Enjoy the Journey

Your career path will be messier than you've been told, and that's okay

My career has had more twists and turns than San Francisco’s famed Lombard Street (IYKYK).

When I share my career journey, I usually skip straight to my time working in startups during the dotcom boom of the late 1990s—but I actually started my career in retail and reprographics before moving into tech.

At the ripe old age of 25, I was a vice president overseeing sales, marketing, and customer service for a reprographics company with an $80,000 per year salary and a company car.

I was never brave enough to drive my company car on Lombard Street, however. Photo by NISCHAL MALLA on Unsplash

I gave it all up for an individual contributor marketing manager role, half the salary, and stock options. 🙄

And here’s the thing—I’d do it all again. In fact, I did do it again.

Fast forward a few years and I was once again a vice president, this time for an e-marketing startup. And once again I took a lesser role and salary to make a pivot, this time into education.

From there my career progressed along a traditional path for awhile. I rose from manager to director to CIO over the next few years, and then became CIO at progressively larger and more prestigious universities.

But just when I was at the top of my career, I made a change—again.

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From CIO to … Senior Manager?

Amazon is notoriously flat—just eight role levels for hundreds of thousands of employees, from L4 (entry-level) to L12 (the CEO). Where some organizations have title inflation, Amazon has title deflation.

Given the scale that Amazon operates at, it’s not uncommon for CxO-level leaders with significant scope and impact in smaller¹ organizations to join Amazon at the L7, or senior manager, level.

So there I was: a four-time CIO, vice president across multiple industries, and board member for an international association, now a senior manager at Amazon.

It can (and did) feel disconcerting to go from a CIO/VP to being a senior manager.

I also missed having my own office. But I digress … Photo by Deliberate Directions on Unsplash

I’ve even known folks who’ve turned down an offer from Amazon because of the title.

But that’s … short-sighted, perhaps?

A title is just words. It can signal the scope, responsibilities, and compensation of a role, but lacks the context within which the role is being performed.

The scope of work you do at a company like Amazon—and the scale you do it at—is far greater than that of the senior-most leaders in virtually any other company.

The Messy Truth

My experience isn’t unique. We have been sold a bill of goods about what our careers should look like:

• a linear path

• eventual transition from IC to manager

• continual progression of titles

This may still be the reality, for a select few.

For the rest of us, however, we come to realize that there isn’t a singular “career ladder” but a series of ladders—some short, some longer, some only reachable by stepping sideways … or down.

My rather rudimentary depiction of these career ladders, thanks to ChatGPT and Photoshop. But you get the idea …

If you’ve reached the top of the ladder you’re on but aren’t ready to stop climbing, you may have to “step back to move forward.”

And that’s okay. Normal, even if that’s not what we’ve been told.

Like life itself, careers can be imperfect and messy—two steps forward, a step to the side, one step back—filled with twists and turns along the path.

Buckle up, and enjoy the ride.

Photo by Jacob Kiesow on Unsplash

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Bonus read: When you are ready to move to another ladder, consider this practical guidance for successfully changing industries or roles:

Pivoting Your Career

1. Smaller is relative. I’ve met some impressive, accomplished, and truly amazing L7 leaders—folks who were company founders, Fortune 1000 CEOs, state CIOs and CISOs, and military generals prior to coming to Amazon. 🤯