6 Lessons From 6 Years of Full-Time Freelancing

Jul 7, 2020

Let’s travel back in time to Monday, July 7 of 2014. That was my first day as a full-time freelance writer. I vividly remember sitting down at the kitchen table in my apartment, staring at my laptop screen, and thinking, “So…what the heck do I do now?”

Fast forward six whole years, and I’m still at this freelancing thing. And you know what? I’m thrilled to say that it’s gone pretty well for me so far.

I’ve more than exceeded my own income expectations. I’ve worked with amazing clients. I’ve had my name published places I assumed were just pipe dreams (hello there, The New York Times). Pinch me, because I must be dreaming.

I have yet to decide if the past six years have crawled or flown by. In some ways, that moment of panic at my kitchen table feels like yesterday. In other ways, it feels like a different lifetime.

Either way, I know I’ve learned a ton—most of it the hard way. So, in honor of my sixth freelance-iversary, I thought I’d spell out six lessons from my own journey.

If you’re just starting out yourself (and maybe currently at your own kitchen table?), I hope they provide some advice and encouragement.

freelancing lessons

1. There’s no such thing as an overnight success story

There’s some sort of quote out there about not comparing your beginning to someone else’s middle, isn’t there? Unfortunately, that’s way too easy to do as a freelancer.

Maybe you look at other successful freelancers and you see their major bylines and impressive portfolios. Or their envy-worthy income reports. Or their big social media followings.

I remember doing that same thing. Embarrassingly, I never gave any thought to the years of hard work those freelancers likely sunk into building their businesses. I assumed that they were lucky enough to find the magic bullet for freelance success, and I needed to stumble upon a similar helpful hack.

Let me state it plainly: There’s no such thing as an overnight success story in freelancing. It only seems like there is because you aren’t seeing all of the blood, sweat, and tears (oh, so many tears) that went into scoring those wins.

Sure, I like to think that I’m successful now. But there’s plenty that isn’t quite so obvious.

There are the countless resumes I drafted for $20 a pop. The 700-word blog posts I wrote about storage unit insurance for $40 each. The hours I spent entering a shoebox-full of business cards into a spreadsheet for a local businessperson who paid me $10 per hour (yep, true story).

THE TAKEAWAY: If you’re comparing yourself to other freelancers, I can promise that you’re only seeing their highlight reel. Take a step back and ask yourself what you’re not seeing. I guarantee there’s a whole lot of non-glamourous work involved.

2. “Making it” involves a whole lot of hard work (and a little bit of luck)

Related to the above, freelancing requires a heck of a lot of elbow grease. I worked tirelessly to get my business up and running. There were early mornings, late nights, and entire weekends spent blurry-eyed in front of my computer screen.

But, as much as I’ll tout the value of breaking a sweat, I have to admit that there’s a little bit of luck involved. In fact, I think that’s true of success no matter the circumstances (and I wrote about a similar concept for The Muse a few years ago).

Did I bust my booty to build my freelance career? Absolutely. There’s no doubt about it.

Yet, I’ll also admit that there was quite a bit of luck involved. I landed some of my best clients and projects because I just happened to be in the right place at the right time. That’s not a helpful sentiment—but it’s true.

Luck is certainly no substitute for rolling up your sleeves and getting work done (and it’s definitely a less reliable tactic). However, I also recognize that oftentimes it’s a dash of good fortune that can take your freelance career from good to great.

THE TAKEAWAY: There’s only so much of your own freelance journey you can control. Sometimes the universe has other plans for you.

freelancing lessons

3. Boundaries are your best friend

Freelancing isn’t a career path that people readily understand. It’s not quite as obvious as being a teacher or a doctor or any other profession that’s widely known and accepted. I can’t tell you how many times I’ve answered the, “So…like, what do you actually do?” question from my friends, in-laws, and everybody in between.

Since people don’t quite grasp the intricacies of the freelance lifestyle, it’s important that you set boundaries with them and help them understand that you do, indeed, work.

Nope, just because you’re home doesn’t mean that you’re available to wait for their cable guy to show up at 2PM on a Wednesday. You’re working. Setting those expectations and reaching a common understanding can be more difficult than you think.

Loved ones aside, you also need to be ready to set boundaries with yourself. Particularly if you’re used to working a traditional job outside of your house, freelancing quickly blurs the lines between your work life and personal life.

One of the best things I ever did for my freelance career (and, you know, my sanity) was set my weekends as off-limits.

After years of working almost full days on Saturdays and Sundays to get my business off the ground, I decided I wanted my weekends back. Now, I don’t even touch my computer on those days—and it means I’m able to head back into my work week feeling refreshed and recharged (rather than full of resentment).

THE TAKEAWAY: Set expectations early. Communicate your plans and needs to your loved ones, and set a work schedule (including some “off limits” hours and days) for yourself right away. You can thank me later.

4. Community is way better than competition

When I first started freelancing, I assumed this career path was competitive and cutthroat. In some ways, that’s true. You are up against other freelancers to land the clients and projects you really want.

But here’s something that might surprise you: Other freelancers have been my greatest source of not only encouragement but also new clients.

A few years ago, I started interacting and corresponding with a number of fellow freelancers through Twitter. I even connected with several of them for regular video chats where we’d trade advice, stories, and just catch up on life.

Through that, I’ve not only built a network I can lean on for tips and support, but I’ve also created a pipeline for potential new clients and projects.

When other freelancers in my network are too busy or not a good fit for a gig that lands in their inbox, they refer me—and I always return the favor.

So, don’t think that freelancing equates to constant competition. Make the effort to help and support other freelancers. I promise it pays dividends in the long run.

THE TAKEAWAY: Reach out to some other freelancers to forge positive relationships. My private Facebook community is a great way to connect with other creative freelancers in a variety of disciplines.

freelancing lessons

5. Highs and lows are inevitable

Do you want to know how many times I’ve been convinced that my freelance business was crashing and burning? Approximately 10,739. Seriously, it’s a concern I have on almost a weekly basis.

Freelancing is a rollercoaster ride, and you’re going to experience your fair share of dips. It’s just the nature of the beast.

I’ve been blindsided when beloved, long-time clients told me they had to move on. I’ve been rejected by opportunities that I thought were in the bag. I’ve wondered where my next paycheck was going to come from.

But, on the flip side of that, I’ve also scored major accomplishments that made me burst with pride.

Freelancing requires a healthy amount of persistence. You need to be willing to grip the handlebars, grit your teeth, and hold on tight for the ride. You can’t hit the eject button the moment you experience the first dip—it’s just all part of the process.

THE TAKEAWAY: Enjoy the peaks and stay committed through the valleys. When things are good, make sure to set some money aside to help carry you through the scary times. It’s way better than searching your couch cushions for spare change.

6. Money truly isn’t everything

When you’re a freelancer, you don’t have a lot of the same success metrics that you have in a traditional job.

There’s no clear path for advancement. There are no regular performance reviews from your manager. There’s no promise of an upcoming promotion.

That makes it way too easy to view income as your only success indicator. Trust me, I’ve fallen into this trap. I assumed that the more I earned, the more “successful” I was.

Here’s a peek at my annual income (before taxes and expenses) for each year I’ve freelanced:

  • 2014 Income (half a year, since I started my business in July): $5,300
  • 2015 Income: $32,000
  • 2016 Income: $80,000
  • 2017 Income: $102,000
  • 2018 Income: $98,000
  • 2019 Income: $120,000

Yep, I’ve cracked the esteemed six-figure milestone twice. But, was I any happier earning over $100,000 than I was when I earned $80,000?

Not really. In fact, if it hadn’t been for my QuickBooks reports, I might not have even known that I had made it over the six-figure hump. I mean that.

The year I earned $80,000 was one of the most stressful years of my life. That was before I had some refined systems in place, and achieving that major income increase meant I made a lot of other sacrifices. Put simply, I worked way more than I should have—and I think that’s just what happens when you’re using money as your only barometer.

So, while I know it’s hard to do, try not to assign so much importance to the income aspect of things. Of course, it matters (and I recognize that it’s way easier for me to say, “Don’t obsess over the money!” now that I’ve achieved a great income for myself).

You obviously need to pay your bills (and you deserve to be compensated fairly for the value you bring to the table!), but just be aware that money truly isn’t the be-all and end-all. There’s no income milestone where you’ll think, “Whew, yep, everything is right with the world now.” I promise.

THE TAKEAWAY: Set some non-financial goals and milestones for your freelance career. Learn a new skill. Achieve a better work-life balance. Land a dream client. Identify something important to you so you can feel a sense of achievement for something outside of your income.

freelancing lessons

Here’s to six years (and hopefully many more)

Freelancing has been a constant learning process. I’m six years in, and I’m still learning. Some days I feel like I have it all figured out, and other days I’m convinced I have no earthly clue what I’m doing. The latter are way more common than I care to admit.

But, even so, I love being a freelancer and I’m so glad I took that leap of faith from my full-time job exactly six years ago. I’ve said it before and I’ll say it again: It’s the scariest riskiest best decision I’ve ever made.