The Best Freelancing Advice I Ever Got

When I was preparing to quit my corporate job, I got really into freelance blogs.

Desperate for any insight into what this scary new life of mine was actually going to look like, I read a number of promising posts, usually along the lines of:

How I Quit My Corporate Job and Never Looked Back

How I Traveled the World While Working Remotely

How I Built a Six-Figure Freelancing Business

All were interesting and valuable. But freelance life is significantly more nuanced than what they imply.

So I want to share the ONE piece of advice I stumbled upon, way back when, that turned out to be the most important tip of all. It’s from a 2017 Ask Polly column, in which Polly, a longtime freelancer herself, offers her insight on taking the plunge. She writes:

“Once you trade in all of the stale burning coffee pots and cheap birthday cakes and dull meetings and incompetent goons of office life for a freelance career, you need to know that you are always, always replacing one team of dehumanizing demons for another.”

No statement has reflected my experience more.

I enjoy freelancing not because it’s somehow superior to other ways of working, but because its challenges are better suited for my own random mix of personality traits and priorities.

For example, hustling for every single assignment can be a tiring way to live. Yet I notice the challenge keeps me engaged and excited by my work. Negotiating rates with clients instead of banking a guaranteed paycheck is also hard, but it makes me feel empowered and forces me to advocate for myself. And this month, managing 30-plus deadlines is proving to be nothing short of a clusterf—well, you get it—yet somehow I’m liking that, too.

These are demons I can handle, in other words. They torture and excite me in equal measure. At the very least, they serve a greater purpose.

I can’t say this for my experience in the corporate world. I had a great job with an even better team, and my brain still found new and exciting ways to eat itself alive every day of the week. No amount of positive experiences—and there were plenty!—could take away the things I inwardly obsessed about.

I would spend hours digging into research on how long “knowledge workers” can actually focus on cognitively demanding creative tasks (HINT: IT IS NOT EIGHT HOURS, THANK YOU VERY MUCH) and then privately seethe about being stuck at a desk for the minimum of nine to five.

I would loathe the meetings that could have been emails and then loathe the emails that could have been nothing at all. I would hear the words “deep dive,” and my soul would temporarily depart my body.

These were frustrations I couldn’t shake. And just like the person who wrote to Polly for advice, I felt ashamed. Why am I such a sensitive snowflake? Why am I such a grade-A pain in the ass? I had so many talented colleagues and friends and family members who managed their awesome corporate jobs without all this neurosis. I envied them (and still do sometimes).

But I can tell you now that the traits that made me feel like a headcase in the corporate world are the exact traits that make my business successful. The critical thinking, the questioning, the desire to innovate, the need to establish and enforce boundaries—they serve me in a million and one ways.

Though you absolutely can leave your corporate job and file a story from some beach in Thailand or blow past the six-figure mark while running your own life, it will likely fall apart if you fail to consider all the frustrations involved in getting there, like tracking down a major payment that’s (**glances at Excel doc**) five months late or enduring endless revision cycles with clients.

Both of these things sit well with me. Spending 10 hours on a deck does not.

As Polly so eloquently sums up at the end of her column:

“No matter what you do for a living, the only thing you’ll get more and more and more of is hard work. So figure out what kind of hard work feels satisfying to you... Your path is unique and very difficult, and it doesn’t lead to some promised land. The path itself is all there is.”

P.S. Want more on this idea? Blogger and author Mark Manson also writes about a similar concept. A fellow appreciator of curse words, he refers to it as the shit sandwich. As in, “What flavor of shit sandwich would you like to eat?”

Jackie Veling