Chomp chomp chomp, like a failure-eating Pac-Man

I wrote this because I know how easy it is to fear failure, especially when taking a big leap. But I want you to see failure the way I do: as fuel.

Another Week Belongs to Death

On the wall of my office, above and to the left of my monitor, is my Memento Mori poster. It’s a series of circles, each one representing a week of life. It goes up to 80 years old, or 4000 weeks (a la Oliver Burkeman’s book).

Every time I go out of my office I walk by this poster.

Every Friday I fill in a circle to acknowledge that another week belongs to death.

I don’t see it as morbid. I see it as a real reminder to be present! It’s why I spend so much time with my kids. It also contributed to me starting my entrepreneurial journey.

People at the end of their lives rarely regret what they did. Instead, they regret what they didn’t do.

Time is fleeting. Tomorrow is not guaranteed.

Better to act - and risk failure! - than to stay where it’s comfortable and let regret hit you on your deathbed.

A One-Way Door…or is it?

Fear of failure stops people from making big moves. What if it all goes wrong?! What if I fall flat on my face?

But most of our suffering happens in our heads, not in reality.

Leaving a job seems scary. The downside is catastrophic!

Yes, failure could happen - I don’t want to pretend that nothing bad could ever happen 🌈 - but there’s a range of failure. There are BIG failures, and there are little failures.

We fear the former, but are more likely to experience the latter.

And those little failures? They’re how we build towards success and avoid BIG failure.

Little failures don’t stop you. They steer you.

Chomp chomp chomp on failure

In high school, my ego was fragile. If I struggled with something, I took it as proof that I wasn’t smart enough. It was safer not to try, than to try and fail.

Over time, experience and necessity forced a shift. I realized failure wasn’t a verdict - it was just information.

Now? I don’t just tolerate failure, I seek it out. I eat it up. I throw myself into things just to see what happens. I can’t wait to get feedback on what’s working and what’s not.

You can’t just pick a point in the future (e.g. successful entrepreneur), make a plan, and then execute without issue. It doesn’t work that way.

You get there by starting. By failing. By learning. You don’t avoid little failures. You consume them. They power you.

You have to be bad to get good

I couldn’t wait to start my first sales outreach process. Why? I knew it would be awful. 🤣

And being awful is just fine! You have to be bad to get good.

I could’ve spent weeks or months doing research (especially as a true noob at this). I could read books. Meet experts. Go back and forth with ChatGPT.

Or I could just get started. For the target I was reaching out to, there are at least tens of thousands of people I could contact. I found 10, drafted a message, and got started.

The planning process would’ve probably been high school Kevin’s approach. Planning feels productive. It gives the illusion of progress, and it delays the judgment on whether your plan will actually work in the real world.

Today’s Kevin knows that you learn best by doing. I need the little failures of an awful outreach process in order to get to a good outreach process.

But sucking at something isn’t enough. If you’re not tracking and reflecting, you’re just failing randomly.

If you’re not tracking it, you’re not learning

The evolutions on your journey from little failures to big successes will be subtle and nuanced. You need data.

If you don’t have the data, you won’t know what’s working, or how to improve it.

You need to track your performance so you can see what’s working, what’s not, and what needs to change.

For my sales outreach it was a simple Google Sheet. I kept track of who I contacted, what I said, where I sent it, and then the milestones as they did (or did not) engage.

This gave me two big diagnostic metrics: volumes and rates. Over time, I’ll see which adjustments improve outcomes, and which make things worse.

The principle here is simple: If you’re not tracking, you’re guessing. And if you’re guessing, you’re not using the failures as fuel.

Reflect on Your Failures

Tracking data isn’t enough. You have to make sense of it.

What did you think was going to happen when you took action? Did it work? If so, why? If not, why not?

I have a space for journaling in my daily note in Obsidian to reflect on failures and feelings. I reflect after major campaigns or other meaningful milestones. I also perform monthly reviews of my Objectives and Key Results (OKRs).

These techniques help me bring data and reflection together so I can choose my next move with intention.

Data and reflection ensure you’re pausing and effectively adjusting. When seen in this light, “failures” are really just information guiding you toward success.

Doing this is how you stop avoiding failure, and start devouring it like a failure-eating Pac-Man.

Call to Action

This week, take stock of your attitude toward failure. Are you fearful? Do you see it as fuel? Or somewhere in between? If fearful, reflect on why.

Are there any areas you’re avoiding making meaningful progress because of that fear? How could you de-risk your action and get started so you get some real feedback?

How’s your tracking? Do you have metrics in place, and a system to pause and reflect so that you can adjust with intention?

Have fun!

I’d love to hear from you about this: What’s one way you failed recently that turned out to be useful?

Have a great week,
Kevin

PS: If you liked this, just hit reply and say “chomp” and I’ll know we’re on the same page 😁