Chapter 1: Office Life Will Be The Death Of Me

A brief history of why freedom and flexibility in my work life matter so much to me

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Last week, I kicked off the process of serializing a book I started working on recently, posting the current version of the introduction chapter.

It’s a book about how I was able to carve out a unique sort of professional life for myself that affords me a lot of freedom, free time, and, quite frankly, dignity. But the book is also about why this doesn’t have to be such a unique story—my hope is that it can serve as a highly practical manual for how to build such a career for yourself if you really want to.

I was struggling to coin a nifty little term for this style of work life, which essentially boils down to putting together a small portfolio of jobs where you’re being paid for something other than a fixed amount of your time each day—your knowledge and expertise or particular deliverables—so that you can control how much money you make, how many hours per day you want to work, and where and when you want to work.

I only got as far as describing this as “beyond work from home,” which is true—it is a step further than just working from home—but I wanted to come up with something better. I imagine it’s something I’ll be workshopping for some time, but for now, I’m liking the term “freestyle freelancing.”

It’s not a style of work that’s right for everyone. But for those of us who feel smothered by the traditional 9-5 career model, there’s a lot to like about freestyle freelancing.

However, it helps to have a clear vision and some specific reasons why a work life with more freedom and free time is important to you. While I do think such a career path and lifestyle is very feasible and more attainable than perhaps most people think, it does require a bit of effort: focus, strategy, hard work, and persistence. So, you have to have something you’re fighting for, and the answer to this question will look different for everyone.

Here's mine.

Or, at least, part 1 of mine.

Back in my college years, there were so many reasons why I wanted the kind of professional life I now enjoy, but there was one that eclipsed all the others in landslide fashion: I had serious concerns that a 9-5 job in a traditional workplace setting—you know, basically an office job—would literally kill me.

I’m not being dramatic. And I’ll get us back to the silly, fun voice I like to write in soon enough, I promise, but insofar as this book is as much the story of my adult life as it is a manual of practical advice, I can’t move on without saying a bit about my history of mental illness.

There’s your trigger warning.

But the story does have a happy ending. The trigger clicks, but the gun fails to fire. And then it’s replaced with the incessant, satisfying clicking sound of a pen.

Summer Bummer

I started experiencing symptoms of…something when I was probably about 16 and really started becoming aware of those symptoms by the age of 17, during my last year in high school.

I was the Salutatorian of my high school class, graduating with the second-highest GPA out of a good 400 or so of my peers—a distinction that I suppose mattered quite a bit once upon a time ago, but which now feels like a hazy dream that has long since lost its social and professional relevance.

But look, I’m not going to completely undercut myself here. I delivered a graduation speech that knocked everyone’s socks off. Minutes after getting off the stage, a classmate I barely knew came up to me and told me I should run for President.

My crush at the time gave me a hug and whispered in my ear, “I love you” (yes, I’m serious; no, this didn’t go anywhere).

And for months afterward, the spell I cast seemed to hang over everyone who was in the room that day: friends jokingly nicknamed me “dirt” in reference to the opening lines of the speech, lines that many people from that day were able to recite by heart; other friends said their parents told them they should spend more time with me.

By all outward indications, I should look back fondly on that summer as a period of basking in the glow of everything I had accomplished up until that point, the immense respect I had earned from my peers, their parents, my teachers, and my family, and the blindingly bright future I had to look forward to, starting with the approach of my college years at an institution that had quickly become a dream school.

There were bright spots from that summer, of course, but I remember it more as a summer of the most profound darkness I had yet experienced in my young life.

I remember holding my high school diploma and all the little physical artifacts from my graduation day—tassels, cords, the funny little mortarboard hat—and being a bit confused by how hollow it all felt. I remember being even more confused about how quickly I was losing all interest in the subjects I had loved the most.

By the time I finished high school, I had aced every Advanced Placement math and science class offered by my high school, got 5s on all the corresponding AP exams (if this means anything to you), and aced three semesters of organic chemistry and biochemistry at a local college.

More importantly, I was a science enthusiast. It’s what I wanted to dedicate my life to. I was sure of that. Until, suddenly and inexplicably, all of that went out the window. Equally inexplicably to me, I was quickly developing a fervent interest in philosophy and religion, things for which I had until that point held absolutely zero interest.

I remember a summer marked by restless nights, existential dread, and long periods of time spent lying on the floor in a near-catatonic state. I felt like a corpse. I felt like the “I” with which I had identified for so long had died and was replaced with nothing more than a gaping void.

I wrote it all off as the boredom and anxious anticipation of someone hanging out in the interstitial chasm between high school and college, childhood and adulthood.

I wrote it off as normal teenage shit: girl problems, a delayed period of angst and rebellion that I had somehow skipped right by in my earlier teenage years, and so on—anything to explain away the terrifying question hanging over my head like a shimmering sickle.

“What if this is all permanent? What if this is just who I am now?”

When I Hit The Floor

The start of college brought a certain degree of distraction with all the exciting freedoms, new friends, new crushes, new frontiers of intellectual stimulation, and new substances of psychoactive stimulation.

But the bony finger of intolerably maddening dread wouldn’t stop tapping me on the goddamn shoulder.

Midway through my second semester of college, I dropped out.

It stunned my friends. It freaked out my parents. I suppose it should’ve done the same to me if I weren’t so disoriented by the thick cloud of confusion hanging over my head.

I spent the first two months back home with my parents. More dark, lonely, restless nights. More spooning sessions with the floor.

Then I spent two months at a retreat center in Big Sur, California, which is a story for another day.

And for the sake of getting back to the story you came here for in a timely manner, I’m going to skip past a few more years of the highs and lows I experienced when I went back to finish my college degree.

By the end of my Junior year in college, the symptoms were worse than ever, but I still hadn’t entertained the idea that I might have a “mental illness.” In my estimation, everything that I was experiencing was one big set of personal failings and weaknesses, and, as such, it was entirely up to me to deal with it all.

And then, sometime early on in my Senior year, I found myself sitting on the kitchen floor in my apartment, back against the wall, knife in hand, blade pressed lightly into my wrist. It was a scene so cinematically cliche that it would’ve been almost comical if I weren’t experiencing it firsthand as the lowest point of my life.

Strange as it may seem, though, I look fondly back on that moment; I am grateful for it. It tipped the scales of mental imbalance just enough so that the stubborn scales of denial could finally fall from my eyes.

“It’s this serious, huh? I’m not just fantasizing about doing this—I’m really about to do it…maybe.”

I sat there for maybe 20 or 30 minutes, really letting myself see the chain of consequences that would follow from such an act of self-annihilation. And beyond the tinge of shameful cowardice I felt when I finally put down the knife was the sense that I had won some important battle in the years-long war that had been raging within me.

In that moment, I decided I would get professional help and, should it prove successful, I would treat each day as a gift: not a gift from God or the universe or some other cosmic entity, but a gift from the part of myself that chose life over death.

Like I said, pretty cinematically rich stuff—slip it into the biopic, Hollywood.

Jekyll & Hyde

A few weeks (or months—who knows? Time passed erratically back then), I was diagnosed with type II bipolar disorder.

Suddenly, a lot of things started to make sense. The catatonic states, feelings of dread and emptiness, and suicidal ideation were textbook symptoms of depression; the restless nights—sometimes I’d be fully awake and alert, almost superhumanly so, for 48 hours or more—were glaringly indicative of hypomania, as was the sudden deep fixation on spirituality, which led me to study religion in college and graduate school.

Bipolar disorder is characterized by fluctuating, unstable moods and corresponding levels of energy. The fluctuations can be quick and sudden or more gradual and prolonged, and do not always come in equal measure. For me, the hypomanic episodes were somewhat rare, while the depressive states became more and more frequent until it was a virtual constant state of being, a new normal.

This is the characteristic distinction between bipolar I and bipolar II. To say one is “worse” than the other would be a fruitless pissing contest. But, in simplistic terms, it is generally accepted that manic episodes are more frequent and severe with bipolar I, while depressive states are more frequent and severe with bipolar II.

There is, of course, much more I can say about all of this, but the main point of the sob story is this: bipolar II can be as unpredictable as it is debilitating.

Sometimes you’re on cloud 9, dripping with rizz, hypnotically captivating a crowd of a couple thousand people with a magnificent speech, or writing the best term paper your professor will ever read in a fiery burst of manic energy at 3:00 in the morning.

But more often, you’re stuck in bed until 3:00 in the afternoon, avoiding social interaction like the plague, deathly worried about what others might think if they were to see you in this condition, and painfully aware that you’re in no condition to be a productive member of society that day anyway.

All you can do is sit there and wait for the dark clouds to pass. But you’re lucky if you can even maintain the sense of higher self-awareness necessary to hang onto that conviction that they will pass.

And when it’s finally time to sleep, you have no idea whether you’ll wake up as Dr. Jekyll or Mr. Hyde.

Now, think about what the career prospects for such a person might be. I sure did quite a bit when I was finishing up college.

If, by the grace of a God I didn’t believe in, I even managed to find an employer who was willing to hire someone with a bachelor’s degree in Religion, what were the odds that the chips would fall on the productive Dr. Jekyll 8 out of 24 hours each day, 5 out of 7 days each week, 40-50 weeks out of 52 each year for the next 40 years?

In my experience up to that point, fucking nil. It just wasn’t gonna happen. And if it wasn’t gonna happen, how was I gonna make any money? And if I wasn’t gonna make any money, how was I gonna survive? And if I wasn’t gonna survive, what was the point of putting the knife down that day?

I had serious concerns that a 9-5 job in a traditional workplace setting would literally kill me.

‘Member that? You with me now? You believe me? This is how much I wanted—no, needed—to get myself out of the rat race before it even began.

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