Jan Almasy, veteran, agency owner, and Head of Community at IndeCollective – a ten week cohort based community dedicated to helping freelancers take their businesses to the next level – joined us for an Office Hours session on Crafting a Compelling Newsletter.
We covered determining what topics matter most to you and your community, building an audience, crafting and growing your newsletter, and more.
Catch up on the conversation here:
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.
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.
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:
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.
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.
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.
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.
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:
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.
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.
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?
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.
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?
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.
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?”
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.
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.
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.
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.
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.
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?
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.
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?
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.
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.
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.
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?
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.
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?
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.
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?
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.
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.
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.
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:
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.
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.
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.
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:
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.
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.
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.
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.
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.
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:
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.
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.
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