Work Habits for the Bossless
How to work when you don’t have a boss
Fish allegedly don’t notice water. Elite athletes don’t know the physics formulas that govern how their bodies achieve excellence. And those of us in independent work forget that the tools that take us through the day aren’t obvious to others flirting with the lifestyle of the bossless.
Everybody knows what work is. You show up on time, do the things your boss asks you for, go home when your shift is over and/or your workload is done—and get a paycheck at the end of the week or whatever. There’s no how or where or when involved, since the boss got that covered, and the HR-negotiated contract states the job description and the hours and compensation package.
Boring.
What we don’t readily know is what independent work is. What do you do? What’s work like? How do you do it? And who decides?
I heard a friend asking for advice for how to live bossless; he found it hard to structure productive life as self-employed person and was wondering if there was a secret trick. Some shit the insiders did, maybe, that would crack the code for successfully working bossless?
He’s not the only one. In recent years, plenty of remote workers, nomads, freelancers, gig workers and other have asked themselves similar questions. And 2020 forward, millions joined their rank: as so often, Cuckoo-19 accelerated that which was already underway. The 2020s will be the decade of the bossless, the independents, the coffee shops and co-working spaces.
Short answer: No, there’s no secret trick. You just gotta work hard for it—like everything that’s worth doing (…but beware the converse: Not everything hard is worth doing!)
There is, however, some scaffolding that can help push you along.
Then again, what do I know? I’m no expert. I don’t know what’s good and what isn’t, what works and what doesn’t. I’ve just been doing this for years—with more or less success—and every single year is some 300+ days of work; and every day is some form of work-life routine. I’m clearly doing something but I can’t promise that it’ll work for you.
Since you don’t have a boss who tells you when to show up and when you can leave for the day, you have to make those decisions yourself. A common trap for the self-employed is to work all hours of the day, all the time—regularly putting in 60–80 hour weeks for earnings that probably don’t match up with what employees pulling those sorts of numbers usually earn.
But there’s a quality-of-life aspect to consider, and part of the reason you opt out from employment is that you you prefer doing the kind of work you’re currently doing, in your ways and in your own time rather than the kind of work your boss wants you to do, in a sticky and busy office.
Still, limits are important scaffolding devices. When do you sleep? When do you eat? At what point do you close up shop and go hang out with the dog or the kids?
Some people like a structure that imitates an employment: sit at your desk between this and that hour and do work. I tend to follow flows: work lots when it feels easy and rewarding; get outside when it’s hard and nothing seems to go your way.
I’m well aware that there are days when I do 2 hours of work—or 6 hours. And then there are days when I intend to do 10 hours but can’t resist the winter light on the mountains and beeline for that glory rather than the income-generating prison I leave behind.
Some days are like that, and I usually feel a little bit bad about it afterwards. If I worked harder, I’d earn more money… I’d be able to do this and that thing. But I find that it’s also totally worth it. This is the play I made, the trade-off I want: the ability to own my time, to work when there’s a snowstorm on or when I’m in the mood, run to the hills when they’re pretty and my body wants it.
It takes a certain personality type for that to work. If you’re not disciplined, or there’s nothing pulling you back to the desk, that kind of liberties can quickly go south — all play, no work. Not good.
There are some tried and tested tricks to ease the transition from commute-office-boss work to independent work: echo that which you are used to. Get up obnoxiously early, shower and shave and get dressed the way you would have for a job—and you actually go someplace. Leave the house. Join a coworking space, go to a coffee shop.
I have even known some nomads who legit turned this sane routine into a farce: they left the house fully dressed, just to come right back in. It sound nuts, but it’s echoing the psychological value of the commute—of getting into the right mindset for work, of leaving home stuff at home and actually going to work.
Life is what we do, and doing certain things signals to your mind and your body that it’s time.
Another common idea is to fit work to your life. Screw schedules and what the watch tells you. If you wanna sleep all morning and work all night, do that. If you need a mid-day break to go pick up your daughter or nephew from wherever (or your family needs you to run some daily errands), plan your day around those commitments.
It sounds strange to plan your day around not having a fixed plan but it’s anything but. Being bossless is about owning your time—so own it. Instead of scheduling work between 8 and 18, with a break for lunch and that daily 1-hour worthless meeting with department X (oh, and that call at 2 p.m.) you schedule your life around the things that matter.
I remember early in the Cuckoo-demic some columnist for the Financial Times complained that their colleague had declined the time for a proposed Zoom meeting, saying that it interfered with their yoga class. “Yoga class?!” interrupted the columnist whose idea of work was about two decades out of touch. “Your priority has to be work; down-dogs can wait”.
No, no they can’t. The life of the bossless is precisely that: *inverting* the ordering of things, back to the way they should be—letting the things you care for most decide the schedule, and fill in the rest of your hours with work.
- Got nothing on that day? Great, then we pound out work for as long as our body allows us—all day, every day.
- Doctor’s appointment at 11 a.m.? OK, decide the day before if you want to work for a few hours before then, or begin the work day after—and approach the day accordingly.
- Yoga in the morning? Alright, have those pesky Zoom meetings after.
When I work American hours for some client, I usually make a mini-timezone adjustment: stay up late the night before and wake up a little later than usual—practically speaking shifting the work routine to a few hours later in the day. Good or bad, I don’t know, but it seems to work alright for me.
Listen to your body
A big no-no is the fight to keep working since it’s “only 4 p.m.” and you somehow gotta keep going. Nope.
As a self-employed person you’re not paid for your time but for your work, and more importantly its quality. That means you better deliver good-quality work—something that rarely gets produced when you’re dragging your sorry ass through another half-hour or so just because it’s only 4 p.m.
When I flirted with an academic career years ago—a lifestyle that shares some features with the bossless lifestyle—a professor of mine gave a piece of advice that stuck with me. Nobody cares if you run your dataset at 3 p.m. in the office or at 3 a.m. at your kitchen table. That’s exactly right.
And because symmetry rules the opposite also holds. Don’t ever stop working in the middle of a flow because, I dunno, it’s too late to work or somebody wants you to be somewhere. You can allow yourself to not work when you’re feeling off and low only by riding the workflow wave when everything is good.
If you’re on a roll, if you’re doing good work and you feel energetic—don’t stop. It’s 1 in the morning and you should go to bed? Screw it. Your friends are at a bar waiting for you? Pff. I mean, I’m not generally recommending that you abandon your social life but if the work you’re doing is high-quality enough and your friends will forgive you—screw ’em. They’ll understand.
Workout routines: another thing that the out-of-touch FT columnist doesn’t grasp is that physically challenging the body—taking time for your practice, hit the gym, go for a run—isn’t “losing out” on potential work time. That’s old-school, linear thinking. Physical exercises are negative time sinks: the time you invest in a hike, a class, a jog comes back to you in the form of more hours in the zone, a calmer and more energised mind, a body more ready to do what you need it to do. Get your ass to yoga class, etc.
Here’s an awkward confession: some of these advice I’m not too good at following. Certainly not in the dead of very dark winter when staying under the blanket is warm and beckoning; when the pitch black sky outside the window deters me and the howling wind tells me I should just stay in bed, postpone today for tomorrow.
Still, though my body is very sluggish in the mornings, my brain is unusually sharp and quiet—so I drag myself to the desk and get going. Often I can get a few hours of good work in before my body has even realised what’s going on or wants food.
Similarly, my brain is very tired in the afternoon but my body is energetic and ready to go. So I usually go for a walk or a mountain hike in the early afternoon.
I hate getting interrupted. So every notification is off and phone is on silent and on the other side of the room. The thing I most hate about office environments, and what I believe we completely botched in the way we organise our workplaces (white-collar, at least), is to shove people in each other’s way—aka an office. Always people moving around; always somebody wanting something minor; always someone greeting you good evening, good morning or asking you to lunch. Always some meeting or someone’s birthday or whatever interrupting the boredom of being in a place you don’t want to be. How is anybody supposed to get anything valuable done when all you’ve done is make sure everyone is interrupted all the time?
It certainly is an office irony that the best work anyone does in that type of environment is done before or after hours. That tells you something about the uselessness of an office with other people in it. Just leave, already.
But I digress.
Here’s a hard rule I never ever break: never, under any circumstances, do I work in the sofa. Sofa is for social, relax, chill, Netflix-mode or anything else—never ever for work. If I’m tucked away nicely, drinking tea and watching a show or whatever and I find that I’m needed for some urgent work (ugh @ American hours…), I get up and move over to the desk. Sofa is off-limits for productive endeavours. Always.
What the office environment does, and what physically going someplace for work actually achieves, is to mentally and spatially separate work from home, production from consumption, value-creation from relaxation.
As a bossless, office-less worker you need that same separation. Make it clear, to yourself and those around you, when it’s time for work and when it’s time for play. Put your phone away; wear certain clothes; play certain music; sit in a certain chair etc. Whatever works.
The bossless life is tricky and probably takes a certain personality type for it to work. You need a drive to work, an urge even, over and above the disciplining that a budget constraint imposes. If you’re not disciplined, or there’s nothing pulling you back to the desk beyond money, the kind of liberties I’ve outlined above can derail you. No good.
Setting up rules like those I’ve described can instead set you free. Very good.
