On mid-career satisfaction

Some observations on career satisfaction for ambitious mid-career folks in tech (from having coached hundreds of talented & ambitious people over the years):

1) Your career satisfaction in mid-career has little to do with how good your LinkedIn looks and more to do with your ability to combat career envy when it arises.

2) Corollary: Some of the most “successful” people on paper feel dissatisfied (and even sad, remorseful) because they haven’t found effective ways to cope with career envy.

This problem is global, but it is especially prevalent in the San Francisco Bay Area (and more so in the South Bay, Peninsula, SF).

3) This is not just a problem for managers and executives. Startup founders and CEOs are similarly susceptible.

4) This problem is getting worse with even more polarized outcomes of hot AI companies.

5) Taking a temporary break from LinkedIn can be a useful tactic when you’re experiencing career envy.

6) Other people will tend to judge your career by one or more of

- Title: big titles > small titles

- Money: “she was early at [hot AI company]”, “he just bought a home in Crescent Park”, etc.

- Scope: “runs 100 person series C startup”, “manages an org of 800 people at Google”

7) No one judges your career by your

- Competence in your role

- Flow when doing your work

- Culture & people fit

- Work-life harmony

- How you feel most Sunday evenings

8) Many ambitious people choose their next job based largely on Title / Money / Scope.

It makes sense, because these factors do actually make you happy when you accept the offer.

But they will stop making you happy starting the very first day of your new job.

This happens because we tend to take the items in #6 for granted once we’ve started the job.

We promise ourselves that we won’t take them for granted but we also reliably fail at keeping this promise.

9) The things that actually make you happy (and keep you happy) after your first day on the job are the items in #7, not the ones in #6.

10) The moment you make your career identity about the items in #6, you’ve made a deal with the devil.

Many ambitious people make this deal without really thinking it through, because they have been conditioned to believe that #6 is the only deal on the table.

11) There is no single career path that will work for everyone. But there is a career philosophy that can work:

In your job, you know you must first understand your users when building the product.

But you never consider that you must first understand yourself as you build the rest of your career.

Because when it comes to your career, you are the user.

12) What is the way out?

It isn’t easy, but consider this: once you reach certain levels of security and competence, your career is not a performance you are doing for an audience.

Your imagined audience doesn’t know you at all, doesn’t understand you, and doesn’t even care about you.

The audience does judge you, but that judging is just for soothing its own insecurities and fears.

The only true audience for your career is you and those dependent on you.

So if you want to perform, perform for that true audience. I hope you make it a worthy performance.