When Jeff Bezos said "no" to my dream

Is the career ladder dead? Here's how you can build your own (relatively safely)

Hello, it’s Ethan & Jason. Welcome to a *paid subscriber* edition of Level Up: Your guide to grow fast, avoid mistakes, and make optimal career moves.

NOTE: The October cohort is the last of the year for Ethan’s signature course Stuck at Senior Manager - How to Break Through to Executive. Over 1,300 leaders rated it 4.7/5 with many sharing promotion success stories (example below):

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I asked Jeff Bezos if I could build “Amazon University.” He said no.

Amazon wouldn’t support my dream.

It was the best thing that ever happened to me.

In this article, I will tell you how you can build your own dream job relatively safely and share details from my process that you can apply to your “career ladder(s)”:

• The Old Ladder is Getting Wobbly, But it Still Works

• Multiple Ladders

• A Ladder to Where?

• Nailing the Steps

• Your First Steps to Freedom

• When You Need A New Ladder

• Be Flexible On The Ladder

The skills and interests that got me to VP at Amazon are not the same skills and interests that have allowed me to build my business after leaving Amazon.

They are related, of course, and I developed many of the coaching and teaching skills that I use now over the course of my corporate career.

However, as I progressed in my career at Amazon, I realized that I was becoming more drawn to teaching, coaching, and mentoring than to my day-to-day work as a VP.

This brought me to an inflection point—I wanted to be developing careers and leaders, but my job demanded that I focus on driving metrics for my business.

At first, I experimented with fitting my coaching work into my life as a VP. I tried holding office hours, streaming on Twitch, and various other methods. But, it eventually became obvious that my VP role was holding me back from being able to do the work I truly wanted to do.

So, I looked for a change.

Initially, I looked to make this change within Amazon. I wanted to build “Amazon University,” a school to teach career lessons from an Amazonian perspective. I talked to the appropriate internal leaders, including emailing Jeff directly.

When that idea failed to gain any internal traction, and I was faced with a choice:

Amazon or coaching and teaching.

I wasn’t going to be able to do them both.

So, I made a five-year plan to “retire” from Amazon and start my coaching business. I have now been running the business for five years, and I am making almost as much money as I did at Amazon while working less than half as much and feeling much more fulfilled.

I share this story because we often are told to think of our careers as “ladders”, but for many of us, we climb a few different career ladders over the course of our working lives. For entrepreneurs and other highly autonomous careers, we are responsible for building those ladders ourselves. And, as AI and other factors rapidly change traditional employment, it is more likely that we will all need to be more intentional with constructing our own careers.

Here is how you can manage and build your own career ladder(s) to climb to the career(s) of your dreams.

The Old Ladder is Getting Wobbly, But it Still Works

There is a lot of discussion about how traditional employment models are changing, as a result of AI, remote work, layoffs, “job-hopping”, and other factors. While I think this is true and immediately relevant for industries like tech, publishing, media, etc., there are many industries in which traditional career ladders are deeply entrenched.

The federal and state/local governments have rigid level structures that are likely to persist as a result of bureaucratic and structural rigidity. However, there are also careers in which the “old structure” is likely to remain intact for a long time—industries that are relatively insulated from the tumult of AI and outsourcing.

For example, I have two stepsons. One is a fireman and the other is working to become an electric lineman (the people who work on power poles). Both are union jobs and have strict hierarchies that explicitly take tenure into account. Also, both are essential jobs that require physical dexterity and strength. The field of robotics is a long way away from being able to replicate those jobs.

As a result, the career ladders that are built into the structure of some jobs (including the ones I have mentioned) are unlikely to change soon. The US and global armed forces, as well as academia, medicine, and established legal and consulting firms with associate/partner structures, are likely to preserve their hierarchies even if the broader industry ecosystems change drastically.

So, declaring the career ladder completely over is incorrect.

It is more fair and accurate to say that these hierarchies are fraying at the edges within corporations and individual careers where we are more free to move from system to system between companies.

But, since corporate information workers are the majority of my readers and the most affected by this fraying, here we are going to be very focused on how to construct new and effective career ladders of our own.

I will describe my process and tell you how you can apply the same approach in your life.