Freelance Interview Series – Creating Multiple Income Streams

Freelance Interview Series – Creating Multiple Income Streams

Elna Cain is content writer for SaaS businesses as well as a mother to twins. Over the years she’s helped Smartblogger, Zapier, GoDaddy, Optinmonster and more grow their traffic and lead generation strategy. Her own blog has been cited as the top 100 best sites for freelance writers seven years in a row. When she isn’t writing, she’s playing with her new kitty and shuttling her twins to sports.

"The biggest piece of advice I can give you is to go at it slowly."

Tell us about your business and the different revenue streams you have created.

I started freelancing in 2014 when my twins were around 15 months old. It wasn’t until around 2016 when I started offering 1:1 coaching sessions. I had an email list and had cultivated an audience around my blog, so I sent out an email asking if anyone was interested in 1:1 coaching with me and many were.

It was difficult managing my freelance clients and my coaching students when I first launched. I would write and pitch during the day, spend an hour or two on the phone with my coaching clients, and then another two to three hours writing up a plan for my students following. This turned out to be too much, and I had to do something to free up my time. Soon after, I decided to consolidate my learnings into a course to help my coaching students. Instead of hour-long sessions, I would enroll them in a course and answer any questions that came my way. This course evolved over time to include a Facebook group, expert training sessions, audits, challenges, swipe files, and templates.

During this time, I also started a new blog, Twins Mommy. I wanted to write about the challenges of working from home, while seeing if I could monetize this channel. I wanted to try affiliate marketing and other ways to grow my traffic. Since my freelance niche is digital marketing, I found the tactics I was using for Twins Mommy helped with the content I was writing for my clients too. I ended up creating a course for this audience too, and more courses for my freelance audience as pain points meshed well with my current learnings.  At this time, through trial and error, I had created a freelance income stream, an affiliate marketing income stream, and a digital product income stream.

Over the next few years, I started other websites and two YouTube channels. I then turned my focus to monetizing those channels, and signed up for Mediavine to gain some ad income.

Why did you start to build additional revenue streams?

My niche is digital marketing and I was learning about different ways businesses monetized their brand. Since I wanted to learn more about my niche, I thought, well, why not TRY these methods out?

And that’s what I did. I started with coaching, then affiliate marketing and then digital products. I was practicing what I was writing about and over time, I added more to my revenue streams.

How do you make time for creating outside of your normal freelance work at a macro-level?

Now, I make it a point to only do part-time freelance work. This means I’m working with no more than three clients at a time. This leaves me room to focus on my students, my email list, my products, and my YouTube channels.

I’m learning to be a content creator and, at times, I lean into content creation more than freelancing. But I have control of my day and that means doing what I want to do. This year, I decided to focus more on freelancing than content creation. This means more pitching, more networking, and more LinkedIn posts.

How do you balance client work and building additional revenue streams on a micro level?

I batch my tasks throughout the week. Mondays and Tuesdays are video production and editing days. Wednesdays and Thursdays are client and blog days. And Fridays are catch up days or educational days. I may have to edit a client article, so I will leave that to Friday and check out a podcast or copywriting training video.

And the weekends are family time. I have two 11-year-olds, and I’m either at a ski lodge or a hockey arena.

What other advice would you give to creators or freelancers building multiple revenue streams and/or distribution channels?

The biggest piece of advice I can give you is to go at it slowly. I think offering another service, creating an eBook, or opening up a paid newsletter or Patreon account is the simplest way to break into the creator economy. Another way to build additional revenue is with affiliate marketing and creating digital products.

For me, many of my SaaS clients had an affiliate program, so I could also become an affiliate for them. I also became an affiliate for products by freelancers. An example is a finance book created by Alexis Grant of the Write Life and her dad, an accountant. She opened up her book for affiliates and I knew this would help out my audience – and it has!

If creating a digital product seems too difficult, you could always start another service. I did coaching, but you could become a strategist or analyst for businesses.


Build Your Dream Team in Harlow

Build Your Dream Team in Harlow

As freelancers ourselves, we wholeheartedly understand the desire to transform our businesses into lifelong ventures. We know that in order to achieve this lofty goal, we often find ourselves in need of additional support.

Let’s face it, trying to do it all on our own can be exhausting. We are firm believers that true success lies in recognizing our limitations and seeking assistance when necessary. And that’s where our journey aligns with yours. We have witnessed countless talented individuals like you, who are relentlessly striving to expand their businesses, turning to virtual assistants, subcontractors, and bringing on business partners to share the workload and maximize potential.

We see you, and we’ve heard you ask for the ability to bring those people into Harlow so you can manage all aspects of your business in one place.

And now we’re so excited to announce that based on your feedback, we’ve opened up Harlow so you can invite additional users into your account to collaborate seamlessly and unleash your collective genius.

Virtual assistants, subcontractors, business partners—bring ’em all in!

How to get started

From the settings section in Harlow, you can add users and determine the level of access you want to assign based on your needs.

  • Teammates:  Teammates have access to all the same great information you do, but are unable to view your billing & subscription details.  This profile is designed for a co-founder or business partner, or even your virtual assistant who might send out invoices or proposals on your behalf.
  • Collaborators: Collaborators are able to see tasks & time tracking associated with specific clients and projects you give them access to. This profile is great for subcontractors who are working on a piece of the project but don’t need to see all your financial details.

Once the new user has been added to Harlow, they’ll receive an email to accept your invitation and start working together. You’ll be able to assign tasks, keep an eye on hours worked, and fully support your clients, all from within your Harlow app.  Get started now.

Cheers to Continued Growth

Let’s raise our virtual glasses to this exciting chapter in Harlow and your entrepreneurial journey! Let’s celebrate the power of collaboration, the thrill of teamwork, and the immense potential that awaits when we combine our strengths. As you navigate the path towards success, remember that we are here, fully committed to fueling your ambitions and propelling you towards your dreams.

Are there other features that you’re dying for us to work on? Email us at

We take customer feedback to heart.

A Checklist for Launching Your Freelance Business

A Checklist for Launching Your Freelance Business

So you’ve decided to launch your freelance business. Congrats! You’re joining millions (yes, millions) of people who’ve chosen to work for themselves.

This tried and true path can offer flexibility, independence, and financial security — but there are some key steps you should take at the beginning to increase your odds of succeeding long-term. We put together this handy freelance business launch checklist to help get you on the right path. 

Freelance Business Launch Checklist:

  1. Form your LLC – Protect yourself from liability and increase your legitimacy by registering your business as a Limited Liability Corporation, or LLC. This helps safeguard your personal assets in the event a client relationship goes wrong, and it shows potential clients that you’re a serious, reputable operation.

2. Get your EIN – After forming your LLC, you can request an Employer Identification Number from the IRS so you don’t have to use your social security number to get paid. Each time you do work for a client, you’ll provide your EIN number.

3. Set up a business bank account – No commingling funds! Having a dedicated business checking account makes taxes so much easier — trust us. You’ll have all your income and expenses logged in one place. Many accountants and tax platforms can also automatically sync to business bank accounts for easy reporting.

4. Outline your elevator pitch – What are you offering? Who do you want to do business with? Answering these basic questions helps you get clear on your strategy, and developing a quick, digestible pitch will serve you whenever you get asked the question, “So, what do you do?” Casual conversations often lead to new clientele, and having a polished pitch at the ready is just good practice.

5. Define your pricing – What are you charging for your services? What does your fee structure look like? The next question after “What do you do?” is often “How much do you charge?” Defining your rates and your rate structure (hourly, project fee, retainer, etc) is another key step in preparing to pitch to potential clients.

6. Put together your proposal template – Grab that elevator pitch and pricing and combine them into your proposal template, which you can use over and over, tweaking based on the project. You can easily get started with one of Harlow’s six professionally designed and easy-to-use proposal templates, created by expert freelancers

6. Outline your contract and terms – What are your payment terms, late fees, and non-negotiables? Developing a solid, legally fit contract template is arguably one of the most important steps for new freelancers. Your contract is your source of truth for all projects. It’s the foundation you can refer back to if clients make unreasonable asks, miss payments, or otherwise take advantage of you. It sets expectations from the get-go. Sounds daunting? It’s okay, if you’re a Harlow user, we have a great contract you can use, put together by a legal expert who knows what you need covered. 

7. Curate your portfolio – Your portfolio will look different based on your industry and niche, but it might contain social posts, visual assets, articles, photographs — whatever it is that captures the quality of the work that you do. Portfolios don’t have to contain freelance work — they can also include work you produced or helped with as a full-time employee or contractor.

8. Put together your promotion strategy – How do you plan to get your first couple clients? Outlining your approach gives you a tangible strategy to commit to. Document the specific channels you’ll leverage (e.g. social media, job boards, word-of-mouth referrals) and the specific tactics you’ll use to maximize your reach (e.g. posting on social twice a week, creating profiles on three gig sites, telling one person about your work every day). Committing to this promotional work can help you build steady momentum and gain visibility quickly.

9. Start networking with other freelancers – There are bound to be ups and downs during your freelance journey. Having people around you who truly understand the challenges makes all the difference. Freelance pals can help keep you motivated and inspired, and empathize when you’re having a tough go of it. Plus, having friends who freelance means you may get some referrals for the gigs they’re not interested in or qualified for — you never know who will send a client your way.

Taking these steps at the start of your freelance journey will save you an immeasurable amount of stress later on and set you up for the kind of freedom and success you’ve been dreaming about. Every freelancer’s path is unique, but if you talk to the most seasoned solopreneurs, they’ll all echo similar advice: Take care of the foundation now. You’ll thank yourself later. Each little step you take is like a vote for creating a more abundant future. Your confidence will increase as you go, and soon you’ll look back with gratitude for how much effort you put into creating the life you want for yourself.

If you need support and resources along the way, Harlow is here to help. Our intuitive freelance tools can help you build a foolproof business foundation, onboard new clients, manage your day-to-day tasks, and get paid. Sign up for a free trial to get started today, and check out the dozens of freelance resources we’ve created for new solopreneurs like you.

How to Remind Someone to Pay You For Your Work

How to Remind Someone to Pay You For Your Work

If you’ve ever had to remind someone to pay you—you know it’s not fun. You do the work, you’re feeling on top of the world and like you just aced this project, the feedback is great, you send the invoice…and crickets.

Now the anxiety sets in, it’s time to send that dreaded payment reminder. We’ve all been there. No one wants to have to continue poking, asking for payment for the work they’ve done once, much less more than once.

While we can’t help you completely avoid this situation (we wish we could), we can help you do everything in your power to avoid late and missed payments.

Here are a few simple (but impactful!) recommendations we have for you.

While we can't help you completely avoid this situation, we can help you limit those late and missed payments!

Add Clear Payment Terms to Your Contract

You should kick off every project by communicating your expectations around payment upfront. And we don’t mean just a verbal agreement. You should have a written contract for every client you work with. That contract should include a payment section that clearly outlines when they need to pay you.

Do you expect a client to pay you within 15 days? Within 30? Document it and get that contract signed. Take it a step further by calling out your terms via email or in a meeting too, that way there’s no confusion, and nothing gets lost.

Voila! You now have a written contract, an email or verbal agreement, and a signature you can refer back to if you are having any issues collecting payment.

We’ve also seen more and more freelancers including late fees in their contracts, which can help as another incentive to get clients to take care of your invoice on time. We’ve seen late fees range from 1.5% to 5% and higher!

Pro tip: You can create, send and get signatures on your contracts in Harlow.

Provide Your Account or Payment Information Upfront

Make issuing the payment as smooth, easy, and convenient for your clients as possible. Chances are, they’ll be more likely to pay on time when the process doesn’t require extra effort.

Before sending your invoice, you should decide how you want to accept payment. If you’re not sure which payment options are available to you, here are a bunch to choose from:

Every invoice should not only include how a client should pay you but the additional relevant details necessary to actually get paid. Some examples of things you might want to include:

  • Your current address and contact information, in case your invoice gets sent on to another person outside of your main point of contact who might have questions.
  • If you’re accepting payment via ACH, make sure to include the correct routing and account numbers from your bank.
  • If you use PayPal or stripe to collect a payment, make sure the link is accessible and obvious.

The simpler you make it, the fewer excuses they’ll have to procrastinate.

Pro tip: If you use Harlow’s payment integrations on your invoices, all your client has to do is click one button and they can pay online through your payment processor of choice.

Automate Your Invoicing and Reminders

Consistency helps! Let clients know that invoices are delivered on a certain day each month—and stick to that schedule. This way they come to expect that email from you and are less likely to lose the invoice in their inbox.

Another simple tactic is to set up automated reminders. Reminders give your client a light nudge, even before an invoice is overdue, without you having to write that dreaded email—or even think about it.

To make your life easier, you can use Harlow to schedule your invoices in advance and set up auto reminders to go out after your invoice is sent.

If All Else Fails, Send a Tactful Follow-Up Email

If you’ve taken all of these steps and are still not seeing that payment come through, you might have to resort to a follow-up email. You deserve to be paid nothing less than what you’re owed and want to be honest and upfront about that, while also maintaining tact and respect if possible. Remember, not every client that doesn’t pay is doing it maliciously! So in your first or second reminder, make sure to give them the benefit of the doubt. We’re all human.

Here’s a template you can customize and send to your clients:

Hello NAME,

I’m reaching out because [INVOICE NUMBER] (also attached), has not been paid. It was due on [DATE], and is related to:

Work done
Work done
Work done

As per our contract, payment is due [PAYMENT TERMS].

Can you please track this down for me and get it paid as soon as possible?

Thanks in advance,

How to Remind Someone to Pay You? Do the Work Up-Front!

I know how stressful it can be to run after the money you’re owed, and how awkward it can be to initiate those conversations with your clients. But here’s the bottom line: You deserve to be paid for the work you do! You don’t have to settle for missed or late payments. Instead of worrying about how to remind someone to pay you, advocate for what your work is worth by putting the payment terms in writing, setting up late payment fees, and automating your invoicing process and follow-ups at the start.

If worse comes to worst, a simple but clear message may still be needed. If that happens, remember the value of your work and embrace that to be confident in your request.

How to Repackage Your Services and Sell the Value of Your Work

How to Repackage Your Services and Sell the Value of Your Work

Pricing and packaging are hard to nail down as a freelancer. No way around that.

Often when you start out freelancing, you don’t have the confidence yet to charge what your work is truly worth. We often set our rates too low and sell ourselves short.

This was true for Samantha and me when we first started freelancing. We were charging hourly and quickly realized that the value we offered was being lost as the hours were tallied up.

The good news is that while pricing and packaging your work appropriately and accurately is challenging, you are your own boss. You run your own business and you can shift things whenever you want to!

So if you don’t feel properly compensated for your work and you want to start charging more, it’s time to make a change. We’re going to guide you through how to reposition your packaging, and raise your rates confidently so you can get paid more.

And, we’re living, breathing proof that these steps work.

If you don’t feel properly compensated for your work, it’s time to make a change.

Shift your mindset from selling services, to selling outcomes.

Repeat after me: the work that you do is important. You don’t simply complete tasks, you help push businesses forward. For example, you’re not selling 3 blog posts for $1,000. You’re selling an outcome: content that’s going to increase traffic to your client’s site and ultimately lead to more revenue.

If you read that and are having a hard time figuring out the outcome and value you’re selling, try this:

Look back on your last five clients. What was the outcome of your work together? What value did they get from that work? It can even be helpful to look through past emails to see what exact words and phrases they used to describe your work.

Use this to build your outcome-based elevator pitch. The goal is to be able to explain the value you provide, in 2-3 sentences. Use this as the basis for sales calls, proposals, your website, and more.

For example, your elevator pitch might be: “I’m a content marketing and SEO expert with more than 2 years of experience working with early-stage startups. I help you scale organic traffic and revenue through optimized on and off-site content.”

From there you can detail exactly what the actual tasks and processes are to fulfill that outcome.

Position yourself as an expert partner.

It’s important that you not only think of what you offer this way but that you communicate it clearly to your potential client as well. When you start communicating the outcome and the actual value of your work (I.E. more website traffic, HR processes that impact the bottom line), it’s easier for you to charge a higher price and get paid what you deserve. It’s all about positioning!

That’s all well and good, but you may be wondering: what do you even mean by “positioning”? Great question! We’re talking about the way you refer and speak to your skill set and the overall value you’re bringing.

When you’re speaking to a new client, or putting together your proposal, be cognizant of the language you’re using.

For example, you might use language in your proposal like:

  • Together we’ll build a paid marketing strategy to…
  • Your in-house designers and I will partner on the creation of assets…
  • As your social media strategist, I’ll work closely with your existing team…

Notice how this language alludes to you partnering, rather than simply doing.

Make the change from hourly to retainer- or project-based pricing.

While this isn’t the right move for everyone, for many freelancers retainer- or project-based pricing is a way to distance yourself from explaining what goes into every minute that you’re working. What you do is worth more than the hours you put into it.

As the popular saying goes, “I’m not charging for the 10 minutes it took me to do this, I’m charging for the 10 years of experience I brought to it!” This is another powerful shift that starts with you (knowing the value of your work!) so your clients can understand it too.

What’s more, clients may not understand how much work goes into something you’re creating (remember, they’re not the experts in this, you are!). Rather than justifying what you know to be a reasonable number of hours, you can wrap everything up into one lump sum. Don’t forget to still be detailed in documenting the work included in that retainer or project so they can still clearly see the magnitude of work being done.

Use your website, marketing, and proposals as a way to communicate value.

You should be using your website, social media presence, and proposals as a way to communicate the value of your work clearly. This can be hard to do—even a humblebrag can feel uncomfy, we know!

But once you shift your mindset, lock down your elevator pitch and positioning, and tie in your pricing, it’s time to share that with the world!

Putting that message out there not only helps to get you in front of the right potential clients, but it allows you to sell value before you even touch base with a client for the first time.

Get a gut check from your community.

If you’re feeling unsure of your new positioning and pricing, run it by someone! Even if you’re running your business on your own, there’s an entire community out there who wants to help—and can provide insights you wouldn’t be able to get otherwise.

Find someone you admire and ask for their feedback. Don’t focus too much on whether you have competitive rates. Instead, get their opinion on whether they think a potential client could understand the value you’re trying to get across.

If you don’t have anyone in your back pocket to speak to already, start connecting with other freelancers through online and offline communities. Check out our list of freelance communities we love if you’re not sure where to get started!

You can also find either Samantha or me on social and run it by us, we’re here for you! Connect with us on Twitter: @SamanthaAnderl and @thelittlestflea.