It is exactly 10:14 on a Tuesday morning, and I am currently having a very intense conversation with a crumb on my desk. It’s a small crumb, likely from a piece of toast I ate while standing over the sink three hours ago, but right now, it is the most interesting thing in my world. In a “real” office, I’d be three coffees deep, nodding through a meeting about quarterly projections or perhaps avoiding eye contact with the person from accounting who always wants to talk about their cat. Instead, I am here. Alone. In my pajamas, wondering if I should vacuum or write this paragraph.
This is the part of working for yourself that doesn’t make it into the Instagram reels. There are no filtered shots of me working from a sun-drenched balcony in Bali (mostly because my Wi-Fi doesn’t reach the porch, and also because there are mosquitoes). Instead, there’s just this strange, heavy, and occasionally beautiful reality of being the only person responsible for your own momentum. It’s something I’ve been thinking about a lot lately—how we talk about “freedom” as if it’s a destination, when in reality, it’s more like a landscape you have to learn how to navigate without a map.
The Myth of the Permanent Vacation
When I first told people I was going out on my own, the reaction was almost universal. “Oh, you’re so lucky! You can sleep in every day! You can work from the beach!” I smiled and nodded, mostly because I believed it too. I had this vision of myself as a relaxed, creative soul who would wake up naturally with the sun, sip lemon water, and then produce brilliant work in two-hour bursts before spending the afternoon at a museum.
The reality? I have never worked harder in my life. And not always on the stuff I love. When you are the boss, you are also the IT department, the janitor, the accounts receivable clerk, and the person who has to decide if the printer is actually broken or just being spiteful. The “freedom” to work whenever you want very quickly turns into the “obligation” to work all the time because if you aren’t doing it, nobody is. There’s no ghost in the machine making sure the bills get paid or the emails get answered while you’re out taking that “freedom” hike.
It’s a weird psychological shift. You spend your whole life being told when to show up, when to eat, and when to go home. When those walls are suddenly removed, it’s not always a relief. For some of us, it’s actually kind of terrifying. You realize that your productivity is entirely dependent on your own internal engine, and some days, that engine just doesn’t want to turn over.
The Heavy Weight of the Quiet
I didn’t realize how much I relied on the ambient noise of other people until it was gone. In an office, there’s a rhythm. The hum of the air conditioning, the distant clatter of the elevator, the low murmur of gossip by the coffee machine. Even if you hate it, that noise provides a certain structural integrity to your day. It tells you that you are part of something. It tells you that it is “work time.”
When you work for yourself, the silence can be deafening. It’s just you and your thoughts, and sometimes those thoughts aren’t very nice. They’re the ones that ask, “Is this actually a good idea?” or “Are people going to realize you’re just winging it?” Without a colleague to bounce an idea off of—or even just to complain about the weather with—the days can start to feel a bit like you’re drifting in space. You have to learn to be your own company, which is a lot harder than it sounds. You have to learn how to talk to yourself in a way that is encouraging but also firm, like a coach who actually likes you but won’t let you slack off.
The Unexpected Loss of the “Watercooler”
I used to roll my eyes at office culture. The “mandatory fun” and the awkward holiday parties. But I’ll be honest: I miss the small talk. I miss knowing that Sarah in marketing just got a new puppy or that the guy in the cubicle next to me has a weird obsession with sourdough. Those tiny, inconsequential human interactions are the grease that keeps the gears of a workday turning. Now, my “watercooler” is a quick scroll through social media, which—let’s be honest—usually just leaves me feeling annoyed or inadequate. Finding a way to replace that human connection without the structure of a workplace is one of the biggest challenges I’ve faced. It requires effort. You have to actually schedule “being a human” into your calendar.
The Feast, the Famine, and the Fridge
Let’s talk about money, because ignoring it feels dishonest. One of the most stressful parts of this life is the unpredictability. One month you feel like a mogul, and the next you’re checking the couch cushions for change. It’s the “Feast and Famine” cycle, and it can do a number on your nervous system. You learn very quickly that a “yes” on a project doesn’t mean the money is in your bank account. It means it might be there in thirty, sixty, or ninety days, depending on how the universe (and the client’s accounting department) feels.
And then there’s the fridge. Oh, the fridge. When your office is ten feet away from your kitchen, every minor frustration becomes a reason to see if there’s any cheese left. Bored? Check the fridge. Stuck on a sentence? Check the fridge. Avoiding a difficult phone call? Maybe there’s a yogurt in there with my name on it. Developing “refrigerator discipline” is a skill they don’t teach you in business school, but it’s probably more important than learning how to use a spreadsheet. You have to learn to recognize when you’re actually hungry and when you’re just looking for a hit of dopamine to distract you from the fact that you’re stuck.
Setting Boundaries with Your Own Brain
When you don’t “go” to work, you never really “leave” work. This is the trap. Since I work from the same table where I eat my dinner, the line between “Professional Me” and “Human Me” has become incredibly blurry. I’ll be watching a movie at 9 PM and suddenly think of a better way to phrase a proposal, and before I know it, I’m back on my laptop. It feels productive in the moment, but it’s actually a recipe for burnout.
I’ve had to get really strict with myself. I have to physically close the laptop and put it in a drawer. I have to tell myself, “The workday is over,” even if I didn’t finish everything on my list. Because the list is never finished. That’s the secret. The list is an infinite scroll. If you wait until you’re “done” to stop working, you will literally never stop. You have to give yourself permission to be a person who doesn’t produce things for a few hours every night.
- Create a “Closing” Ritual: It sounds silly, but I started lightling a specific candle when I finish work. When the candle is out, I’m just a guy in a house, not a business owner.
- Get Out of the House: Even if it’s just a ten-minute walk to the corner and back. You need to remind your brain that the world is bigger than your screen.
- Stop Working in Bed: Seriously. Just don’t do it. Your sleep will thank you, and your brain needs to know that the bedroom is a “no-stress zone.”
Finding the Rhythm That Actually Works
Despite the crumbs and the silence and the weird relationship with my refrigerator, I wouldn’t trade this for anything. There is a specific kind of satisfaction that comes from building something with your own hands (and brain). When a project goes well, you know it’s because of your effort. When you decide to take a random Tuesday afternoon to go to the movies because the weather is nice, you don’t have to ask for permission. You just go.
But that freedom has a price, and that price is discipline. It’s not the discipline of a drill sergeant; it’s the discipline of a gardener. You have to show up every day, even when nothing is blooming. You have to pull the weeds of self-doubt. You have to water the projects that show promise and have the courage to prune the ones that aren’t working anymore. It’s a slow, iterative process of learning who you are when nobody is watching.
I think we’ve been sold a version of “working for yourself” that is all about the “hustle” or the “exit strategy.” But for me, it’s just about the life. It’s about being able to look at my day and see my own fingerprints on it. It’s messy, and it’s inconsistent, and sometimes it’s lonely. But it’s also mine.
A Final Thought for the Curious
If you’re sitting at a desk right now, staring at a clock and wondering if you should make the leap, my advice is simple: Don’t do it because you want to work less. Do it because you want to care more. Do it because you want the problems you solve to be your own problems. It’s not easier—in many ways, it’s much harder—but the rewards are measured in something better than a paycheck. They’re measured in the quiet realization that you are capable of standing on your own two feet, even if those feet are currently wearing mismatched socks.
Anyway, I think it’s time I dealt with that crumb. And then, maybe, I’ll finally get around to that vacuuming. Or maybe I’ll just write one more page. After all, I’m the boss, and the boss says it’s okay to stay in these pajamas for another hour.