In the last edition, I promised to continue the exploration of how AI is reshaping engineering careers. I still want to explore that question.
But with my LDX3 talk now less than 10 days away, I have been thinking quite a bit about my workload and bandwidth.
And since this is Labor Day weekend in the US, another subject has been on my mind: vacation.
A while ago, I joked with a longtime coaching client that I no longer have PTO. As an entrepreneur, it’s now UTO for me—unpaid time off. 🙂
Technically, I have the most unlimited vacation policy possible. I can take off whenever I want, for as long as I want, without compromising the support I provide my clients.
But when I am not working, I am not getting paid.
That has made the cost of vacation much more visible to me than it ever was as a salaried employee.
And yet, I have set a rule for myself: I want to take at least two meaningful vacations every year, each one lasting 1–2 weeks.
I know there will be a financial cost, and I have decided that the time away is worth paying for.
Unlimited does not always mean usable
This has made me think differently about the unlimited PTO policies that have become common across tech companies.
People are often suspicious of them.
Is “unlimited” really unlimited? Or is it a clever way for companies to avoid committing to a specific amount of vacation while employees quietly take less? It also reduces the administrative and accounting burden of tracking accrued PTO.
The policy alone cannot answer that question.
A salaried employee may continue getting paid while on vacation, but that does not mean the time off carries no cost to the employee.
Maybe nobody covers their work, so they return to an overwhelming backlog.
Maybe their teammates rarely take more than a few days off.
Maybe senior leaders respond to Slack messages throughout their vacations.
Maybe people worry that taking two weeks off will make them look less committed, less visible, or less essential during the next promotion or layoff discussion.
If one engineer taking two weeks off creates operational panic, the issue may not be vacation at all. It may be weak ownership distribution, poor documentation, or a team that has become too dependent on individual heroics.
The costs are less visible than the ones I experience as a business owner, but they can still shape behavior.
The real employee benefit is not unlimited vacation. It is the feeling that you’re genuinely able to take the vacation available to you.
A generous policy on paper tells you what the company formally allows. The behavior around that policy tells you much more about what people actually feel comfortable doing.
Behavioral interviewing goes both ways
This is one place where I think candidates underuse behavioral interviews.
We often approach statements on job descriptions with healthy suspicion. A company says it has “great work-life balance,” “unlimited PTO,” or a “people-first culture,” and we reasonably wonder what that looks like in practice.
But then we ask interviewers abstract questions such as: “How is the work-life balance?”
Unsurprisingly, we often get abstract answers.
So instead of asking people what they believe about their company culture, ask them what they have actually done.
For example:
When was the last time you took a real vacation?
Then get curious:
How long were you away?
How did you feel about the quality of that time off?
How did you feel about returning to work on the last day of your vacation?
You can ask similar questions about the team. When was the last time someone took one or two weeks off? How does the team handle ownership when someone is away?
Don’t expect the answer to match some perfect standard because different people have different preferences and constraints.
What you are looking for is evidence.
Someone who can comfortably describe taking two weeks away, disconnecting, and trusting their team to continue the work is giving you useful information. So is whether they were looking forward to coming back.
That tells you something very different from someone who cannot remember the last time they took more than a long weekend.
There will always be another reason not to step away
I also think vacation is becoming easier to postpone in the current environment.
Layoffs have made many engineers understandably anxious about job security. AI is changing our work quickly enough that there is always another tool to learn, another workflow to rethink, another skill to build, or another reason to wonder whether we are keeping up.
If you are ambitious, it is remarkably easy to turn uncertainty into a reason to keep working.
Just until this launch is over.
Just until the promotion cycle.
Just until the job market improves. Or just until I understand AI better.
But the conditions creating this uncertainty may not change anytime soon.
If you are waiting until your career feels completely secure before allowing yourself to rest, when exactly do you expect that day to arrive?
I have been asking myself a version of that question too.
I could postpone my next vacation until I build another AI automation or finally replace my spreadsheet with a CRM. There will always be one more thing I could optimize.
But if constantly postponing rest eventually leads to burnout, the cost is much bigger. I become less able to show up fully for the clients I have committed to supporting.