How I avoid trading happiness for money
Dealing with the 4 types of stress
I hate waking up in the morning. It’s something I’ve done every day of my life, and somehow, I’ve gotten worse—not better—at it.
When I quit my W2 job in 2022, it felt like ripping off the warm sheets of financial security, putting my two inexperienced feet on the ground, and going for a run.
I knew it would be hard. But I knew I had to do it.
That’s what everyone says about entrepreneurship: “it’s hard.”
But at the time, I didn’t know HOW, specifically, it would be hard. It was just a general sense.
What I’ve found is that being responsible for a business unleashes a pattern of mental torment that’s encoded in human nature, but not always productive or valid.
A few examples:
Worrying about problems before they even exist
Focusing on what you don’t have instead of appreciating what you do have
Fixating on the future instead of living in the present
The good news is that these bad mental patterns are timeless, and some of history’s baddest boys have shared remarkable wisdom on navigating the stress associated with them.
That’s why Seneca and Marcus Aurelius are so popular among entrepreneur types.
Obviously stress isn’t unique to entrepreneurs, and I hope this post is relevant to anyone reading. It’s just that starting a business was the catalyst I needed to solve stress for myself.
Why solve stress?
I’ve spent a good amount of time trying to understand the drivers of successful people, and here’s one takeaway:
Succeeding in business is all about taking advantage of compounding.
Compounding is all about longevity - staying in the game.
And longevity, I think, is all about keeping your head on straight long enough for your effort to pay off.
For this reason, keeping my head on straight has become something I actively work on. And it’s not just about unlocking compounding; I owe it to my family to not be a neurotic maniac.
(“You used to be so carefree”, my wife tells me.)
So, being a weird guy, I’ve come up with a specific protocol for managing stress.
In case it helps you, I wrote it out.
I’m about to spell out what I’ll call the “Four Types of Stress” and my process for dealing with each. But first, there’s a great quote from Jeff Bezos that gets at the core this whole thing.
In a sentence: If you’re feeling stressed, take immediate action.
“Stress primarily comes from not taking action over something that you can have some control over. So if I find that some particular thing is causing me to have stress, that's a warning flag for me; what it means is, that there's something that I haven't completely identified perhaps in my conscious mind, that is bothering me, and I haven't yet taken any action on it.” - Jeff Bezos
The Four Types of Stress
The big unlock for me was realizing that “stress” isn’t a precise term. It describes a broad category of bad feelings.
I’ve found that the stress I feel falls into 4 buckets:
Worry
Mountain of Work
Looming Uncomfortable Task
Decision Not Made
For each one of these, I have a specific set of steps I follow.
Worry
“He who worries before it is necessary, suffers more than is necessary” - Seneca
Worry may be the most nefarious flavor of stress. It’s limited only by one’s imagination and it tends to persist even when things are going well.
It also seems to lurk in the background of the other 3 types of stress.
Part of the reason that worry can easily infect an entrepreneur is that some amount of worry is productive—even responsible. Anticipating bad things before they happen is part of keeping a business afloat.
But the tendency is to overdo it. Evolutionary biology goads us into overestimating the number and the severity of threats.
How I deal with worry
I have a page in Notion that I call my “Worry Register”. When I am worried about something bad happening, I add it to this document.
I have a screenshot below, which I’ve edited a bit for clarity (some stuff is context-specific and/or sensitive).
The document has 5 fields:
What I’m worried about
Whether or not it mattered (I go back and update this later as things shake out)
Updates that I add periodically
Created date and time
Last update date and time
I’m a little embarrassed to share that I do this. I recognize that it’s overkill and reeks of the kind of “hyper-optimization” stuff that is cringy and excessive.
But it’s helped me for a few reasons.
The very act of writing down a worry takes the sting out of it. A worry in my head feels abstract, nebulous, and scary. A worry in writing is tangible, specific, and solvable.
Writing it out often inspires a specific next step that I can take to resolve the worry.
Maybe most importantly (and least expectedly), writing down a worry in this document forces me to look at all of my past worries, most of which never ended up mattering. I almost feel goofy writing down each new one. When I read prior entries, the voice sounds like a scared, naive simpleton. “Why was I ever worried about that?”
This approach has helped me realize 2 truths about worry: most things I worry about don’t end up mattering. And over a long enough time horizon, even the worries that were justified end up mattering less and less as time goes on.
This approach was inspired by Shaan Puri’s Decision Register.
Mountain of Work
What I’m calling “Mountain of Work” may be the most common type of stress people feel. Just a ton of things to do, and seemingly no time to do them.
The tactic I use for this type of stress is boring and unoriginal, but hear me out.
How I deal with the mountain of work
The pain that comes with having a bunch of work to do is composed of a few different emotions:
Worry about what will happen if the work doesn’t get done
Overwhelm from an unclear idea of what work actually needs to be done
The dread of having to do uncomfortable and/or energy-intensive tasks
I’ve already talked about #1, so let’s talk about #2 and #3.
My first step is defining the actual list of work. And that means spending some time with a good old to-do list. Boring and unoriginal, like I said.
Like the Worry Register, half the battle here is just disarming the mental monster by writing it down.
But the key is the step 2: breaking the to-do list down until I’m no longer stressed.
For example, this might be version 1 of the to-do list.
Version 1
Figure out insurance renewal
Hire one of two driver candidates
Follow up with {{big important prospect who isn’t responding}}
Hmm, still pretty daunting. So I break it down a bit.
Version 2
Figure out insurance
Skim current insurance policy and costs
Skim new insurance policy and costs
Write down the differences
Make decision on whether or not to renew or shop around
Hire one of two driver candidates
Call Bobby (my lead driver) and get his opinion/buy-in on the 2 candidates
Review interview notes from each
Make decision
Call each candidate with yes/no decision
Follow up with {big important prospect who isn’t responding}
Draft email to prospect to get my story and ask straight
Call them
If they don’t answer, send them the email
This feels better to me.
The very act of breaking down a short, heavy list into a longer, but lighter one is therapeutic. And the result is a clear body of work that feels less daunting and gives me clear marching orders.
Sometimes I think: taken to the extreme, you could continue breaking down any task again and again until all that’s left are single keystrokes. And no single keystroke has ever made me feel stressed. Kind of true, but a bit of an exaggeration.
Even with a crystal-clear, broken-down, and specific to-do list, some of the things on there are still daunting. This causes stress.
Looming Uncomfortable Task
I don’t want to call that candidate I decide to reject and give him the bad news. That sucks.
If the prospect answers, I’ll be happy, but it’ll still be an intense, high-stakes call.
This sense of foreboding makes me feel stressed, and it compels me to do unproductive stuff like look at my phone or work on something easier instead.
It’s the same feeling that leads me to putter around the house before a hard run. I should charge my headphones to 100% just in case. Better drink more water. Wait! I need some gum.
An impending uncomfortable task causes stress, and it’s natural—but not productive—to avoid it.
How I deal with a looming uncomfortable task
Once again, the demon behind the scenes is worry. I’m worried that the rejected candidate will be sad or upset. I’m worried the prospect will turn me down. Worry is a bitch.
With these painful tasks, I’ve found the following to be a good formula:
Prepare, but don’t putter
Act swiftly
Relish the serotonin boost from having completed it
Prepare
If I’m about to have to deliver some tough news, I write out my talking points. At least some of the pain of any difficult task comes from winging it and not being sure what you actually are trying to say or do. This can also be a trap, since it’s easy to over-prepare and fool yourself into putting off the actual thing. Once I’ve prepared, my excuses have run dry, and it’s time to act.
Act Swiftly
Nothing groundbreaking here. See the Jeff Bezos quote - acting immediately is the antidote to hard and uncomfortable work. Sometimes I’ll just rip out my phone and dial the number before I can talk myself out of it.
Enjoy the feeling
There is a unique rush that comes with ripping the bandaid on something hard. I try to sit in that feeling for a little bit. The feeling fades, but it hangs around in my memory and gives me a “carrot” for next time.
Decision Not Made
Sometimes, the specific reason behind a bout of stress escapes me. I can’t put my finger on the cause, and it doesn’t seem to fit any of the first 3 flavors of stress I talked about. When this happens, it usually means I have a decision to make, and I haven’t made it yet.
“Just make the decision” isn’t a satisfying remedy, so I’ll try to expound on it (but that’s really what it comes down to).
How I deal with a decision not made
Any traction I can claim to have made in my business has come 70% from a few important decisions, and 30% from “work.”
I used to believe that work only happened when I was toiling away at my computer. I think this is a leftover habit from 8 years of working in W2 jobs, where optics matter, and you’re judged based on inputs, not always outputs.
It took me a while to realize that some of my most productive hours as a business owner have happened on runs, at the grocery store, in the shower, and a bunch of other places away from my computer. These are the places where I make decisions, and for too long, it was a passive activity.
Now, I’m deliberate about my decision making time, and it rarely happens at my desk.
It still tends to happen on walks, drives, runs, or during conversations.
But I have a tactic I use now: I plant a flag in the ground and tell myself, “By the time this is over, I need to have a final decision.”
Boxing off decision-making like this forces me to do the thing that actually matters: just making the decision and moving on with conviction.
As I was writing this, I began to doubt whether my internal mental toiling and the specific solutions I’ve come up with apply to anyone else. But I’m publishing this anyway, on the off chance that there’s a nugget in here that might help someone reading. I hope that’s the case.