Hello everyone,

Thank you for your feedback to last week’s newsletter. Sorry if I couldn’t get back to everyone. Appreciated as always.

A special thank you to my friend Jonas, who’s responsible for me getting last week’s newsletter out and getting back on the wagon with this.

This week is a change of pace: we’re talking about failure.

Two Kinds of Failure.

Robert Greene - the author best known for his book, the 48 Laws of Power - draws a distinction between two kinds of failure.

There’s the first kind of failure - inaction. It comes from holding off on your ideas. It can be due to fear, procrastination, waiting for the right time, the list goes on and on. But simply put it’s failure from not doing the work.

As Greene points out, “this kind of failure you can never learn from, and such timidity will destroy you”. I, perhaps more than most, have struggled with the tendency to fail like this for a very long time. 

Then there’s the second kind of failure. The kind that comes from “a bold and venturesome spirit”. The type of failure that comes from action. From trying and learning from your results. Those who fail with bold action - and actually sit down to reflect and learn - are getting ahead, even if it doesn’t seem like it on the surface. Greene put it eloquently: “If you fail in this way, the hit you take to your reputation is greatly outweighed by what you learn.”

This second type of failure can be seen as closer to a scientific process. “Repeated failure will toughen your spirit and show you with absolute clarity how things must be done.” You can gain a lot of agency and knowledge by treating every action as an experiment - something you can learn from and improve yourself through. Each one a step to your ultimate goal.

The best projects develop you. As Alex Hormozi says, you become the reward of your hard work. 

If you make the first type of failure a habit - time becomes your enemy. You’ll inevitably be miserable.  If you make the second type of failure a habit - time becomes your ally. You’ll inevitably be successful.

Failure Through Inaction is a Mistake.

The first type of failure is the one you want to avoid at all costs. Charlie Munger and Warren Buffett made multiple fortunes largely through a simple mental model: avoid mistakes.

Inaction is the greatest mistake. It weighs us down, undermines our confidence, wastes our potential. It creates bitter people. Make inaction your enemy.

There is no shame in trying and failing. There is only shame in not trying. The only fatal failure is inaction. Treat it as such.

This is a lesson that has evaded me for 99% of my life - and one I am trying now to internalise.

Experimentation > Failure.

As mentioned above, the second type of failure is much closer to experimentation. 

When reading a biography of Warren Buffett, I was absolutely blown away by the sheer number of business ideas he tried in his youth. Even for him, the majority of them failed - but they informed the few that worked. Those few gave him the financial foundation that snowballed into one of the largest fortunes in human history. 

He didn’t care about reputational risk from failure - he saw it as an unavoidable part of his path to wealth. All of it was a learning opportunity.

Last year, I fell flat on my face with a pressure washing business. Not an idea I tested the waters with (pun) but an actual partnership that I registered, took insurance out on, and put a lot of time (and a decent amount of money) towards. Long story short: it failed.

In hindsight, the business was destined to fail from the beginning. I made all the mistakes I had read over the years to avoid. I wasn’t interested in the project, we had no experience in the field, we didn’t validate demand ahead of time, and on and on. Essentially, if there was a mistake to be made - I made it.

But I was surprised by how I felt when we decided to pull the plug. Sure, it didn’t feel great losing money and wasting time - but I was glad that I had tried it. I ended up writing out 23 lessons from the experience in my Repose notebook. Those lessons have informed my current projects and choices. The investment of time and money paid knowledge dividends I’m glad I now possess.

Failure Reveals.

I’ll write more on the failure itself another time - and share some of the most important lessons I took away.

One thing that I’ll share now though: failure reveals.

It revealed parts of me to myself, it revealed I had more work to do, it revealed that my fears were largely unfounded, and mostly, it revealed people in ways I wouldn’t have expected.

I got to learn a ton about my business partner that I probably would have never known or noticed - even after years of friendship.

The advice I got from people I respected (many of them on this list) was all the same: It’s good you did this, now learn from it and get on to your next project. They understood that it was a part of my path to where I want to be.

Meanwhile, other people - all of them unaccomplished, it's worth noting - enjoyed my failure. In fact, one friend got drunk (on mead of all things) and admitted to me that he had been hoping I failed from the start. 

He claims it's because he didn’t like my business partner - but the effect was the same, he was rooting against me. He told me about how happily he had told his mother about my failure (weird, right?).

There’s a line from Mark Manson that applies well here - and it’s a heuristic you should take away: If you wouldn’t ask for their advice, you can ignore their criticism.

Understanding Risk.

Failure is just a part of the path. Read any biography of someone you admire, and their life is littered with failures and obstacles. You shouldn’t fear them.

As I wrote earlier this year:

Real risk isn’t trying and failing. It’s not having to deal with some short-term pain, minor obstacles, or having your image changed in the minds of others.

Real Risk is ending up in a life we hate. That’s a 100% guarantee of failure and misery - nothing else could possibly carry so high of a risk or so high of a toll on you. The greatest risk is accumulating regrets and mistakes until you’re in a spot where you wonder where everything went wrong.

Call To Arms.

This week’s newsletter is a call to arms. Get out there and start pushing your limits. Challenge yourself. Don’t just rest on your knowledge - use it or lose it.

Don’t let ideas just sit in your head - where they’re safe from reality but ultimately useless. Bring them to life.

Do you want to feel good now or great later?

Only you can decide. Avoid the first type of failure, and let the second type be a natural consequence of your “bold and venturesome spirit”.

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Thanks for reading. Let me know if you’re someone who still struggles with the first type of failure, or if you’re someone who’s going to put it on the line and risk the second type of failure as you pursue your goals.

My own resolution is to ramp up my rate of the second type and eradicate the first type. I hope you’ll help to hold me accountable.