Freelance Interview Series – A Gentle Approach to Productivity

Freelance Interview Series – A Gentle Approach to Productivity

Genevieve Michaels writes to make complex topics engaging and accessible. She started her career in the contemporary art world, then pivoted to life as a freelance writer. She’s written for brands like Atlassian, Shopify, Hootsuite, and Hubspot, and her creative writing has been published in Elle Canada, Vice Canada, and Canadian Art Magazine.

Find her on Substack at gentle chaos, where she shares her creative writing and thoughts about freelancing, reading, travel and living a self-determined life.

"Your to-do list is a menu of exciting possibilities, not a list of obligations."

Talk to us about what gentle productivity means to you.

We’ve all heard that procrastination is a problem with emotional management. Gentle productivity is about staying in tune with your emotions, and using them as a guide.

To me, negative feelings like frustration or disengagement are not an inconvenience. They are precious signals towards where you shine, what inspires you, and where you should focus your energy.

So many traditional productivity methods, like time blocking, involve rigid, predetermined rules and obligations. That’s never worked for me.

Instead, I aspire to work with my natural impulses, curiosities, and inclinations — or at least listen to them, without judgment. Those feelings are just data, and I can use them to improve how I work.

I’ve learned from experience that I’m more productive when I’m inspired, excited, and curious.
When you’re highly engaged in an activity, you are working faster, being more creative, and doing better work.

It’s not lazy to want to chase that feeling — it’s using your mental resources effectively. And more importantly, it improves your experience of work, which means elevating your life as a whole.

Read more thoughts about gentle productivity on my Substack here.

How do you incorporate this approach to productivity into your daily routine?

Creating space for your own interests, curiosities, and emotions doesn’t happen by accident. It takes three crucial components to work this way: reducing distractions, removing time pressure, and breaking down your work into different kinds of tasks.

Here’s a little more detail on each of these three strategies:

  • Protect your time (and brain) from the internet: Because smartphones and social media are designed to be addictive, they put us out of touch with our natural curiosities and inclinations. By limiting your access to these distractions (or whatever else tends to throw you off track), you give yourself space to discover what does make happier, more inspired, and more productive. I wrote an step-by-step guide to these strategies on my Substack — read it here.
  • Give yourself plenty of time: If something is due tomorrow, it doesn’t matter how you’re feeling — you’ll have to do it whether you’re in the mood or not. That means padding your deadlines, and starting on projects way before you need to. That is its own special kind of discipline, but it gets easier with time.
  • Understand the building blocks of different types of work: What specific tasks does it take to get a project or assignment done? These will depend on your profession — since I’m a writer, mine include research, outlining, drafting, and editing. This allows you to choose the work that feels right for you in each moment, instead of scheduling your time based on clients or projects.

Together, these elements add up to a life where you know what you’ve committed to, and what it will take to get there. But nothing is imminent, so how you use each day and hour is entirely up to you.

Each new day becomes a fresh, inspiring blank page. Your to-do list is a menu of exciting possibilities, not a list of obligations. Instead of “I need to start X project,” you could say “I feel like some research today, what’s coming up?”

Not every day will look like this — we all have to do things we aren’t in the mood for now and then. But I find that pushing down negative feelings just makes them worse. By holding space for inconvenient feelings like boredom, this approach helps me with all parts of work, not just the ones I’m excited about.

What are some indicators that more traditional approaches to productivity might not work for someone?

You wouldn’t expect to change your body to fit into a pair of jeans. So why should your brain conform to a certain way of working?

Our working habits, methods, and routines are supposed to enable you to do your best work. But since we spend so much of our time working, they should also make your life more enjoyable.

If your current work routines feel painful or discouraging, that’s a sign they’re not not the best fit for you. Similarly, if you see yourself as lazy or lacking discipline, that could be a clue that you’re not inspired.

These feelings can, of course, signal larger issues like attention deficit disorder or executive dysfunction. But why not start by working towards a professional life that feels good? You won’t be able to eliminate all the work you don’t love right away, but listening to those feelings can make them easier to live with in the meantime.

On Substack, I wrote about my journey to realizing traditional productivity didn’t work for me — read it here.

How do you navigate negative self-talk when it surfaces?

Negative self talk is just feelings — shame, judgment, fear, anxiety.

Seeing those feelings objectively, as data I can learn from, helps me not get caught up in them. It helps me not to give those thoughts more power than they actually have.

Coming back to what I said above, obviously, reality isn’t going to match up with this vision all the time. But somewhat counterintuitively, this approach helps me tackle even the tasks that don’t feel flowy, that I do have internal resistance towards.

Those feelings are easier to handle, because I’m not judging myself for having them. They are what makes me human. They’re valuable data that I can use to improve my life and work.

What advice do you have for new freelancers who are struggling to find productivity practices that work for them?

I would suggest thinking about what motivates you, and designing a working style that puts those things first. “Motivation” isn’t going to be a problem when you’re living your dream life, or at least getting closer to it. So how can you make that a reality?

Even when I’m not that excited about the specific topic I’m writing about, it’s part of a career and life that brings me joy. You’ll be so much more engaged with work if it’s part of creating a life that feels fulfilling and exciting, generally.

For me, freedom and seeing the world has always been the thing. I travel often, and people have asked if I find it distracting or hard to concentrate when I’m in a new place. The answer is no, of course not — it’s not hard to focus on living your dreams.

Maybe caring for your family, or spending time in nature makes you happy. If you can clearly see how your work routines bring you closer to those things, they will be so much easier to stick to.

Office Hours: Outsourcing to Grow Your Business

Office Hours: Outsourcing to Grow Your Business

Serial entrepreneur, former consultant, and founder of EditorNinja and Credo, John Doherty, joined as our guest for our July Harlow Office Hours; Outsourcing to Grow Your Business.

We chatted about when to consider outsourcing, what you should outsource, hiring full-time vs. part-time, shifting pricing strategy once you hire, and more!

Catch up on the conversation here:

 

Stay in touch with John on ThreadsTwitter, and LinkedIn!
And follow along with EditorNinja on Twitter, LinkedIn, and Instagram!

 

Transcript:

Samantha

Welcome to today’s Harlow Office Hours for those of you that don’t know me yet, I’m Samantha Anderl, co-founder of Harlow, and for those of you who don’t know a lot about Harlow, Harlow is an all-in-one freelance tool and community to help freelancers grow thriving businesses. We really help with everything from pitch to paid and beyond. We also have Andrea here, who is my co-founder, and Madi from the Harlow team, who’s our amazing community manager. They’re both with us today to say hello and field questions as we go.

Before we dive in, I’m going to go over some housekeeping items, just to let you know what to expect. This is going to be a 45-minute Q&A, all about outsourcing to grow your business. I know that’s broad; we’ll cover a lot of topics here today. So, John Doherty is with us. John is a former consultant marketer and CEO and founder of EditorNinja. I’m going to hand it over to John in a couple of minutes to go deeper into that and tell you more about himself. But before we do that, just letting you all know, this is going to be a recorded session, so for anyone that couldn’t make it today or anyone that you feel would benefit from tuning in, we can send the link out afterward and you’ll all have access to this session.

We have a handful of questions that were sent over in advance. We’ll start with those to kick things off. But if you have any questions during the Q&A, go ahead and drop them in the chat or just raise your hand, and we’ll let you chime in. You are welcome to participate in whatever way feels most comfortable to you. So if you want to speak up, feel free. If you’d rather type something out, feel free to do that too. Either way is totally fine. John, I’m going to hand it over to you and let you tell this crew a little bit more about yourself.

John

All right, hello, everyone. Thank you for that intro, Sam. I appreciate it. So as Sam said, my name is John Doherty. I am a serial entrepreneur, so I’ve started three six-figure service companies since 2015. It’s almost been years now, here in just a couple of months. I have generated a ton of leads for marketing agencies through my other company, Credo, and then Editor Ninja has been my recent focus. We are just 41 words shy of 3 million edited in the last 18 months. So if anyone wants to go submit 41 words, I will love you forever. All right, sounds great. So my background is as a marketer, as an SEO. I did SEO professionally for many years. I don’t even know how many, but I started in about 2008, stopped doing consulting and mostly doing consulting into 2018, done a little bit since then.

I worked agency side for a couple of agencies, most notably Distilled in New York City. I was the first hire in their New York City office after Tom, who moved over from the UK to start it. And then I went in-house with Zillow for a couple of years and ran SEO content growth for a couple of their nationwide brands. And then went out on my own, and you know, I’ve kind of built a company since then. So I’m kind of a jack of all trades. I can, I’m a front-end developer, I’m a marketer, I’m a writer. The only thing I don’t do is design, but I married a designer, so we’re good to go there. And also, I am, in the last number of years, my superpowers kind of become hiring because I’ve just come to recognize that I can hire people who are way more affordable than I am or who have skills that I don’t have, who love doing things that I hate. And so overall, that is my goal, and that’s how I’ve grown my companies.

At Credo, the largest the team has ever been is nine. It’s a little bit smaller than that now, and at Editor Ninja, we currently have, it’s myself and seven editors. So one of those editors is more of an operations managing editor, kind of handling the workflow of assigning documents that are submitted by customers to their editor, queuing it, returning it, etc. But I’ve built our own software, kind of workflow software that facilitates all of that. So yeah, I kind of do all the things, but I love hiring, I love talking about hiring. I am firmly convinced that the best way to grow usually is via hiring, but you have to do it correctly. So I’m here to share my knowledge.

Samantha

I love it, and John and I have actually, we’ve known each other for what, nine years now? So back when you were at school, I think I was at Campaign Monitor. And so it’s really fun because we’ve both seen each other start these various businesses and go through our careers together and seeing how we’ve grown businesses and shifted and hired. So I’m super pumped to be having this conversation here with him today. So, oh, we’re gonna dive in. And I know, John, you just mentioned that you’ve gone through starting a number of businesses, whether that’s consulting businesses, whether it’s service businesses, whatever it is. When did you first start considering outsourcing? As a solopreneur or somebody who’s starting their own business from scratch, when do you think people should consider outsourcing?

John

So I think there are a couple of ways to answer this question. The first one is, it kind of starts with knowing yourself and knowing what you’re really good at and what you enjoy, and also what you don’t. For a business owner, even a freelancer for a business, even a freelance business under 10K a month, something like that, I don’t really recommend outsourcing simply because you’re cutting into your margin so much that you’re most likely just going to let that person go pretty quickly. That said, I do think there are definitely ways to outsource earlier on. For example, using Freshbooks or Harlow subscription is way cheaper than hiring an accountant and that sort of thing. I definitely recommend hiring a tax accountant as a self-employed individual, but really, once you get above about 10-15K a month in revenue, that’s when everything starts to get really busy, as I’ve found. So, you’re ending up working a ton of hours and doing a lot of things that you don’t really know well or that you once you learn, you realize that you don’t really love, and sometimes you actually hate them.

My kind of framework for considering when to outsource is basically, do it as soon as you can afford to do so and outsource things that are core to the business that you hate, that you don’t like, or that need a trained eye, like accounting or something like that. So, things like counting payroll, even marketing potentially, but probably not sales. I think for most freelancers, you should be the one doing the selling, but you also have to be the one doing the delivering.

At EditorNinja, for example, or even at Credo, I believe it was about two to three years in that I hired someone on a part-time basis, hired a few people on a part-time basis, to basically do all the lead qualification issues to agencies and that sort of thing. But I still did the account management. Over the years, as the business was growing, I was able to hire a full-time person that also did account management, and now I’m basically stepping back from the day-to-day of that business. I was able to fully replace myself. But at Editor Ninja, I am not an editor, I’m a writer. So I’ve had to outsource, I’ve had to delegate to editors, and then pretty quickly got the managing editor in place so that I didn’t have to show up every single day at 7 A.M., assigning documents to editors, and at noon, QAing documents and sending them back to customers, and at the end of the day, assigning documents that came in during the day to editors, all that sort of thing. I don’t handle any of that, which frees me up to do things like this, to do marketing, to do sales, you know, that kind of thing, to go on a walk in the middle of the day if I want to. I have that freedom in my calendar these days.

But, you know, I will say though, the first thing to consider outsourcing is your inbox, scheduling, calendar, so hiring an assistant, hiring a virtual assistant, a part-time virtual assistant, or just an assistant, I think is what we should call them because we live in a remote world now. I mean, look, we’re all working from home. So just hiring an assistant that can handle those sorts of things. Mine lives in El Salvador, and I pay 800 a month. I get 20 hours a week of her time, 3 to 4 hours a day. So, you know, you don’t have to hire full-time, you can outsource things like this pretty easily, cost-effectively, and really the goal is to get these things off your plate so you can focus on higher leverage activities, which we’re going to get into further, but also the goal is to buy back your time and then take that time and apply it towards things that are higher leverage that you’re great at and that you love doing, which is ultimately how the business is best going to grow.

Andrea

Sorry, I want to interject because I am curious about this specifically—outsourcing your calendar and your inbox. It’s something that I struggle with because it’s like, “Oh, but are they gonna know what to do?” and it feels like giving up so much control. How did you even structure that with your assistant in terms of how they’re to manage your inbox and your calendar?

John

Yep, it is definitely a control thing. It is something that I’ve had to learn over the years. Basically, my assistant keeps my calendar. The way I’ve kind of worked it over the years, and I highly recommend reading Dan Martell’s book “Buy Back Your Time.” I actually learned my process for hiring and delegating from him. But basically, yeah, I see Claire mentioning SOPs. One of my oldest assistants actually put together a document about me and how to manage my inbox and calendar, including information about my family and birthdays and all that sort of stuff. So there’s literally a guide to John that each assistant I hire gets.But for me, they manage my inbox by putting anything that I need to look at into a specific folder that I look at so that becomes my inbox, but they handle getting everything else out of there—anything I don’t need to see. If they have a question on something, they put it to me. If it’s something like, “Hey, do you want to have a meeting with this person or not?” Instead of them saying, “Hey, do you want to meet with so-and-so,” they’re like, “Hey, there’s an email from someone that looks legit, it’s not a guest post pitch or something like that, take a look at it.” Then, basically, I handle the back and forth.

When I’m reaching out to someone, I handle the back and forth, and when it comes to sending the calendar invite and that kind of thing, we use Trello. I will forward that email to my assistant’s Trello board, which is “Things to Do,” and I’ll just say, “Can you please schedule this meeting with so and so?” Then, they take care of it for me. One other thing that we do that really helps is we have a review at the start of the week and at the end of the week. On Monday, it’s about what’s coming up this week, and on the end of the week, we look back at what we did and if there was anything that was a waste of my time and I shouldn’t do anymore. Then, we look forward to the next week and be proactive about it. So, we have a couple of different ways, the folder in my email and Trello boards. They also put stuff on my Trello board, things they need me to do, which is awesome, and they’ll bug me about it too. I ask them to bug me, but I’m like, “You’re not bugging me, actually. You’re just making me get things done,” which is great because I’m an ADHD all-over-the-place founder. I need someone who has checklists about their checklists. That’s kind of where we start.

Also, just your quick question about, are they going to know how to manage your inbox and your calendar from the start? No, you have to train them. You have to show them what you need and what you don’t need. It’s going to take the first month, two months, something like that for them to really get up to speed and learn what’s important and what’s not. But then, after that, they’re rocking and rolling. That’s how I do it personally.

Andrea

Thank you. That was really helpful. Yeah, good, awesome. So you mentioned very briefly that you used a service to find your most recent assistant, and I would love to dig a little bit more into that because what I hear a lot from freelancers is they’re like, “Okay, I want to bring on subcontractors. I want to bring on a VA. How do I do it? Where do I find them? What does that look like? How do I even start?”

John

Yeah, it’s a big question. It’s something that I got wrong many times before I started getting it right. For me, I kind of think about it a couple of different ways. Number one is if you decide that you’re going to hire an assistant, and you can pay them 15 bucks an hour, 20 bucks an hour, whatever that is, work from home, that kind of thing, there are a few different ways that you can do it.

First of all, you can source them yourself. So, you can either put up a job rack, put it on LinkedIn, or you can pay to promote it on different sites. It kind of depends on how big your business is. For example, at Credo, doing 40, 50, and 60k a month, I would basically go and I’ll pay 500 to a thousand dollars to promote a position on different sites like We Work Remotely and Career Contessa to get a wide variety of applicants, to get a diverse variety of applicants because I believe we have to go and actually prioritize that and then use an applicant tracking system to basically sort through the resumes. I actually have my assistant sort through the resumes and move them on to the next level, and then I take a look at it and then we basically have a process there that’s mainly for full-time people, though. For part-time people, especially like part-time virtual assistants, it can often be easiest to hire them through a service that specializes in it. There are a bunch of different services out there. Mine is one that specializes in helping US companies hire El Salvadorian employees, so it’s super cost-effective because their cost of living is a lot less. But if you’re going to hire military wives, there’s a service for that. There are multiples of what I pay, but they’re in the US, highly trained, and professional with what they do. I mean, they’re military wives and moms, and so, they have to be super organized. I love hiring stay-at-home moms, by the way, just because they’re super organized, super communicative. They work out really well. But yeah, that’s kind of how I start.

Then, the whole vetting of them and that aspect is a whole other level. We can get into that. But, it’s kind of where I start with looking at how do I find the right people. Too many people just go, ‘Oh, I’m looking to hire someone. Hey friends, do you know?’ and I just find that doesn’t really work well. You can go and source them yourself like at EditorNinja.

When we have a customer come in that has a specific need, we were working with a large Marketplace and updating a lot of content for SEO for them, I didn’t have anyone on stop that could do it. I did the pilot project but then I needed to hire people, so once again I was out of delivery so I could focus on Marketing, sales, etc. So, I actually went and sourced them. In that case, I used Superpath, which is a Content Marketing Community. I think that’s where I found them through, but I tested out five, six, seven different potential contractors, paid them all for the work that they did, but ended up hiring two actually from there. So, I sourced them myself through there and kind of put them through our vetting process. So, there’s kind to lean back like, ‘Hey friends, who do you know?’ and then there’s like, go and search for them and who’s actually done it before. So, yeah, that’s kind of how I approach it.

Samantha

Awesome! I’m gonna name drop one other service too for finding virtual assistants, which is shesagiven.com. Actually, a pal of mine, Emily, specializes in helping, whether you’re a solopreneur or a small business owner, actually go out and find the right virtual assistant for you. So, she has a vetting call; she matches you, very much as Credo does, with agencies and people looking to hire them. So, that’s also a really great service to check out. Yeah, she’s really, really awesome. Okay, so you touched on this briefly about, you know, going through and having to hire like five different contractors, try them all out, really figure out kind of who fits your business. So, I want to kind of go into mistakes that people make when bringing on subcontractors or virtual assistants, especially when they’re hiring maybe for the first time. Like, talk to us a little bit about what you’ve experienced and maybe how to avoid some of those mistakes if avoidable.

John

Yeah, yeah, I mean, there are definitely a bunch and some of them are avoidable, some of them are not, but there are a few things. Number one, and we touched on this with the question about, are they going to know how to manage my inbox, my calendar, and that kind of thing? And that is, too often, people, especially people who are not super experienced with hiring, will basically bring someone on and be like, ‘All right, go do it,’ and they’re like, ‘I don’t know what to do,’ right? So you have to train them. Not training them is one of the most common mistakes I see. You have to let them know that if they’re a writer and they’re subcontracting for you, you have to let them know the expectations around length and keyword usage and tone and voice and when it needs to be submitted and all of these sorts of things, right? Turn them on to the workflow system that you use. It seems like everyone has built their own like workflow system in Asana or Trello or wherever I build my software. Everyone has kind of built their own, but you have to train them on the tools that you use because even if they’ve used Trello a lot, they might not know your Trello setup, so you have to train them in that. Another one that I see is not hiring people with experience.”

So going really cut-rate and going junior usually ends up unless you’re, you have a long time and a lot of patience, and your clients do, too. Especially if you’re subcontracting work. It doesn’t really end up working out well, so I hire people with experience. Even if it’s just a year or two of professional writing experience, that can make a big difference over someone that has had one client that they’ve done some writing for.

Then, along with that, to take it even a step further is not hiring people with experience, uh, at your type of business, that is at your stage. So there are some people that work really well. Like I worked, you know, for Zillow, a publicly traded company. We went from 600 to 2400 people when I was there in the two years I was there. That included a big acquisition of our biggest rival. The company I was at went from I was number 18, and we grew to about 60 in those years. So, like, I’ve seen that, or you know, early early-ish stage growth. I’ve also worked, you know, I’ve started my own companies and built them up to, you know, 8, 10, 12 people. So yeah, it’s, and this is regardless of like if you’re hiring a subcontractor, you’re hiring someone full-time, you need, you need to find that you’re hiring an agency, find the people, find the entities, organizations, whatever, that have the cut, that have experience doing the thing that you need: CEO blog writing, whatever editing with the type of business that you are. So not like e-commerce or SaaS, but also in your vertical and then also at your stage.

Because people that are used to working at an early stage, they’re going to be like, if your process is a little bit, a little bit all over the place, they’re gonna be a lot more forgiving than someone that’s like, I’ve worked for only companies that have over 2500 people and like I need a, you know, I need someone that is like on call for when my keyboard breaks to get me a new, like all that sort of stuff. Small companies don’t have that luxury, right? So you need people that really understand that.

Then, just a couple more things, just real quick, are number one is not setting expectations with them about what success looks like. So I kind of talked about that already with style guides and like that kind of thing, but you have to give them expectations about what it means to succeed that also lets you hold them accountable. And if they’re not meeting those, are not able to meet those, even after, you know, repeatedly being like, hey, I need you to do this, that gives you a really good out to let them go and to find someone new.

Another big mistake that people make, that I’ve made before, is hiring people to do new things, not to do things that are already working. So I’m a big believer in replacing yourself or delegating stuff that’s already going, as opposed to hiring someone, you know, to build out a brand new Google ads campaign for your company. You can do that, but I personally have been taking the approach of hiring a coach that can coach me through it. So, I can do it, and then once it’s working, I can hire someone to actually take it and run with it and do it better.

But hiring someone to do new things just doesn’t really work well, and then just the last two are numbers, or the last one really, is not measuring results. You know you need to hold them accountable, but then also are the numbers going in the right direction, right? And are you actually taking that time that you’re buying back and are you using that for things that are higher leverage, like marketing, sales, that kind of thing? And this is all about holding yourself accountable to that as well because I see too many entrepreneurs, and I’ve been guilty of this in the past myself, they’ll hire someone to buy back their time, but then they’re not going and taking that time. They’re basically just not working. But they should take that time and go put it into higher leverage activities that are going to continue to grow the business.

And also, it’s okay to not have your business be growing, and you know if you have an insane profit margin and you know you’re working 80 hours a week and you have a crazy profit margin spending a thousand dollars, two thousand dollars, you know a month to buy back 30 hours of your time, that’s probably going to be worth it for you to take that personal income, that profit hit to work way less and actually be able to see your family and go on trips and that kind of thing. So those are the main mistakes that I see people making.

Obviously, there’s a lot of them, there’s a lot of pitfalls to avoid.

Samantha

Yeah, that was actually a great list. I think a couple of the ones that stood out to me specifically were finding somebody who is used to working with the same type of clients at the same type of company. I think that was really big when Andrea and I were running our consulting business Interimly. All we did was work with early-stage companies to help them get up and running. But with early-stage companies and with tech startups, there were constant shifts in strategy. Andrea and I have worked at a number of startups, and so we were used to this constant shift in strategy, but when we bring on a subcontractor that was not used to kind of the ups and downs and the roller coaster of startup life, it could be really difficult for them. You know, we’re like, okay, yes, you were working on this project, but we’re de-prioritizing that, and we’re actually shifting to this project because the business goals have shifted, right? And so, it’s just really important to find somebody who understands the way certain types of businesses work.

John

And sometimes you don’t really know that until after you’ve hired them. Unfortunately, we’ve had some editors come to work for us who were just really uncomfortable with any uncertainty and it just didn’t work out right we start working with them they’re a great editor their work product was fantastic BUT it wasn’t uh successful for the long term or for both of us long term simply because they weren’t able to work with uncertainty.

Samantha

Uncertainty is a great word to bring up in general because I think whether you’re a solopreneur or whether you’re a small business and you’re going after those first couple of hires, whether it’s a subcontractor a virtual assistant, those people have to be okay with some uncertainty and I think that’s really hard but like you’re an entrepreneur starting a small business and there’s a lot of uncertainty for you so whoever you bring on board they have to be okay with uncertainty too. And I think that goes back you know you were talking about setting expectations and that’s one of those expectations to set right it’s like hey I’m I’m trying to grow this business and here’s my plan and here’s where I’m heading but there’s a lot of uncertainty when you’re in a one to five person business and the people that are joining you have to really understand that so I love that.

Something that we’ve touched on you’ve touched on briefly in a couple of answers but we haven’t gone into specifically is if you’re a solopreneur and you’re just bringing on your first assistant or you’re bringing on your first subcontracto,r you really have to go back and reassess your pricing right so you’re not going to charge the same that you’ve charged you’re probably not going to charge the same hourly rate the same project rate so how would you recommend a solopreneur or a small business owner going back and assessing their pricing when they start hiring?

John

That’s a really good question though so there are a few things that first of all you need to understand before you even go higher the first one is uh what’s your current profit margin right so if you’re you know if you’re charging and some and often if it’s you’re a solo person kind of working out your own effective hourly rate it’s like, okay how much you know if you’re making 10,000 a month but you’re working 200 hours you know uh working 200 hours a month what’s that number it’s 50 an hour right? You might say I charge $125 but your effective hourly rate is actually 50 an hour so you actually really need to know what that is and then you know that that’s where the uh you know percentage of uh your hourly rate your actual hourly rate is uh that’s that comes into into play for hiring another one to know is what’s the amount of profit you want to make or you need to make in a given month so I’ve heard multiple people say and I’ve come to believe it is “Revenue feeds the ego profit feeds the family,” so you know if you’re running you’re like yeah you can have you know twenty or twenty-five thousand honestly I’ve made this mistake with EditorNinja and I’ve been rectifying it you can have 15, 20, 25,000 a month in revenue and have no profit – it’s very easy to do.

And so that’s where you need to understand what your profit margin is and what you’re willing to take. Agencies are really tough, service businesses are really, really tough to make work because you have human capital. The market will only bear a certain, you know amount as well. But basically, you need to say okay if I want to make ten thousand dollars a month as a freelancer, I probably need to charge 20 or 25 based off of how much I can get, you know, basically work for, and the level of work and all that sort of thing. You’re going to pay more for more experienced people, but also it’s gonna be less of your time right, but you know but there are trade-offs there as well. Because if you hire a less experienced person you have to spend more time, but you’re spending your time instead of spending the dollars right? It’s the constant like balancing act. At the start, usually, you’re going to hire people that are more junior and you’re gonna have to spend more time and then over time that allows you to go and hire more experienced people that can take more things off of your plate, but you’re charging more because you’re having a better work output, and so you actually end up making more. You just need to keep an eye on this.

I have a spreadsheet that I use where every single week, it’s in every month as well, is how much cash do we collect, how much did we pay our editors, how much did I pay, how much do we pay me, what are other expenses, and basically at the end of the month I know how profitable were. But, I also look at paying editors, is my calls my cost of goods sold, and then what’s my percentage there and I like to keep mine at like 60% to 70% because then we have other expenses for software and technology and all that sort of stuff and then I like to get paid, too.

And then I also need to keep some cash in the business in order to go and invest in new things, so it’s it’s a balancing act across all of those. But I think the takeaway really is pay people more if they’re doing more senior, more valuable tasks and take other things off of your plate. And if they’re just writing and they’re not doing any strategy, they’re not doing any client management, that sort of thing, they should be paid less than someone who is also doing some of those things, and you can over time establish a rubric there and move it around. So that’s how I start thinking about it. Then with pricing as well, a lot of people ask me about setting pricing. Where do I even start? The way I do it is to look at what is the market charging, but that is just the starting point for me. People will be like “All right they’re charging $1500 a month for five blog posts, I’m gonna go charge 1200.” Right? And that’s just a race to the bottom.

Instead what I think is “Okay, how can I get someone to pay me $2500 or $3000 a month for that same amount of work by adding on more value or just leaning into the value that we already bring?” Whether it’s subject matter expertise or it’s ready to publish, we’re going to upload it into your team, whatever it is, adding on that additional value and therefore being able to charge more. You’re just going to get better clients as opposed to just a race to the bottom because if someone’s charging $1500 and you come in charging $1200, someone else is going to come in charging $1100 or a thousand dollars, right? It’s just a constant race to the bottom, and that’s where I see freelancers get into trouble. Instead, look at how can we charge more, how can we charge premium prices, that better clients are going to want to pay and be able to pay, and the people that aren’t going to be great clients, you know, they’re just not even going to consider it, and that’s okay.

Samantha

Absolutely, and I think you know, with charging more in general, if you’re a freelancer and you’re bringing on a subcontractor, you’re bringing on a virtual assistant, it should be so that you can provide a more well-rounded service and a more valuable service, right? So if you’re in a position to do that, to bring on people to help you with your team and to bring in more perspective, you should be charging more because now you’re offering a more valuable service to your client, right?

John

If you bring on if you’re like if you’re taking forever to send out invoices, bringing on an assistant that is responsible for sending out invoices, you’re going to get paid faster, and that right there has a measurable impact, so it means you can maybe go from like negative cash flow to positive cash flow. That right there can have a huge impact, so don’t forget to look for those things too.

Samantha

Absolutely. I think one of the things that’s very important to state around pricing and when you’re first figuring this out and first bringing on subcontractors and virtual assistants, you’re probably not going to get it right the first time, and you mentioned that, John, right? You’re like, I’m still working through it. I’m still working through how much I should be paying people for what type of service and how it impacts my business and what the how valuable the outcome is, and that’s okay, right?

Andrea and I brought on a couple of subcontractors when we were running our consulting business, and we were kind of constantly shifting, you know, how much does it make sense to pay people, how many hours can we bring them on, what exactly should they be doing, where are they providing the most value, how can then we, how then can we provide more holistic value for our clients? It’s a constant conversation with any small business, any startup. You’re constantly learning, you’re constantly shifting, and that’s okay.

Andrea

Yeah, and I will say at times we found it was better for our business to not subcontract but directly connect our client with that other freelancer and let them manage the relationship because we weren’t going to be able to profit off of offering that service, but we were able to generate a lot of goodwill with our clients and with the other freelancer by making that connection and still like holistically being able to provide these services by bringing in other freelancers and consultants. So just kind of I would say consider that sometimes it doesn’t make sense to do the subcontracting.

Samantha

Yeah, one thousand percent and that’s also, I mean, that’s a great way, like, you know, Andrea mentioned Goodwill, that’s a great way to build out your network and build out your community is by passing off the work that you’re not going to do well or that you’re not going to make margin off of, and it doesn’t always have to be passing up that work to a subcontractor or virtual assistant. It could be somebody else in your community, and that’s a beautiful relationship to build as well.

Okay, another question that we received, so the question is, I’m based in Canada, and it’s not as easy to subcontract here, and I know that we are all probably not super in tune with Canadian law, but the question really is around hiring versus subcontracting and how to figure out which is the right move for you. Right, do you want to hire someone full-time, do you want to subcontract, do you want to bring on a virtual assistant, like, how do you figure out the right path?

John

I’m not a Canadian employment attorney, so I’m not quite sure about all of that. I’ll just give you my framework for kind of how I think about this. If it is something that needs to be done semi-often, well, there’s kind of, I think about it as a breakdown of what is the task or what are the things that this person I need this person to do, and then what’s the right type of hire for that. For example, if your business is under probably a million, two million a year, you don’t need a full-time Finance person. You need a bookkeeper, you need a bookkeeper, you need an accountant, is what you need, right? You don’t need a chief revenue officer, like, that sort of thing. Basically, you hire them to do the things that they do every single month.

For example, they go through they reconcile my books, they do a little bit of invoicing and that sort of thing, they tell me quarterly taxes are due and here’s what you need to pay and this is where you send it and that kind of thing, but it would never make sense to hire someone full-time for that. Part-time or subcontractors, that kind of thing. So, at Editor Ninja, I’m the only person that’s full-time, and I’m not even drawing a full salary yet. They’re all 1099 contractors. We’re based in the US, I pay them basically by the amount of work, by the amount of words that they edit, and the type of editing that they’re doing and that sort of thing. For my managing editor, it’s a little bit different, that’s hourly for stuff that he’s doing but also kind of have an expectation for a number of documents he can get through in an hour, that kind of thing, have a budget there that we don’t, that I don’t really go over. And so, these are things that need to be done, I mean, I need these editors to show up every single day and to, you know, to work to do work for us, so I have an expectation of a certain number of hours.

But it’s 10 hours a week, and if they have more, then that’s great, but I know they can get through two thousand words an hour, and so 20,000 words, you know, a week, and so 82,000 words a month, and that allows me to build capacity from there. At some point, it may make sense to bring on someone, you know, full-time, like a full-time editor, a full-time account manager, or someone like that, once we’re at a certain point where it’s taking enough of my time that I can then go and hire someone full-time. So it’s both the like, what is the role, who is doing those things currently, how often do they need to be done, and then basically, can you afford to bring in that person, you know, to kind of replace you in that? Usually, I say start off with, there are certain things like accounting and whatever, maybe even development, right? Like, I will occasionally find freelancers to build out a feature for us, you know, for the software that we use to kind of facilitate all the intros or all the assigning work to editors and that kind of thing. But I’m not going to keep a developer on a retainer. I can go to Codable and find someone to build out this one thing, and yeah, it might cost me a little bit more per hour, but I don’t have that ongoing overhead versus a managing editor or a marketer or someone like that.

Usually, I like to start off with freelancers. That kind of I’m directing the strategy. Eventually, I’ll bring in someone on a part-time basis who is directing the strategy, who is managing those freelancers, and then eventually, assuming they’re good at what they do – and this applies to sales or any of those things as well, kind of take it and apply it to your business – then eventually I will hire someone full-time once their work has basically gotten us to the point where I can afford someone full-time. And it might not be that same person because they might be a fractional marketing lead or whatever, and so, and they’re not open to full-time work, and so I’ll go and hire someone full-time, but I’ll get that part-time person to help me with hiring the full-time person so I don’t have to do all of that. That’s a hack for you right there. But that’s kind of how I think about the type of organization or person or whatever to hire, and we could get into the like done for you, done with you, do it yourself.

So you know, like consultants you’re working with, freelancers you’re working with them, DIY is obviously you’re doing it, and then done for you, that’s more like an agency or an individual like a senior contractor or someone like that who is very much executing on the work and not just giving you strategy, and that’s important to kind of differentiate between. I actually say freelancers are the ones that are doing the work, consultants are giving you strategy, but you still need freelancers or someone else, maybe you, to implement it, but then you’re still also having to manage the people versus you hiring an agency, they’re responsible for me, or a service like mine, they’re responsible for managing the people, right, and that’s also a value that you can charge for because, like, you know, we get people coming into Editor Ninja that they need, they’re like, I have 150,000 words of content that I need edited in two weeks. There is no way they’re going to be able to go and hire freelance editors that are vetted, that are trained, etc., to get all that done in two weeks.

We can do it. We have the people, right, but they’re going to pay us a premium because we’ve taken all that off their plate, and they’re actually able to get it done. So, you know, that’s something to also think about in your own work as you’re freelancing. Like, are your customers that they actually prioritize getting things done on time, or they’re like, hey, if we don’t get this done in two weeks, this client’s gonna fire us, and it’s a ten thousand dollar a month client, right? It’s 120k a year contract. They’re gonna be super happy to pay you five grand potentially in order to not lose that additional like 100 grand of revenue, right? The people always surprise me, and often then sometimes people will be like, oh no, I can’t do that, and I’m like, what was the trade-off, you know? But what I find is usually people are willing to do it.

Samantha

That’s awesome. I was actually, I know that we are, we’re about five minutes. I initially going to ask you, would you kind of dug into just then, is like how content writers specifically can leverage EditorNinja to expand their business, right? So I know that you have companies of all shapes and sizes that come to EditorNinja for their editing needs, but specifically, I know that we’ve talked about previously that you have some pretty big, you know, or well-known names in like the content freelance space that have started using EditorNinja to expand their business and using EditorNinja in place of maybe a subcontractor or virtual assistant to do certain things. So can you talk to us a little bit about that?

John

Yeah, for sure. So yeah, I mean, we work with everyone from small, like two-person agencies to, we have some publicly traded companies as well that are customers. For freelancers specifically, there are a couple of ways. And freelancers, I’ll be completely candid, it can be challenging to work with freelancers simply because your work can be kind of all over the place. It’s the same challenge we have at Credo and why Credo focuses on agencies, not on freelancers and solo consultants because freelancers and solo consultants only have a certain amount of capacity, right? And so if you’re able to produce 10 pieces of content a month, like, that’s where you’re capped. And most, I also find most freelancers do not actually know their numbers and know their profit percentage and that kind of thing, and they think about hiring another service or a contractor or something.

Like that is like that money directly coming out of their pocket and I get that, and I’ve had that mindset before. I’ve just been doing this for long enough that I now know my numbers but so for uh freelance writers specifically, there’s a couple of ways. Number one, if you have consistent ongoing work, you have long-term clients, that kind of thing, you know how much you’re producing and editing is just taking up a lot of your time, we can save you 15-20 hours a month, two to three days of effort per month just on the copy editing, proofreading, fact-checking, that sort of thing so that can make sense for people that are producing more and actually get that “okay I’m doing 10 pieces per month right now, but if I can get back those two to three days I can do two more pieces of content every month and charge a thousand dollars for that right so I’m paying 500 to make 2000. Totally makes sense economically right?

The other thing I tell freelancers is we have the ability for you to just order a single piece edited, so editor-ninja.com/single-doc, uh, will get you to where you can basically price it out and say, ‘Alright, 1500 words copy editing proofreading, you know I need it back in two days,’ you can kind of test out the service that way if you’d like to and you can just keep on it, you’ll then be prompted to create a free account and then you can go and you know just pay for documents one-off, and so what I tell Freelancers is this is a great way for you if you’re like, you know all of a sudden you know something happens, your kid gets sick or you get sick or something like that but you’re like, ‘I owe this piece of content to them in two days’ time, it’s whether it’s me to go pay editor-ninja 50 bucks to get this done so I can get it you know on time so that I don’t lose that client or I’m not having to re-manage expectations or that sort of thing. As you can tell, it really comes down to what are not just the upfront cost, but also what are the hidden costs, right? What do you get, what could potentially happen, or what will probably happen if you don’t go ahead and do this thing right? You don’t need to commit to a full monthly subscription with us. If you want to, great! Let’s talk about it. But if you go to editorninja.com and click ‘get started’ that’ll take you to schedule a call with me, happy to chat even just to help freelancers solve their problems with scaling. I’m good at this, I’ll be honest, I’m good at this.I love talking to freelancers, but consider using it just for one-off documents where you need a rush job or something like that. We’ve got that, we’ve got the editors and you don’t have to go and hire them, so we can help you out when you get yourself into a bind.

Samantha

Awesome! I love that. Well, we are right about at time so quickly. I know that you just mentioned where people can go on the editor-ninja website to either submit a document or get in touch with you, but outside of that where can people find you if they have questions after this, if they want to get in touch, or they just want to follow along with you where can they find you?

John

The best place is on the social media – Twitter and Threads – I’m @dohertyjf on both. This is the first time I’ve actually gotten to say that, but I’m the same username pretty much everywhere except on LinkedIn but just type ‘John Doherty’ and you’ll find me in there. LinkedIn is really the best place to find me then my email is john@editorninja.com, which is the best place to reach me professionally or if you just want to ask one-on-one questions.

Samantha

Awesome! And if you have any questions for me or the Harlow team, you can find us on threads, Twitter, etc. at @MeetHarlow, or you can get in touch with me specifically! All of my handles are just @SamanthaAnderl.

Freelance Interview Series – Freelance Finances 101

Freelance Interview Series – Freelance Finances 101

Treyton DeVore is a creative entrepreneur, freelancer, financial planner, and founder of Creatorbread, a blog and newsletter created to answer all of those questions the self-employed have about money and business. Subscribe to his newsletter if you’re ready to take your business game to the next level.

Freelance Finances 101

How do you recommend freelancers structure their business?

For those just starting out, it makes sense to keep it simple and operate as a sole proprietor (which means you’re acting as a business but you have no established entity). You can accept payments, write off expenses, and offer professional services all without an LLC. But if you plan to stick with it for a while, I recommend setting up a single-member LLC. It’s essentially the same thing as being a sole proprietor, but you get a few extra benefits:

  • You can apply for an EIN, which is like a social security number for a business (so you can use that rather than your SSN when filling out W9s)
  • You can apply for business bank accounts
  • You can apply for business credit cards
  • You have more legal protection

If you plan to grow into an agency or you’re consistently hitting $10k months, it may make sense to establish an S Corp to save money on self-employment tax. This is complex and rules vary by state so you need to speak with an attorney or accountant before doing so. This’ll help ensure the right steps are taken and that it makes sense for your situation.

Why is it important to have a separate business bank account?

Mixing personal and business transactions in one account would be like managing work for two separate clients in one folder that they both have access to. When you go to file taxes, you need to know what expenses are tied to the business and what income is subject to self-employed taxes – so I recommend having separate business accounts to make your financial life 1000x easier. Without separate accounts, you’d have to go transaction-by-transaction through your personal bank and keep track of the numbers in a spreadsheet to maintain proper records.

You’ll also have cleaner insights into your business when you have accurate numbers. By connecting your business account to accounting software, like Freshbooks, you get all sorts of financial data and reports. Understanding these will help you make better decisions and ideally, make more money.

At what point in the freelance journey do you recommend bringing on a bookkeeper and/or accountant? 

I recommend working with an account for tax filing from day one. It’ll cost a little bit of money ($200-1,000+), but even tools like TurboTax typically charge to file self-employed taxes. I like paying for peace of mind so the couple hundred dollars it costs to work with a CPA is beyond worth it. For bookkeeping, it typically makes sense once you’re doing more than $100,000 per year in business revenue. The monthly fees can be a little steep, which is why I recommend doing it yourself until you have extra money in the business to start outsourcing tasks & responsibilities.

What money management advice would you give to year 1 freelancers who want to plan appropriately for things like taxes and retirement?

Most importantly, make sure you’re setting aside something—anything—for taxes from every payment you receive. I recommend 25-30% as a general rule of thumb but the accurate percentage will depend on your unique situation. 

Get paid $2,000? Move $500 into a separate account. Some banks, like Found or Novo, will do this automatically. Then you can make the necessary quarterly tax payments (which is required if you expect to owe more than $1,000 throughout the year) and have the funds ready to go. 

For retirement, there are a few options available. The easiest way to get started is by opening a Roth or Traditional IRA. These can be opened at places like Vanguard or Fidelity and they’re almost like a bank account that lets you buy stocks. In 2023, you can only put $6,500 into either a Roth or Traditional IRA and there are also some income limits that start at $68,000. The limits change each year so be sure you’re staying up to date with new laws & numbers. 

Outside of those two accounts, the best options will depend on how your business is set up. I wrote a fairly in-depth post here about the following accounts:

  • Solo 401k
  • SEP IRA
  • Taxable brokerage
  • Roth and Traditional IRA

Contrary to what most financial advisors would recommend, I don’t think retirement should be a priority when you’re just getting started, especially if money’s tight. There’s massive upside to getting started early, but there’s also value in financial stability and peace of mind – even more so if you have variable income. Personally, I haven’t invested much in retirement since I started the business. Less than $500. I’ve put all the money back into the business to grow it, paid myself, or saved it in cash. When the business is more established and I have a solid financial foundation, I’ll have more income to ramp up retirement savings in the future.

What expenses should small business owners be keeping track of?

Anything that’s “ordinary or necessary” for your business. That’s how the IRS defines a legitimate business write-off. Need a computer to write? Keep track of the expense and you can probably deduct the full amount on your taxes. Pay for a course to learn a specific skill? Write it off. If you want to learn more about taxes, I wrote a full breakdown of how tax write-offs work here.

What are your go-to podcasts, blogs, or other resources you’d recommend to small biz owners interested in learning more about finances?

How We Built a $1M Consulting Biz by Outsourcing

How We Built a $1M Consulting Biz by Outsourcing

It’s common for freelancers and solopreneurs to reach a point where their workload becomes overwhelming and help is needed. Sometimes it’s a simple matter of capacity — they’re burning out trying to meet their clients’ demands — but sometimes it’s a skill gap that calls for an extra set of hands.

This is typically the moment when freelancers take a step back and ask themselves what they really want from their business. Usually, it’s a choice between scaling back their workload or outsourcing to grow. Reaching this critical point can be scary, because it forces you to change your approach. But hiring support is also an incredible opportunity to take your business to the next level.

Figuring out where to start — and how to find the right people — can be a daunting task. That’s why we’re sharing our story. We’ll go through the steps we took to grow our boutique consulting firm using subcontractors, including how we found them, how we priced our services, and how we managed a growing team. I hope that it helps you with this next big decision in your business.

Our Story:

When my business partner and I started freelancing, we had the unique advantage of being a duo. This gave us access to a wider network of connections and bigger projects because together we offered a diverse skill set. But as our business grew, we discovered that most of the companies we worked with needed even more support than we could manage between the two of us. We were constantly helping them bring on additional freelancers or consultants to manage parts of the project, and that’s when we had our aha moment. What if we just brought on the talent our team needed to service their needs top to bottom.

We decided it was time to reassess our team structure. We worked great as a team of two, but we recognized the opportunity to diversify our clientele and grow our revenue by bringing on subcontractors. The extra help would be a value add for our clients, which meant we could charge more for each project. And having additional support would allow us to delegate the more hands-on tasks, so we could focus on strategy.

Off we went to find our first subcontractors. Shortly after putting the word out, we hired someone to manage our clients’ paid marketing programs and help with content creation. This move transformed our business and helped us scale tremendously. Bringing on just 1-2 people shifted the way we could serve our clients. We were closing bigger deals, executing faster, and truly enjoying the work we were doing.

TLDR: Bringing on subcontractors really did change our lives and helped us to take the business to a level we didn’t know was possible.

How We Hired Subcontractors

Before we began our talent search, we got really clear about the type of work we wanted our subcontractor to focus on, and the type of work we no longer wanted to do. For example: We were too bogged down by other clients’ strategic needs to manage execution tasks, like launching paid programs and writing short-form content. We knew that outsourcing these tasks would free us up to focus on the work we really loved to do. By getting specific, it helped us find the right subcontractor for the job — someone who would both enjoy and excel at that work.

We tapped into our network to find marketers who were looking to leave full-time work and try freelancing without taking a huge risk. We offered them consistent but flexible remote work and the freedom they’d been craving. It was a win-win for all of us, because we got support in tackling the tasks we didn’t enjoy, and our subcontractor got a stream of well-paid work without the responsibility of managing client comms or business operations.

Other Ways to Find Subcontractors

Don’t have an extensive network to tap into? That’s okay. There are a number of routes you can take to find the right subcontractor:

  • Put the word out anyway — Talk to your friends, family, and acquaintances about the kind of support you’re looking for. Even with a small network, you never know who will make the right recommendation. People are looking for work all the time.
  • Post on social — Twitter and LinkedIn are packed with freelancers and job-seekers who are constantly chatting with each other. Ask people to share your post or refer friends if it’s not the right fit for them.
  • Scout job boards and communities — Dedicated sites like Freelancing Females, MarketerHire, and Peak Freelance are homebase for freelancers looking for work.

How to Price Your Services When You Hire Subcontractors

One of the trickiest parts of outsourcing work is making the profit margin worth the extra effort of managing a freelancer. It basically means you have to raise your prices once you bring someone on to help you, or you’ll need to take on more clients to make it work.

We did both.

We got really good at estimating how long certain tasks would take, and then allotted 1.5-2x that time when assigning it out to a new team member. We’d account for this time and effort in our up-front project pricing to make sure we were covering our costs of labor and were going to make a margin. We paid our subcontractors up to $100 per hour and still made a profit because we were providing so much value.

You might not get pricing right the first time, so it’s smart to reflect on each project and assess where you’re making margin and where you’re not. You can shift your prices and packaging as you go. Don’t be afraid to raise rates as the value you provide increases.

We did this a number of times and most client’s didn’t bat an eye at the price because we were providing so much value. A few months into this new team structure, we were bringing on 3 month $60k deals.

How to Manage Your Subcontractors

When you first start freelancing, you’re often managing your biz a little chaotically — scribbling on sticky notes, logging tasks in your phone, and keeping a running list of ideas in the back of your mind. This approach can get you by while flying solo, but you’ll definitely need a centralized business management tool once you bring on subcontractors, virtual assistants, and/or collaborators.

Using a comprehensive tool like Harlow can help you streamline your business operations as you grow by keeping all of your client info, project details, proposals, contracts, and invoices in one place. You can invite your subcontractors and collaborators too, and assign out tasks as needed. By having this single, centralized dashboard, everyone’s job gets easier, and you can keep your business movin’ and groovin’.

Outside of just having the right tool to manage your biz, make sure you’re being a good boss and collaborator. Make sure your subcontractors have the information they need to do their job well, make expectations clear, and make sure you give them flexibility and room on deadlines. If the job starts feeling too corporate and rigid, you’re likely to lose those people looking for the perks of freelancing. Treat them how you want to be treated by your clients, it’s as simple as that.

 

Outsourcing can be a powerful strategy for solopreneurs looking to grow their businesses. By leveraging subcontractors, you can delegate tasks, streamline processes, and focus on your core strengths.

Remember, the key is to first understand exactly what kind of support you need. What do you dread doing every week? How much more could you accomplish if you were freed up to focus on the work that brings you joy and adds to your energy? Outsourcing can not only take your business to the next level, but it can help you fall in love with your work again.

Plus, having another person to brainstorm and collaborate with can be refreshing, especially if you’re used to working solo. Freelancers tend to bring a wealth of skills and experience with them, and a fresh perspective that can aid you in all sorts of ways you never imagined.

Taking the leap can be scary. But it was well worth the risk for us and countless others. With a little bit of prep and the right talent, you could transform your business. Are you looking to grow your business by bringing on subcontractors? I’m here for you as a resource, don’t hesitate to reach out.

Office Hours: Mastering Mindfulness

Office Hours: Mastering Mindfulness

Freelance writer, editor, and business coach Jenni Gritters joined us as our guest for our May Harlow Office Hours Zoom Q&A, Mastering Mindfulness, where we discussed developing a mindfulness routine as a solopreneur, prioritizing personal well-being, setting boundaries, and more.

Tune into the recording here:

 

 

Jenni works with fellow solopreneurs and small business owners on writing projects and strategic business planning. In addition to her coaching and freelance practice, Jenni has a monthly newsletter called Mindset Mastery that’s full of real-life stories and exercises for solopreneurs who want to prioritize their well-being and incorporate mindfulness into their day-to-day.

Follow along with Jenni on Twitter and LinkedIn!

 

Transcript: 

Andrea

Harlow’s an all-in-one freelance tool as well as a community and our goal is to help freelancers grow thriving businesses. With us today is Samantha, my co-founder, who is on mute because she is sick and not well today, and Madi, our wonderful Community manager who a lot of you are probably familiar with.

Before we dive in just a couple of housekeeping items – I know a lot of people couldn’t join us today, so this session will be recorded. If there’s somebody that you want to send this over to, we’ll send over a link to the recording. Afterward this session, it’ll be available on YouTube and our website. 

Today will be a 45-minute session on mastering mindfulness and prioritizing your well-being with the amazing Jenni Gritters. We’re so excited to have you with us today! We have a handful of questions that were sent over to us beforehand that will go ahead and start with, but if you have any questions during this Q&A, please drop them in the chat or you can raise your hand using the raised hand icon. We’ll call on you and we’ll let you chime in so can participate in any way that feels comfortable and good to you.    

Before we get to the questions, Jenni, would you mind giving a quick intro and telling everybody a little bit about yourself?

 

Jenni

My name is Jenni Gritters and I am a business coach for freelancers and creative entrepreneurs, so most of my clients are individual workers – most people are solopreneurs, and a lot of them are freelancers. I’m also a freelance writer and editor. My background is as a journalist, so that’s how I started my career over a decade ago. Things have changed a lot but I still do a lot of writing. I also live in Central Oregon with two tiny children –  an almost one-year-old and a three-and-a-half-year-old. So, my life is very full. I work mostly part-time or three-quarters time depending on the week. I also have a background as a yoga teacher and a meditation teacher, too, so you’re going to hear all these things kind of married together in the way that we talk about running a business. 

Today, my focus on running a business is really teaching people how to run sustainable businesses that work through seasons of life that are challenging, difficult, or complex. We all end up dealing with those at times and sort of prioritizing our life over our business and having a relationship between our life and work that feels really good.

At the end of this session, I’ll share more resources and things about how you can you can work with me in the future. But, yeah that’s me in a nutshell! 

 

Andrea

Awesome! I feel like you touched on this a bit in your freelance interview series, but our first question for you is what does mindfulness mean to you and why is it so important? 

 

Jenni

Of course! That’s a great question. So when I think of mindfulness, I think of being present and literally noticing what’s going on and being mindful. I would say that that’s very counter to the way our culture teaches you to work. You know, the hustle culture mindset is pretty opposite of being mindful. You’re going going going, you’re moving really fast, you’re often not checking in and, to me, running a sustainable business is about actually checking in and being present. Having a lovely life is about experiencing the present moment. So, to me, when I say mindfulness I think of being in the here and now, and when I teach my clients to be more mindful about their businesses, they’re also able to be more intentional about what they’re building.

So mindfulness sounds like this “woo-woo” word, but, I think for a lot of my clients – and for me – it’s a weekly check-in of how things are going, how I feel in my body “is this working, what needs to change,” and so on. It’s having moments where you’re touching down on Earth instead of just speeding along and it’s a different approach to running a business. Frankly, it’s not what we’re taught in school and it’s not what you would learn at a university. It’s really counter. But as a person who has a lot going on in my life and someone who has mental health challenges – I have a panic disorder and have two young kids – I can’t move at that pace and not check in, or I end up in a corner where things are really compressive and I feel like I’m not doing the type of work I want to be doing. So, when I say mindfulness, that’s what I mean – sort of that check-in and that awareness. It’s what we learned in our first jobs, right? Be reactive, if your boss needs something, get it to him immediately. I personally carried this mentality with me into freelancing of “Oh my gosh a client needs something they’re gonna think I’m terrible if I don’t respond right away or if I’m not like on Slack 24/7”. For me, it was really hard to let that go and put in place some boundaries. 

 

Andrea

What inspired you to really focus on this mindset shift in your coaching practice and your business?

 

Jenni

By doing the opposite. My very first job was at a viral media company and I was working probably three people’s jobs in one person’s body. I was that person that you could go to to ask questions and I would know the answers. I would get it done really fast and so much of my identity was really built around reactivity and it fried me. So I worked at that job for two years and I left without a job to step into because I literally could not keep going. My mental health was suffering, my body didn’t feel good, and I was on a laptop for 12 hours a day. That was eight years ago I would say it’s been a very slow evolution and I still, when I’m stressed, will step back into that reactive space. Again, it’s been a slower evolution over time to sort of dismantle some of those thoughts, like am I still going to have good work? Am I still going to have clients if I slow down a little? As my life has gotten more complex, it’s almost become like I don’t have a choice anymore. I do have to use these tools and, frankly, I get a lot of people in my coaching practice who have the same story – they’re burnt out and they feel like

they’re running a business that’s not exactly aligned with their needs and they can’t figure out how to make the switch. So, I started teaching this over and over again and eventually realized that this happens about two to three years in for most people in a freelance business – the reactivity, the being always available –  these things aren’t sustainable long-term for most people.

 

Andrea

How do you incorporate mindfulness into your routine and into your business?

 

Jenni

I have a lot of what I call “touch points.” I’m really not a lover of habits because those are very rigid in most people’s minds. Every day I wake up and do the same thing and so on. I’m not the same person with the same needs every day, my children don’t wake up at the same time every day. For me, having those very regular concrete practices doesn’t work. So, I have rituals or touch points. I do a lot of walking, which is one of the things for me. It’s very mindful, it gets me back into my body, and I get my best business ideas when I’m moving. That’s a mindfulness ritual that I have Sunday evenings. I sit down and reflect on what I need to do for the week ahead which is also a mindful ritual because I’m not just planning my days based

on my inbox, which is so easy to do. But, I’m actually figuring out what is the most meaningful work I can be doing. I also stand up and try to take a deep breath every hour. Sometimes I need to shake out my body because I’ve been holding it weirdly or because I’ve been on Zoom. I also do a yoga nature meditation every night before bed so I can slow my brain down. Those are my touch points when I’m working with people, like “What are your full feet back on the ground touch points throughout the week?” and those will be different for everybody. We don’t all need to have a fancy morning routine, and, for a lot of people, that actually is not waking up at 6:00 am to meditate and drink warm water and do yoga. I wish it was! But it’s more frustrating than helpful oftentimes when we try to slot ourselves into these predetermined ideas of what would be good for us because it’s so individual and about what feels good to you and what slows you down.

 

Andrea

Do you have any recommendations for implementing mindfulness techniques to help manage clients? 

 

Jenni

Yeah, this is where the reactive versus intentional shows up in your business shows up. People get offered an assignment and you say “yes” right away. It’s reactive and that’s because that is how you have probably run your business since the start. It’s like survival and so the way that we start working in that mindful pause is by taking a moment between the email that says “do you want to do this work?” and your response – there’s a Victor Frankl quote that states that between stimulus and response, there’s a space and in that space is where there’s freedom. So, we’re not robots, things don’t just happen and we respond, there is a moment, and in that moment between the project offer and the yes – or no – is where you start to get a little more control. I usually help my coaching clients figure out a little checklist of questions to ask during that pause, so you train yourself to turn off your email, put your email on pause, or have a canned email that says something like, “I’ll get back to you in 24 hours” then, you go for a walk, then you come back and there are these questions you ask: 

Is this project aligned for me right now? 

Is the pay right? 

Do I want to do this? 

What would be the cost of doing this? 

So, you start to sort of interrogate to determine if this is working for you. That’s the first little step that I have people take toward moving in the direction of being a little more mindful and intentional.

 

Madi

I love that advice. I’m a yes girl, I say yes to everything very fast and that’s always been something that I do. I’ve noticed that especially in friendships and personal relationships I’ll sign myself up for something even if I don’t want to do it and then I  dread it. So I think that

Advice resonates in so many different areas of your life. Take some time step away and really think, “Do I want to do this for real or am I just saying yes because I think that that’s what’s expected of me.” 

 

Jenni

Yes, because it’s safe to say yes, too, right? I think for a lot of us that’s been our training. I didn’t grow up in a family where you would really say no and it seemed like there were consequences to saying no, so it is sort of training your nervous system in little ways with friends and relationships and things like that so you feel safe. Also, then you don’t have to cancel last minute after dreading it for five days right? 

 

Madi

Or go and be in that mindset that you’ve been dreading it for so long that there’s no way you’re going to have fun and you’re also gonna kill the vibe for everyone else because you’re already in that negative headspace. 

 

Jenni

Yep, exactly and that’s what happens with clients, too, right? The drag of the dread means projects take you longer, you’re not making as much money, and your business starts to slow down. It’s also a bad business decision to say yes to things that are misaligned and burnout is a result of misalignment. Burnout isn’t just because you’re working too hard, it’s connected to your value system and doing what feels good to you, and then you’re doing something that is not aligned with that and it erodes and starts to feel really horrible. Your nervous system doesn’t feel right. I always tell people that it’s not selfish, it’s actually better for everyone involved. There are always freelancers out there who might love that project, even if it’s not right for you. But it is a tough switch to make. Saying “no” is really hard for most of us. 

 

Andrea

I definitely have more of a scarcity mindset when it comes to freelancing. I get so scared that

the next thing isn’t going to come along, especially in this market right now. How do you stay true to yourself when you know you should do something, but you’re terrified?

 

Jenni

You figure it out and tell me! My best advice is this – sometimes you do make the decision and you feel really good and then sometimes it feels safer to take the thing anyway. It’s a both

and. One of the exercises I’ve been working with lately with clients is that abundance is a very squishy word, right? And scarcity is the idea that there’s like not enough and abundance is the idea that there’s endless everything. We’ve started to work on noticing abundance in other parts of our lives because scarcity is a very capitalist thing that’s ingrained in our entire way of being. So your brain is not trained to even have an awareness of there being enough, that’s not normal in terms of the way we live. But starting to notice it like “Wow look how many trees there are!” or “Oh there’s enough air to breathe,” you know like those basic things start to switch your brain just a little bit and then you also take those small risks, right? You’re not saying no to the $2,000 thing, you’re saying no to the $500 things, and you start to get more used to it, but it’s really a complicated cocktail. This is why coaching is great because we sit for an hour and dissect what your brain thinks is gonna happen and whether or not it’s true and what you would do if it happened. Walk down the road a little so you feel like you have a fallback plan, too. 

 

Andrea

How has practicing mindfulness changed your business? 

 

Jenni

My son was born three months before the pandemic started, and I had a really rough pregnancy. I had PTSD after he was born, and he was in the NICU, which was genuinely horrible. I couldn’t go back to work in the same way, unsurprisingly. The pandemic added another layer of complexity. The more I did internal work and practiced presence, the more I realized I had to change my business model. I worked 15 hours a week for the entire first year and a half of his life and still made enough money. I had to make intentional choices about who to work with and who not to work with.

Adjusting my business to match the season I was in has changed my business structure over and over again. I’ve made frequent pivots, such as leaving the company I was running with Houdinien. I adjust my schedule, client load, and the work I’m doing based on my capacity and needs. The result for me has been frequent pivots, which is complex but also the benefit of running a business is you have that choice, you have that ability. So, do I need to turn up the volume? Do I need to turn down the volume? Do I need different clients to meet these financial needs? It’s like those little practical questions that adjust my schedule, my client load, and the work I’m doing based on the capacity I have in my brain. I do a lot more coaching now because that’s the season I’m in, but that may not always be true. 

 

Andrea

Are those small decisions and pivots happening in real-time as you’re running your business, or do you actually schedule these reflective periods where you analyze what’s been going on and what you need?

 

Jenni

I do a lot of reflection because otherwise, I won’t notice necessarily. I will feel sort of dread and frustration, but I won’t know what actively I need to do to fix that unless I sit down. I have a very structured process. Once a month, I sit down offline, no computer, no phone. There’s a Bookshop in my town that has an attic, so I go sit in the attic with colored pencils, and I ask myself these questions: What is working? What’s not working? I audit my clients, figure out what my capacity needs to be, how many hours do I actually have, and what’s my brain feeling like? Based on that, I’ll make a little to-do list of things to tweak. I don’t think it’s possible to make these changes when you’re in the forest; you need to step back a little to see what’s going on. This is what I do in coaching too, so when people come in and do business audits, that’s what we’re doing. We’re asking what’s working, and what’s not, and then we can make little tweaks about once a month.

 

Andrea

Talk to us a little bit about boundaries and what boundaries you’ve set up with clients to help you and how you use those boundaries to protect your own well-being.

 

Jenni

Boundaries are hard for most of us, and we often think of them as brick walls and “None Shall Pass,” and then somebody tries to, and we get really angry. The way I like to think about boundaries is that it’s kind of a negotiation. So, you’re going to put your needs on the table, your client’s going to put their needs on the table, and then you’re going to figure out what works for you. I do have boundaries around availability. I am not available in the evenings to my clients. I say I’m available Monday, Tuesday, and Wednesday from 10 to 3, and that’s when I’m going to get emails from them, and that’s when I might be able to respond. Otherwise, I have a 24-hour lag time, basically. That’s in all my emails, so that’s a clear boundary that I have because I have small children, and they are with me On Thursdays and Fridays most of the time, so that’s important to me. But again, sometimes there are clients who have needs outside of those hours, and I’ll work with them to figure out how to accommodate those needs without taking something from myself, basically. So, that’s important to me. I really like to work with people who are kind, so I will sometimes say no to projects or work in a coaching relationship if someone is abrasive or makes me feel not great. I try to protect my emotional well-being in that way.

Then I have a lot of boundaries in the workplace around how many rounds of edits clients get. That’s all showing up in the contract. When are you going to pay me? How are you going to pay me? What’s the length of this project? There are some very specific guidelines that I have with my clients to make sure that I am protected, and that we have similar expectations for what’s going in. Again, I’m offering what I need, they’re asking for what they need, and we’re sort of creating a tapestry of needs in a contract. So, that feels important to me too. That’s why contracts matter.

 

Andrea

Yeah, definitely. We put a lot of things in our contract around that. And Samantha is always very good at creating boundaries around communication as well. Like, I’m not going to respond, we’re not going to join your Slack room. We can have a dedicated Slack channel, but we’re not going into your company’s Slack because we would never get our project done and just be reacting. 

 

Jenni

Yeah, exactly. So, I don’t do attending meetings. I don’t want to be involved in the company or whatevers going on. I’m like a hired hand. I’m going to come in, I’m going to do the thing, and I’m going to leave. So, those are the questions again that, like, when you take that pause between the offer and the yes, sometimes the answer is maybe, if. That’s this list. Maybe if I could do this project in two months and I had three weeks to do it and you were paying me this and the communication was XYZ, then it would work for me. And that’s what you pitch back to them. So, it is part of that. I call it your business rule book. Most of my clients will create a little business rule book that they have on a sticky note in their computer so that when they get in those moments, they’re reminded of, “Oh, those are the things that are important to me so that this project feels really good.” Not every project does, but most of them do with that intentionality in place. 

 

Andrea

Yeah, I love that. That’s a good idea to just write it down.

 

Samantha

Well, I was just thinking about Andrea and my previous experiences, and for us, toward the probably the second and third year of our freelancing career was when we started including a lot of those boundaries in our contracts and actually putting them in writing. But for us, we really had to go through some mishaps to get to the point where we started including those things, right? It was like a learning experience. Okay, and the next contract we’re going to include this, and the next contract we’re going to include this. So, I was just wondering if that’s what happened to you. Did you kind of Have to experience a mishap and then set a boundary, or did you think through your boundaries very clearly from the early stages? 

 

Jenni

Oh no, I only learned them from them being stepped on because I felt angry, right? Because when you’re angry, it’s because the need hasn’t been met, and that’s a sign that that’s a boundary you probably want to set with a future client. I’m thinking about, like, I had two or three clients right when I started freelancing who were just the worst fit for me. I mean, everything they were asking me to do, the way they were communicating with me, all the things, it was just not good. And I made a lot of money from those projects, but it wasn’t ultimately a fit. So, I think you’re exactly right. The only way to learn it is through not getting it and then realizing you need it. And that is most of the people who come into my coaching room around two to three years. That’s why this is the conversation that we’re having, right? What got you here doesn’t get you there. And at two to three years, you have enough confidence usually that the process, there are clients out there who are going to meet your needs that you’re willing to start setting some of those lines in the sand, if you will, with who you’re going to work with and who you’re not going to work with.

 

Andrea

Do you have any recommendations for freelancers that are at that exact point, right? They’ve hit this mark of like, “Okay, I know I can be successful, but man, this isn’t sustainable. Where do you start?” 

 

Jenni

Yeah, I’m actually running a coaching group this fall for this exact group of people because I have a long waitlist, and like most of them are in this space. The group will be called Sustain. If you follow me, you’ll see information about it. It’s a monthly program. But I start with asking some of those big questions about what you want because usually what you want has changed two to three years in. What you wanted at the beginning was to run your own business, and you did it because now you’re three years in. However, now it’s done enough. You know, that was survival. And so, what’s next? And so, we’re asking some of those more significant questions. What do you want? What do you care about? What do you value? What feels good? What are you excited about? Some of it is that self-interrogation again, like mindful awareness. And then we’re building those thoughts and needs into your business.

So, the question is, okay, which of these clients meet those values? Okay, this one doesn’t, so we’re going to make a little game plan on how to pull them out and recruit a new client. Usually, in this phase, there’s a need to find new clients because the clients who worked for you don’t work for you anymore based on pricing and the way they treat you. There’s a need for a different business infrastructure usually, in terms of your schedule, in terms of the way you’re invoicing things like that because you’ve sort of been making it work, and now you need something that’s going to work for like 10 years. And then we do a lot of planning. What’s going to happen in six months, nine months? What big projects are on your radar, and how do you start picking at them? This is when people start touching on some of those ambitious creative projects, usually books, you know, something they want in their portfolio that they don’t have, so there’s a lot of stuff.

This is why I’m going to do a group on it, and every month I’ll have a different theme because there’s also a lot of money stuff that comes up at this point too in terms of rate pricing, confidence, all of “I want to make more money, how do I do that?” All of that is wrapped up in getting your needs met, well, so hitting the financial things. So, it’s very multi-pronged. I could talk about it for a year, which is why it needs to be a program, but most people hit this point two or three years in. It’s almost everybody I know, they do.

 

Samantha

One, I love that you’re running that group and that it’s called “Sustain.” It’s just like a really, really beautiful and I remember hitting all of those exact same pain points in our business. Can you talk to us a little bit, you know, outside of that group, who kind of hits these pain points at year two or three? Where else are your sweet spots for coaching and helping people bring mindfulness in? Are there other specific moments in the journey for freelancers and small business owners that they could really benefit from coaching? What does that look like?

 

Jenni

Yeah, so the two programs I’m launching this fall, one is “Sustain,” and then one is a program called Build. And the idea is that most of us just kind of go flailing into starting a freelance business, and like, it works, but also then you hit three years in and you’re like, “I really need to change something.” So, the “Build” program is oriented to doing a lot of the stuff at the outset, so not just building a business and figuring out your services, but also figuring out how to build a life adjacent to your work and having those things be married together. So, it’s a four-week program, it’s one-on-one coaching. I find there’s a lot of benefit in setting yourself up for these things right away. And a lot of us didn’t have that ability, but because so many people are getting laid off and getting requests for this all the time, it’s really important to me that it’s not just business 101, it’s also mindful awareness of what you care about and building something that will last. So, that’s happening.

 

I do a lot of business audits with people as well throughout, and often those are annual. And I think that’s a really good moment to get somebody else’s subjective brain in the picture because working alone is really hard, and you get a little bit tunnel-y, and so having someone else just look at your business structure once a year and talk with you about what you want and need is wonderful, worth every penny. I do a lot of that annually with people.

 

And then I do have a small subset of people who have hit the 5-6 year mark, who are scaling up into agencies or adjusting their business models in a variety of ways to build passive revenue streams, you know, kind of do things that are more… I would call it scaling. And so, that is a point that people usually hit that’s a little variable, somewhere between 5 and 10 years, where they just kind of actually want a different career, frankly. They want the size and shape to be different. And that is also where you need a lot of coaching because that level-up is big in terms of money and hiring help. I’m actually in the midst of doing that in my business, and so I’ve been doing a ton of coaching because you need someone else to help you feel grounded as you’re making partner like a thought partner to sort of help you figure out how to jump over that little liminal space.

 

Samantha

I love that so much because you can get so in the weeds of your own business, right? It’s so hard to take a step back, even when you’re making the time to reflect, right? Even when you’re, you know, going up into your attic space and bringing your colored pencils and being really thoughtful about assessing your business, it can be really hard to do that on your own and think bigger without having someone there to challenge you and ask the right questions. So, I think that’s great. I think the annual review would be really beneficial. 

 

Jenni

Yeah, I mean, you get that in a full-time job, right? You get a point to reflect and say, “I grew these skills, and I’m proud of this, and this thing was hard, and this is what I want to do next year.” And so, that is kind of what this is. You know, I think that’s the hardest part about freelancing is the lack of structure in terms of advancement, and so that is the role I play for a lot of people, right? Like, you don’t have a manager anymore. I’ve worked as a manager in full-time jobs. I was always running teams. If there’s a similarity there in terms of the reflective sort of like somebody else who’s not in your brain, the thing that just is so… It’s so good. It’s so important. That’s why I love doing this too, watching people’s businesses jump is really fun, frankly. 

 

Samantha

I love that. When you start talking about mindfulness and reflecting on your business and doing these assessments, it can feel really overwhelming. And so, if you had to, you know, talk to everyone here and just give them advice on just like, what is the simplest way to start dipping your toe into being more thoughtful with your business. 

 

Jenni

That’s a great question. The simplest way is to pause in the middle of the day and notice how your body feels. Like, close your eyes for five seconds because our brains have about 20% of the information, and our bodies have about 80%. And so, oftentimes, even if mentally you’re not noticing because there’s an inertia that’s happening and you’re just going, your brain is not really tuned into that, your body will have some sort of tell if things don’t feel very good. For a lot of us, it’s like, “I will keep my shoulders here and it will protect me,” or like, you’re not super breathing, your stomach feels a little weird. So, that is like a very basic way to just start noticing what’s happening. And that’s my question, it’s really, “What’s happening right now?” That’s the small version of the big question. And then, yeah, like you get into sitting down for 45 minutes and asking, “What’s working? What’s not working? What do I love? What do I hate? What am I dreading?” Some of those questions, but really, what’s happening?

 

Samantha

I love that. I think I have those moments often where I’m like, “Oh my God, why do I feel like if I don’t stretch right now, my body is going to absolutely snap?” Oh, it’s because I’ve been sitting in this stressed pose for so long because I can’t actually solve this problem right now, so I need to play. 

 

Jenni

Yeah, but there’s inertia that makes that actually quite difficult so it’s like this training thing that we have to train ourselves to do to take a second. 

 

Samantha

I know we’re getting to we’re about 35 minutes in so we’re gonna we’re getting kind of to the end of this, but anybody else here have any questions for Jenny? I know we’ve dug into a lot, but any questions, nothing’s too big or too small. 

 

Tess

I’m wondering if you have any tips for remaining mindful when one is stuck in a project that perhaps five or four months ago when we signed the contract was serving our needs then and there, but right now really isn’t, and we have to see it through, but for God’s sake, I don’t want to. I can’t. This isn’t serving me right now. Like, how do you deal with a situation like that?

 

Jenni

Yeah, it sucks. I’ve been there. Everybody I know has been there. The frustration is real. So, in a coaching session, I would ask you a few questions. Like, one is interrogating that idea of, do you have to stay? And what makes you think that? What is the evidence to suggest that you have to stay? What is the evidence to suggest that you don’t have to stay? And we work with that a little to make sure that you do have to stay stuck in it. If the answer is yes, then it’s a question of, like, how are you gonna feel good about the rest of the time there? What boundaries do you need to set so you can get your needs met during that final month or whatever it is?

Sometimes I work with clients who realize that the tax of staying for that extra month is actually not worth it because it has such a drag factor in your business. So, you get another freelancer, and they step in for you, and you leave, and you risk making someone upset. That is option number one. But I do think there’s this question of, like, okay, so what do I need to get through the next month or however long it is? Sometimes the answer is distraction. I was pregnant and horribly sick, and finally, my therapist said to me, “You know what, Jenny? There’s a lot of value in just distraction.” I think we’re taught that distraction is like running away from the sensation, sometimes yes, but sometimes also it’s necessary if something is really bad. And then, I always want you to have something in the mix that does feel good. So, it’s not just like you’re not just tunnel-visioned on this tough thing, that there is. It feels like there’s a future because when we’re in survival mode, it’s hard to see the future.

So, we talk a lot about what’s coming and how can you start to move towards that right now so you feel like there’s momentum for the exit. That’s what I would say. It’s a… Someone told me the other day too, this type of thing widens your window of tolerance. While it’s uncomfortable, it does mean that you’re gonna be able to tolerate a lot more in the future, and that is really a silver lining, for better or for worse. So, I don’t know if that answers your question quite. I mean, it’s just solidarity because it sucks, but there are mental things I think that you can do to sort of work through. Like, where do you have control here is basically what I’m asking you, right? Where do you have agency, and what could you do about it?

 

Tess

Yeah, I feel like I’ve been so conditioned to just tough it out, you know, from being an athlete or just a hard worker in school. That’s just the mode i enter in so even when the project or thing that isn’t serving me is over, I’m just crushed by it. 

 

Jenni

If your body and brain are used to the suffering mentality, that is a slow process of unlearning. But, you don’t have to suffer – what a weird concept! Quitting can be incredible. I work with a lot of people who have fired clients or left things and it is the absolute best thing they could’ve done for themselves. But, someone is also still mad at them because they left. And that’s hard to tolerate but it released them from a structure in their business that was locking them in. If you did leave, what would that look like, feel like, or so on? Reflect on that.

 

Samantha

I remember the first time Andrea and I had to break up with a client. It was daunting and a really big project. It was people that we really liked but we were not aligned on the direction and there was a lack of focus there was a lack of feedback that was being given to us like we just got really really off track and we could not do the project. At this time, we actually didn’t have a termination clause in our contract which that’s another mishap that we learned from that we include. But I remember how hard it was you know. Andrea and I really agonized over it, right? We had lots of phone calls with one another being like how are we gonna do this, what are we going to say, how do we maintain these relationships, but at the end of it we’re like we’re going to actually lose these relationships if we keep pushing forward with this project and charging them and nobody’s happy with the outcome. The only way to actually maintain these connections and make this work for everyone is to recover this relationship. 

 

Jenni

Tess, I’m thinking about I fired a client a few months ago and I literally walked outside afterward and threw up. I’m not saying that this is pleasant, right? It’s tremendously difficult and you can still do it. It was a misalignment, it’s like what Sam said, I love the person but the project was absolutely wrong for me and it would have taken so much for me that it was not worth it. It would have taken time with my kids and it would have meant I couldn’t make more money. It was all the things and these things are just so difficult and you actually can handle them when you have a tool kit available to you and a support system that helps you manage your anxiety that helps you rethink. This is like coaching and therapy and all the things, right? You don’t just want to cut ties and then flounder around alone you need people around you, but it’s also liberating as much as it is miserable. Yeah, Sam, I feel that deeply like you have to leave to maintain the relationship. Andrea, did you have one more question? 

 

Andrea

I did because you touched on this a little bit in your interview and just any like schools and apps and small little things that you use to help remind you and bring you back to mindfulness in your day?

 

Jenni 

Yeah, great question. There are a few podcasts I love and one’s called Pulling the Thread, that’s very philosophical and kind of reminds me of big themes insight timer has been really great for me and a lot of my clients it’s a free app that has all kinds of meditation breath work Yoga Nidra is something I do a lot I mentioned it like helps me go to sleep because my brain likes to ruminate on work questions and so Yoga Nidra is a technique that is like very much brings you back into your body I fall asleep in the middle which is wild for someone who usually takes an hour for me to fall asleep uh so those are two key ones. There are a lot of books I love things like that but I think insight timer would be the one I would offer to people and then pulling the thread is like a good perspective giving thing. And, honestly, being in community with other people who are talking about this sort of style of business and work on social media wherever you find your community I think is something that has been so important to me uh it’s this again is like pretty counter to what a lot of those pros are talking about and so you need to be surrounded by people who can support uh the idea that you might fire a client right or something like that. You need a support system and that to me is actually like a mindfulness tool that is so important you need people to bring you back down and back into your space with people who love you and are cheering for you.

 

Andrea

Awesome! This was such a wonderful way to spend 45 minutes thank you so much for your time  Jenny and before we take off do you want to tell everybody where they can find you and to reach out if they have any questions or want to learn more about your coaching services?

 

Jenni

Totally! I’ll drop my email or my website in here and my newsletter I think those are the two best places although I’m across all social media at Jenni Gritters. But my website has a list of some of those coaching offerings those are opening up in the fall so you can just join my waitlist and you would get information about that, and in my newsletter, I talk about this every week. It’s free so pop in there there’s always reflective questions it’s like one of my favorite things I’m doing right now it’s such a creative like generative space for me so I love to be having those discussions in those places what does it look like join a business like this why is it hard like Tess I just wrote one about firing a client so you can go in there read it but yeah I would love have you all hanging out there and then I’m on Twitter and Instagram and the places. 

 

Andrea

we’ll include all of this stuff in our follow-up email and if you guys have any questions for Harlow or Samantha, myself, or Madi, feel free to reach out directly. We’re on all social channels. If you have any input on these office hours sessions, please don’t hesitate to reach out and give us that feedback thanks so much.