What happens when the optimizer over-optimizes?

I looooooove the process of improvement. I was born with this desire to optimize everything. Optimize business, optimize sleep, optimize nutrition, optimize workouts, optimize relationships.

Everything. Must. Be. Better.

That’s a story that I bought into for a long time.

I would track everything I possibly could. I would monitor, tweak, iterate, scrutinize. If everything was running like a fully optimized machine at 100% capacity, maybe then I’d be happy and successful.

Turns out the key to happiness is not in trying to make something perfect. Perfection is a constant, never ending quest of disappointment. There’s no way to win that game. No matter how well its played it will never be good enough.

We are seeing this play out on a global level. If only we could be a little bit more profitable this quarter. Maybe this time we reduce the quality. Or cut corners. Or decrease headcount. We must improve the machine. At all costs. Or else.

I’ve found that after a certain point, it’s time to step off the hamster wheel of optimizing everything. What if I step off that wheel and I am happy, I am enough, and this life is beautiful… just as it is. What happens if we collectively step off of this optimizing wheel we’ve held as gospel, and we find that we have all that we need. Perhaps it is the endless seeking of optimization that is causing us to miss the abundance that has been here all along.

What is the upgrade?

I would totally crush it if I were Phil Connors in Groundhog Dog.

I'm an optimizer. I see things how they are and want to make micro improvements to make them better.

If I had to live the same day over and over again, sure I'd have to go through the sanity check phase, but then I'd like to think I'm take a similar approach as Bill Murray. Meticulously iterating on every moment of the day until it is fully optimized.

Thankfully (maybe?) I don't re-live the same day over and over again in Punxsutawney, but I am always looking at the best places for optimizing and upgrades. My optimizer had been off line for a bit as the pandemic began, but it's peaking its head out again.

In Atomic Habits, James Clear neatly articulates this optimizer mentality with his graph "The Power of Tiny Gains." If we get 1% better every day for a year, we are over 37 times better than where we started. And if we get 1% worse every day for a year, we are at 3% of where we started. Quite the swing.

Currently, I'm optimizing my morning routine during this "Shelter in Place" phase. Little tweaks and tests here and there and we'll re-find that magic.

Obviously, it's not attainable to actually achieve that 1% gain every day, otherwise I'd be flying and walking through walls by now. But it is a wonderful aspiration. Squeeze the juice out of each and every day in a way that makes Phil Connors proud.

How do I expedite the no's?

I'm skipping over the part where we accept and embrace the fact that we are going to receive boatloads of no's in our adventures. That's a given.

Taking that a step further, we want to get through all of the no's as quickly as possible so that the yes's come through loud and clear.

I'm an optimizer and am always looking for greater efficiency. By expediting the no's, I can save lifetimes of maybes, time wasting, mental energy, stress and disappointment. Give me the "fuck yes, or no" as Mark Manson so eloquently put it.

Whether it's about hiring, fund raising, dating, where to eat dinner, or even (especially) what idea or business to start, it's our job to clear out all of the no's. We live in a world of virtually unlimited choices where we can spend 40 minutes scrolling through Netflix with a bunch of maybes. Stop that. If it's not a complete and total yes, it's a no.

Something might not be a no forever, but if it's a no right now, be thankful for the no and move on. If it's meant to be a yes later on, it'll find a way.

The best way to expedite the no's is to ask the really difficult questions that cut through all the pleasantries. If you know what you want, ask for that up front regardless of how awkward it might be. You'll save everyone involved lots of time and that's way more valuable than a few moments of difficult conversation.

Steve Schlafman has a simple and powerful way to do this when pitching investors. Ask them directly, "What are your concerns about our business?” You cut through lots of fat with that question. It's our goal to find questions like this in all that we do.

Give me all the damn no's until there are no no's left. Then the beautiful yes's can shine down upon us.

Why do I choose to make practice so difficult?

We're about to connect some really old threads that have been in my subconscious for decades. We're going down the rabbit hole on this one.

Why do I choose to practice in extreme conditions? Short answer: it's been programmed in me since childhood.

Childhood Practice Memory 1:

There's one season of the cartoon Dragon Ball Z, one of my favorite shows as a kid, where Goku has to travel far away and fight some aliens who are way more powerful than him. On his trip, he has a Gravity Machine that allows him to train in higher gravity levels than on earth. It breaks and goes up to 100x Earth's gravity. Goku goes from not being able to move to training in 100x gravity like he's walking on air which then allows him to put a whooping on the bad guys.

Childhood Practice Memory 2:

Over the holidays, we were teaching my 8 year old nephew how to bowl. I explained the way that my brother and I learned as kids. Our grandfather had taught us a certain step by step method and then made us repeat this process. Talk about training in a difficult environment. Our grandfather was a strict German man who not only owned the bowling alley but also was one of the best bowlers around, and he was watching our every move. I had to be younger than my nephew when we did this, and it stuck with me all these years.

Childhood Practice Memory 3:

I had just changed soccer teams. My old team won pretty much every game we played, won our league and won a few tournaments. My new team was not nearly as good. I was probably the best player on the team, and I wasn't all that great. At a practice midway through the season, my new teammates were goofing around, and my coach was laid back and laughing with the kids. I don't think our team had won a single game at that point, and I completely lost it. I yelled at my teammates, yelled at the coach, said some inappropriate words for a kid my age and then ran laps by myself for the rest of practice.

What do these 3 seemingly random memories about practice have in common?

These formed my own internal belief system about practice which only became apparent to me very recently.

Today, I choose to actively practice in situations way more difficult than anything I'll experience in real life, so that the real world operates in easy mode in comparison.

There's a few ways that this plays out for me. I never really made the connection as to why I did things this way until now, but it all makes sense from this new perspective.

In yoga, my favorite teacher is a woman in San Francisco who has the most notoriously difficult classes I've ever encountered. I didn't realize this when I showed up to her class the first time for what would be the third ever yoga class of my life. She warned us that it was going to be an advanced class and instead of rolling up my mat and leaving, I vowed to myself that I would not let this woman break me. Over 100 of her classes later, I have not given up in her class yet, and she has pushed me further than I ever could have imagined.

I do breathing exercises in the sauna and steam room with the extreme heat and humidity. I meditate in loud gyms and on the subway. I read books that are way above my comprehension level.

I don't get mad at myself when I struggle in these situations. It's practice. We're talking about practice. The opposite normally occurs. I'm grateful for failing in these situations, because I now know my current breaking point and have a new baseline to surpass next time.

It's important to keep in mind that this only applies to practice. Don't drink and drive so you're a better driver sober. Don't pick a fight with your boss or significant other just to improve your arguing skills. Common sense helps here people.

One of the keys to having a growth-focused mindset is to always be looking for opportunties to improve. An easy way to accomplish this is to see how you react when the switch gets ratcheted up 100x and you can't get up off the floor. It also shows incredible inner dialogue when you are in an unwinnable situation.

If we want to get exponentially better at the things that matter most to us, practice harder.

How can I create a bias toward action?

One of the coolest parts of living full time in San Francisco was all of the incredible conversations and discussions that happened. Visionaries, future thinkers, philosophers and spiritual wisdom seekers. I feel like I was always finding my way into a truly fascinating conversation, and I haven't found that level of depth and frequency anywhere else.

This was also something that was frustrating to me.

It appeared to me, at least in some of my circles, that there was a direct inverse correlation between how visionary a person or company was and their ability to execute and operate. And that's not a knock against anyone or anything thing. The world needs both operators and visionaries. For me personally, I think the ideal balance is somewhere around 80-20 with a bias toward action.

This all has given me a greater appreciation and respect for people who execute at the highest level.

These people, as a default, are action oriented as opposed to discussion oriented. They want to build, create, iterate, improve, optimize, test and prototype. With everything they do.

This ties directly into my previous thought: "How can I think 14 steps ahead?"

Applying this bias toward action means repeatedly taking that first step toward the North Star. With the minimum time necessary to recalibrate, it becomes time again for action.

The way I see this becoming more prevalent for me personally is through:

1. Simplifying the complex into tiny, bite-sized pieces and ruthless executing on them
2. Making more space and time blocking specifically for taking action
3. Creating regular checkins for completion of action items
4. Being aware of when I get pulled into the world of the theoretical, hypothetical and futuristic

This isn't the first time I've thought about these things. I've tried various to-do lists, time blocking, and checkins but never from this perspective. I'm excited to see what structures drop in on my quest to rebalance my own method of operation with a bias toward action.