Today, in 10 minutes or less, youâll learn:
đ§âđť The shift from traditional to modern careers (and why it matters)
đ How to measure your career growth using the S-Curve of Learning
đ¤ The surprising truth about "enough" money and choosing happiness

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đ When to make a career pivot
If youâre reading this, youâre probably a high-achiever.
Youâve attended a top-ranking university.
Youâve climbed the career ladder faster than your peers.
Youâve been promoted, gotten multiple raises, and grown your income rapidly.
Everything is just groovyâŚ
⌠or is it?
On the flip side of the coin, you feel the hum of low-grade anxiety.
You feel like youâre 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.
Thatâs when I seriously considered the career pivot.
In this newsletter, Iâm going to examine the question: âHow do you know if and when to pivot your career?â
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 personâs 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
Iâm 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.
Letâs 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 Richardâs 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 youâre learning and growing, things are peachy.
But when youâre stagnant, all hell breaks loose.
Contrary to popular belief, I donât believe learning in careers is linear.
Instead, I see learning and professional growth following an S-Curve:



