Mental Fitness for Operators

Treating cognitive resilience like physical training (with reps, recovery, and reflection.)

What’s more important: physical fitness or mental fitness?

Trick question - they both are equally important.

There's a misconception that somehow, what you see in the mirror matters more than what's happening inside your head.

And it makes sense why physical fitness traditionally gets more attention, right? Physical fitness is visible to the naked eye. You can look in the mirror and see whether you look fit or not.

Mental fitness is not as visible. Same thing with sleep fitness.

But all of it compounds.

The good news is more people are taking all of it seriously now. Mental fitness, physical fitness, sleep fitness are all valid forms of fitness.

You can see this with the rise of brands like Headspace, Calm, and Eight Sleep - all companies that focus on mental and sleep fitness to improve and compound effects in physical fitness.

How you're sleeping, how you're eating, how you're feeling, whether you're working out, and especially how you feel impacts the decisions you make. If you take even two seconds to think about it, of course mental fitness matters, especially for high performers.

This is a common pattern I see: I work with founders who really take care of their mental health. They connect with family and friends. They have community. They sleep well.

These are the founders that make decisions from a place of possibility. That's what allows them to make bets that are calculated and bold. They don't let fear or anxiety rule their decision making.

On the other hand, you have founders that don't sleep enough, they use substances, they don't see a therapist. They're not doing the things they need to do to take care of their mental health.

Those are the founders that typically will have their companies go under because they make decisions from a place of fear. Or they'll make good decisions but burn themselves out in the long run. Those are the ones that usually have some sort of existential life crisis even after they've achieved success.

A Story About Fear-Based Decision Making

I once worked with a founder who had maybe about five months of runway left. Our work together was really a hail Mary: it was a last-ditch attempt to try to solve the problem and prevent his company from going under.

When we unpacked his first session, it became super clear that he was making decisions from a place of fear, and that this was something that was deeply rooted in the way that he grew up.

He had a really hard relationship with his family. He didn't feel like he could be honest with them, which made it hard for him to be honest with himself, and that bled into the way that he ran his company.

He was afraid of losing investors' money, afraid of not finding product-market fit, and afraid that he would never be successful.

It was even to the point where he was afraid that if he was anything short of successful, nobody would love him, nobody would care for him, his partner would leave him, and he would die alone.

Our first session together was a really hard session. Before we met, he struggled to admit that fear was the way he ran his life for as long as he could remember. Our coaching call was the first time that he was willing to admit that this was the case, and that it was not sustainable.

So what did we do?

We identified first that he was in fear. He had no idea how fearful he was until we really talked about it.

Then, I encouraged him to do what I tell all my coachees to do when they're in massive fear: fear journaling.

Fear journaling is basically writing out the absolute worst-case scenario of what will happen if your fear comes true.

P.S. The chances of most people that read this newsletter actually dying from poverty and being completely ostracized and blacklisted from all of Silicon Valley is pretty much zero. And even if there are people that this applies to, it's probably not you, the reader.

Part of the impact of fear journaling is looking at the ludicrousness of just how absurd your fears are once they're written down on paper.

Once we were able to fear journal, the advice was to do the opposite. This is a dialectical behavioral therapy tactic where you do the opposite of what your brain is telling you to do.

So if your brain tells you "don't take the big bet because it's not going to work," you imagine what would happen if you did take the big bet.

"Is this really an existential crisis?"

If you're able to realize through working with a coach or partner that no, it's not existential, you do it anyway. If it turns out you made the wrong decision, you have learnings. If it's the right decision, you come out better for it.

My coachee and I did that for a week or two, and it was like magic.

It was almost like overnight he became a completely new person.

His partner actually ended up reaching out to me about a month or two after we started working together and was like "I don't even recognize my partner anymore. He's not paralyzed by fear, I feel like he has a renewed sense of self, I am more in love with him, our dates are better, even our sex is better. Everything is better."

That really just shows how when you take care of the mental fitness, everything else improves alongside with it.

His company turned around. It is extremely successful now.

He took bigger, bolder bets. Some of them paid off, some of them didn't, but that didn't scare him. He was able to make the right hires. He thought with a lot better clarity.

He's physically fit, too, and the mental fitness was actually helping his physical fitness as well.

Now, my former coachee is motivated by desire and drive rather than by fear of disapproval, of shame, of guilt. It helps him as a better leader. He leads board meetings better. He fires people that are underperforming. He promotes people and pays them better when they do well.

We don’t need to work together anymore, because he now knows everything he needs to know. And that came from being mentally fit.

The Playbook: Building Mental Fitness Through Reps and Recovery

Mental fitness is like any other kind of journey or fitness.

It's all about consistency, and consistency is always better than intensity.

Here are my six steps on building peak mental fitness.

1. Fear Journal 😱 

I write about fear journaling here, and you should go read that for more information.

When you notice fear showing up, write out the absolute worst-case scenario. What's the most extreme, catastrophic outcome you can imagine?

Then look at what you wrote and ask yourself:

  • How likely is this really?

  • What would I do if this actually happened?

  • Can I do the thing I'm afraid of anyway?

Some of my coaches become so good at fear journaling that they do it mentally. They don't have to write it down anymore.

They just go "okay, what's the scariest, most extreme form of this?" and then "how can I overcome it?" and "can I do it anyway?"

2. Do the Opposite ↔️ 

This is a dialectical behavioral therapy tactic.

When you have a compulsion to run away from your problems or do the thing that is more automatic - whether it's yelling at someone or running away or getting angry or snapping at someone - do the opposite.

For most operators, doing the opposite means doing nothing.

Sitting on your hands. Being still. Not reacting.

3. Practice Mindfulness 🧘 

This can look different for everyone.

For some people it's praying. For some people it's going out in nature, taking walks without devices. For some people that's meditation, sitting still.

I've spoken frequently about the different kinds of meditation I like. I like See Hear Feel by Shinzen Young. I like mindfulness meditation, especially ones following Thich Nhat Hanh's practice.

Some sort of disconnection from electronics to center on the present moment is really important.

One quick note: Perfect is the enemy of good here.

10 minutes is better than zero minutes; 5 minutes is better than zero minutes.

This is probably one of the few places where my advice is different from that of Naval Ravikant. (Twitter Bros, don’t come at me!)

Naval has previously said that if you're not going to spend an hour meditating, it's not worth it.

I completely disagree.

I think that even just to build the habit, to form the habit, spending 5 minutes is better than trying and failing at doing an hour every single day. Too many people who start with an hour just give up after a couple of sessions.

Make the practice towards your mental fitness challenging but doable, whatever that looks like for you.

4. Therapy (Once a week) 🧑‍⚕️ 

I highly, highly recommend therapy.

I think everyone could benefit from seeing a therapist to help them either with performance (becoming a more evolved version of themselves) or aligning the things that they say they care about to the actions that they do.

Therapy is also super helpful for developing a sense of self-awareness, which obviously leads to better mental health and also leads to more happiness.

And if nothing else, therapy serves as a really great place to look yourself honestly in the eyes and have an unbiased person tell you what's going on.

Going to therapy weekly is a worthy investment. You're spending one hour of your week talking to someone who can help you see the most objective version of yourself. You develop that self-awareness that compounds into really incredible self-awareness. That will lead to better decisions for the rest of your week.

Given that you have 168 hours per week, one hour of that towards therapy is not a lot of time.

5. Never compromise your sleep 😴 

Sleep is so essential for your brain to not be brain fogged. It's essential for memory. It's essential for making good decisions.

Sleep is so important that it's one of the things that you should absolutely never skimp on.

I am a die-hard fan of the Eight Sleep mattress. I use it. I recommend it to all of my coachees.

6. Medication (If needed, under psychiatric supervision) 💊 

This is a bonus one that I think could be helpful for mental fitness: potentially exploring the use of medication under psychiatric supervision.

There are some people that are just prone to anxiety or depression. I don't want anyone to believe that they should do this without using prescription medication.

I'm a huge proponent of taking care of mental health in whatever way is healthy and sustainable.

I do not recommend seeking prescription medication without supervision because a lot of these substances can be addictive.

But if you're an operator that struggles with OCD, with ADHD, or with depression or anxiety, it's completely okay to look for whatever help you need to take care of your mental health. Sometimes that includes medication.

The only thing I really care about here is that it's done under strict supervision, especially if you have addictive tendencies.

If you're seeing a psychiatrist for medication, once a month unless otherwise advised by your doctor is usually a pretty good cadence. Once every two weeks or every four weeks to see how you're responding to medication.

The Transformation

Do all of those things over and over again until your self-awareness improves and until you feel like the work you're doing is truly joyful.

Mental fitness changes everything.

Not just how you feel, but how you operate.

Mentally fit operators make different kinds of decisions. They handle their teams differently. They approach board meetings differently.

They take calculated risks instead of playing it safe out of fear. They fire under-performers. They promote and pay high performers well.

They don't allow short-term thinking to impact long-term benefits.

That's the operator you're working toward becoming.

Until next time,

📌 Resources mentioned:

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About Regina Gerbeaux

Regina Gerbeaux was the first Chief of Staff to an executive coach who worked with Silicon Valley’s most successful entrepreneurs, including Brian Armstrong (Coinbase), Naval Ravikant (AngelList), Sam Altman (OpenAI / Y Combinator), and Alexandr Wang (Scale).

Shortly after her role as Chief of Staff, then COO, she opened her own coaching practice, Coaching Founder, and has worked with outrageously talented operators on teams like Delphi AI, dYdX, Astronomer, Fanatics Live, and many more companies backed by funds like Sequoia and Andreessen Horowitz.

Her open-sourced write-ups on Operational Excellence and how to run a scaling company can be found here and her templates can be found here.

She lives in the Pacific Northwest with her partner, daughter, and dog, and can be found frequenting 6:00AM Orangetheory classes or hiking trails nearby.

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