Dan has been a software engineer for 25 years, more than 15 of them at the same telecom company.
He wants to move into a senior AI role, and for three years he’s been hoping a layoff would make the decision for him.
I loved that. I told him he was the first person I’d spoken to that month who was waiting for a layoff that never came.
His plan was simple. A layoff would come with a package worth nine or ten months’ salary, and he’d take it and go.
But the package never came, and he knew exactly why: “If you work hard, they keep you. They don’t want to cut you.”
So the push Dan was waiting for was never going to come from his company. Being good at his job made sure of that.
I asked what had stopped him from leaving on his own three years ago. His daughter was in high school, and he wanted to be around before she left for college.
Fair enough. Then came the real answer: “I don’t have any specific reason. It’s just the artificial barriers I put.”
Another barrier was the interview. It’s been 17 years since Dan sat on the candidate’s side of the table, even though he’s interviewed people himself.
Facing a young, smart guy from a good college and not knowing an answer is the last thing he wants, so he kept waiting to feel fully ready.
Dan already knows the catch: “You’re never fully ready.”
And he isn’t starting from zero. He uses AI coding agents in his regular work, leads an AI project at his company, and is studying for an AI architect certification.
The skills are moving but the decision isn’t.
I told Dan none of this is unusual.
Early in his career, he was putting in 14-hour days, hungry to build a name. Now the name is built, the pay is good, and the company values him.
Getting comfortable is a byproduct of that success. The problem is that it gets in the way.
I’ve seen people with four kids get jobs. Most of the time, these barriers are excuses we give ourselves.
So Dan doesn’t need a layoff, a better time, or the feeling of being fully ready. He needs a date he picks himself.
He’s picked one: February.
That’s hiring season, and he wants to walk into those interviews ready. Work is quieter for him in November and December, and he has a lot of PTO to use up, so he plans to spend those two months learning.
P.S. If you’re a senior engineer and part of you is still waiting for a layoff to make the decision for you, apply here. I’ll tell you what I’d do in your shoes.