A Lesson at 40: Happiness and Hard Things

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Why This Episode Exists + Nerdy Stuff Not In The Pod 💡

Today’s episode exists because turning 40 is a bit of a trip and it made me think about my life. Specifically, about what I’ve learned and what might be useful for entrepreneurs to know.

The core idea is around the connection between happiness and discomfort, and the mechanics of making uncomfortable stuff manageable so that you can tilt the happiness equation in your favor.

Here's some nerdy stuff that didn't make it into the pod:

1. The Physics of Life Inertia: I dove deep into research on psychological inertia and cognitive biases. There's fascinating work by Daniel Kahneman on System 1 and System 2 thinking that relates to why we avoid discomfort. System 1 (fast, instinctive) often steers us away from discomfort, while System 2 (slow, deliberative) can recognize the value in it. More on that in this book.

2. Neuroplasticity and Discomfort: Studies show that pushing ourselves out of our comfort zones actually promotes neuroplasticity. Learning new skills or facing fears creates new neural pathways, literally reshaping our brains. This ties directly into the happiness equation I mentioned – by increasing our capacity, we're expanding our potential "reality" outcomes.

3. Storytelling and Neuroscience: The bit about using stories to overcome inertia is backed by neuroscience. When we engage with stories, our brains release oxytocin, which enhances empathy and cooperative behavior. By telling ourselves future success stories, we're literally chemically priming our brains for action.

4. The Compounding Effect of Discomfort: One concept I wish I'd expanded on is how seeking discomfort compounds over time. Each uncomfortable action not only moves us forward but makes the next uncomfortable action easier. It's like compound interest for personal growth.

That’s the nerd deep dive. Hope you enjoyed 🤓

Pod References

• Tacklebox

• The Daniel Tiger SOP

Timestamps:

00:30 Intro - Discomfort Leads to Happiness
01:33 Discomfort is Front-Loaded + The Happiness Equation
07:43 Observation Number One: The Idea Comes Later
09:26 Pivoting Isn’t Linear
12:32 Observation Number Two: Fiction is Way Harder Than a Documentary
15:37 Observation Number Three: Taco Bell Prioritization
17:39 The End: Execute Through Stories

Transcript - Feel Free to Read it Like a Long-form Article:

Today, we’re going to talk about a few things I’ve learned in the last 40 years. Really, one thing. How discomfort leads to happiness and how we’re all very much ignoring that despite the fact that it’s the only thing we should be paying attention to. It’s the only direct line.

I know that’s a bit of a vague opener, and my podcast consultants are very clear that a good podcast starts by telling your audience exactly what you’re going to tell them, then tells them that thing, then ends by telling them what you told them, but those same consultants also told me that the pun restaurant names were getting, quote, distracting, and I get emails about those all the time so today I’m going to let the vibes be my guide.

Also, that phrase let the vibes be your guide came from a shirt I saw a girl wearing this morning at my local coffee shop. My first instinct when I saw it was, now there’s something I should never under any circumstance say, but here we are.

Which, sort of, brings us back to today’s episode. So, let’s get started.

Discomfort is Front-Loaded + The Happiness Equation

I turned 40 a few weeks back, and that’s … something. 40 is an age where, unless you’ve got your head entirely up your ass, you can’t help but to have learned a few things. I’ve spent a lot of time the last month or two trying to figure out what those things are.

40 is a funny age because people younger than you think you’re old, people older than you think you’re young, and you can feel either depending on the direction of the breeze. I felt old walking around my old neighborhood in NYC two weeks ago and I felt young this past weekend in my suburban Connecticut town. I feel old on Youtube, young on Nextdoor, and like I want to put toothpicks under my toenails and kick a wall on Linkedin.

40 is also funny because once you turn 40 there’s a really good chance you can go the rest of your life without taking any sort of voluntary risk. It’s like that stat that 90% of people over the age of 30 will never sprint again. I bet that 90% of people over 40 never do anything that purposely makes them uncomfortable again. We gather debris and baggage and wounds and whatever else those first 40 years like we’re wiley coyote tumbling down a mountainside picking up sticks and tumbleweed, and we eventually get so big we lose all our nimbleness. The more mass you have, the stronger the inertia will be to just keep doing what you’ve been doing.

If this was plotted on a graph, with things you do that make you uncomfortable on the Y axis and your age on the X axis the line would start high and then go diagonally down until it eventually hits zero. Probably, somewhere around 40.

Look at my son.

A few weeks ago at a brewery he wandered over to a group of kids a bit older than him playing with trucks in the gravel. He grabbed a truck that no kid was playing with, started playing, and then the owner of that truck, a kid maybe a year older than the little guy, aggressively slapped his hand and screamed “mine.” That kids parents watched and did nothing, which isn’t relevant to the story but still pisses me off, and then my son got up, gave a little shrug, and wandered to a new group of kids he’d never met and played with them instead. He had a blast. He’s still nimble.

It got me thinking that over the next 15 or so years he’ll try out for sports teams and take tests and maybe go audition for the lead in the school play. Some of those things will go well, some won’t. He’ll write will you go out with me on a little piece of paper and drop it on someones desk and they’ll check one of the boxes and he’ll be elated or he’ll be crushed. Maybe he’ll apply to college and get in some places and get rejected some places and he’ll show up on campus somewhere not knowing a soul.

Risk, and general discomfort, is front-loaded for humans.

Which might not sound like a problem at all. You get your lumps early, then cruise, right? You can tell by my tone that, no, that isn’t right, because if we were to do another visual math thing on the podcast, well known as the best medium for visual graphs and equations, we’d draw out the equation for happiness.

This equation is simple, but it still took me 40 years to learn.

Happiness equals reality minus expectations.

Put simply, happiness is when you surprise yourself. When you do something you didn’t think you could. When something is better than you’d expected.

Now, there are two ways to weight that equation and stack the deck for happiness - first, you can try ambitious stuff and be successful at it, or second, you can lower your expectations so reality consistently rises above them. I wholeheartedly recommend both.

But what usually happens when you get older is you do less ambitious stuff but raise your expectations. You want great, but you aren’t willing to pay the uncomfortable tax to get it. Maybe you think that you’ve already paid your lifelong uncomfortable dues, but that’s not how this works. Discomfort doesn’t work like rollover minutes.

So, you’ve unconsciously tilted both variables in the equation the wrong way and stacked the deck for unhappiness. We think avoiding discomfort makes us happy, but it all but guarantees the opposite.

So, what’s the point of this intro?

I was looking back at all the things I’ve learned over the years and the things that made me happy. I’ve also looked at all the things I’ve seen our founders do to be successful.

A bunch of things jumped out - I’ll cover some today and some in other episodes at some point - but such an enormous amount of it had to do with that inertia I mentioned. The wiley coyote ball of mass that, eventually, gets us on a track that guarantees the opposite of what we want.

Unless we do something about it.

So, that’s what today’s pod is about. Doing something about it. Things I’ve seen other people do to avoid it.

My son has no problem walking up to every kid he sees and trying to play with them, because he’s only thinking about the upside - what if they’re the best truck player on the planet? I avoid talking to the parents of the kids he plays with because I’m worried about the downside - what if they’re boring and saying hello ropes me into a 7 minute conversation about their job as a strategy consultant at Deloitte?

Kids maximize for upside, adults protect against downside. One group is much happier than the other.

So, let’s jump into a few things I refuse to call hacks because that word is dumb, but for today we’ll call observations that might be helpful for you. It’s less organized than usual, maybe, but as our good friend at the coffee shop says, we’ll let the vibes be our guide. And with that, I promise I won’t say that phrase again.

Or will I… find out, after…

The pod consultants are going to love that cliffhanger.

a little smooth jazz.

Hey!

We’re starting to offer some new products, specifically a few one-off workshops. There’s one on setting up your life to support a startup idea on the side, one on finding your north star and setting up a long-term vision, and one where we’ll kick off customer interviews.

Head to gettacklebox.com/workshops and click on the details to let us know which you’re interested in being on the list for. We’ll go first come first serve.

Back to it.

Observation Number One: The Idea Comes After

There’s a story I’ve heard a few times but have never been able to confirm, so it might not be true true. But I’ve heard, and seen, versions of this play out so many times that even if it’s not capital T true, it’s definitely lower case t true.

The story is that JK Rowling, author of the Harry Potter books, came up with the idea for Voldemort, the bad guy in those books, when she was mostly through writing book one of the series. The whole thing was initially just about a boy who didn’t know he was a wizard and got thrust into the wizarding world at the age of 12. Which is, honestly, interesting. But it’s just fine. With Voldemort, it becomes generational.

The Simpsons writers have talked about something similar. They rush to get the first version of an episodes script out so that they can figure out what the episode is actually about. They figure out the key points after the script is written, then go back and edit it with the focus they found.

As I’ve started writing a fiction book on the side of the pod and Tacklebox, I’ve trusted this process and it’s extraordinarily weird. I sit down with a blank document and a very vague whisper of what I want the book to be about - basically all I started with is a guy who goes to live in a northeast beach town to try to figure out his life - and I write. Eventually, things happen on the page. And then I think about those things and mix them with other ideas and build on them. The story sits in my subconscious and when I’m driving or showering I’ll think of something that might move the plot forward. And now, after a month or two of this, I have an idea for a book. The idea came after maybe 50 hours of writing and two months of thinking. And now I can start.

Entrepreneurs often talk about “pivoting” in a linear way. The idea for Instagram for dogs popped into your head while you were on vacation, so you built instagram for dogs. But, people used it as a dating app instead, noting that they were single on their profiles and commenting on other single people’s dog photos and organizing meetups in parks. So, you pivoted and built that app. And yes, in that scenario the dog dating app is called Fetch.

But the general idea of an idea will come to you fully formed, then you’ll pivot to a different fully formed idea is so wrong it pains me to even say. And I think it comes from the X for Y days - the, I’m building Uber for Dentists or whatever.

The actual way these things work is, sure, you might have the idea for instagram for dogs, but then you do some customer interviews and realize that idea doesn’t solve any real problem, so it’d never get enough momentum to get to a pivot. It’d just be nothing. But, along the way you learn about a different bleeding neck problem this customer has, which is maybe that they’re back in the office four days a week and their dog no longer gets a morning hike and they’re gaining weight. And so you thrash on that for a bit, and, four months in, you’re running a concierge mvp with people walking each others dogs and then something starts to take shape.

There’s a clear and obvious tax on interesting stuff in this world.

That tax is doing uncomfortable things with a lot of uncertainty around them.

Building Instagram for dogs isn’t uncomfortable and has no uncertainty. You can play entrepreneur and hire a development shop and get good branding and launch. That’s comfortable. And it won’t work, and then you can say - aw shucks 95% of startups don’t work and head back to whatever job you had.

Paying the tax is doing things most people are unwilling to do. There are no $20 bills on the sidewalk. You’ve got to search high and low for it in places other people haven’t been with no guarantee that you’ll find anything.

The tricky part here is that when you flounder, you feel uncomfortable and that certainly doesn’t feel like happiness. It seems like a straighter path to happiness is a clear set of goals. But that wandering gets to the ambitious, unique thing that can truly shift that happiness equation.

So, I guess the moral here is, you’ve got to set up your life to flounder. To do stuff every day that, as a byproduct, will produce interesting, and more importantly, unique startup ideas. Or, unique opportunities, if you’re just thinking about this as life advice.

Every one of our successful founders has gone this route. They came in with something that was immediately and entirely wrong. They thought they’d found a $20 bill on the sidewalk but it was a starbucks receipt. Then, they dig around places where they’re interested and, after a bunch of false starts, find the solid core of an idea worth building.

So, you probably need to recalibrate what you think it looks like to work on something new. This impacts the happiness equation on both sides. It ensures you’re after something ambitious, and creates a realistic expectation for your first idea. It’s a double whammy.

Which brings us to the next idea.

Observation Number Two: Fiction is WAY harder than a documentary

The obvious next question is, how the heck do you look for ideas in unlikely spots? Or, find these unique threads that other people can’t find? Where’s the ambitious stuff hiding?

Well, here’s another lesson I learned from the writing thing.

I reached out to a number of authors I admired about getting ideas for first books, and every single one suggested starting with an existing story. A direct quote was “writing fiction is WAY harder than writing a documentary. Your book can still be fiction, you can add in the gaps, but start with a story or a number of stories and stitch them together. Great stories are true stories. Get a few people to tell you their stories, then write them out and combine them with your twists, and they’ll feel true.”

Looking for startup ideas is the same.

The best way to thrash around and chase down an idea is not sit at home and read a bunch of articles and tweets and rack your brain to combine AI plus a customer plus a problem.

Tons of founders have shown up on our door step and said something like, “I bet auto dealerships would LOVE to get an email each day with email addresses of all the local people who have cars that are 10 years or older. We can easily use AI to do that,” then went and tried to build and sell that thing. They end up writing copy for a theoretical customer, build a product for that same made up person, then try to sell it to them with a bogus view of their experience. It’s a work of fiction.

Documentaries are so, so, so much easier.

The way to come up with ideas, or find meaningful insights, is to pretend you’re making a documentary.

Want to build something for people who own car dealerships?

Go pretend you’re writing a documentary on them. Not literally, although it’s not the worst idea I’ve heard. Figuratively.

Go and watch them work for hours, days, weeks. Look over their shoulder as they try to sell cars - to people on the lots, to people over email, to people over the phone. To past customers, to new customers. Look at how they fulfill orders. And do what any good documentary does - match the action of what’s happening with the depth of the emotions the person feels during that thing.

Then, go to the customer side. Watch people buy cars. Watch them talk about buying cars. Understand the lead up.

You’ll have twenty ideas, and you’ll have actual context. And, those ideas are things you got by chasing discomfort. Because, how the heck are you going to shadow a car dealership guy for two weeks? I don’t know. But that’s your job to figure out.

Do the thing. Don’t pretend you’ve done the thing and then try to create something you think would be helpful in that theoretical scenario.

The world is full of people doing backflips to avoid doing the thing or watching someone do the thing. That’s not ambitious. That won’t help our happiness equation.

Unique inputs deliver unique outputs.

Which brings us to Observation number three:

—

Observation Number Three: Taco Bell Prioritization: Prioritize Your Day By Physical Pain

One of our best alums did a call a few years ago with some current members and a great question was asked:

“How, especially early, do you prioritize what you work on?”

This is a tough question for entrepreneurs because you can literally work on anything at any given moment. The shock of not having a boss or a quarterly plan or yearly set of KPIs to meet once you leave a regular job is jarring.

His answer was what I now call Taco Bell Prioritization.

“I look at my list of things that I want to get done,” he said, “and I pick the one that makes me feel queesy. The one that’s most uncomfortable. The one I most want to avoid. If there’s nothing on the list of things that does that, I spent 10 minutes and try to think of one. The reason is that basically everyone working on the same idea as you will come up with the same stuff to do. And if our goal is to be meaningfully different, we need to do stuff that other people don’t do. Everyone pushes away from discomfort, so if I prioritize leaning into it I’ve guaranteed that I’m doing stuff different than my competitors. And, if I’m doing something that feels comfortable, that’s what everyone else is doing which means I’m wasting my time.”

The follow-up question was, what about the other tasks. The stuff that maybe doesn’t make you feel queasy, but needs to get done.

“For those,” he said, “I rank them by best case worst case. I look at everything I need to do and think, what’s the best case scenario for this task and what’s the worst case scenario if it doesn’t get done. Then, I rank everything by highest ceiling and lowest floor. And I attack it that way. I handle the stuff that can destroy the business first, then I handle the stuff with the highest possible ceiling. Then I get to the stuff in the middle. But I never actually get to those. They don’t usually matter.”

There you go.

Taco Bell Prioritization. Do what makes you feel queesy. This ensures that, if the thing works, you’re working towards something ambitious. Something that helps with that happiness equation.

—

The End - How to Execute on these: Tell Stories

If I asked chatgpt to give me a ten word synopsis of this podcast, it’d probably be something like “discomfort leads to happiness, so build a world where you consistently do uncomfortable stuff.”

Actually, let’s try it. Here’s what I came up with:

"Discomfort fuels happiness; consistently pursue challenges for personal growth."

Meh. It’s a little too conference slogan-y for me, but not terrible, robot.

The important part of this, though, is how to actually do it. Because there’s a reason people push away from being uncomfortable regardless of how many times I say that everything good in life needs to get worse first. They’ve got a bunch of inertia pulling them towards what they normally do. They need a way to break that inertia.

Constantly writing stories is the best inertia breaker I’ve found. Specifically, two types.

First, the best case scenario story. The story of your future self being successful with whatever thing you’re scared of doing.

So, if you want to speak to those auto dealerships but are understandably hesitant, take 20 minutes and write the story of yourself a few months out. The wild success story. In a few months, you might be knee deep in a concierge mvp with one dealership, and be using that positive experience to sign LOIs with a few others. Suddenly, the uncomfortable piece is a small part of a big, ambitious story.

The second type of story is the Daniel Tiger SOP we’ve talked about. Where you just describe exactly what’s going to happen to make it less intimidating. So, for the auto example, You’ll call up a dealership, ask if you can come in and buy the owner lunch and ask a few questions, and they’ll say yes or no. If they say no, you move on to the next. If they say yes, you buy them lunch and talk about their business, then ask if you can come in and watch them for an hour while they solve a specific problem. There’s a yes or a no. The idea is that spelling all of this out breaks the discomfort spell. Because nearly everything big and scary isn’t bad when it’s broken down.

All of this allows you to build up your endurance and capacity for doing hard things. It’s just like any skill. You get better and do it more. Except this skill leads directly to you being happy.

A bit of a random episode, but some stuff I’ve been thinking about at 40. I let the vibes be the guide.

I promise, that’s the last time.

Also, someone should start Fetch.