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What I Learned from Becoming My Own Boss

Ditching the nine to five is great in some ways, challenging in others, and as a whole, incredibly rewarding. Here's how.

I gave in my two-weeks notice just over a year ago.

I asked my manager to grab a cup of coffee for our weekly one-on-one chat, and as we walked through the city streets in the cold, I explained that I’d be leaving. No job is perfect, but I assured her that I didn’t make that decision because I was unfulfilled, unhappy, or jumping ship for a higher paycheck. There wasn’t a different position I wanted or another assignment I was angling for. Quitting wasn’t about that at all.

Instead, I had projects of my own that I wanted to work on. Routines of my own I wanted to establish. Graduate school loomed around the corner for me, I knew, and I felt like it was time to clean up my long to-do list before committing to a career — or else let those goals go.

It was now or never. And choosing “now” usually teaches you a whole lot about the world, about yourself. Here are some of the lessons I’ve gathered in the year since.


Sleep Like You Mean It

I’ve always been a night owl — I especially stay up late to read and write, while the stars are out (light pollution notwithstanding) and most other people have gone to sleep. It’s comforting and inspiring to feel like the world is yours. But give a night owl a full-time job, and what do you get?

Sleep-deprivation, of course. And although this is my story, it’s not mine alone: more than one-third of adults in the U.S. are sleep-deprived, missing that 8-hour snooze mark by enough to potentially harm their well-being. I won’t overload you with the science or the statistics, but suffice it to say that sleep-deprivation can have some seriously negative short- and long-term effects on just about everything.

One of the greatest unexpected advantages of quitting my full-time job and working on my own schedule has absolutely been the chance to get the sleep I need. Walking through my days fully awake, I can recognize how much of an impact under-sleeping had on my daily quality of life beforehand. I won’t be a freelancer forever, but from here on out, I’ll think twice before making the decision to sacrifice the sleep my body and brain needs.


Budget Better

The first thing I did after quitting was get a drink, naturally. But the second thing I did was post up in a coffee shop, open a spreadsheet, and create a detailed budget plan. Not exactly the sparkling image of newfound freedom, but it’s necessary.

Freelancers need to track their money carefully to prepare for tax season, plan for major expenses like rent and health insurance, and figure out their cash flow for smaller costs. With a less predictable income, we’ve got to be smart about what we spend. Tracking your revenue and bills is the way to do that. That said, planning ahead is one thing — sticking to that plan is another challenge entirely.

It’s much easier to set a budget for yourself than to actually cut back on those purchases that seem innocuous alone but, together, can make a serious dent in your savings account. A dinner with friends here, a movie ticket there, and suddenly your budget’s gone to the wind. If you have savings and don’t overspend wildly, you don’t necessarily need to feel alarmed… But there’s also the principle of sticking to your plan at stake.

It took some time to adjust, but eventually I learned an important truth from budgeting for my part-time work: Generally speaking, you don’t need as much as you think.

Whether that means figuring out different ways to spend time with friends, cutting out some small purchases, or never taking a taxi again is up to you. Personally, I made a dedicated effort to cook meals for the week ahead of time, and started to revel in those kitchen tasks as a part of my new routine. Budgeting is always important, but the emphasis on simplicity and prioritization that budgeting brings is just as vital.


Be Comfortable with Yourself

“So, what do you do?”

Whenever you meet someone new, chances are pretty high that you’ll get asked this all-American icebreaker in five minutes or less. And why not? Everybody’s got an answer because everybody’s got a job.

Yet somehow, answering this question as a part-time teacher and freelance writer didn’t feel quite as satisfying as it did when I worked at a technology startup and my job title was buzzword heaven. In my first few months of freedom, I found myself qualifying my response, adding that I “used to work in tech” or was “planning to go to law school.”

That reaction never felt genuine to me. It wasn’t a lie, but it wasn’t being true to myself, either. It was as if I felt compelled to normalize my current status by tying it to something more conventional, maybe because I was anxious about what other people would think. But then I realized: who cares what they think?

I quit my full-time job to sprint out of my comfort zone. It absolutely made sense that measuring my sense of self-worth by the metrics of old, full-time me might cause some anxiety, but those aren’t the numbers I try to hit anymore. I care about happiness, fulfillment, and personal accomplishments, and damn the rest.

These days, when I’m asked what I do, I’ll answer that I write short stories, read fantasy novels, and go hiking. I put my hobbies, passions, and interests front and center, not only because they more accurately describe “what I do,” but also because it strengthens my conviction that I am not my job. Sure, it’s a Fight Club truism, but no less true for it. I became my own boss to pursue what I love, and freelancing is fuel for that fire.


Don’t Mistake Uncertainty for Danger

My high school English teacher (hey, Mr. D!) once announced that wisdom is the ability to tolerate ambiguity. Maybe it sounds hokey, and it’s certainly a debatable definition, but it stuck with me in the years since. And if that’s what wisdom is, then boy, I was as unwise as they come.

To plenty of people, the idea of leaving a full-time job without much of a backup plan sounds exciting, emancipating, maybe even brave. To me, it sounded insane. I’ve always been averse to big risks, and the thought of withdrawing from an enjoyable, well-paying, and challenging job for a whole lot of question marks felt as risky as it gets. I constantly asked myself worst case scenario questions: How will I make enough money to manage? What will I do all day? What happens if I get bored, lonely, or complacent? Was my vague to-do list of personal projects and my desire for freedom really worth sacrificing a comfortable lifestyle for?

Comfortable. That was the word that finally convinced me. As if by gravity, I was drawn to security, routine, predictability. I craved comfort. There’s nothing wrong with any of those things — we all want them, even need them — but there’s a precariously thin line between stability and stasis. I wanted to conquer my dependence on the expected route and take a leap, not to escape the known but to explore the unknown.

Ambiguity and uncertainty have been my bedfellows this past year. At times they’re frustrating and distressing guests, but learning to tolerate and at times embrace what they offer has made me more confident and composed. Life often rebels against our best designs, but believe that things will work out in the end, in some way, and it all gets a little easier to deal with.

Whether I’m wiser or not, I’ve learned that unpredictability, while stressful at times, is also exhilarating and unavoidable. Walking away from your most comfortable routines puts you in a sink-or-swim scenario where you either accept the challenge or give into the fear. I’d bet that most people can swim.


Striking out on my own has had its ups and downs. At times it’s boring, lonely, and slow; at others, frustrating and stressful. Aimlessness can erode the conviction that this was the right choice. By no means has it been an easy year. But when we step back from our daily lives to take a deeper measure of how we’re doing, though, we ought to ask ourselves the question: In 10 or 20 or 40 years, will I feel proud of the choices I’m making?

I decided to take a break from the full-time grind to dedicate myself to hobbies and passion projects, yes, but also to challenge myself, to learn how I would adapt, and to act based on the expectation of future pride rather than future regret. Quitting my job to become a part-time teacher and freelance writer was my big leap. Wherever I land, I’ll be happy to be there.

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