I’ve found one principle particularly useful in my work and life: whatever you’re doing that’s important or complex enough, plan for 10 attempts before you get it right.
Starting with Realistic Expectations
For example, I’m thinking about restarting my blog. I’ve been away for a while and gained a lot more experience. How do I synthesize that into something meaningful? There’s no point trying to make the first post perfect. In fact, I find it useful to expect it will be bad and write it anyway. I know that before the first good one comes, it’s going to take 10 attempts.
Why Short Iterations Beat Long Projects
Consider someone becoming a software engineer. You might think: “Let me take on this huge project that takes four or five months. By the time I’m done, I’ll have learned everything about software engineering.”
This approach completely goes against the 10-iteration philosophy. If you do the math 4 months times 10 attempts that’s 40 months. Way too long.
What if instead you had projects that could be done in a week? Now you can get where you’re going in 10 weeks, and you learn so much more in the process.
Building Habits Through Iteration
I’ve seen this work even in habit formation. Habits is one of the only things I find reliable in getting anything done. When I want to build a new habit, I tell myself I’m going to stick with it 10 times before evaluating success.
For example, if I want to start going to the gym:
- Day 1: Maybe I just check in and check out—that counts as one
- Day 2: I come again
- Keep going until I hit 10 times
- Then I can start evaluating success
Applying It to Important Conversations
When I’m about to present a major idea or propose a foundational shift in how we’re doing things at work, I ask myself: Have I had this conversation at least 10 times before?
Talk to an engineer, talk to a product manager, talk to a data scientist, talk to another engineer. The point is to have 10 conversations before the big one.
The Benefits of This Approach
This discipline does two powerful things:
First, it reduces pressure. The first attempt suddenly doesn’t carry so much weight—it’s just the first of many attempts to come.
Second, variety helps you see more. Your first interpretation is almost always wrong. You’re seeing things based on your bias, based on unfair comparisons, based on what you think the world should look like versus what it actually is.
When you impose this discipline on yourself, you start encountering the world as it is.
Staying Open to Change
Of course, you should let that reality influence you. You don’t want to be so stuck on your ideas that after 10 attempts, you’re still where you started.
By the 10th iteration, you should be able to look back at iteration one and think: “Oh my God, that was so wrong. This is so different now.” Or you might realize there are variations, but you were on the right track—and that’s good too.
Even if your idea completely changes, that’s okay. You’re now more harmonized with the truth. What could be more valuable than that?