The feeling of being trapped by your job

Meet Burt (names changed to protect the innocent)

Burt is a software engineer, male, mid-30s, worked both in bigtech and startups. In his 20s he joined a Series A technology startup in a high cost-of-living (HCOL) area. Most of his compensation was in the form of stock options, but the company ultimately went nowhere and his options expired worthless. Afterwards, he joined a tech giant with a reputation of having a difficult culture, but ultimately returned to startup life.

When I asked him how he felt about money, this is what came up...

The vulnerability and powerlessness of being a cog in the machine

Burt expressed fear and anger about being powerless to influence the system he was a part of:

• "The social fabric of the company was unstable. The CEO didn't treat people well. I felt like I could fall out of favor with the CEO at any moment, and if I did, that would be the end for me"
• "An organization making dumb choices... I felt like the rot perverted everyone's incentives"
• "My fear, being powerless to fix these broken systems"
• "I felt fragile... like the sand could shift under my feet at any time"

I suppose it's fine to encounter a broken system that you are powerless to influence if you can escape. But many people feel like they can't escape.

Being vulnerable to circumstances outside of our control is part of life. We all understand this. I wonder if corporate leaders and managers get how this sense of powerlessness and vulnerability affects their employees.

Being trapped

Burt described the fear he felt observing his friend (let's call him Chuck) at a different company:

"I have a fear of being crippled or hamstrung, entrapped by the sickness of the system. Curtis comes to mind. I feel dread of being in his shoes... depending on a salary is like owing a debt, and having a bad boss is like having a high interest rate on that debt... institutions are sick and broken... sickness propagates through"

Burt was describing basic lifestyle creep--the obligations that come from being an average middle class person, and the financial dependence that comes with them. Chuck's obligations included:

• Mortgage
• Supporting the spouse and kids
• Car payments
• Saving for college
• Unexpected out-of-pocket medical expenses

In his view, no matter how bad the situation was at Chuck's employer, Chuck was trapped:

"This is classic situation I want to avoid--having a desk job and a high level of obligations. You're in a career, you're on a hill that keeps going up, and you can't escape. It's like having too much debt, too much interest payment"

And the deal just isn't good enough

Reflecting on his career, Burt's dominant emotions were anger and regret.

He felt anger because his expectations didn't match his reality:

• "The way I want the world to work: I want to show up, do great work and have great impact, and be fairly compensated for it. But it feels like that world doesn't exist for me."
• "I made a bad bet at the startup--living in an expensive city, with a low salary, and huge risk not just about the company's financial success but also the risk of getting on the CEO's bad side. I'm angry at myself for making a bad bet."

And his regret?

• "I burned out in my 20s, I pushed myself as hard as I could, had multiple health issues, depression, and I took years to fully recover. If I got laid off, does that mean I did a bad job?"
• "My feeling is regret... I gave so much and got so little"
• "There's a period in your life when you have to have a surplus... without it, you can't get married, have a house... I never got to build up that surplus"
• "A job--an agreement, selling your time--it's just not good enough."

A caveat

I want to remind the reader that there are upsides to W-2 life at a big corporation and there are upsides to working at a startup. Burt is also aware of these.

This post is about the raw emotions underneath all of the logical knowledge about tradeoffs and risk. If you're a manager, you need to understand that this is what's going on for a lot of the people that work for you. If you're a CEO, recognize that small actions by you have a large impact on other people. Don't be an asshole. Life is too short for that.

Questions for reflection

As you look at your career situation, I invite you to ask yourself these questions...

1) Where in my career or life do I feel trapped?

2) What aspect(s) of my career feel like the sand is shifting underneath my feet, or I'm at the mercy of people or circumstances I can't control?

3) What part(s) of the career bargain I've made feel like they are just not good enough?