I Was An Anxious, Awkward Perfectionist—Until I Started Freelancing

I overcame my people-pleasing tendencies when I became a solopreneur.

I Was An Anxious, Awkward Perfectionist—Until I Started Freelancing
[Photo: Hero Images/Getty Images]

My path to going freelance didn’t happen in a fit of cubicle rage. It was quite the opposite: I was in the middle of a dream trip to Italy when I realized working for myself was what would really make me happy. The scrimping I did to afford the trip also made me realize I had what it took to build a savings cushion to help me get off the ground.


When I was asked to write about how I was saving to go full-time freelance, I did so in true Leslie Knope fashion. (Friends often refer to me as the Parks and Recreation character, and only partly because I host Galentine’s Day every year.) Thanks to my Type A personality, I made exhaustive outlines, asked for second opinions, and agonized over every word before finally submitting my draft.

The story went live on my first day as a full-time freelancer. As I read over my own experiences, I frowned and chewed my thumbnail. Now what?

Anxiety can be a catch-22. Many of the anxious behaviors that defined my professional life–perfectionism, hyperorganization, multitasking–are praised in today’s workplace. But would they hold me back as a solopreneur?

Related: How To Balance Freelance And Family Life 

As it turns out, they wouldn’t. In fact, going freelance helped me work through my anxiety by keeping me focused on each step of building my business–which ultimately enabled me to strike out on my own successfully.


Building My Client List

First things first, I needed clients. There were just two obstacles in my way: my people-pleasing tendencies and a fear of rejection.

In the past, I’d gone above and beyond to make others happy, like making regular trips from Virginia to New York to interview in-person for unpaid internships. But bending over backward tells others your needs aren’t as important as theirs. I soon realized if I wanted to survive freelancing, I had to make sure I valued my time and quality of life, too. So I’ve learned to decline requests for free trials of my services; I also avoid the impulse to drop everything to answer an email.

Given the hours I laid out for myself and my monthly financial needs, I calculated that I could live comfortably with up to six clients on my roster at a time. I jumped in by pitching as many clients as I had open spots each day. I wasn’t picky about where I pitched either. I’ve earned clients everywhere from my network of publishing contacts, writers and former clients; to cold pitches on Upwork, Reedsy, and the Editorial Freelancers Association job board.

Getting a lot of no’s out of the way early on paid off. My response to rejection is a powerful choice: I can be upset, or I can learn from it and move on. Now, I’m constantly booked two months in advance, and my fear of failure has lost its teeth.

Related: Three Freelance Clients You Need To Steer Clear Of 


Setting A Schedule

Exhaustion, double-booking, under-eye concealer–yet more reasons why I so deeply identify with Leslie Knope. (Hosting a telethon while sleep-deprived sounds exactly like something I’d do.)

But marathon multitasking is not sustainable. That hit me full force back in May, when I found myself strung out on caffeine balancing client work, email, blog posts, accounting, and developing a webinar curriculum– usually until 5 a.m. (I’m tired just thinking about it.)

In order to run a sustainable business, I had to let go–the kryptonite of control freaks everywhere.

Delegating was doubly challenging, because it meant transitioning from a savings-focused lifestyle to one that occasionally meant I had to pay to save time. I now balance frugality with responsible outsourcing of tasks I can’t bill to my clients, like balancing my books or blogging about my business. Luckily, such expenses tend to be tax-deductible, which is a nice incentive for being kind to myself.

I’ve also learned to set work-life boundaries. I set deadlines throughout the day to block out my schedule, rounding up to the nearest half-hour just in case. I set off every morning by 9 a.m., and around 5 p.m., I reach a stopping point and take a stress-relieving jog. Then I enjoy dinner with my boyfriend, Paul, before going back to work or relaxing, depending on the night.


Time management is a work in progress for me, but I’m happy to say I’m getting there.

Managing The Books

If you’re self-employed, quarterly estimated taxes are no joke. Not paying them can mean facing penalties that accrue daily interest on your annual tax return.

I’m prone to ruminating on important subjects like this, so I outsource my anxiety to my trusted accountant, Chad. Chad has helped me in many ways, like helping me apply for my local business license and allocating money for my quarterly estimated taxes (i.e., 25% of every incoming payment.)

Related: Five Creative Ways These Freelancers Landed Gig Work 

Speaking of taxes, if a client pays me more than $600 per year, I give them a Form 1099 for their next annual return. I do this at the outset of our collaboration so that there’s no confusion or unfortunate oversight come tax time.


Budgeting For My Personal Life (Again)

Budgeting is different for freelancers than it is for traditional employees. Payroll doesn’t deposit checks into our account every other Friday, so we can’t plan for incidental expenses or savings until we actually have the money in the bank.

Because of this, I’m not just better at hearing “no,” I’m better at saying it, too. Until I make enough to cover my fixed expenses each month, I counter my friends’ invitations out with invites in. Fun traditions have sprung up as a result, like October’s “Monster Madness,” in which we watch scary movies and then debate which villains should move on to the next round of our brackets.

It’s also hard to anticipate savings ahead of time, which is the toughest part of freelance life for me. However, by keeping incidentals within reason and maintaining a full client list, I’ve been able to save up to $1,000 per month, which I spread across a few goals: a down payment on a home, a travel slush fund, and a retirement account.

Reaching My 1-Year Freelancing Anniversary

Freelancing isn’t for everyone. I knew this, which was why last year I sat at my desk, feeling that anxiety would keep me from succeeding.

But so far, it hasn’t. By embracing challenges and shifting my perspective, I’ve worked with clients on four continents, I’m comfortable in my own skin, and I’m even launching a goal-setting planner for writers this fall. If not for the sink-or-swim nature of my industry, none of this could have happened.


This October, just before my freelance anniversary, I’ll return to Italy for a writing workshop. I got my invitation as I was drafting this article–and I had to sit back for a moment, dazzled by karma.

The fact that I’d trusted myself to build a business meant I had the time–and money!–to accept the invitation. I once would have seen this opportunity as risky and last-minute, but now? Now, it feels like an adventure.

This article originally appeared on LearnVest and is reprinted with permission.