Borrowed Wisdom

This week: Change the timeline to change your business

Debt mountain is keeping you from shipping projects on time.

Jason Fried had a realization. Long project timelines destroy teams because of one dangerous word, LATER.

When you're working on a 6-month project, "later" becomes a dumping ground. A problem you can't solve? Move it to later. Design not coming together? Toss it in the later pile. Technical debt piling up? Push it down the road.

The timeline tricks you. Six months feels infinite when you're in month one. There's always tomorrow, next week, or next month to fix it.

So you keep piling. Every unsolved problem, shortcut, or "we'll clean this up later" gets stacked on top of each other.

Then month five hits. You turn around and see this massive pile of stuff you promised to deal with.

Now you have two terrible options.

Ignore the pile completely and ship broken work. Or panic and patch everything up in the final weeks with crunch time and guilt.

Both options create more problems. You either ship garbage or create another project to fix the garbage you just shipped.

37signals works in six-week cycles to kill this pattern.

When you only have six weeks, "later" means something completely different. There's no invisible space to hide problems. Later doesn't mean "we'll get to it at the end of this cycle."

Later means we're dropping it. Later means another time, not this time. Later becomes a decision tool, not a procrastination tool.

You can't build debt mountains in six weeks because the timeline won't let you. Every "later" becomes a hard choice right now.

Do we tackle this problem in this cycle, or do we cut it entirely?

When later isn't an obligation, it becomes freedom. You're not carrying debt into the final weeks. You're not guilting yourself over broken promises. You're not facing late nights trying to patch six months of avoided problems.

Most teams would've kept the long timelines and complained about crunch culture. 37signals changed what later meant and eliminated the crunch time.

To-Go Bites

1. Short cycles redefine "later"

2. Short timelines prevent pile-ups

3. Six weeks forces hard choices now

4. Long timelines create invisible debt

5. End-of-project panic is self-inflicted

6. Later becomes a decision tool, not debt

7. Shorter cycles eliminate late-night panic sessions

8. Later tricks you into thinking you'll eventually fix everything.

9. Limited time forces you to identify what actually matters versus what you're avoiding.

10. Unsolved problems, design issues, and technical debt stack up because you keep pushing them forward.

Worth The Open

My favorite content from surfing the web this week

1. This has been all over my socials lately. Leaving early yesterday?

2. Dealership parks their cars close together

3. Healthcare showdown for the Super Bowl

4. Most people aren’t like you

Thanks for reading

— Cam