A little over a year ago, I took on a day job for the first time in seven years. When most people are off getting coffee with colleagues and planning how to avoid the weirdest person at their office Christmas party, I was editing transcripts and running livestream events for colleagues I would never ever meet in person.
Remote work only went mainstream in the last five years. It was pretty interesting to come up doing work that most people found weird or sketchy, only to find out that I had been “living the dream.”
I kept waiting to be judged or labeled a sellout for getting a day job. But thankfully, all my entrepreneur friends saw it as just a step I needed to take then and really supported me. What job I had didn’t define my personality or intellectual independence to them. It felt really nice.
But I can’t lie, the transition to freelancer to entrepreneur to working stiff was tough. I faced a lot of challenges that wouldn’t even register for someone who had a more conventional career path. Sometimes, it was hilarious how small my stressors seem compared to the grand picture of Work Stress. But hey, they’re mine.
You realize that jobs take up, like, a lot of time.
This is something to which most people with normal jobs figure out right away. But for someone who had worked unconventional jobs forever, this fact hit me like a freight train.
Eight hours a day. Five days a week. Until you’re 65, if you’re lucky or don’t sacrifice a lot of time and money to save enough money to do so.
I don’t always have the option of going off to the store to get something when I need a break. I have more freedom than most at a fully remote job. But I still have to complete 40 hours of work a week. There’s no shortcuts if I’m extra efficient. There’s always something to do, and my time is worth most of all.
You respect your successful friends so much more.
“How does anyone do… anything?”
I probably asked this question a dozen times my first year of work. It sounds stupid! But it’s exactly how it felt. I’ve had weeks between vacuuming and months between cleaning my car. Two days of maintaining a proper, 100% efficient routine usually results in me binging on pizza and getting high the third day.
That’s the section. I have no solution. Send help.
Your ambition has violent mood swings.
In my area of the world (the Pacific Northwest), there’s an odd anti-ambition undercurrent. We don’t talk about how much money we make with people we don’t know very well, and rarely with non-family members. If we get promoted at work, we’re happy about the prestige and the “new challenges ahead.” Before you even talk about your career, there’s an unspoken agreement on the idea that Career Isn’t Everything.
Now, this is a great attitude in a lot of ways. Pacific Northwesterners value personal health more than folks of a lot of different regions. We value philanthropic giving. There’s a lot less resistance to people taking a pay cut because they believe in the company’s mission.
But it also leads to a lot of stagnation. Many, many people my age in the Pacific Northwest have given up on the idea of ever having financial freedom. They will die with debt. They will never own a home. So why try? Why not just go to work, smoke weed with their friends, and try to enjoy the life that’s available to them at this level?
After taking on a 40-hour-a-week job, I understood where these folks were coming from more than I ever wanted to admit. To transition to a “real job" comes with expectations that you’ll live a more conventional life. Those expectations can grate on you, and you start to wonder why you do so damn much for money.
If you’re like me, you eventually come around to the other side and realize the real meaning of money in your life (independence, choices, freedom to pursue something, etc.). But if money just stays money, it’s easy to lose interest in giving up a lot of life to pursue it.
You realize the value of imaginative play.
This may be heavily dependent on a person’s career choice. I have no idea about the relation between people who program computers for a living and their imaginations (though I’d absolutely love to hear about it).
My imagination has been my closest friend most of my life. I’m building worlds for at least three “universes” for my book series at any given time. I choreograph dances in my head when I listen to music. I love seeing pictures of where people live on social media because imagining where they live makes me happy.
Even if you have the most loosey-goosey job in the world where everyone gets months of vacation off every year and there’s an MLB-size company sports league, work is still the antithesis of pure imagination. Weirdos like me do their best to harness the power of their imagination and make it earn them money. If we get lucky, we end up like Stephen King and we can just create-create-create for a living.
I explained this once to my family as the concept of “go off and write.” To “go off and write” is to set aside time for creating things with no obligations or needs on your part. Nothing will stop or deteriorate if you don’t do anything. No children will need you. No chores will languish. You can just go and play in the worlds you’ve created, listen to the people your mind has sprung, and listen so you can write about them better in the future.
This sacred space is rarely achieved. High-paying writing jobs used to provide it. Publishers once acted as if it as their duty to pay writers enough so that they could “go off and write.” They invested in writers because they believed in that creative space. They believed in the worth of imaginative freedom.
But today, to “go off and write” requires more than ever. You have to have the money. You have to have everyone in your life on board with giving you that space. In an age where writers are responsible for running their own marketing and to be a regularly successful writer is to sign up for running your own business in perpetuity (especially if you’re a self-published author), it’s rare.
This is what people talk about when they talk about the gender gap in writers. Or more accurately, when women talk about making time for writing and how it seems impossible. Children need them. The home needs them. They “have” to support their partners and downplay their own career — because it’s what they’ve been taught is right. To challenge this would make them feel Very Uncomfortable and guilty.
The joy of having a day job is that you’re closer to giving yourself the ability to “go off and write” whenever you do something creative outside of work. Anything you produce during that time doesn’t have to pay your bills. Your art no longer has that responsibility. That often leads to new ideas exploding into you… and it is glorious.
Burnout becomes the ultimate enemy.
I did not expect my thirties to start by worrying about a lot of people. But we can’t control everything.
A great deal of my friends suffer from burnout, and they suffer happily because it is acceptable. It’s goddamn acceptable for them to look ten years older than they are, have bags under their eyes constantly, live off caffeine and three hours sleep a night, then wake up and cater to their boss’s every request.
It’s not normal. It’s accepting lesser than they deserve because pickings can be slim these days. But it’s unnatural. Worse, it doesn’t even benefit you.
The people I know like this have ambitious drives to always be pushing forward. But it’s at the cost of their mental and physical health. I’m a writer, I get the brain-in-a-jar way of thinking that discounts health for temporary raises in creativity or productivity.
But the body doesn’t forget. It punishes, and it refuses to let you get off the hook for acting like it’s nothing but your jar. And just when you need it to obey most, it will refuse to do so if you haven’t needed its warnings.
You can think more and more about the future.
When you have a paycheck that’s due to be regular for a minimum of three years (typical for my industry if you really like where you work), hunting for money and meeting a quota isn’t always at the front of your mind.
I don’t at all regret jumping from entrepreneurship to a conventional job. In fact, I came across the job at just the right time. I had experience working remotely when not many of my contemporaries did.
But freelancing also prepared me for this job more than I expected. I am no longer at the same level of my career as I was at my last conventional job, a housecleaner: I had had mentors, especially wonderful women who were principled and had made diligent moves at every step of their careers. I had attended conferences. I had had to make difficult decisions about my career’s direction and think hard about my priorities. Objectively, I still progressed in my career.
There are a million articles about why you should quit your day job and start your own business. They’re all correct in what they say about day jobs. But what they neglect to say is that day jobs really really work for some people. They just do.
This doesn’t make those people sheep. In some cases, they’re people who realized a truth about themselves and chose to follow it. They didn’t want to strive to work a career that would have been “cooler” life but would have ultimately stressed them out. To them, it wasn’t worth it.
Believe me, they’re not judging you.