Today, in 10 minutes or less, you’ll learn:

• 🧑‍💻 The shift from traditional to modern careers (and why it matters)

• 📈 How to measure your career growth using the S-Curve of Learning

• 🤑 The surprising truth about "enough" money and choosing happiness

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🖊️  When to make a career pivot

If you’re reading this, you’re probably a high-achiever.

You’ve attended a top-ranking university.

You’ve climbed the career ladder faster than your peers.

You’ve been promoted, gotten multiple raises, and grown your income rapidly.

Everything is just groovy…

… or is it?

On the flip side of the coin, you feel the hum of low-grade anxiety.

You feel like you’re running on a hamster wheel.

You dread the arrival of Mondays.

This was me a few years ago.

My colleagues were patting me on the back for my rapid career trajectory. While on the inside, I felt empty and lost.

It felt like my life dreams were getting further out of reach.

That’s when I seriously considered the career pivot.

In this newsletter, I’m going to examine the question: “How do you know if and when to pivot your career?”

Traditional vs Modern Careers

In the 21st century, the definition of careers is changing quickly:

• Traditional Careers: 1 career across ~45 working-years

• Modern Careers: 4-6 careers across ~45 working-years

According to this definition, I am 110% pursing a modern career.

Here is how I view the nature of 21st century careers:

• A person’s lifetime is a series of 4-6 career seasons, each spanning 7-10 years

• Each season is long enough to build expertise

• Each season is short enough to go deep in multiple areas

• Each career change is an opportunity for reinvention

I’m 33, so I can see the second season playing out in my life and the lives of my friends.

Here are a few examples:

• Friend #1: Worked in corporate marketing/strategy for 6 years, MBA for 2 years, and now bootstrapping a B2B training business

• Friend #2: Built startup communities/content for 8 years, and now teaching dance

• Me: Worked in internet product management & growth for 10 years, and now building an online education business while consulting

Even before the 21st century, you can find fascinating examples of career seasons in history.

Let’s take one of my favorite case studies, Ben Franklin:

• ~24 years as a printer, running his own printing shop, and publishing the immensely popular Poor Richard’s Almanack

• ~6 years as a scientist, from his first experiments with electricity to getting elected to be a fellow of the Royal Society in London

• ~40 years working in politics as a postmaster general, congressional delegate, governor and even as a US diplomat for 9 years

This is imprecise because a lot of his career paths overlapped.

But if Ben Franklin could pull off career seasons 250 years ago, then we can too.

Do you feel stuck in your current season?

Try one of my favorite career tools - measuring your Rate of Learning:

Measure your Rate of Learning

For high-achievers, learning is absolutely crucial.

When you feel like you’re learning and growing, things are peachy.

But when you’re stagnant, all hell breaks loose.