How To Set Deadlines That Feel Real

You’re your own boss. And your boss is kind of a dick.

It’s simple.

If you’re like me, currently working from home, likely unemployed, attempting some kind of work on a personal project or hobby, you, literally, have your dream job.

Didn’t you always want to set your own hours? Work on something you cared about? Work from home? Sure, you might have preferred the ambiance of a coffee shop, but the lucky shouldn’t be picky.

You’re living the dream. The guy in the kitchen makes coffee exactly how you like it. Your office is exceedingly pet-friendly. Naps are allowed, and maybe even encouraged.

Your situation, in some respects, is extraordinarily easy.

I’ve told myself things like this the past few weeks and months in an attempted mix of self-shame and self-motivation. As in, “you ungrateful loser, how much easier could you have it? And you’re still procrastinating? Still unproductive?”

(If you’re lucky enough to be employed right now, and are still looking to work on your passion, congratulations: you now have two jobs. You’re working a night shift. Good on you for burning the midnight oil to make your dreams come true. This all still applies.)

Since this all started, I’ve cleaned my entire house to the molecule, twice. I’ve started to learn to cook — not because I wanted to, but only because it was satisfyingly very much Not Work. I’ve done three loads of laundry just while writing this article.

Even more embarrassing is performing my weekly ritual of googling “how many days since March 13th, 2020” and seeing the number tick up over 100, and 120, and 150, and continue climbing. It very well may be 365 (or depressingly well past it) by the end of all of this. And it’s rather upsetting to see that number of days — full days — where, by definition, there was nothing to do except work, and comparing it to my output. Or lack thereof.

Quarantine has exposed a lot of weaknesses in our society, in our systems, and in ourselves. And a lot of us, in a lot of ways, truly are out of excuses.

This is the real truth: your days are your own. You have the time to learn how to make bread. You have the time, really, to do anything. You always did, but now it’s nearly non-negotiable.

So why, after five and a half months, has there not been a flood of new Great American Novels clogging Amazon’s self-published section? You may have noticed the boom of new podcasts and TikTok accounts popping up in late March — why have so many of them gone silent?

Because working diligently and consistently towards our dreams, especially if they’re relative longshots, is one the hardest things any of us ever do — if we do it at all.

And the power of self needed to believe in ourselves enough to try, and maintain the discipline to keep doing it over and over again, even when it’s hard, even when it’s embarrassing? Who could do it?

Lots of people do. They’re called professionals.

I think that, while distractions and busy schedules and “lives” were always helpful excuses, they weren’t the real thing keeping millions from getting work done. It’s more of a subtle, complex mindset problem — a bundle of intangibles that no one ever taught you how to keep in order.

There’s just a different energy at work. Often you’ll have some kind of boss figure on your back, poking you to remind you to stay on schedule. You likely have co-workers to compete with, or support, or worry about somehow disappointing. You got in some kind of vehicle to go there. You wear clothes that are more “presentable,” or whatever. There’s just a different emphasis placed on the things you do in that building.

It’s why you hear people talk about dressing up in real actual work-type clothes before walking into their home office, only using their home office exclusively to work, physically leaving the room take a break, leaving it vacant on weekends— they’re all tricks on the mind, that, because we’re all dummies with monkey brains, often really work.

If you can recreate that work environment — whatever that means for you, whatever that requires — I’d wager you’re halfway there.

If you’ve ever read a productivity article on Medium or watched a Matt D’Avella video on YouTube, you probably know these things. And we can get pretty far in designing our workspace and our headspace into something primed to mimic real work.

But there’s one final flaw in our intrepid self-designed Personal Productivity System.

We still don’t have a reliable system for finishing work and turning it in on time. Procrastination is too strong. Pressure is too low.

Without the structures of work and other people relying on you, there is no necessary timeline on any project. No sprints. No target projections to hit. There’s no reason to turn in work on time for any reason other than “you want to,” and plain old willpower. And we know how unreliable those two things can be.

Previously, the only ways we had thought of to recreate real, pressure-cooker deadlines for yourself were to install honor systems. You’ve probably heard about creating bets where you have to pay your friends money after missing a deadline, or where your friends are allowed to set your Facebook status to something “embarrassing” like “i should have finished my essay on time cause now i’ve been hAcKeD!!!”

Those consequences may have seemed compelling at first, but they turned out to be ultimately rather dull. In my experience, even the fear of a five-dollar Venmo charge can be washed over by the apathy that swallows up all my other feelings of motivation during The Big Procrastination.

So once you know you’re willing to give up actual hard money to procrastinate, what’s left? What else could reasonably recreate the subtle dread and the lump in the stomach and the restless leg you get nine hours out from a deadline?

The fear of disappointing someone you respect.

Like yourself.

The person who hired you for this job, this job where you are your own boss and you do whatever you want, liked you then, and trusts you now. They’re a lot like you, actually. Kinda look like you too — but you don’t mention that.

This person read your resume and cover letter, and it felt like they saw in you the things that not everyone else saw. They even appreciated, or at least pretended to appreciate, all the dumb filler stuff everyone else skips over.

“Wow, you did that summer job three whole summers in a row?”
“Wow, that social media account you managed had no followers and now it has 90?”
“You’re a great multi-tasker and a team player?”

Of course, you fabricated and exaggerated a bit on your resume to in order to get this job, but it was only stuff you knew you could stretch to learn, or pick up quick on the job if you needed. (Photoshop can’t be that hard, right?)

Your boss kinda knew that. It’s always easy to tell. But that’s not why they gave you this job. They gave you this chance because they saw something in you.

So you got lucky. You got your dream job. Thanks to the charity of this person.

And like we’ve established, it’s a pretty plum gig. Your boss seems reasonably laidback. He’s lenient about things that most bosses aren’t lenient about.

Bosses usually hate people coming in late or leaving early, because it denotes a lack of respect for them or the job. But your boss knows just as well as you that you have a stressful life, and that sleep is the number one priority for someone’s health, and while your now-forty-second commute doesn’t really cut it as an excuse in the same way it used to, she knows if you’re sleeping in or running a couple steps behind today, it’s for a good reason.

You can watch YouTube for half the day if that’s how you work. You can take one of those super-encouraged workplace naps with your workplace-friendly dog right before lunch, and then again right after lunch, if that’s how you work. Blow off weekends, sure. Blow off Fridays while you’re at it. Again, that’s not what your boss cares about.

But your boss also knows you. He knows what he can expect of you on the important stuff. He knows your capacity, and how much you can achieve if you push yourself. She doesn’t expect you to push yourself to the max every day, but she would love to see you improve towards that point consistently, if not daily.

She knows how many pages you can write a week, or lines of code you can compile, or emails and outreach numbers you can hit, on a base week. He’s observed you for long enough, in various stages of productivity, to know how hard to push you.

If you’re struggling for a week, for legitimate reasons, the last person to be a pill about it is your boss. But at some point, your boss is going to know when you’re not pulling your weight.

And your boss can be kind of a dick.

Your boss has this unique ability to know when you’re absolutely full of it. And he’ll call you out on it.

“Oh, you’re feeling a little tired? All you did yesterday was sit on the couch.”
“You always do this. You always over-promise and under-deliver. If you deliver at all. Why don’t you deliver something, anything, for once?”

They will make you feel so terrible if you truly disappoint them. They’ll call you into their office and yell super mean, super specific things at you.

“You should just give up and try to get a desk job somewhere.”
“Ashley from sophomore year was right to break up with you.”
“You ungrateful loser, how much easier could you have it? And you’re still procrastinating? Still unproductive?”

They’ll make you feel worse than if you had failed at something you don’t care about, or for people whose opinions you don’t care about. This one stings, because you do care. And they know just where to hit you.

But really, your boss is only hard on you because he thinks it’s important to be. And at the end of the day, she’s there for one major reason: to tell you what you really needed to hear — the core of our issue with self-imposed deadlines:

You have to engage with the seriousness of your task.

This is your dream for a reason. You’re scared of it for a reason. You want to devote your life to it for a reason. And you’re procrastinating for a reason.

And taking all of these things seriously means putting things on real timetables. And it means sticking to those schedules. Having discipline. It’s within you and it’s been there the whole time — you just have to activate it.

Try it. Set a deadline for tomorrow, or sometime this week, at 9am. (I like to give myself this option so I technically have access to the all-nighter if I need it — freedom to putter around and end up getting it done halfway calmly at 2 or 3am, instead of actually bursting a real blood vessel at 11:58 — but you do you. Your boss gets it either way.) You can’t change the deadline once you set it.

If you care as much as you claim to, and take it seriously as you know you should, this deadline can feel as intense as your senior thesis in college.

I don’t even care if the work is good. Because you care both about hitting this deadline and not disappointing the boss, it will probably be fine. You can edit it and improve it later if you need to.

If that goes well enough times, make it a weekly thing. This will be a bit easier if you’re working on something public that people see, like a blog or podcast. You’ll start to be slavishly dedicated to publishing consistently, no matter what gets in your way. If you’ve set your output at something you know is manageable, it shouldn’t be a problem.

And that’s it. All your boss expects of you is to consistently work, and work towards your potential. Show progress. Show effort. And finish. That’s all they want. You can give that to them, right?

So: you’re your own boss. There’s a lot that comes with that, both helpful and challenging. But more than anything, it brings a responsibility to be the master of your own domain. To remain self-aware — of your output, your growth, your effort, and how they can all be improved.

This requires a lot of thought and focus and discipline to pull off. But it’s also painfully simple: just don’t disappoint yourself. And you know exactly what disappointing yourself looks like. Set your goal, know it’s possible, and work in whatever way you need to to get something done, and make it happen.

You owe it to yourself. In at least one time or another in your life, you believed in yourself. Remember that when “your boss” is asking you to stay late tonight to hit this deadline.

Turn in work. On time.

Note: This was not written from a place of “I figured it out and so can you.” I basically wrote this at myself. I’m gonna try, right now, to get some stuff done. Hope you join me. Let’s go to work. Traffic isn’t too bad today.