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.

Contrary to popular belief, I don’t believe learning in careers is linear.

Instead, I see learning and professional growth following an S-Curve:

The S-Curve of Learning

In startups:

• Business growth follows the trajectory of an S-curve

• If growth slows, you may have saturated your market

• To re-ignite growth, you must expand to new channels, segments, products and markets

• Over time, you stack multiple S-curves to sustain business growth

In careers:

• Professional growth also follows the trajectory of an S-curve

• If growth slows, you may have saturated your learning opportunity

• To re-ignite growth, you must navigate to new skillsets, roles, industries, and markets

• Over time, you stack multiple S-curves to sustain professional growth

What’s the takeaway?

Pay attention to your growth rate.

if it’s slowing down, ask why?

If you believe you’ve saturated your existing S-Curve…

… then perhaps it’s time to navigate towards a new challenge.

However, sometimes growth isn’t the only dimension that matters.

Sometimes it’s about the money:

Define what’s “enough”

This is the age-old question.

What’s your freedom number?

Hampton recently surveyed their group of high-net worth founders.

What they discovered was a moving goalpost:

At every net worth level, respondents aimed for a goal roughly 2x-10x their current wealth.

My take on this:

If you don’t understand your why, it’s almost guaranteed you’ll move the goalpost after hitting your goal.

And this just sets you up for another rat race.

So how do you decide what’s “enough?”

I would start with clarifying your personal values.

Then clarifying how you’d spend your time:

What would you do with your time if you magically won the lottery and never had to worry about money again?

Write your answer down in excruciating detail.

Map out a Google Calendar for A Week in the Life of Jessica Post-Lottery.

This is much harder than it sounds.

Pro-tip: Treat your schedule as a hypothesis, then validate it.

• Use a sabbatical or mini-retirement to experiment with implementing the schedule and see how it feels.

• E.g. 90% of people I ask this question to say they want to “travel,” but in reality, most people start tiring out from it after 6-12 months.

Once you have this set of activities, work backwards to the numbers.

How much do you really need to pull this off?

Chances are, it’s less than you think.

Build the courage to choose happiness

I’ll end this edition with a story of Derek Sivers I love.

In 2009, he wrote about selling his company, CD Baby, for $25M and then giving it away to charity.

Before the sale, he moved the company into a charity trust – The Independent Musicians Charitable Remainder Unitrust.

In practice, the sale proceeds were no longer owned by him. They belonged to the trust.

This meant the trust’s investments will grow tax-free until Derek’s death and then be used to benefit musician education (his charitable cause).

And while he’s alive, he’ll be paid 5% of the trust’s value per year.

Why did he do it?

Yes, he saved on taxes (to the tune of $5M). But I doubt that’s the only reason.

This is what he had to say:

In other words, don’t be afraid to choose happiness and “enough.”

In Summary

Figuring out if and when to make a career pivot is hard.

Here are a few tools I’ve used to help:

• Measure your Rate of Learning

• Define your “enough”

• Build the courage to choose happiness

🌐 Beyond your borders

🇸🇬 Why young Singaporean professionals abandon high-paying careers to be in business or pursue passion projects (TIS)

🧑‍💻 HENRY -> NENRY: A cautionary tale from FAANG-land (Reddit)

📱 Khe Hy: Don’t quit your high-paying job to become an influencer (Youtube)

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📆 How I can help

That’s all for today!

Whenever you’re ready, here’s 4 ways I can help you: