I'm Making an App to Help Procrastinators, as a Procrastinator

Confession time: I’m the queen of procrastinators.

I’ve turned the act of putting things off into an art form. You might think that’s not something to brag about — and you’d be right. But it does give me a certain expertise when it comes to understanding the procrastinator’s mind.

My struggles with productivity are the stuff of legends. In college, my study ‘technique’ was a blend of fervent hope and caffeine-fueled all-nighters. I’ve tried every trick in the book to get my focus on track. Rising with the birds at 5 a.m. only turned me into a sleep-deprived grouch. Meditation led to some impressive mental gymnastics, but calmness and focus? Not so much. And bullet journaling felt like I needed a Ph.D. in stationery.

But through this haze of half-starts and near-misses, a few strategies did shine through:

Pomodoro method

Pomodoro is as simple as a door handle: you set a timer for 25 minutes, focus on deep work, and when the timer rings — take a 5-minute break.

I’ve discovered there are several reasons why Pomodoro got so insanely popular and why it actually works:

1. 25 minutes is never as scary as your never-ending to-do list.

   25 minutes are manageable.

   You know you can do 25 minutes.

   
   

2. Something called “psychological priming”.

   
   

   Humans are a little simpler creatures than we like to think of ourselves, which is good news. Because you can actually teach yourself to get triggered to work, like Pavlov’s dog, setting a timer can be one of the cues your body uses to get into hard focus mode.

   
   

3. Time awareness.

   
   

   One of the things you’ll often hear from chronic procrastinators is, “I’ve been putting this thing off for weeks, and it actually took me 15 minutes to do it”. Once you learn how much you can actually accomplish in just 25 minutes of focused work, every next Pomodoro session will feel even easier.

Planning for failure

No matter how motivated I am, there are still times I will experience extremely strong resistance to doing things I know I have to do but don’t want to do.

In those cases, you’ll see me straying off to check email, getting into an argument on Twitter, or staring at my phone.

But knowing yourself and what you’ll do when you’re about to give up can actually be helpful: it’ll make it easier for you to cut off those back exits.

The easiest thing you can do is set up obstacles in the way of doing things you don’t want to be doing:

• Use a website blocker so you won’t be able to access funny cat videos while you’re working.
• turn off your phone and quit all the messaging apps so you won’t be tempted to work on your co-workers’ problems when you should be solving your own.
• log out of your inbox, so it’s not too easy for you to get lost in those back-and-forths

The possibilities are endless, but the bottom line is you need a safety net to fall onto, and it shouldn’t be too easy for you to get distracted and lose focus.

Reward vs. Punishment systems

Humans are notoriously bad at delayed gratification.

If you’re working on something that does not bring immediate results, a sense of accomplishment, or joy, you have to know: long-term goals simply mean nothing to your brain in the moment.

And that’s why you’re struggling so much: working without an anticipation of a reward that’s coming soon is hard and unpleasant; no one actually enjoys that, and no one is good at it.

The good news is that you can build yourself an artificial system of rewards and “punishments” that will reinforce your brain’s perception of the things that bring you positive results and those that hurt you. (Important thing: both rewards and punishments have to come quickly.)

If you fight delayed gratification with a slightly less delayed gratification, it won’t work.

The reward/punishment systems that I’ve found to be working best for me were often based on monetary incentives.

Positive reinforcements would often include celebratory purchases of things that aren’t necessary but wanted.

They don’t have to be big or expensive.

Sometimes, I go for a fancy dessert or a new vinyl record after checking off everything I planned for the day. Other times, I’d celebrate launching a project with a new Lego set (which is a passion of mine). Anything that can give you that extra boost at the moment and that feels easy to reach will do.

The second tactic is loss aversion.

Or, in simpler terms, paying in case of failing to do what you wanted to do. Loss aversion also usually works best because, in most cases, it requires some sort of public commitment. E.g., make a bet with a friend that you’ll stick to a gym routine or that you’ll launch something by an agreed deadline. If you’re not too keen on bets or making your friends richer, promise to donate to a charity if you fail to deliver on your commitments.

Can we Eureka tomorrow?

And then, finally, it clicked.

When I was a few months into my sabbatical, licking wounds after the worst burnout I’ve had so far, I’ve been thinking about building something from scratch, something I’d know people would use. Something I could use. Because at the end of the day — I’m a very regular person with very common problems.

But I’m also a try-hard, so the idea that I could actually bring something new to the world wasn’t that outrageous.

And that’s how I realized the things I’ve implemented manually in my own life can actually be packed into a simple product. I wanted to start with something that would be easy to build in a relatively short time and budget so we could get a proof of concept and build upon that foundation.

That’s how I came up with the concept of Pomodollar — a productivity Chrome extension that combines my best productivity tactics:

Pomodoro timer — for easier dives into deep work Website blocker — to make getting distracted much harder and put some obstacles on your way Loss aversion — if you decide to get distracted, you still can, but it’s not going to be free.

The way it’s going to work is simple:

You start a work session, and Pomodollar will block all the “naughty” websites until the work session is over. If you still want to go ahead and watch a cat video instead of working, you’ll have to either end the session earlier or add the website to a whitelist, but both of these actions will cost you $1.

As of now, our launch is planned for November 30.

But what I’m wondering is:

1. Will we launch on time?

   
   

   and

   
   

2. Is anyone on here willing to bet a $100 we won’t? :)

   
   

P.S. If you’re invested by now and want to see if we actually manage to deliver on time, subscribe to our beta waitlist here.

Also published here.