January 13, 2023
On Sabbatical
I'm out. Today marks my last day of work until March. I'm taking my first sabbatical in 23 years. It's embarrassingly overdue. I do the 8 hour day, 40 hour week thing just fine, but when it comes to taking extended time away from work, I'm terrible. Subtracting time away when my kids were born, and aside from from personal days dotted ...
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January 6, 2023
The new normal
Normal comes on quick. First it starts as an outlier. Some behavior you don't love, but tolerate. Then someone else follows suit, but either you miss it or you let it slide. Then people pile on — repeating what they've seen because no one stepped in to course correct. Then it's too late. It's become the culture. The new normal. This ha...
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January 2, 2023
Where's the bug?
The feature doesn't work. It's not critical, but there's a rush to fix it. Two people are pulled off something else to deal with this. The code is sloppy, but the original problem is gone so the fix is deployed. A post-mortem is scheduled so 9 people can review what happened. New QA procedures are applied to every project moving forwar...
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November 19, 2022
On company size
I have no idea how the the Musk-era Twitter saga plays out. That's a time will tell situation. And this isn't a post about Elon, his personality, his management style, decisions being made, talent drain, morale at the company, or the thousands of people who've been laid off or outright quit. There's plenty to be said there, and plenty ...
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November 16, 2022
Collaborating away
“"But how do you brainstorm remotely? Or riff remotely? Or collaborate creatively remotely? Isn't it better when you're in a room, tossing ideas back and forth?"” I hear some version of this fairly often from people who aren't used to making things with others from far away. There's an assumption that four walls, a whiteboard, a table,...
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November 7, 2022
Against Maximization
In business, maximization is the minimization of joy. I can’t imagine anything less interesting in business than maximizing shareholder value. Yet this is what public companies are pressured — if not legally required — to do. A lot of non-public companies follow the same path towards performance and results. To take it further, maximiz...
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October 27, 2022
Do you have to love what you do?
Attend enough business conferences, read loads of LinkedIn posts, or listen to enough motivational speakers and you’ll hear one piece of advice repeated over and over again: You’ve got to love what you do! If you don’t love what you do, you might as well stay home. No less a giant than Steve Jobs famously told Stanford’s 2005 graduatin...
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September 20, 2022
Just get moving
In business, moving is one of the hardest things to do. People think change is hard. It is. But moving is harder. Morphing from thinking and talking to actually doing and moving is the hardest. It's hard because talk is easy. Theorizing is easy. Imagining is easy. Waiting is easy. Second guessing yourself is easy. Third and fourth opin...
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September 14, 2022
It's not an experience
Alto.com is a wonderful pharmacy that offers same day delivery. I have nothing but great things to say about them. But they're following a pattern I'm seeing far too often these days. They're trying to track everything, and asking people to attribute "experience" to things that are mere, routine happenings. Most things just don't need ...
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August 30, 2022
The longer
The longer you do something, the more you'll be asked "what keeps you motivated?" People are typically looking for a goal-based answer. Or some big mission. Or some sort of target you just haven't hit yet. The question is often aimed at revealing a deep, purpose-filled motivation. The assumption is that you're still doing it because yo...
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August 25, 2022
Tossing a key
This weekend I was riding my stationary exercise bike when I noticed a sharp poke in my pocket. I reached in, pulled out a house key, and looked for a place to put it. But since I was on a bike, there's really no where for it to go other than not here. So I tossed it on the ground, broadly aiming — without accuracy or expectations of p...
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August 9, 2022
How it goes downhill
Comparing warning labels on gym equipment. From the 80s on the left, from the 2000s on the right. The one from the 2000s says a lot more, but the one from the 80s means a lot more. -Jason
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July 22, 2022
Binaries over priorities
Low, medium, high. 1, 2, 3, 4, 5. Must have, should have, could have, don't need. These are various forms of priorities. People seem to love them. I've always hated them. Especially when it comes to product development. When it comes to choosing what to do, it's always binary for me. Yes or no. Now or not now. Do or don’t. What about m...
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July 20, 2022
Down in front
Look around YouTube at car reviews, and you’ll see a lot of people standing in front of cars. Below I’ve snapped captures of early frames in three car reviews. These represent the first time the car is shown whole, in profile. Who’s on review here? The car reviewer or the car? Get out of the way people! Take it from Doug DeMuro. His re...
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July 14, 2022
Return On Effort
Over the last few days, a few department heads at 37signals got together for an offsite gathering, lead by Bill Joy from The Joy Group. We've worked with Bill in a somewhat different capacity in the past. This time he was here to help us understand some truths about how we really run the business, make decisions, and value what's worth...
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July 8, 2022
Like a squirrel
Stick with me on this one. I've been spending more time watching birds, squirrels, and insects lately. Nature has always fascinated me, and the longer I observe, the more I notice. And one thing I've noticed in general is that birds, squirrels, and insects stop and start a lot. They're headed somewhere, but context plays an enormous ro...
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July 2, 2022
Working around people
We all know it’s important to work with people. That’s collaboration. But it’s perhaps even more important to learn how to work around people. To uncollaborate. Not by ignoring them or dismissing them. But moving without them because they simply aren’t available to move with you. This isn’t about avoidance, it’s about “ah, you’re busy,...
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June 21, 2022
Heard Something, Read Something, Saw Something [#13]
Hey! Back again with another installment of Heard Something, Read Something, Saw Something. So, what do we have this time... Heard Something Really enjoyed this heady Making Sense episode that asks "Do you really have a self?" Theoretical conversations like these feel like a massage for the mind. They get down to root assumptions upon ...
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June 6, 2022
Risk, decisons, and scarcity
This weekend I took a long walk with a fellow founder/CEO. We talked on the phone before, but never met in person. We found ourselves in the same city, so it felt like it was time to shake hands and catch up IRL. He runs a company that's an order or magnitude larger than 37signals, so his experiences, responsibilities, and perspectives...
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June 2, 2022
Wait to concentrate
Procrastination is often tagged as a negative. If you're putting something off until the last minute, it's assumed it's because you don't want to do it, or it's too hard, or you've been avoiding it for some other reason. Maybe I'm making excuses, but lately I've found procrastination can be aimed to your advantage. Not always, but more...
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May 26, 2022
Don't defer quality
Ever find yourself about to ship something that isn't good enough? You know it, you feel it, but you still want to get it out there because regardless of outcome, lots of work went into it. You want something to show for it. You can often make yourself feel a lot better by wrapping the uneasiness with a statement like "We can always co...
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May 3, 2022
37signals: Hello again
When we launched our company in 1999, we were called 37signals. We started out as a web design firm that ultimately transitioned into a software company. As 37signals, we made a bunch of products over the years including Basecamp, Backpack, Campfire, Highrise, and others. We wrote a number of books, and blogged like crazy too. We were ...
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April 7, 2022
Heard Something, Read Something, Saw Something [#12]
Hey! Back again with another installment of Heard Something, Read Something, Saw Something. So, what do we have this time... Heard Something My friend Bob Moesta is out with a new podcast on product development and innovation, and this 27-minute episode is an especially good one. By the end, you'll have a new framework for thinking abo...
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March 26, 2022
Getting together again
We've worked remotely for nearly 20 years, but we've sustained the distance by lining up intense, one-week-together-in-person bursts twice a year. Over the last 10 years, we've mainly held these bi-annual all-company meetups at our Chicago office. But the combination of the pandemic, and an expiring office lease in July of 2020, conspi...
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March 4, 2022
Reframing it
A friend of mine is pissed off. He hired someone to replace a bunch of windows at his house. The guy did the work. Poorly. And now it turns out he needs to have everything redone. Given how badly the job went, he's going to work with someone else to get it done right the second time. What's there isn't really salvageable. Even the wind...
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February 22, 2022
How to land the job you really want
As someone who's been hiring people for 23 years, I've seen, read, and reviewed tens of thousands of job applications. The ones that typically rise to the top are the ones that demonstrate effort to get this job, and not just any job. We recently hired our first Email Marketing Manager. Nearly 400 people applied for the position. As ap...
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February 15, 2022
Watch out for 12-day weeks
Way back when, we used to release new software on Fridays all the time. That often meant working Saturdays and Sundays to fix an urgent problem with the new stuff, wrecking the weekend for whoever did the release. It was stupid yet predictable, because we kept setting deadlines at the end of the week, as most naturally do. But Friday i...
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February 10, 2022
Getting better vs. feeling better
Over the past few months I've been taking guitar lessons from a friend of mine who happens to be an exceptional teacher. I got lucky. I used to play years ago, but probably only retained 10% of what I knew, so I was as close to starting from scratch as any barely-experienced player could be. Basically, I could dabble and play some chor...
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February 1, 2022
Heard Something, Read Something, Saw Something [#11]
Hey! Back again with another installment of Heard Something, Read Something, Saw Something. So, what do we have this time... Heard Something While this is a video, it's really about sound. If you like cars, or simply dig physics, I bet you'll find this video (and audio) fascinating. I sure did. Why do engines sound they way they do? I ...
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January 28, 2022
No big deal or the end of the world?
Here’s something that should be obvious: People don’t like to have their grievances downplayed or dismissed. When that happens, even the smallest irritations can turn into an obsessive crusade. Imagine you’re staying at a hotel, and the air conditioning isn’t working right. You call the front desk to mention it, and they say, oh yeah, ...
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