A Career That Lasts

Happy Sunday Friends!

Here’s one quote I’m musing on this week, two ideas, three favorites, and one question to take with you into the week ahead.

One Quote I’m Musing

“Waste no more time arguing what a good man should be. Be one.”
| Marcus Aurelius

I had a first this week.

Someone I admire asked me for advice to give to a young person trying to “find a career that will last for the next 20 to 30 years.”

That sounds normal until it happens to you.

It was an unusual feeling when the question comes from someone you’ve only ever asked questions of. Not bad. Just… different.

A small, uncomfortable truth: you do not get to stay an apprentice forever.

Behind the Question

The question was simple. Too big, actually.

“What should I tell them?”

We want careers to be one clean decision. One perfect pick. One door that stays open forever.

I don’t see a career that lasts 20 to 30 years as a title. It is a skill stack. It is reputation. It is adaptability.

Careers are not found. They’re built.

And they’re usually built in the least romantic way possible: through reps, drafts, and awkward early attempts that feel like failures.

We aren’t stuck because we lack talent.

We’re stuck because we’re trying to reduce uncertainty before we act.

In this realm, thinking isn’t enough.

You act your way into clarity.

If you expect to fail 80% of the time, that sounds discouraging… until you do the math.

Ten attempts at life gives you two wins.

A million attempts gives you 200,000 wins.

Same hit rate. Different life.

Your 20% is much larger if you try a million times than if you try 10 times. The failures still “amount to zero” because they stop mattering once your wins compound.

The real skill is not avoiding failure.

The skill is lowering the cost of failure, mostly in your own mind, so you can take more shots. Do this by engaging in disciplined initiative and reflection in your iterations.

Advice to the Young (and to myself?)

1) Time is your unfair advantage when you’re young.
There are more than eight billion people on the planet. If you love something, there are millions who also do, and some will pay for mastery. Early on, your edge is simpler: you can be wrong and recover. Elders expect you to try and to fail. They are looking for ways to help.

2) Run experiments while your life is still light.
When you have fewer attachments (wife, children, loans, mortgage) you have more vectors. Later, you can still pivot, but you pivot smaller, smarter, and safer. So explore early. Fail early. Cheaply. On purpose.

3) Apprentice with masters, with boundaries.
Take internships, shadowing, low-paid entry roles with masters who are where you want to be. Not forever, not blindly, and not in abusive environments. Time-box it. Learn fast. Extract the pattern. Move. Worst case, you learn what you never want to become. Best case, you earn proximity to someone great.

4) Take advice as input, not chains.
Take freely given advice gladly. But never surrender your agency to it. Take what’s useful. Test it. Discard what isn’t. Stay grateful.

5) Build the T, then stack it.
Broad base of competence, then depth in a first, single craft. Becoming an expert gives you a lens through which you will understand new concepts faster.

It also buys you respect with other experts. Not because you are special, but because you both know what it costs to become dangerous at something.

Then you stack your depth. Your T grows a second leg, then another, and becomes an M. Not because you’re collecting hobbies. Because you’re building leverage.

6) Adopt a philosophy.
Pick something and wrestle with it. Stoicism. Epicureanism. Religion. Machiavelli. Your own stitched-together code. Return to it often, especially after milestones and observe your changes in perspective.

7) Read like it matters

There is little difference between a man who chooses not to read and a man who can’t read. But the former can never improve.

Reading is your conversation and relationship with history.

No matter what problem you encounter, someone much smarter or much dumber than you, ran into it already. They succeeded or they failed, and they wrote about it.

And there’s a reason this matters: in many places and times, the powerful tried to keep reading away from the powerless, slave owners hid money in books knowing that slaves had no reason to open them. That should tell you what power lies in books.

8) Write, draft, and expect ugly first attempts.
Hemingway tells us, “The first draft of anything is shit.”

Your early work is supposed to be rough. Stop interpreting early clumsiness as a sign you picked wrong. It’s usually a sign you just started.

9) Apprentices are Anonymous.

When you fall flat on your face, no one cares enough at the beginning to judge you. You’re new.

Most people are too caught up in their own lives, problems, and plans to give you more than a fleeting glance. And even if they do notice, they don’t remember.

We track the masters and what they’re doing.

So enjoy the anonymity of being an apprentice.

Two Ideas From Me

1. Clarity is a reward for motion. Waiting to feel ready trains you to be still.

2. Your career is a numbers game with an identity wrapper. Protect the wrapper (your values), then increase the attempts.

3 Things This Week

Something to help you think, reflect, and act in your own voice.

1. A book: Range (David Epstein)

2. A book: Mastery (Robert Greene)

3. A song: “In the Middle” (Jimmy Eat World)

One Question to Take Into Your Week

Who is one person doing what you want to do, and what single question will you ask them this week?

Write it down. Time-box it. Take the rep.

Until Sunday, my friends.

Think Dangerously.
–e