And I see everyone gettin’ all the things I want

And I’m happy for them, but then again, I’m not

Just cool vintage clothes and vacation photos

I can’t stand it, oh, God, I sound crazy

Their win is not my loss

I know it’s true

But I can’t help gettin’ caught up in it all

jealousy, jealousy by Olivia Rodrigo

There are many paths to hit your financial independence numbers. In Connection 95 – Your Starting Point, I said I was currently focused on my career, consulting, and building an audience.

Today let’s talk about the psychological landmines of building an audience.

We defined building an audience as:

Putting out so much value via content (Twitter, a podcast, newsletter, etc.) that people pay attention.

I’m trying to crack my “consistency code”, which means publishing a blog post or newsletter biweekly. I’ve also been spending more time on Twitter.

A few things have become clear:

  1. Building your audience is hard. If you’re going to do it, you do have to treat it like a full-time job. Thoughtfulness and consistency don’t happen by accident.
  2. There is a long tail of success. I’ve come across so many examples of people who built audiences and leveraged that social capital for financial capital. Some do it via big tech exits, others are small SaaS builders, and others are creators. It’s an inspiring amount of data points.
  3. “Motivation” and “jealousy” are two sides of the same coin. My friend Buford nailed the sentiment with this tweet

Source

There are people on Twitter genuinely trying to give advice. The problem is digging through the mountain of humblebragging to get there:

  • “We grew from $400M to $4B in the last 10 months. That’s a 10x in 10 months. This wasn’t an accident, but it also wasn’t a given. The shift? We started making EVERY day count. What exactly does that mean? Let’s break it down” source
  • “Now that I have money, I see some people treating me differently. Don’t do this. I’m just a version of you that’s been in the game for more time. You can do this too. Never put anyone on a pedestal.” source

Here’s a typical spiral I plunge into when combing Twitter:

  • “That’s cool they did that!”
  • “I wonder what I can learn from them…?”
  • “Oh wow, they’re 25 years old…”
  • “Oh that’s just a project they do on the side…?
  • “How come I don’t have that?”
  • “What have I been doing wrong all these years?”
  • “Am I the kind of person who’s jealous of other people’s success?”

It’s exhausting. It’s distracting from doing the actual work.

Three mindsets have helped me navigate these psychological landmines. If you’ve felt something similar, hopefully they work for you:

1. You chose this

In case it wasn’t clear, there is no managing editor of The Connection. There’s no boss checking if this issue will ship. There’s no board I report to.

I choose to spend 30 minutes each morning writing things down, then re-organizing those ideas into a newsletter.

If you’re building an audience, you probably don’t have anyone to report to either. It’s your own ambition driving you, because you have something to teach, to say, or to prove.

You have total freedom. Which also means the freedom to abstain from the game.

If the FOMO gets too strong, you can stop listening to podcasts and quit Instagram. You can take your weekends back. Read a trashy novel. Take up frisbee golf. It’s probably an amazing, terrific life.

But…

If you do want the audience, you have to learn to navigate the FOMO and the jealousy. That’s the toll you pay to build an audience. To paraphrase Morgan Housel:

“It’s the cost of admission, and the trick is to convince yourself the cost is worth it. There’s no guarantee it will be. Sometimes it rains at Disneyland. You have to be willing to pay the price.”

2. You have enough

True story, Word of Honor:

Joseph Heller, an important and funny writer

now dead,

and I were at a party given by a billionaire

on Shelter Island.

I said, “Joe, how does it make you feel

to know that our host only yesterday

may have made more money

than your novel ‘Catch-22’

has earned in its entire history?”

And Joe said, “I’ve got something he can never have.”

And I said, “What on earth could that be, Joe?”

And Joe said, “The knowledge that I’ve got enough.”

Not bad! Rest in peace!”

— Kurt Vonnegut, Joe Heller

When I first moved to LA, I wanted a job — any job — to start my entertainment career. When I landed my first assistant’s desk in 2011 I was elated to answer someone else’s phone and read scripts. After two months, the novelty faded; what I really wanted was a writer’s assistant role. When I got that job, I had barely settled in before I started angling for a staff-writer role.

When I first shifted into tech, I was elated to just be in the room. In my first month, I was at a dinner with Directors and VPs of buzzy SF start-ups. The optimism, intelligence, and energy was intoxicating. Naturally, the high didn’t last long: I wanted to be the one DRIVING IMPACT and I coveted all the accouterments (pay, equity, recognition) that followed.

Looking back at these junctures, the problem wasn’t any of the roles, or the salaries. I didn’t always earn a lot of money but I always earned enough.

The problem was me.

The problem was this flavor of ambition, so prevalent and common in our culture of performative social sharing.

Ambition is a curious thing. It’s helpful for achieving career or financial freedom goals, but is it really useful if it distorts your ability to feel happy? Unchecked ambition dooms you to a life trading one set of handcuffs for another.

I’m proud of my career and personal trajectory but the incessant self-loathing caused by this type of ambition wasn’t necessary.

If you’re reading this newsletter, you probably have people in your life who love you and will miss you when you’re gone. You probably have the means to provide for yourself and your family. There are things you want to change, and you have the agency to do so.

In other words, you already have enough. Everything else is just extra.

If you ever feel like you just need that raise, that relationship with that one person, that one credential on your LinkedIn profile, and then you’d be happy, spoiler alert: you won’t.

3. Success = Pretty Good Returns X Patience

Any modicum of success I’ve had is the result of consistently showing up. I think that’s a definitive trait of success itself, and hardly unique to myself or anyone else.

Seth Godin puts it like this:

“Outcomes are important. But the outcome isn’t the practice, the practice leads us to the outcome.”

The problem with studying successful people, is you rarely see all “the showing up.” You only see the outcome, the 2% as they near the finish line. That makes “consistently showing up” appear terribly inefficient. So what do you do? You hunt for their roadmap, their secret, their shiny tactic. And it’s this wild goose chase that distracts you from both inputs that lead to success.

It’s another way in which success is like money: objectively an average 8% return YoY over 10 years is pretty good. But it’s difficult to be satisfied when you’re reading about 30% returns in 6 months due to some DeFi arbitrage hack, or YOLO’ing on GME at the right time.

To paraphrase Morgan Housel again:

“Good investing isn’t necessarily about earning the highest returns, because the highest returns tend to be one-off hits that can’t be repeated. It’s about earning pretty good returns that you can stick with and which can be repeated for the longest period of time. That’s when compounding runs wild.”

Why is any of this important?

Because blindly pursuing something like financial independence and money targets is a great way to flame out. You only need to look around at the Rich & Depressed to realize this is a journey littered with psychological land mines.

The worst outcome is not not reaching these goals.

The worst outcome is reaching these goals and stillbeing unhappy

Knowing (1) you choose this (2) you have enough and (3) success = pretty good returns X patience might give you the kevlar needed to make it through.

Sources:

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