Jason Zimdars

July 10, 2024

Decisions are hard

Ask anyone early in their career and they'll certainly agree that, "things would be better around here if I was in charge and called all the shots". But seasoned managers know better. Making decisions can be a huge burden—exhausting, isolating, anxiety-inducing. Who hasn't longed to go back to the days when someone else told you what to do and all you had to do was do it?

This dynamic plays out at even at home. After a long day at work, my wife and I negotiate not so much what we're having for dinner, but who has to decide. I'll cook, but you have to pick. Relief from having to make decisions is the reward.


One of my favorite bits of advice about decision making comes from the late Clayton Christensen, who once wrote, "It's easier to do something 100% of the time, than 98% of the time." In the accompanying anecdote he explained how he applied this to his family's Sunday church attendance. They never had to agonize when one of the kids had a basketball game that fell on a Sunday morning because the decision was already made. They wouldn't go to the game because they'd already decided that their family goes to church on Sundays. Easy.

Making the decision ahead of time means you don't have to decide again every time you face that decision. You've already made it so you can just act and move on.

I recently learned that St. Augustine (354–430 AD) said something similar (much earlier) that flips it to the negative to address avoiding vice: "Complete abstinence is easier than perfect moderation." It's easy to see why. Someone who struggles with alcohol abuse, who has decided once, "I don't drink anymore", has an easier time than the one who thinks, "I really need to keep it under control this time." In the former case the decision and actions are very clear. In the latter, there is a lot of leeway for hand-wringing, if not outright failure.

But this isn't just some life hack to make your decision making easier. Ultimately this advice is a way to grow as a person. A decision made 100% of the time is part of forming your character; the decisions become who you are.

Instead of being a person who works out when I can you become someone who exersizes. Someone who doesn't drink rather than someone who struggles with alcohol. You  become a person who does the right thing, aligned with your beliefs and values, every time rather than on a case by case basis.


As a part-time manager of product designers at 37signals, I'm not usually concerned with managing people's daily work, making sure they show up, or correcting bad behavior. After all we're a remote company so we're able to hire very experienced people—the best available, anywhere in the world—who are experts in their craft.

My job is to teach decision making. They already have the skills and experience to do the work and many of the designers we've hired were design managers, art directors, or creative directors in their previous job. They have expertise and experience in abundance but they're brand new to the 37signals way of working.

So I'm more of a coach or mentor who helps them learn to make decisions the 37signals way. The same way I've learned to make decisions working with Jason Fried and David Heinemeier Hansson over the past 15 years. 

Designers here internalize the values and decisions we've made up-front that allow us to build successful, beloved products with very small, highly-productive teams. 

What kind of decisions? Here are a handful:

Those are the bigger picture ideas but there are tons more at the micro level involving taste, tone, voice, and style. Helping our team grow into product designers who can do this with ease is what I do. Talent and skills come and go but this is the real secret sauce. 

About Jason Zimdars

Product designer at 37signals working on Basecamp, HEY, and ONCE since 2009. Illustrator of It Doesn’t Have to Be Crazy at Work and the Prince Martin Epic series. You can find me on X, Instagram, LinkedIn and at jasonzimdars.com.