I Don’t Know How to Be a Beginner Anymore

When I was a kid, I wore holes in my parents’ carpet running the imaginary bases in imaginary Comiskey Park.

Not metaphorically. Actual holes.

I was obsessed with sports. My brother was much older than me, and I was the four-year-old following him and his friends around, begging to play whatever they were playing. I watched baseball and football and then recreated them throughout the house.

The kitchen had the five-and-a-half hole (the area between where the shortstop and third baseman play). I’d make diving plays in it. I’d spring up to my knees and fire the imaginary ball through the kitchen wall where I’d be the first baseman on the other end of an incredible 5-3 putout.

I’d jump over the couch pretending I was a running back going over the pile on 4th and goal.

I played hockey with a broomstick in the foyer and made the sound of skate blades cutting into the ice as I moved around.

My mom still tells the story about how I’d flip down a pair of sunglasses inside the house, announce, “Night game,” and take off.

And, of course, when Game 7 of the World Series came down to its final at-bat, I always hit the walk-off. I’ll also add before that walk-off, I routinely made home run robberies in the top of the 9th to keep the game tied. I also put my heel through some drywall by the stairs. My dad just saw the drywall but I don’t think he ever appreciated that was a heckuva catch (in my head)!

I loved sports.

That was it

Before there was a scoreboard.

.

Nobody was watching. Nobody was evaluating me. There was no audience, no ranking, no money, no followers.

Eventually, though, I got pretty good at actual sports in real life.

And that’s when the scoreboards started appearing.

Can you make the tournament team?

Yes.

The travel team?

Yes.

The All-Star team?

Yes.

Can you play at the next level?

Can you get invited to the Area Code Games tryouts?

Can you play Division I baseball?

Can you get drafted?

Can you make All-Conference? All-Region? All-American?

Can you play professionally?

And slowly, almost imperceptibly, something that started as I love doing this became I need to be good at this.

Then good stopped being enough.

There was always another level.

Another accomplishment.

Another way I could have been better.

That mindset served me incredibly well for a long time.

It also created a game I eventually became incapable of winning.

The scoreboard followed me

When my professional baseball career ended and my professional career began, I found another game that fit my brain almost perfectly: sales.

Sales literally gives you a scoreboard.

Here is your quota.

Go.

I loved it.

Hit the number. Beat the number. Blow through the number. How quickly can I get there?

Then, eventually, hitting the number wasn’t enough.

Okay, what’s my W-2?

It became like one of those carnival games with the giant hammer. How hard can I swing this thing? How high can I send the marker? Can I hit the bell?

So I swung.

And for a long time, the scoreboard kept moving in the right direction.

The funny thing is that eventually I started discovering that even winning wasn’t particularly satisfying.

Because I had developed an incredible ability to add two words to almost any accomplishment:

Yeah, but...

Yeah, but I could have made more.

Yeah, but I could have executed that better.

Yeah, but someone else did more.

And if the result was good but the process wasn’t?

Well, the process mattered.

If the process was great but the result wasn’t?

Suddenly, the result mattered.

It’s a pretty ingenious system if your objective is to make sure you can never win.

I’ve become a sore winner

I’ve always thought of myself as someone who is comfortable being a beginner.

I’m starting to think that’s bullshit.

Cooking is a great example.

I got really into cooking a few years ago, and in the story I tell myself, I was willing to suck at it. I learned. I practiced. I got better.

Except that’s not really what happened.

I kicked my own ass constantly.

I’d make something my family genuinely enjoyed and then explain to them why it wasn’t actually very good.

The plating wasn’t right.

I overcooked something.

The sauce wasn’t quite there.

Something could have been seasoned differently.

My family would essentially be saying, “This was great.”

And I’d argue with them.

No, no. Sit back down, let me present Exhibit A on why this steak is actually a failure.

I’ve somehow learned how to be a sore winner.

And I’ve done the same thing with golf.

I only started seriously playing a few years ago. Yet I would stand over shots with a tiny fraction of the experience of a truly accomplished golfer and evaluate myself against standards that made absolutely no sense for my level of experience.

I was applying a professional-level grading scale to amateur-level experience.

Ten hours in, grading myself against someone with 10,000.

Then wondering why I was frustrated.

Five essays should be enough, right?

I started this Substack because I felt like I had things to say.

That was basically it.

Writing seemed like an interesting conduit for some of the thoughts bouncing around in my head, and the barrier to entry was incredibly low.

So I started writing.

And I enjoyed it.

For maybe five essays.

That was apparently the probationary period I had graciously given myself to be a beginner.

Then the executive producer in my head showed up.

Okay, I’ve done this a few times now. Where are the readers?

Shouldn’t there be a couple hundred people by now?

How do I use this to launch a YouTube channel?

Could this become a platform?

Could this eventually become something big enough that I don’t need my primary career anymore?

Reading that back now is hilarious.

Five essays.

I had written roughly five essays and apparently expected the market to provide evidence that I had found my second act.

When it didn’t, I got discouraged.

Ten people read something I spent considerable time creating, and instead of thinking, Ten people read something I made, I saw the scoreboard.

10.

Not enough.

Therefore, maybe I’m not good at this.

Maybe nobody cares.

Maybe this isn’t it.

I’ve done the same thing with real estate

I’ve been interested in real estate investing for years.

I love the long-term nature of it. I love the idea of building something that produces income, appreciates over time and can eventually be passed to my children.

I’ve underwritten deals. I’ve gotten close to buying multiple times. Every time I’ve gotten close, I’ve learned something new.

And yet I haven’t bought one.

There are completely rational reasons for that. I’ve yet to find the combination of price, risk and opportunity that makes me comfortable enough to deploy the capital.

You could interpret that as discipline.

My brain has another interpretation:

You haven’t done it.

Zero.

No property means no point on the scoreboard.

Eventually that becomes: Maybe I’m never going to do this.

Which is an impressive conclusion to reach about something I haven’t actually tried yet.

I know how to pursue a target. I don’t know how to choose one.

This is the strange place I’ve found myself in lately.

For most of my life, someone gave me the target.

Make the team.

Get the scholarship.

Get drafted.

Win the deal.

Hit quota.

Make the money.

And I became really good at pursuing targets.

But I don’t think I ever learned how to choose one.

That’s a very different skill.

I’m fortunate enough to be at a stage of life where I have more freedom than I’ve ever had before. I have some financial flexibility. I have time. I have a family I love. I’ve had professional success.

These are the things I was supposedly pursuing all those scoreboards to obtain.

And instead of freedom being completely liberating, I’ve discovered it can also be incredibly uncomfortable.

Because now nobody is pointing toward the next goal line.

I have to choose it.

And I keep trying to use my old framework to do it.

Maybe I’ll start a podcast.

Yeah, but what’s the theme? Who is the audience? Why would anybody care?

Maybe I’ll make videos about cooking, golf, watches, sports, craftsmanship, or whatever else I’m fascinated by at the moment.

Yeah, but that’s not a coherent content strategy.

Maybe I’ll write again.

Yeah, but only ten people are going to read it.

The executive producer arrives before I’ve even made anything.

Maybe I need to be a beginner again

I’m not interested in pretending scoreboards are bad.

They’re not.

Competition has given me an incredible amount. Ambition has given me an incredible amount. I like getting better. I like winning. I don’t particularly want to become someone who doesn’t care about the outcome.

But maybe I’ve gotten the order wrong.

Maybe the game has to exist before the scoreboard means anything.

Maybe I need to record a podcast before deciding whether I’m good at podcasting.

Maybe I need to write more than five essays before deciding whether I’m a writer.

Maybe correctly rejecting a bad real estate investment doesn’t mean I’m failing at real estate.

Maybe I can hit a terrible golf shot without treating it as evidence presented by the prosecution.

Maybe I can stub my toe without kicking myself in the other shin for doing it.

Maybe I need to give myself permission to be comically bad at something again.

Because there’s something incredibly freeing about that idea.

Not lowering my standards.

Not abandoning ambition.

Just delaying judgment long enough to find out whether I actually love something. Or heck, even like it.

Before I knew whether I was good

I keep thinking about that little kid in my parents’ house.

Before sports became part of my identity.

Before anyone told me I was talented.

Before the travel teams and college coaches and professional baseball.

Before I needed any of it to tell me something about myself.

I just played.

I played hockey with a broomstick.

I dove through the kitchen.

I jumped over the couch.

I wore holes in the carpet running imaginary bases.

There wasn’t a coherent strategy.

There wasn’t an audience.

There wasn’t a business model.

There wasn’t even a real scoreboard.

I just loved the game.

I’m not trying to become four years old again. And I’m certainly not giving up on ambition.

But perhaps the next thing I need to learn isn’t how to work harder, accomplish more or raise the bar again.

Maybe it’s how to start something before I know whether I’ll be good at it.

So I’m writing again.

I’m not waiting for the perfect publishing schedule. I’m not figuring out how this becomes a YouTube channel first. I’m not building a growth strategy before I hit publish.

I’m just going to publish it.

Maybe ten people read it.

That’s ten more people than were watching me wear holes in my parents’ carpet.

And somehow, that kid kept playing anyway.