5 Lessons from 5 Years Freelancing

In March 2021, I crossed the five-year mark as a full-time freelance copywriter. In many ways, the career has been about what you'd expect. I've endured the scary volatility of living project to project. I know what it's like to own my calendar and have choice about who I work with. I make a good living - but I have had multiple clients ghost me without payment. I lived as a digital nomad, earning money through my laptop as I explored the world.

And recently, I had to learn the hard way that no one hands you a congratulatory plaque for making it to five years in this business. (Maybe by year ten?)

This felt like a moment worth commemorating. But how do you celebrate a work anniversary as an entrepreneur? I'm sure there are plenty of ways. As for me, I decided to reminisce on my freelance career in the most writerly way possible: by drafting a short listicle about my experience.

Here we go.

1. Mitigate risk to put the odds of success in your favor

The most successful investors aren't huge risk takers. They meticulously look for opportunities with high potential upsides and capped downsides. 
I believe the same is true for freelancers. The most successful among us find ways to mitigate the risks of flexible work. In particular, there are two areas where managed risk is vital to freelance success.

Add "risk" to your pricing: Freelancers and insurance companies have something in common. We both must charge a premium for carrying risk in professional engagements. To work as an on-demand professional service provider, full-time freelancers carry the risk of not holding a 9–5 job. That risk should be factored into how you charge for your services. In other words, raise your rates.

Balance your financial risk through aggressive saving: Even the most veteran freelancers experience financial fluctuation one month to the next. If you plan to freelance for the long-run, you must become an avid saver and investor. De-risk you business by building a generous rainy-day fund - and investing to build wealth even as you sleep. I run this freelance business full-time with my wife. A few years ago, we decided to become aggressive savers and investors. Our safety net allows us to push through the lower revenue months without much trouble.

2. Time is your best marketing advantage

Last week four new high-quality leads booked meetings with us in the period of about 48 hours. We weren't actively looking for a new client, so the fast influx of leads surprised us. We had no idea where these leads came from. And as we jumped on calls with each prospect, it turns out they all came from different places.

The first person found our website on Google.

The second person read a post by my wife on LinkedIn.

The third person was in a Facebook group where one of our past clients referred us.

The fourth contacted us after reading briefly about our business in an ebook I wrote six months ago for one of my clients.

The point is: The longer you freelance, the easier it becomes for people to discover you. For me and my wife, every new article we write or client we help is a seed planted for future opportunities.

We never know which seed will blossom into a new project someday. But the longer we freelance, the more seeds we plant. Finding high-paying work gets exponentially easier each year.

3. Every business needs a freelance writer

Yes, perhaps this is a little exaggerated. But it doesn't feel far from reality.

Think about everything an average business is expected to create these days. Blog posts, social media, website copy, case studies, in-app copy, brochures, cold emails - who's going to write it all? Most business owners have no interest in writing. And it's cheaper to work with a freelancer than to hire an employee.

I read blogs all the time about how crowded freelance copywriting has become. My experience is that more businesses need good writing than there are writers available for hire. There's enough work for all of us.

4. Passion follows progress

I've enjoyed freelance copywriting since day one. But it took me a couple years to really decide that I wanted to make a career out of working for myself.

Let's be honest: the first year or so of freelancing is pretty rough. At least for me, I seldom knew where my next paycheck was coming from. I was bad at managing my time. No one knew I was a freelancer, so finding each client took a lot of effort. Freelancing is a grind at the beginning.

But the longer I stuck with it, the more my passion for freelancing and copywriting grew. My love for this craft grew with my knowledge and experience.

Now, as I enter my sixth year in business, it's hard to imagine ever working another job again. What started as simply my latest gig turned into my vocation. Passion follows progress.

5. Rainmakers outlast virtuosos

I believe the most successful copywriters - the ones who are always booked weeks or months in advance, charging industry-leading rates - are better marketers than they are writers. Let me explain.

Obviously you need to be a good writer to be among the top-paid copywriters. Bad writing won't get you far in this business. But after a certain point, writing talent offers diminishing returns. It's better to be a decent writer with some marketing chops than to be the best writer who doesn't know how to sell their talent.

(Of course, if you're exceptional at both marketing and writing then you're in a league all your own. But most of us probably aren't there yet.)

At the end of the day, you're running a business. And the only way to sustain a business is to consistently find customers. Since you're reading this article, I assume you're already a halfway decent writer. One of the best skills you can learn now is marketing - so you always have more inquiries for your work than you could possibly handle.

Stay tuned for my ten-year version of this listicle… in about five years.