The Most Undervalued Force for Building a Successful Freelance Career: Patience

Working for yourself gets better (and easier) once you push through the first few years

Source: Stencil

When someone tells me they stopped freelancing after one year, I can’t help but feel a little bad for them. If their first year was anything like mine, then they endured the absolute hardest aspects of freelancing while enjoying very few of its rewards.

Don’t get me wrong, I have loved freelancing since day one. But at the beginning of 2016, during my first several months as a freelance copywriter, being self-employed felt a lot like being unemployed. My calendar was empty (in a bad way). I often went for several days or even a few weeks between projects. The projects I did have all paid pretty low. I maintained multiple nonwriting side hustles — sometimes involving all-nighters — just to support my infant writing business. One month I had to borrow money to cover rent. And the whole time, marketing my business felt like shouting into the void.

Your problems don’t suddenly end once you cross the one or two year mark. There will always be challenges to overcome when running your own business. But as I approach five years of freelancing, I am more confident than ever about this statement:

Most of the hardest days of being a freelancer are frontloaded onto your first couple of years in business.

If you’re willing to invest in freelancing for the long-term, I believe your best days are ahead.

Don’t Judge Freelancing by Your First Two Years

The reputation of your freelance business ripples further outward every year. Happy clients refer their friends and contacts to you. Those new clients eventually refer even more.

Your website becomes easier to find on Google and social media. Every new article you publish adds to the growing body of work that advertises your business even as you sleep. The compounding nature of online publishing steadily raises your reputation — and your discoverability. And as demand for your services climbs, so do your fees.

When I began freelancing in 2016, my total writing income barely cleared the minimum wage. My wife and business partner Sarabeth joined the business soon after. Our business has grown steadily year over year, to the tune of 82% in the last few years — and 93% in 2020. Sarabeth and I surpassed what we made in 2019… by July.

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Level Up: From Tedium to Strategy

As your fees go up, the work tends to get more interesting. Some of our earliest freelance writing projects could be described as creating content for the sake of creating content. We were hired to put fingers on a keyboard, to output words onto a page. The name of the game was publishing often, and we were the two-person production team for several companies.

That’s how many copywriters start. We must endure long hours of tedious, low-impact writing about mostly uninteresting subjects before we’re entrusted with higher-level challenges. That’s what it takes to improve as a writer and marketer: hours of learning and producing.

“In physical exercise, resistance is a way to make the body stronger, and it is the same with the mind.” — from Mastery by Robert Greene

As you acquire freelance writing experience, you learn what works. You notice what separates your best work from everything else you’ve produced. Those trends become the building blocks for future assignments, the foundation of your writing processes.

Yes, your writing improves, but more importantly, the way you think about writing improves. Writing transforms from a task you perform to a lens through which you see every business and its inherent problems.

Just as you’re beginning to notice this lens within yourself, so do your clients. They begin hiring you to access your mind instead of just your copy. The longer you freelance, the more you begin to look like a consultant instead of a writer. You’re hired for the way you think about words more than your ability to put them on the page.

Outlast the Competition

I think most people stumble into freelancing like I did: by accident. It’s a fun gig for a while, like working at a local coffee shop. Then after a year or two many freelancers start looking for full-time employment. For the freelancers who remain, that means most of the competition at your level will fade away with time. The longer you’re in business, the more you’ll see people who were once at your level suddenly abandon freelancing to get real jobs.

Sure, there will always be new people trying their hand at this work, but as they start, they already lack your experience. In fact, you’re probably the one they’re learning from.

Become a Rainmaker

Starting a freelance business can be risky. Most businesses do not make it to five years. But again, I believe the risk is frontloaded. Every year you’re in business as a freelancer increases your chances of making it another year.

Freelancing begins as financial insecurity and, with time, can evolve into something more secure than the cushiest full-time job. This is a direct result of all the factors already mentioned. But there are two additional factors that eventually make freelancing more financially secure than your standard salaried job.

  1. Freelancing means learning how to sell yourself in any situation. When work slows, you know exactly where to go, what to say, and how to pitch yourself in order to fill your calendar with more work. The ability to make money becomes second nature.
  2. Freelancing means working with dozens of clients, instead of one. When a salaried employee is fired, their only consistent paycheck is gone. That’s a desperate situation. On the other hand, in freelancing, you may need half a dozen people to all fire you at once to be in the same situation. Diversity is power.

Cross the Tipping Point

In the first few years of freelancing, your work will feel like moving a heavy rock up a steep hill. You must labor for every step. Nothing comes easily. But the further you go, the more your vertical climb bends horizontally. Things steadily become easier. The path flattens.

Somewhere along your freelance journey — and you can’t precisely point to when — the gravity that once worked against you begins working for you. Clients come to you more often than you approach them. Your best writing work comes more easily and more often. While you used to pay for marketing, now people offer to pay you to speak on stages and write about your expertise. Yes, people will literally pay you to market yourself.

Maybe I’m getting ahead of myself. I’m not trying to suggest that freelance writing ever becomes easy. I believe that the hard work you love is better than easy work. So if you enjoy freelancing now while it’s new and grueling, just wait until gravity turns in your favor.

In the best way possible, it’s all downhill from there.

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Freelance SaaS copywriter. Subscribe for weekly tips on writing, marketing, and launching a freelance business:

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