How To Set Deadlines That Feel Real

This one may feel like a bit of a higher concept, but just go with me here. This is a mindset change that helped me reframe my perspective with my own work, and hopefully it will do the same for you.

Luckily, it’s actually pretty simple.

If you’re like me, and have the freedom to devote time to work on a personal project or hobby during the day, you have your dream job.

It might be a part-time job right now. You might be splitting time with another obligations. You might have to go into an office, or attend video calls with other people, for eight-plus hours a day. That’s not ideal, but it’s okay—we all start somewhere. Think about those times when you’re working on your personal projects. You’re probably at home, or in another environment where you’re comfortable. Maybe sometimes you dedicate an entire day or two on the weekend to this work. You’re in an environment where, for the hours you have at your disposal, you set your own schedule. You create the ambiance. In those moments, you’re living the dream. Your “office” seems perfectly suited to you. The guy in the kitchen–you–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 fortunate.

And this is the argument I’ve levied at myself in recent weeks and months when, despite all the comforts I enjoy, I struggle to get my “dream job” work done: “How much easier could you have it? You’re still procrastinating? Still unproductive?”

During the quarantine a couple years ago, I learned the expansive and mind-blowing extent of my ability to procrastinate. Cleaning my entire house down to the tiniest speck of dust. Learning to cook, not because I wanted to, but because it was satisfyingly very much Not Work. I’ve done two loads of laundry just while writing this article, when I definitely could have stopped at one.

I realized that procrastination was still there, when – literally – there was no excuse. There was nothing to distract me or keep me busy. More than any other time in my life, I had whole blank days to fill with “whatever I wanted.”

And still, I did nothing.

Here’s the real truth: your time outside of your day job is your own. You have the time to learn how to bake bread. You have the time, really, to do anything.

But if that’s true, why has there not been a flood of new Great American Novels clogging Amazon’s self-published section? You may have noticed the glut of new podcasts and TikTok accounts popping up in March of 2020, when people were at their most bored—why have most of them gone silent?

My theory: because working diligently and consistently towards our dreams, especially if they’re relative longshots, is one the hardest things we’ll ever do—if we do it at all. And the self-confidence needed to believe in ourselves enough to try, and the dedication needed to 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?

A lot of people do. They’re called professionals.

Going pro


I believe that, while distractions and busy schedules and “lives” were always helpful excuses, they weren’t the real things keeping millions of people from getting work done. The real culprit is a subtle, complex mindset problem—a bundle of intangibles that no one ever taught us how to keep in check.
There’s a different energy at work. Often, you have an authority figure on your back, poking you, prodding you to stay on schedule. You likely have co-workers to compete with, or support, or worry about somehow disappointing. You left your comfy home to go there. You wear clothes that are “presentable,” or at least not sweatpants. There’s just a unique importance placed on the things you do in that building.

This is why you hear people talk about dressing up in real work-type clothes before stepping into their home office, using their home office exclusively to work, physically leaving the room take a break, leaving it vacant on weekends—these are 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—I’d wager you’re halfway there.
If you’ve ever read a productivity piece on Medium or watched a Matt D’Avella video on YouTube, you probably know these things. And we can get pretty far with designing our workspace and our headspace to mimic “real work”.

But there’s one fatal 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 structure of the workplace and other people relying on you, there is no necessary timeline for any project. No sprints to the finish line, no target projections to hit. There’s no reason to complete a task by a certain date 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 to re-create real, pressure-cooker deadlines for ourselves 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 away by the apathy that swallows up all my feelings of motivation during The Big Procrastination.

So once you realize you’re willing to give up cold hard cash to procrastinate, what’s left? What else could reasonably mimic the subtle dread and the knot in the stomach and the restless leg you get nine hours out from a deadline?

The fear of disappointing someone you respect.

Like yourself.

You are your own boss

Collaboration coworkers


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. They kinda look like you too, now that you think of it, 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 sees. They even appreciated, or at least pretended to appreciate, all the dumb filler everyone else skips over.

“Wow, you kept that summer job three whole summers in a row?”
“Wow, that social media account you managed had no followers and now it has 80?”
“You’re a great multi-tasker and a team player?”

Of course, you embellished the truth and exaggerated a bit 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 necessary. (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 a chance because they saw something in you. You got lucky. Thanks to the charity of this person—this person, of course, being you—you got your dream job.

And like we’ve established, it’s a pretty plum gig. Your boss seems laidback. He’s lenient about things that most bosses wouldn’t appreciate. 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 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 knows you. He knows what she can expect from you when it comes to the important stuff. She knows your capacity, and how much you can achieve if you push yourself. He doesn’t expect you to push yourself to the max every day, but he would love to see you improve consistently, if not daily. She knows how many pages you can write in a week, or lines of code you can compile, or email and outreach numbers you can hit. He’s observed you for long enough, in various stages of productivity, to know how hard to push you.

If you’re struggling 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 jerk.

Your boss has this unique ability to know when you’re absolutely full of it. And she’s not afraid to 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 can’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.”
“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. The things they say sting, because you do care. And they know just where to hit you. But truthfully, your boss is only hard on you because they think it’s important to be. And at the end of the day, they’re there for one major reason, which is to tell you what you really need to hear. They know the core of our issue with self-imposed deadlines:

You need 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 tasks on real timetables. And it means sticking to those timelines. It means cultivating discipline. It’s within you and it’s been there the whole time—you just have to help it flower.

Put it into practice

plans


Try this: 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. It gives me the freedom to putter around and end up getting it done halfway calmly at 2 or 3am, instead of bursting a 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 as 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 that goes well several times, make it a weekly thing. This will be a bit easier if you’re working on something public, like a blog or podcast. You’ll become 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?

Let RescueTime help

When you sit down to work and work seriously, the RescueTime Assistant can help get you deep into the zone where you do real, serious work. Start a Focus Session, and know you’re being helped in your journey towards healthy productivity with website and app blockers and helpful interpretations of your data.

You’re your own boss. There’s a lot that comes with that, both benefits and challenges. But more than anything, it brings the 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: don’t disappoint yourself. And you know exactly what disappointing yourself looks like. Set your goal, know it’s possible, work in whatever way allows you to get something done, and make it happen.

You owe it to yourself. Remember when you were a kid and you believed in yourself. Remember this when “your boss” is asking you to stay late tonight to hit a deadline. Turn in work. On time.

By the way, I’m right here with you. I’m gonna try, right now, to get some stuff done. I hope you join me. Let’s go to work. Traffic isn’t too bad today.

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Robin Copple

Robin Copple is a writer and editor from Los Angeles, California.

4 comments

  1. I’ve been struggling with this for ever. This was a great article with good practical tips to get things rolling better.
    I love the idea & feeling of being pro at my dream job! I see being pro is about taking something abstract (dream) & turning it into something more concrete (action).
    Thanks Robin!

    1. Yes yes yes! We all should take our dreams as seriously as anything else! And we all have the capacity to be professional, and bring that kind of focus and energy to our passion work 🙂

  2. This is such a relatable article… Felt like every word was written from my experience. And, thank you for the helpful advice – “So once you realize you’re willing to give up cold hard cash to procrastinate, what’s left? What else could reasonably mimic the subtle dread and the knot in the stomach and the restless leg you get nine hours out from a deadline?

    The fear of disappointing someone you respect.

    Like yourself.”

    1. Gosh, I can’t thank you enough for the kind words – and I’m so so happy it resonated with you! Felt like a lot of things I needed to hear myself as well, haha.

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