The Uncomfortable 20

I did a podcast forever ago on time management that’s gotten a bunch of listens over the years. In it, I talk about “sand” and “stone” tasks — how it’s important to prioritize deep, proactive work and create sacred 3-hour blocks for it (stones), and fill in the rest of your time with reactive work (sand).

I still agree with it in theory — big chunks of time are ideal.

But, I'm realizing that for most founders, 3-hour blocks are rare (or wholly unrealistic, especially if you've got kids).

Worse, the episode implies that if you've only got small amounts of time, you should use them for sand tasks and save the stone tasks for those illusive bigger blocks of time (if they ever happen).

The whole point of Tacklebox is to be a blueprint for regular people to start exceptional businesses and if you don't have a 3-hour uninterrupted block each day, we've got to find a better way.

Which is where the Uncomfortable 20 comes in.

A few founders in the program pioneered this approach over the past year, branding the realistic 20-minute blocks of time most people will have to work on their startups throughout the day and creating a framework around them. I love the approach and I use it.

Let's dive in:

The Uncomfortable 20

The idea with the Uncomfortable 20 is to use the short bursts of time real people get throughout the day as a feature, not a bug. Twenty minutes is short enough that you can sprint on something incredibly uncomfortable, knowing it'll be over soon. And it replaces what people usually do with those shorter windows of time — reactive stuff like clean out email.

Here's how it works.

You start with an Avoidance List — a list of things you’re currently avoiding because it seems daunting or intimidating or uncomfortable. You should make a new list at the start of each Uncomfortable 20 — it shouldn't take more than a minute.

Next, pick the thing from that list that creates the most amount of anxiety. That’ll be our sole focus for this Uncomfortable 20.

Now, sprint. Take a minute or two to think about how you can make the biggest dent in this problem before your twenty minutes are up. It's a race against the clock — cover as much ground as you can.

Usually, starting with, "Why does this make me anxious?" leads you to the exact place you'll want to start. Knock the painful thing out immediately so it's done with.

During the last minute of your sprint, write a note to your future self on how, exactly, to continue working on this problem during your next Uncomfortable 20.

Here’s an example:

During a Working Wednesday session last week, I had a founder create an Avoidance List. The thing that made them most uncomfortable on the list was an update newsletter — the first iteration of an email to friends, family, potential investors and anyone else interested in their project going over their progress. They absolutely knew they had to do it but had been dragging their feet for weeks.

After the call, they did an Uncomfortable 20 on it where they found a number of examples they could use as a guide, then wrote a draft of the email. Their note at the end of the twenty minutes reminded them to pull together email addresses and add a few images to the newsletter and then send during the next Uncomfortable 20.

Why it works so well

The Uncomfortable 20 works extraordinarily well for two reasons:

1. The hardest part is always starting. The 20-minute time box makes it far easier — there's a clear end to the “pain.”

2. The stuff that separates you is the stuff you reflexively don’t want to do. Everyone else working on similar problems will push away from the same stuff that makes you uncomfortable — if you do that stuff, you'll end up places they won't.

There’s a founder who does two Uncomfortable 20s each day — before work and during lunch — and that's the only time they work on their startup. They literally don’t touch their idea any other time. Over the past three months they’ve made as much progress as founders working 5x as many hours.

I still think Stones (3hr+ blocks of time) are incredibly powerful. But, if you don't have time for them, lean into Uncomfortable 20s. I've been blown away with how well they work.

The Uncomfortable 20 Process

1. Create your Avoidance List

2. Pick the highest-anxiety item

3. Sprint for 20 minutes

4. Leave yourself a continuation note