Between layoffs and early retirement programs, a lot of people in midlife are now on the other side of a long corporate career. They might be mired in some of these questions: What did I actually accomplish? Oh god what did I give up for all that? Will I ever find meaning again? 

This internal audit can get uncomfortable, so that’s what we’re talking about today. When you’re in the middle of a reckoning, who’s the judge of your success?

The Midlife Reckoning

It’s normal to take stock of your career and compare yourself to others. At this very moment, you might be dwelling on the gap between where you are and where you thought you’d be by now. You look at your own meandering career path and think, why didn’t I become a doctor? Or a lawyer? Why didn’t I pick one lane and stick with it for my entire career?

For a hundred very valid reasons. You didn’t want to. Your circumstances made it impossible. Your interests were too wide and you felt like trying other things. And yet, there is still a weird kind of grief we feel when we abandon a goal we never even worked toward. This is an ambiguous loss – something we once really cared about or thought we wanted. Maybe it was your family’s expectations about who you’d become. 

I remember years ago, when my mom told me she was proud of what I’d done in my career. I was at a low point at that moment, so my response?  “I could have done more.”

Listen, if you lived your life over again with the same circumstances, same family culture, same set of choices in front of you, you would have done the exact same thing. 

Besides, we’re not living in a kid’s story book where every person has a clear job and that’s all they do. Doctors and lawyers have messy career paths as well, and their initial investment was so high that many feel trapped in professions they no longer love. 

And then you fall into the social distortion of LinkedIn. Hundreds of corporate rockstars sharing humblebrags and promotions. It can make you feel like your career was just a messy doodle that you called a resume.

The whole thing creates a kind of cognitive dissonance: you feel the sting of others waving their success in your face, you acknowledge that you didn’t achieve your goals, and you admit you stopped caring about those goals somewhere along the way.

Who’s Keeping Score

A lot of this internal deliberation is bathed in judgement. But who is the ultimate judge here? In the corporate world, that answer was clear. You had bosses and HR departments who doled out titles and compensation. Who decided how many heads your department needed. Even if the system was convoluted and aggravating, it was legible. You knew where you stood.

Maybe you helped to design the metrics. I’ve been in that position, too. You try to create a system that feels fair, is based on research. You tell yourself that people like rules, even if they rail against them. Rules keep the peace. 

Then one day you realize that all the metrics are arbitrary and borrowed. And they are helping you to become someone you no longer recognize. When you step back and look at the panoply of metrics you’ve measured your career against, the cracks start to show. A parent’s expectations, the career ladder at your company, what your friend group is doing. 

You might look for replacement metrics that will tell you how well you did. How you contributed to your city’s economy, or your own household. How you advanced your technical skills. But it still feels like a setup. I could measure my own career against a thousand imagined external metrics that all result in my failure. And that creates the conditions for a juicy rumination spiral.

The Rumination Tax 

I am a champion ruminator who replays career moments and awkward interactions over and over ad infinitum. That employee review conversation that went so poorly. My flopped presentation to a client. My clumsy and hurtful mistakes with friends – I can fret about all of them for months on end. 

All of that rumination comes with a cost. I can recall conversations with friends where I enlisted them to help me sort through what I worried about, only to understand later that I took up all the space and wasn’t available for them. I gave my friends a front row seat to my argument with the omnipotent judge in my head who I invented, then let that judge berate me for my failures. That took up a lot of my time and attention. It drained me of energy and blotted out the present moment. 

When I look back at my anxiety, I now wonder what I could have been doing instead. Swimming. Making that caftan I still haven’t made. I could have been spending time with friends who do not care at all if I have a marketable skill or if I was passed over for a promotion. I can dig up a lot of journal entries with tiny writing and remember what I was so spun up about, but not remember what was happening in my actual life at the time.

Focusing on the ways you came up short in the past robs you of the present. And it puts all the power into the hands of someone who doesn’t even exist. Someone you made up just to be mean to you.

You can stop being mean to you now. 

What to Do With the Time You Have Left 

This is more about a change in orientation than becoming a new person. 

You’re getting ready to leave the corporate world, or you already left. What are you going to do with the time stretching before you? It would be easy to slip into old productivity habits, but let’s make this about the expression of your values instead. 

One former client had a side gig as an animal communicator for years while she toiled away in  corporate. Her layoff was a wakeup call that pointed her to what she loves and believes in. The side gig is now the main gig. 

Let your fervent beliefs and most cherished ideas guide you. It might be service to others, or fostering belonging.

Or now might be the time to start the therapy you’ve put off for twenty years to sort out a pattern because you believe in personal growth and evolution.

You may have a long list of things you’ll get to when you aren’t working so hard. Rather than keeping them in side quest territory, they might become the thing itself.  It’s what you get to do when you stop measuring yourself with someone else’s scorecard.

The One Audit Worth Running

After you strip away the judgment and imagine a focus for the stretch of time before you, there’s one other audit worth running: what you’re good at that you like doing. When my clients start listing their skills, they often rattle off things like improving spreadsheets and handling difficult team conversations. Do you LIKE doing those things, I ask? No, they say, I hate it. Great. Take them off the list. 

Cataloguing the skills you actually enjoy using helps you salvage what was real about your career. It becomes a set of abilities that you feel proud of and shows you how you like to work. That will be the core material for what you build next.

You’re the Judge of You

You did enough. You could have done more. Who cares. The people you imagine judging your career path never earned the right to be the boss of you. Even if that judge is a parent or your high school Math teacher. And anytime you encountered someone bold enough to deliver judgments right to your face, consider whether that was coming from a place of joy or pain. I have a hunch which one it is.

The only question that matters now is what you’ll do with what you have.

If you stopped measuring your career using someone else’s definition of success, what would you find? 

Episode 43 cover art for Burn the Map podcast. A woodcut-style bird's-eye illustration of a winding, non-linear path through an open landscape with scrubby vegetation, split diagonally against a terracotta background. Text reads: Episode 43: Did You Do Enough?