How to Avoid the Pressures of Fitting Into the ‘Successful Freelancer’ Box

By Jackie Lam August 11th, 2021

A few years ago, I reached a crossroads in my freelance writing career. I had a steady rotation of clients with a healthy mix of work in personal finance writing and content marketing. I was making a decent living and enjoyed what I was doing. But I had a nagging feeling that something was missing. It left me wondering, what’s next?

A friend suggested I take my freelance business to the “next level.” I decided I could do this by launching a boutique content marketing agency. After all, isn’t going bigger, doing more, and earning as much as possible a natural progression of success?

I set up a website for my new endeavor. I registered a domain. I plodded through my anxiety and booked time for professional headshots, even though I abhor having photos taken.

But about a month in, I had a startling realization: This wasn’t actually something I had a modicum of interest in doing.

In the same way that climbing the corporate ladder is the traditional way to “make it,” there’s a certain “successful freelancer” path that people feel pressured to pursue. But falling into bouts of compare and despair is counterproductive. After seven years of freelance writing, I now have a clearer picture of what success looks like for me.

Align your strengths with the market

“Do what you love and the money will come” often gets an eye roll. It’s not practical to expect a divine act of the cosmos to make your dreams come true. But in my case, I was able to find the intersection between my know-how and a market need.

Early in my career, I was an aspiring fiction writer, hand model, and blogger. I entertained many creative ideas, like curating a Twitter account that featured daily pizza jokes. I didn’t make a single cent on most of these ventures. But one of them did end up becoming the bedrock of my career: blogging about money—frugality and saving money, in particular.

It’s not practical to expect a divine act of the cosmos to make your dreams come true.

While I daydreamed about “making it” as a writer, it wasn’t until I was introduced to the world of content marketing that it became a reality. In 2014, I met Contently’s VP of talent at a conference and learned there was a big need for personal finance writers on the platform since Contently had a lot of clients in the financial services industry.

Shortly after that meeting, I was added as a contributor on Contently. Within the first month, I earned just as much as I did from my day job. Writing about personal finance was a great fit for me, given my love for the topic. Ultimately, it helped me connect my passion with with my income.

Make your own blueprint for success

There are still aspects of being a “successful freelancer” that I try to avoid. For instance, while I know Twitter is fertile ground for connecting with editors and stumbling upon calls for pitches, I don’t spend much time on the platform that way.

Instead, I focus on subtle community-building. I tend to be service-oriented, so I tap into my natural abilities as a connector. I network with other freelancers through direct messages and emails. I also refer fellow freelancers to work opportunities, offer them advice, and serve as a sounding board.

The tactic has helped me gain clients through referrals. It’s an under-the-radar way of building my network, which relieved me of doing something I really don’t enjoy—and that I’m not terribly good at. There are added benefits too. By developing a trusted network, I haven’t had to do much cold pitching, and I don’t recall ever sending an unsolicited letter of introduction.

Realize that not every side project needs to be a “hustle”

Freelancers often have more flexibility than their full-time counterparts to take a sabbatical, work on passion projects, and pursue their whims. For me, the ability to make my own schedule has been a huge benefit. Peppering my schedule with personal projects has helped me become both a better freelancer and creator.

Sometimes, I scale back on work, take days off during the week to spend time with my mom, or volunteer at a nearby food pantry. I’ve allocated time off to help my partner with business endeavors, to wander, and to just kick it and rest. It may appear like slacking to some, but it’s always what I need in the moment.

Sometimes your path to success might not line up with conventional wisdom, and that’s okay.

If you’re just starting out, figure out what works for you and arrange your schedule accordingly. Take what you’ve heard about being a successful freelancer with a grain of salt—rely on your intuition instead. For instance, a lot of standard productivity hacks don’t work for me, because I work in blocks of time based on my energy. Some weeks, I might work a little each day without ever taking a complete day off. Other times, I front-load to give myself mental space at the end of the week.

Just as there’s no right or wrong way to arrange your calendar, there’s no “correct” way to fill your pipeline. I’ve turned down high-paying work because it didn’t align with my style of freelancing. Alternatively, I’ve accepted work from lower-paying clients because I found it to be more interesting. I’m currently working on becoming a financial coach for artists and creative freelancers—which will probably pay less than writing, but it’s something I find fulfilling.

Seven years into freelancing, I’ve found that I don’t have to keep score with a constant focus on boosting earning potential, scaling my business, or, well, doing that whole #girlboss thing. Sometimes your path to success might not line up with conventional wisdom, and that’s okay.

Image by Mykyta Ivanov
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