Why I hated self-employment.

Yes, the rumors are true: I’m back to commuting, vacation requests and starting emails with “Hi so-and-so” even when there are nine previous emails in the thread all CLEARLY addressed to so-and-so. (Kidding, I would never. First name + comma, MAX. If so-and-so has a problem with it, you can let him know I charge by the word.)

I fully expected to love freelancing. And I did…for a while. It’s liberating to call the shots on your own day — what hours you will and won’t work, what projects you will and won’t take. It’s luxurious to roll out of bed, log a few productive hours in your PJs, hit the gym and the grocery store when there are no crowds, wrap up your work over happy hour and spend the evening as you please, with the knowledge that there will be no alarm to wake you should you stumble into some good times on a Tuesday. It’s especially satisfying to sign on from a hotel pool deck, reapplying sunscreen between emails and feeling like you’re getting away with something illegal.

Furthermore, I’m glad to have the knowledge that I can support myself freelancing. It’ll make me less likely to stay in a job that’s not the right fit, or to freak if I find myself on the wrong side of layoffs (more likely than not in my industry). This time around, I stumbled into the best-case freelance scenario: a steady gig with a great team that valued my contributions and paid me like clockwork, meaning I had relative stability during the three years I was self-employed. I don’t know that I’d be so lucky again, but I understand the rhythm of freelance life, and I’m confident I could make it work with some hustle.


There’s a tendency, particularly among millennials, to glamorize the HASHTAGBUILDINGMYEMPIRE lifestyle over more traditional paths. Perhaps naively. After the honeymoon period ended, I found that self-employment — even best-case-scenario self-employment — had some serious drawbacks.

This isn’t to say that one is point-blank better than the other. I think both could suit different types of people, or even the same person at different times of life. But having a more balanced understanding of the pros and cons could have saved me from the panicky grips of this is not my beautiful cubicle-free life. I thought I’d share my experience for anyone considering ridin’ solo, ridin’ solo…or simply wondering what it’s like when you can do a full day’s work without pants on.

Read the job description. For me, the appeal of freelancing was being able to focus only on the parts of my job that I liked. Three years ago, that meant writing, hard stop. I didn’t want to be going to meetings or wasting the hours I wasn’t creatively “on” sitting at a desk. And heaven forbid someone disturb me when I was.

The reality is…that’s not reality. When you’re a contractor, you’re always looking for your next gig — which means you’d better be down with self-promotion, and you’d better be prepared to spend a good chunk of time pitching things you’ll never be paid to write. Hopefully, if you’re creative, you enjoy that process somewhat. But you can’t bill brainstorming hours, or the considerable time you’ll spend marketing your skills and promoting your work to strangers.

Then there’s invoicing, which is a pain in the ass but the only way you’ll see a paycheck. For some clients, you’ll also have to do post-invoicing, or v professional nagging to figure out when or whether you’ll ever see said paycheck. Saving money is always important, but especially when you don’t know whether you’ll be paid in six days or six months. Running out of cash can put a real damper on your bohemian best life.

This seems like a good time to mention taxes, which are even more terrible for self-employed peeps than they are for everyone else. For starters, there’s a significant “self-employment tax” to cover Medicare and Social Security costs. Another tax if you live on the edge and don’t get independent health insurance. Since you’re being paid in full for your work rather than having a percentage of your income withheld from each paycheck, prepare to be staggered by the amount you owe, especially if you don’t file quarterly. Even with write-offs, I was nowhere close to breaking even. Lemme tell ya, it was rough.

Know thyself. Being self-employed means being your own boss! Awesome, right? Well, not if you’re a really mean one. Imagine if all of your conversations with your boss went like this:

You: I did a thing!

Boss: Wow, this…this is shit.

You: What? I worked really hard on it! I think it’s a good start!

Boss: Terrible. Dreadful. What are you even doing here? I don’t know why we hired you.

You: What?!

Boss: Burn this. Make sure nobody ever sees it.

You: Yes ma’am, burning it now ma’am.

Boss: And then you should probably just quit for the day. Better luck next time.

Yeah, so clearly I have issues. But if you’re prone to perfectionism and/or negative self-talk, you might find that you have a hard time getting out of your own way long enough to do half of what you’re capable of, much less to really thrive. In my observation, the most successful solo riders are the ones who aren’t afraid to learn as they go, produce unfinished and occasionally bad work, and constantly course-correct without being overwhelmed by self-doubt.

Many ~sensitive artists~ I know don’t function this way. As much as we might resist structure (or actually need some flexibility to capitalize on our creative ebbs and flows), it’s helpful to have things like deadlines! and constructive feedback! and people who hold us accountable to how we’re using our time. Without those things, it can be easy to start lots, finish little, and wind up with pretty much nothing to show for the tortured hours you gave to ~the process~. 

Of course everyone should challenge those imposter-y feelings. They’re something that even the most confident person will struggle with occasionally, and they’ll hold you back whether or not you’re self-employed. But it’s worth asking yourself honestly if the risk of getting stuck in your own negative feedback loop will be good for your career, to say nothing of your mental and emotional health.

On that note…

People need people. Look, of course your job isn’t (hopefully) your only social outlet. But as banal as small talk and office gossip can be, a daily dose of socialization plays a huge role in making us feel human. There’s a reason solitary confinement is the highest form of punishment short of death.

I never set out to be a mole person. But going freelance while living alone, moving across the country and trying to build a friend group from scratch was not ideal.

If only I’d joined a co-working space. (These are freaking expensive, by the way. I’m sure it would help, but there are ways I’d rather spend half my monthly rent.) If only I’d had a great relationship or a social life robust enough to balance out the fact that I was spending my days at home. If only I were raising a family. If only I had the type of head-down obsession with work that made everything else obsolete. All valid! But I didn’t, and if YOU don’t, you might really struggle with the isolation factor.

It’s nice not to put on pants. But it’s also nice to have a reason to wear pants. It’s nice to have people to compliment you on your pants! It’s nice when putting on pants feels quick and easy and natural, because when getting ready and leaving the house aren’t part of your daily routine, they suddenly seem like way more effort. It’s nice for putting on pants to be the norm and not the exception, so you can fully savor every pantsless moment.

Pants are a metaphor, by the way.

Boredom is (still) the enemy. I was thrilled to discover that I could get by doing way less than 40 hours of work while living in an affordable city like Portland. That’s the dream, right, Tim Ferriss? Less work, more everything else?

IDK, man. Like anyone who’s ever wished for a glut of free time, I had big plans for how I’d use it — for new hobbies, frequent travel, volunteering, cooking all of my meals from scratch, and having wild adventures I could leverage for my writing.

I did some of that, sometimes. But I really believe that for 90% of humans, too much free time breeds a lack of urgency to do much of anything. And a lot of time to feel anxious about everything.

It makes sense. When we’re busy, we’re highly aware and respectful of our limited free time. We pack it with cool, exciting activities because we know that’s the only time we’ll get to do them — or we laze hardcore and OWN IT, because we’ve earned it and need to replenish our energy for later. I’m always amazed by how much I can do in a day on vacation, or how much I accomplish during the packed weeks I think will be miserable. At the end, I feel tired, but satisfied — and inspired to do even more.

When any day can be a weekend, you don’t feel the same drive to schedule cool, exciting activities, because there will always be time to do them later. I’d rarely work a full 8-hour day, but rarely take a full day off, so I never felt truly rested. I fell into a ho-hum routine of doing minimal work, super-long workouts (fun for me, but maybe excessive, and certainly at the expense of other things I wanted or needed to be doing), spinning the hamster wheel of chores and errands, spending a lot of time on social media and spending a LOT of time wringing my hands over insignificant things that would have worked themselves out if I’d simply had more to distract me from them.

This is on me. Maybe you think I’m lazy AF. I can be, sometimes. It’s fun to be (mindfully) lazy AF! But I also know I’m not the only one to experience this. Think about all the celebrities who turn to drugs, or influencers who feel “overwhelmed” by grueling days of taking selfies with flat tummy tea. Too much free time (and isolation, which often comes with it) is mentally and physically draining. Anxiety is compounded by missing the sense of self-worth that comes from working hard.

If you’re good at filling your plate and/or have unlimited disposable income to spend your free time doing glamorous goals-y things (but maybe still not, see: celebrities)…you might love having a 4-hour work week. As for me, I’ve come to realize that LESS work means MORE stress. And right now, I benefit from having some structure to make sure I keep doing the most, in a good way.

OK, OK — I didn’t HATE freelancing. It taught me a lot and allowed me to take my own path in my own time. I admire people who can do it well, and I reserve the right to revisit it if and when I feel ready. I hope you found this illuminating, or relatable, or at the very least, I hope it infused your Sunday scaries with a glimmer of gratitude.

Now I gotta go laze hardcore. I have work in the morning.

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