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Ask Gorick: “Career pivot at 37?”

Last Updated:

May 29, 2025

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Welcome to Edition #24 of Ask Gorick Anything. This AMA is part of Gorick's Newsletter, where Harvard career advisor and Wall Street Journal bestselling author Gorick Ng shares what they don't teach you in school about how to succeed in your career.

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→ Read time: 5 min

ASK GORICK ANYTHING

“How to make a career pivot at 37?”

Have a career question? Ask me here.

Subscriber’s question:

“I am struggling with pivoting to a new career; I am 37 years old and have been at the same company for almost 15 years. I like where I work but have been feeling stagnant and know I am capable of much more. I have let comfort take over me. I am sad and stressed but determined to make a change. Do you have any tips or any specifics on how I can break this down? I appreciate your time.”

— Anonymous from Houston, TX, USA

Gorick’s response:

Hi Anonymous,

Thanks for sharing your story with me and for your trust!

First off, I want to acknowledge that what you’re feeling is totally normal. In an era where it seems like people are switching jobs left and right, it’s easy to wonder: “Should I be moving around too? What am I missing out on by staying?”

In contrast to many job switchers, though, you have a big advantage on your side, which is that you actually like where you work. At the same time, it would be disingenuous of me to also not acknowledge that switching jobs as a 37-year-old won’t be as easy as switching jobs as a 27-year-old, so it’s also important to be realistic.

Overall, I’d take the following 3 steps:

  • Step #1: Identify what’s going well
  • Step #2: Identify what you’re missing
  • Step #3: Identify the easiest transition

We’ll dive into each step shortly, but first, I’d like to share a framework that we’ll return to. It’s taken from my book The Unspoken Rules, chapter 14 (“Resolve Conflicts”), page 207 in the hardcover edition, and it looks like this:

Figure 14-2, “Potential root causes of your problem.” From The Unspoken Rules (https://www.gorick.com/unspokenrules)

The idea is this: When your job isn’t giving you as much energy as you’d like, it can be helpful to diagnose whether you’ve got a problem with the people, the position, or the place.

Why? Because a lot of people overreact when making a change:

  • They have a people problem and quit—not realizing that they could have simply switched teams and fixed the issue with a fraction of the effort.
  • They have a position problem and quit—not realizing that they could have staffed themselves on different work and again fixed their issue with a fraction of the effort.
  • They have a place problem and quit (the right thing to do this time!)—but didn’t diagnose the exact issue at their former workplace, so they end up somewhere different but with the same problem(s).

With this framework in mind, you might already have an idea of what you might be able to do. Could you…

  1. Switch teams (but stay at the same company)?
  2. Sign yourself up for different work (but again stay at the same company)?

If either of these options sounds compelling to you, pause here and start looking for people who can pull you into a new position or a new project. (Check out my “Oscars Bait” article for more tips on how to make yourself visible enough to get pulled into top projects and promotions.)

If you’re set on switching workplaces, keep reading.


Step #1: Identify what’s going well

Consider the above framework and ask yourself: “What ingredients of my job do I like—and want to preserve no matter where I go next?”

Make a list! You might, for example, tell yourself that you like (and want more of)…

People-wise:

  1. Coworkers who also have kids and who can empathize when you need to work alternate hours when things come up at home
  2. Managers who also have a technical background and who like digging into the details
  3. Clients who don’t sell or do something that doesn’t align with your values

Position-wise:

  1. A day-to-day that involves project management in healthcare and with minimal travel
  2. Long-term potential that includes eventually having P&L oversight
  3. Compensation/benefits that include fertility benefits

Place-wise:

  1. A company that’s stable and not a hypergrowth startup that hires and fires quickly
  2. A leadership team that has domain expertise
  3. A company that isn’t overly bureaucratic

Step #2: Identify what you’re missing

Once you’ve identified the ingredients that your current workplace has, you’ll also naturally start to see what it lacks.

At this point, the most important thing you can do is ask yourself:

“Who do I know (or could get in touch with) who seems to have a role that gives me what I lack without sacrificing what I like?”

Then, get in touch with them, ask for a 30-minute call, and ask questions to validate whether your hypothesis is true! (Here are some Keanu Reeves-inspired scripts to try.)

If your hypothesis proves true, move to step #3. If your hypothesis proves false, keep repeating the process until you find the path that gets you the most pros for the fewest cons. (And remember: I’m not necessarily encouraging you to stay, but there’s no shame in deciding that the grass is greenest where you are now. Celebrate the fact that you didn’t waste your time.)


Step #3: Identify the easiest transition

There are 4 career transition types to consider. (I write about them in more detail in my Battleship Method article here.) In order of easiest to hardest…

  1. Stay in the same industry and same function
  2. Switch industries but stay in the same function
  3. Stay in the same industry but switch functions
  4. Switch industries and switch functions

I’m sorry to hear that you’re sad and stressed. I hope this process makes an otherwise stressful process seem more manageable! And I also hope that you’ll feel slightly less sad knowing that you’ve got a lot going for you that many other people don’t have!

For example, you have experience. You have a workplace you like. Moreover, you have self awareness. In short, you’re already doing great!

See you Tuesday for our next story and unspoken rule,

Gorick

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