The past few months I’ve been a Lean Startup class instructor with ILT Academy. I’ve absolutely loved it - I teach class a couple nights a week, help students (founders) refine their business plans and pitch decks, and work through their big ideas. It’s awesome.

Part of the gig is assigning and grading homework — mainly to hold founders accountable for getting stuff done and to give them feedback on it. Overall it’s more of a formality, maybe entails a few hours of work max throughout the entire program.

And it’s funny, because despite the relatively low stakes (it’s an elective course) and minimal effort required, some students get pretty worked up and overwhelmed by it. I frequently get slack messages at 11:50pm from founders in a panic over their homework due at midnight.

The main culprit for feeling overwhelmed, of course, must be procrastination.

Everyone deals with it. I’m the pot calling the kettle black here. And there are many valid reasons to feel overwhelmed - sometimes life just hits you faster than expected. But now that I’m on the other side of the fence as an instructor my perspective has been ever-so-slightly broadened.

In reality procrastination is kind of a ridiculous thing.

Really, it’s not inherently unproductive — in fact procrastination can actually be extremely productive when used correctly. What is unproductive (and perhaps even destructive) about procrastination is that it makes small things feel much much bigger than they really are.

Countless times I’ve put off some tiny thing like cleaning my apartment for a few days, and by the time I get around to doing it, it feels like its 100x dirtier than it was before. Then of course eventually I actually clean it, and it’s about 80% less effort than I’d dreadfully assumed it to be. This type of mental balloon-anmial act is not helpful for anyone.

The good news, my friend, is that all it takes to overcome procrastination and overwhelm is a little… ~change in perspective~.

The Cure to Overwhelm / Procrastination

Recently I’ve started a little collection of anecdotal antidotes and tips to curing overwhelm. I will share them with you here:

1) Procrastination = Your Mind Saying It’s Not Important Yet

First, I’d argue that most procrastination-induced overwhelm is brought on when you feel like you are supposed to be doing something that you haven’t, or feel like you should be scheduling time for something that you don’t fully understand the scope of.

I think the remedy is to simply lean in to it. I remember reading some quote on Twitter about some-mega CEO (maybe Elon) who said that they don’t really believe in proscrastination — if you are putting something off, it’s probably for good reason. Your mind is telling you that you it’s probably not actually the top priority yet, and until it becomes the top priority, there’s not much use worrying about it yet.

Simply do the thing at the moment you need to do it. And until that moment, forget about it. As Gandalf famously says in the Lord of the Rings: “A wizard is never late. Nor is he early. He arrives precisely when he means to”. Just be the freakin’ wizard you know you are.

2) Practice “Structured” Procrastination, like Marc Andreessen

The idea above is easier said than done. So sometimes I lean on an idea from Marc Andreessen’s guide to personal productivity. He basically says:

• Never fight the tendency to procrastinate-instead, you should use it to your advantage in order to get other things done

• While you're procrastinating, just do lots of other stuff instead

I find this really useful. Because often times procrastinating a big task is when I get my best work done on smaller tasks. It’s when I respond to emails or do my taxes or write blog posts like this. All of that is ‘productive’ stuff of course, just with a different goal in mind from the big scary goal.

Channel it baby.

3) Just Say “I’ll Only Do A Tiny Bit of it”, like Paul Graham

When the time comes to actually do the big scary thing you have (rightfully) been putting off, then I’ve found another anecdote from the great Paul Graham helpful.

In his famous blog post Good and Bad Procrastination from 2006 he says:

And this is inevitably true. Most of the time the hardest part is simply tricking your mind into sitting down and starting the thing. It’s overwhelming to think of doing everything, especially if you are coming from a different, dissonant task. Context switching is a difficult thing for anyone.

But if you just sit down and read the first little bit or just open the document, more often than not you’ll make good progress. I tell myself the same thing about working out… “all I have to do is walk down to the gym. If I leave after 5 min that’s perfectly acceptable” and after that first 5min most of the time I have enough juice to stay for 30.

4) When all else fails, take things “Bird by Bird”

Finally, if you get to the red zone of scary procrastination, you’ve depleted the tools and tricks above, and it really is 5-min to the midnight hour, there is still hope.

Whenever I reach a moment like this, I am reminded of one of my favorite quotes from Anne Lamott in her book Bird by Bird:

The final key when your back is up against the wall is to simply take things one. step. at. a. time. It’s a bit refreshing to think of it that way.

Anyways, I know these little tricks have helped me — I hope they’ll help at least one person reading this. And of course if you’ve come up with your own little hacks for conquering procrastination, I’d love to hear them :-)

Peace,
Ramsey