A Question?

Hi My friend,

Are you still the same person you were when you started?

That's the question that wouldn't leave me alone a few nights ago when I was sitting in my office late, finished with the day's work, no phone in my hand, no music playing, no podcast in the background, just me and the room.

For the first time in a long while I actually let myself sit there in the silence without immediately reaching for something to fill it, and the questions I had been outrunning for months started catching up with me one by one.

Instead of distracting myself the way I normally would, I let them stay, and I sat there with them long enough to actually answer them honestly.

I don't mean the question above in some abstract personal growth way.

I mean it in the practical sense.

Am I still the same kid who was sleeping on a couch with $258 in his bank account, who took meetings with anyone who would give me 15 minutes, who had no leverage and no reputation and was hungry in a way that made every interaction feel like it mattered?

Or have I quietly become one of those guys who gets a few wins under his belt and starts believing his own marketing?

Because there's a version of me that the audience and the success and the income could turn me into, and that version is somebody I would not want to spend any time around if I met him at a dinner.

The honest answer is that I'm still mostly the same person, but I had to admit there are some places where the rot has started to creep in, and most of it shows up in small things.

Skipping conversations I would have made time for two years ago because they don't seem worth my hours anymore.

Getting impatient with people asking the same beginner questions that I was asking five years ago when I knew nothing.

None of these things are huge yet.

But they're the kind of small drifts that, if you don't catch them early, accumulate into a person you don't recognize anymore.

The next question that came up was harder.

What would the 19 year old version of me think of who I am right now?

I want to be careful with how I answer this, because the easy version of this question is to imagine your younger self being impressed by your current life.

But the more useful version of the question is whether your younger self would actually approve of how you got there, the values you held along the way, and the person you became in the process.

Because most of us, if we're honest with ourselves, would have to admit that the route we took to where we are now involved some compromises we wouldn't have made if we had been able to see them clearly at the time.

And the question worth asking isn't whether 19 year old you would be impressed by the income or the lifestyle.

The question is whether 19 year old you would still recognize the person looking back at him from the mirror.

The last question was the one that took me the longest to actually sit with.

What am I actually afraid of right now?

Most of us are walking around with a list of fears we've never really articulated.

We feel them in the background as a kind of low grade anxiety that we never sit with long enough to identify.

But when you actually let yourself name them, they get smaller almost immediately, because most of them turn out to be way less dangerous than they felt while they were lurking in your subconscious.

I'm not going to share the full list of mine because some of it is private and some of it is the kind of thing you only share with people who have earned the right to hear it.

But I'll tell you this.

The biggest fear that came up wasn't about money, or business failure, or any of the obvious external things.

The biggest fear was about becoming a person whose work I produce no longer reflects what I actually believe, because somewhere along the way I started optimizing for what people wanted to hear instead of what I actually had to say.

That fear was useful to identify because it told me exactly what I needed to do next, which was to keep writing newsletters like this one even when they don't fit a content strategy or a marketing calendar or any of the other things I'm supposed to be optimizing for if I were running this the way a business should be run.

Here's why I'm sharing all of this with you, and here's the part you actually need to take from this email.

Most of you have never sat in a quiet room and had this kind of conversation with yourself.

Not because you don't know it's possible, but because the silence is uncomfortable and the questions are scary and there's always something on your phone that can fill the gap before the first real thought has a chance to surface.

You go from one input to another input to another input, and the version of you that would have something honest to say if you ever stopped feeding it noise never gets the chance to speak.

The cost of never having this conversation is that you slowly become someone other people designed instead of someone you designed. Your values get borrowed from whatever feed you scrolled this morning.

Your goals get borrowed from whatever influencer you follow this week.

Your idea of success gets borrowed from whatever culture happens to surround you.

And by the time you're 40 or 50 and you finally do sit in the silence, you realize you've been chasing a life that was never yours in the first place, and now you have to figure out how to build something authentic with whatever years you have left.

The shortcut to avoiding that fate is to start having these conversations now, on a regular basis, while you still have the energy and the time to course correct.

Sit in the silence.

Ask the hard questions.

Let the answers come up even when they're uncomfortable.

Pay attention to the small drifts in your character before they become large ones.

And keep checking in with yourself to make sure the person you're becoming is somebody you would actually want to be.

Whoever you were when you started is the most valuable thing you have.

Don't let the journey turn you into a stranger.