Stefanie O’Connell considers her life as a freelancer and why she’s exactly where she needs to be—with or without crisis.

In April, my bank account was in a sorry state. Having cleared out my savings to finance some unexpected personal drama and depleted most of my checking, I stressed over the dwindling numbers. I tallied how many days I had left until the start of May and my next round of recurring bills due. Meanwhile, I needed to maintain the smooth operation of my business while my biggest clients made excuses for delayed payments.

Faced with the prospect of reaching zero balance (in the bad way, not the good), I considered my options—take on extra gigs with immediate payment policies, liquidate a portion of my non-retirement investment accounts, or sublet my apartment on AirBnB.

I wound up settling on option one and within a few days, some substantial payments appeared in my mailbox, saving me from my impending demise and replenishing a portion of my emergency savings.

Despite the temporary crunch of financial stress, what struck me most about that time, other than the fact that it should not have been happening to me, was that I turned down several salaried job prospects. With as close to zero dollars in checking and savings as ever, I was saying no to near-six-figure salaried positions!

On multiple occasions, I’ve found myself presented with several well-paying job prospects, complete with perks and benefits, over the past two years—something I’ve never experienced before, having spent the first seven years working in musical theater and the past few building my own business.

The erratic nature of my employment history has made for an admittedly stressful career, chasing down payments from rogue clients, losing myself in spreadsheets and invoices, budgeting with wildly inconsistent income, and researching my healthcare and retirement options.

Every time the promise of stability arises in the form of a (normal) salary, I find myself saying no.

Maybe it’s because I’ve already learned how to live without a steady paycheck, so the promise of stability doesn’t offer enough appeal.

Or maybe it’s because I despise the seemingly arbitrary norms of workplace culture—set hours, nonsensical meetings, and bureaucracy.

But there are a few things I know…

My career vision is greater than a steady paycheck.

Most jobs, even high-paying ones, are static, meaning you eventually hit an income ceiling. Employers will only pay so much for a given position, and once you reach that top earnings limit, you’re kind of stuck.

I am self-employed, so there are no such limits. As long as I continue to grow and expand my business, I can earn as much as my time, talent, and effort will allow. How exciting is that?

I want to create solutions for people on my terms.

I’m results-oriented. I like having my performance measured that way, not by my process. How I do my work, when I do my work, and where I do my work are, in my mind, nobody’s business but my own.

I love the flexibility.

It’s not just the flexible hours and locale that make self-employment so appealing; it’s the flexibility of the work itself, too. My primary income stream has shifted at least three times in the past year. I love the challenge of finding ways to match my shifting goals and priorities with the similarly evolving wants and needs of my clients.

I love deciding whom I work for.

As much as I love working with awesome people, one of the best aspects of being self-employed is not working with people who cause me undue grief. Yes, I will turn down perfectly good money to avoid problem clients—and I do!

I work well alone.

Certain settings—like planes, buses, and offices—irritate the hell out of me. Being in an environment where there’s even a chance of hearing the sound of an apple being eaten in an otherwise silent room with any measure of frequency sounds like my personal hell. I know it’s weird, but it’s true. I love the privacy of my personal workspace, and I do my best work that way.

I love dictating the value of my work.

Maybe it’s the trauma of being heinously underpaid for the many years I worked as an actress, but I like being the one to dictate the value of my work, not my employer.

I need ownership over my income.

On a surface level, a full-time salary may seem more secure than the unpredictability of self-employment—especially given recent personal experience—but being the child of parents who were unexpectedly laid off from their cushy corporate jobs just as the first of their five children started college, I’m not so sure.

Real security comes from control. From my point of view, self-employment provides far more control and ownership over income than the lease on income that is a traditional salary.

In short, I know myself. And for me, the six-figure job—in all its supposed stability, security, and benefits—doesn’t fit my vision of career satisfaction. I certainly don’t expect everyone to agree with my perspective, but I do think it’s critical that everyone be in touch with their needs and consciously make career choices that are in line with what they value.

Stefanie O'Connell
Stefanie O’Connell is a Millennial money expert
and author of
 The Broke and Beautiful Life.

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