Why I Still Have A Day Job

In short: because I like it

The fact that many writers have day jobs is not new — most aspiring writers do (and many of the successful ones did, too, before they made it big.)

So to say I have a job isn’t all that interesting. Where people get hung up is when I clarify:

I’m not trying to leave it.

Because “escaping a job” isn’t every writer’s primary motivation.

I know that it is the main goal for a lot of aspiring writers, especially bloggers and freelancers, but for a lot of us (myself included) it’s not. (And to be honest, I’m always a bit surprised when folks are confused by this.)

Some writers aren’t writing in hopes it will “save” us. Rather:

  • A lot of writers like their day job, and equally important:
  • A lot of writers’ motivation for writing is simply: to write


John Gorman is another Medium writer who not only has a day job, but isn’t gunning to ditch it. He and I once talked about this on a call and agreed.

Gorman wrote,

“I am so blessed, lucky and privileged to be able to do the things I love (write, play music) for a career, in the city I wanted… It didn’t have to be so hard.”

No, it doesn’t.

1. I LIKE working

In general. I like the transaction of value in exchange for value. Work, however you define it, is one of the most important things to human morale. The happiest times of my life (and my idea of “perfect happiness”) all involve work.

2. I like “the sandbox” of work

Work is play. Life is play. It’s all a series of experiments and learning.

3. I like the human interaction

Left to my devices, I can (and happily will) be alone for days on end. When I first started my business, I spent days on end with Top 40 songs as my only form of “human contact.”

But this isn’t how anyone is supposed to live. And while it feels good at the time, this isn’t where we thrive in the long-term. We need external engagement.

I know that there’s the obvious suggestion of writers groups, etc., but it’s not the same. I need real life.

4. I love working on product teams

One of my favorite topics is management philosophy — how to run a team to build product. When I get my colleagues out for drinks, even my buzzed chatter is about the product, the team, and how to manage it.

5. I like earning an income

It’s not that I live lavishly, because I don’t. I prefer “shoebox” apartments, own 4 pairs of cheap black skinny jeans from Walmart, and as long as I can afford a few books, and indulge in food and drink from time to time, I’m happy.

But money is part of the game, and I like it — both a.) the “muscle” it offers (I couldn’t pay my parents’ mortgage with writing alone rn) and b.) the motivation it creates (I want to.)

6. I like the structure

Eliminating some decisions from our lives is incredibly freeing. There is no joy in negotiating every single aspect of my life, and I’m quite content to fall within some frameworks already in place. And while I may dislike some parts of the system, the reality is: I like knowing it’s there.

Gorman agrees,

“I am, truly, very ordinary… Came from a working-class family in a medium-sized Rust Belt city. No true gifts that I didn’t acquire through total immersion, sweat equity and repetition… I am your standard American dude-bro.”

But sometimes standard and ordinary can be very nice. Growth requires foundation, so in the same way I like “boring” love, I believe some constancy breeds good.

G also wrote,

“I am happy… I spend like 50% of my waking hours at my day job, 20% of them doing various side-hustles… and 30% of my time being a functioning human — eating and running and showering and rabble-rousing with friends. That’s not just career fulfillment — that’s life fulfillment. That’s happiness and health.”

I agree.

My most productive writing days are those I have to organize around work hours. When I’m left with huge, yawning spans of time, I write less. I’m not alone in this.

7. I like the security

This is the toughest one to admit, but I do. I like knowing where my next meal is coming from. I like providing it for myself. And while no job is guaranteed, having one offers some small foundation on which to build.

As Elizabeth Gilbert, who kept working even after she had articles in GQ and three books published by major houses, wrote in Big Magic,

“I wasn’t taking any chances, so I kept my day job.”

She adds,

“You must be smart about providing for yourself… I beg you not to infantilize yourself.

Other self-infantilizing dreams include: the dream of marrying for money… inheriting money… winning the lottery… a peaceful cocoon, utterly sheltered from the inconveniences of reality.

This is a world, not a womb. You can look after yourself in this world while looking after your creativity at the same time — just as people have done for ages… Just do it.”

It wasn’t until Eat, Pray, Love that she “allowed” herself to become “nothing other than a writer,” and even still she reminds us, “there is no job security in creativity, and there never will be.”

8. I LIKE my job

Meaning the specific role I have, and the company for which I am fortunate enough to do it.

I don’t talk about my job a lot, mostly because Medium is a big platform and I assume at least a few colleagues read me. But that doesn’t mean I don’t like what I do — because I do.

As Gorman wrote,

“I do what I love… I wake up every morning thrilled to death that I spend eight hours spitting words into a computer and, on occasion, those words get used in global marketing pieces that shape the way people perceive one of the world’s most well-known brands.”

Similarly, I am thrilled that I get to spend eight hours a day driving tiny product decisions that are just specks of an overall enterprise solution.

I haven’t liked every job I’ve had — I’ve had some I didn’t (and a few I outright hated) — and I am, as I said, very fortunate to like this one. I know that.

But even if I didn’t like this job, I’d fall back to point one and keep looking.

9. I’m good at my job

If I may say so myself. (But also echoing the sentiments of my manager and most of my team, as well as many I’ve managed in the past.) Why would anyone want to give up something they enjoy and are good at?

10. I prefer “the real world” of a job

This is the biggest overarching point, and what I’m really saying with everything else: work keeps me in the real world.

I’m not saying this is always a healthy coping mechanism — obviously, people can take it too far, losing “themselves” to their titles or becoming workaholics (which I am not.) But I am at greater risk of the opposite — of losing “myself” to some white abyss on the other side; to nothingness. Work is concrete.

While we recognize the shortcomings of the everyday — its assault of the infinite — we also recognize its safe-keeping. I’m not the only one who bolsters and protects myself with “work” in this way.

Gorman wrote a really beautiful piece, which (pardon me, G) I’d like to take a light liberty with. In it, he juggles the concepts of worth and morality:

“I’m constantly incorporating the totality of my life as recorded by a watchful, omnipotent eye… a kind of mental gymnastics no one’s equipped to medal in. Not without a cascade of self-doubt to the point of madness… how are we supposed to assess ourselves?

I think about morality often… there’s no real way to know how we’re doing.”

He admits,

“Since there’s no blueprint to how to live life — no agreed-upon or holistic metric as to what constitutes contribution to society, happiness, fulfillment or success — I’ve often attempted to calculate one, and use it to provide an objective, unbiased answer… a summary and conclusion... ‘I did X, Y and Z’… I went to work today. Pitched a new project… Went to a board meeting. Caught up with a friend over coffee.”


“Fine, I guess. Feeling fairly accomplished and wanted.”

This is, Gorman knows, “of course fundamentally flawed,” begging the questions,

“Who am I devoid of context? Extracting oneself from the trappings of life lived so far has proven to be a herculean challenge. How, and who, are you when you take it all away?… If I were to lose my job tomorrow, who would I be?… If you take away what I’ve accomplished and what I have, I am not sure how to answer who I am

And yet at the same time, maybe sometimes that buoy can be enough — if for nothing else than interrupting these spirals by giving you a place you need to be from 9 to 5.

“There are no easy answers. There are no clear conclusions. I realize, now, seemingly, that… life is meant to be lived … not so obsessively measured or thought about.

So… who am I? I suppose a work in progress.

Maybe that’s all life is: a series of beta-tests where each decision yields a new iteration, each version slightly different from the previous one.”

Yes. And as long as we keep living it, not drifting off, then we, too, are real.


1. I just want to let my writing “be writing”

When racehorses retire, they have all kinds of issues coming off the track after spending their whole lives galloping (and only going left.) They often have to spend up to a year in a pasture to learn how to “just be a horse.

Similarly: sometimes writing can just be writing.

Elizabeth Gilbert wrote,

“I never wanted to burden my writing with the responsibility of paying for my life… I’ve always felt like this is so cruel to your work — to demand a regular paycheck from it… I held on to my day jobs for so long because I wanted to keep my creativity free and safe. I maintained alternative streams of income so that, when my inspiration wasn’t flowing, I could say to it reassuringly, ‘No worries, mate. Just take your time. I’m here whenever you’re ready.’ I was always willing to work hard so that my creativity could play lightly.”

I have been writing since I was old enough to know how, had a blog with like 8 followers in my 20s, and at times wrote as much as a million words a year… meaning: I like writing.

2. My writing’s isn’t save me or “earn its keep”

I didn’t monetize my Medium account for nearly two years. I made about $200 total from writing before that.

Money is not the reason I’m here. I like making it, but, again, that’s not what I ask of the writing — that wasn’t how this started.

When you make writing your source of income, you’re not “escaping” the need for income — you’re just binding those dependencies to a different area of your life. And I get the potential upsides here — freedom, work hours, location, no ceiling — but we have to be careful to understand: when we ask our writing to earn its keep, it doesn’t “save us;” rather, it becomes our job.

And the problem with thinking it is, is that this changes your entire relationship — in the same sense that financial dependency within a relationship does. It puts strain on things where they weren’t.

Gilbert wrote,

“Financial demands can puts so much pressure on the delicacies and vagaries of inspiration… There’s no dishonor in having a job. What is dishonorable is scaring away your creativity by demanding that it pay for your entire existence.”

And if the time comes where our writing does return monetary reward, then this is a windfall; a beautiful upside to a job well done; a good relationship.

3. My writing’s job isn’t to “make it big”

I didn’t start writing on Medium to “get big.” I just wanted a place to write. The rest was more or less “by accident.”

Gilbert shares a similar sentiment,

“I once wrote a book that accidentally became a giant best seller… it was never my intention to write a giant best seller, believe me. I wouldn’t know how to write a giant best seller if I tried. (Case in point: I’ve published six books — all written with equal passion and effort — and five of them were decidedly not giant best sellers.)”

I know there are tons of people out here tying to “game the system” and “figure out” how to “make it big” in writing. That’s great for them.

But all many writers, myself included, want is: to write what we want to write.

4. The real world (and work) inspires writing

I don’t want to write in a vacuum! I don’t like it, I don’t want it, and if I ever found myself with nothing but “writing” in front of me (short of a serious, short-lived intention), my first order of business would be: find a reason to get out of the house.

Gilbert’s jobs included: au pair, private tutor, teacher, bookstore clerk, cook, flea-marketeer, waitress, ranch hand, and bartender… the latter two of which yielded some most successful “pre-Eat Pray Love” pieces (Last American Man and Coyote Ugly, respectively.)

Similarly, most of my work comes from real life — my own experiences, talking to others, going out. I need life in order to write; it’s what I write about.

Gilbert writes,

“There is a profound sense of honor to be found in looking after yourself, and that honor will resonate powerfully in you work; it will make your work stronger.”

5. On “enough time:” creativity loves constraints

Tons of people like making the “enough time” argument, but I’m just going to stop you there, because: those who see “time” as their demon choose to.

Everyone has the same 24 hours. “Time” is actually a “priority” problem.

As Yahoo! CEO Marissa Mayer said in 2006,

“Constraints shape and focus problems, and provide clear challenges to overcome as well as inspiration. Creativity loves constraints, but they must be balanced with a healthy disregard for the impossible.”

Gilbert wrote,

“Most individuals have never had enough time, and they’ve never had enough resources, and they’ve never had enough support or patronage or reward . . . and yet still they persist in creating. They persist because they care. They persist because they are called to be makers, by any means necessary.

6. Writing gets to stay joy-first

Because I didn’t bundle expectations and bills into my writing, I get to preserve what it does best. If writing earns me some money, that’s fine — but it’s icing on the cake.

By keeping a job, I get the best of both worlds.

Writer — www.krisgage.com reach me at krisgagemedium (at) gmail (dot) com

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