An employee asked if her mom could call me about her PTO

The question that taught me PTO had become psychological warfare

I hired Jessica, a 25 year old in an entry level role, to start in November. Two weeks in, she asked about time off for Christmas. She hadn’t earned any PTO yet — new employees had to accrue it over a few months — but I told her she could “work from home” for a day or two to still enjoy some time with her family. I mean, I’m not a monster and the truth is that most of our clients were fully shut down during that time.

A couple of days later, Jessica came into my office requesting two and a half weeks off over the holiday. I had to reexplain that technically she had NO time off and I was kindly looking the other way for a couple of days. She explained that her family was driving to Florida (from Michigan) and so she needed the whole time off if she was going to be with her family at all. When I again said I had no way to do that for her fairly, especially with multiple days on the road preventing any remote work, she asked if her Mom could call me to discuss further.

My mouth said “no, I’d rather she didn’t,” but I’m sure my face showed the full range of emotions from confusion to horror that I found myself processing in the moment.

As we approach the holiday season, and subsequently an influx of PTO requests for many in leadership roles, I’ve realized that PTO has become psychological warfare disguised as a benefit. I’m not blaming employees for being confused when I’m confused. When policies are deliberately vague and consequences are arbitrary, of course people try to figure out what they can get away with. The problem is that leaders like me get stuck enforcing rules that don’t exist, which makes everyone miserable.

We already know that in the US, very few are taking enough vacation time. Add to that our obsession with presence over performance (i.e. who’s worked the longest hours or arrived the earliest) and you’ve created a system where time off feels like a trap. Layer in that in recent years, many companies, especially start-ups, have adopted “unlimited PTO” which gives companies the two-for-one benefit of not having to pay out accrued time off when an employee departs AND seeing employees take the same or less vacation time anyway.

When I worked for one particularly narcissistic CEO where “unlimited PTO” was supposedly the policy, I learned from my team that they had all been told in July that September 1-December 31 was the “busy season” and they shouldn’t expect any PTO to be approved so to be sure to try to take some over the summer. I initially told them they must have misunderstood, but they provided links and screenshots of past emails and Slack messages being quite clear on the topic.

In one of many conversations about company culture, the need for which was a red flag on its own, I brought up that people were afraid they’d be fired if they took PTO. The CEO was “shocked” and denied it but, at that point, I’d already had her get mad at me for approving too much PTO (not holiday-related in this case, but rather two different employees who had valid family emergencies and followed all HR protocol in requesting). The truth here is that she wanted a culture like a police state where everyone felt bad if they didn’t work as hard but instead of everyone feeling bad and working harder, they all just complained, contributed to a toxic culture, and looked for other jobs. Once people know “unlimited” actually means “we’re always judging you,” they don’t want to give their best.

On the other side of the spectrum, I had a (notably underperforming) employee at one company who requested nearly ten full weeks of PTO in one calendar year. At previous companies, handbooks at least defined “unlimited” as roughly four weeks. But this company had gone through multiple mergers and had conflicting policies in multiple handbooks, so technically there was no limit. When I asked HR what/how to navigate the situation, I was told that if the employee had coverage for her work, it was my problem to manage. It was clear nobody understood how PTO worked anymore — not employees, not executives, and definitely not the people writing the policies.

I had her manager go back to her and ask her who she intended to cover her work, and the employee looked her manager in the face and said “I thought you could.” In this case, the message was clear that lack of clarity rewards the most brazen.

Time and time again, it seems that PTO policies reward those who are shameless and punish those who are conscientious. If you’re the one trying to enforce invisible rules, you’re automatically the villain. And if you care about your team’s burnout, you see that the people who most need breaks never seem to take them. One wildly overworked employee asked about a sabbatical, and when I said we didn’t offer them, she admitted she’d considered having a baby just to get 12 weeks of paid leave. That’s what we’ve created: a system where having an actual child feels more viable than asking for rest.

The dirty truth is that from the business impact standpoint, it’s exactly those burnt out people in the middle who no one wants to take PTO because they’re doing the most work in the first place. Jessica, a brand new hire, was not going to add any value to the business for those two and a half weeks she wanted to drive off to Florida.

I was forced to decline her request not because of direct business impact but because, indirectly, not adhering to a policy that other fully onboarded and high performers had dutifully followed would create bitterness among those on Jessica’s team who were most critical to the business long-term. What a silly dance we’re all doing where what’s meant to be a benefit ends up benefitting so few.

Incidentally, despite getting two extra weeks of “work” over the holidays, Jessica didn’t really get much better. While HR’s process for a PIP was going to take at least three months, I spotted a faster window for resolution: I took Jessica out for a drink and told her I could just tell she and her boyfriend were meant to be, that love like that was worth chasing, and she should absolutely move to Utah to be with him.

She gave notice two weeks later.

They broke up within six months.

After 20 years of managing PTO requests, I’d learned that sometimes the only way to win is to make your own rules.

A note for readers (added on 12/4/25):

The post above is unchanged from when originally published. This note provides additional context.

This post describes and anonymizes multiple examples across past roles. When I wrote this for my original 100 subscribers, I ended with a flippant anecdote about encouraging Jessica to move rather than enter formal performance management. The abbreviated version of her story didn’t capture months of conversations or Jessica’s own agency in deciding what she wanted.

I had an honest conversation with someone about job fit and supported a choice that made sense for her life - one I made myself in my 20s. This advice column is more reflective of how I actually think about these decisions.

The point wasn’t “look how I handled this employee” or to position myself as preventing holiday time off. It was about how broken PTO norms create challenging situations for everyone involved.

I’m grateful this resonated with so many people, though I wish I’d anticipated how it would read to strangers. My goal with Stepping In It is to talk honestly about messy professional and personal dynamics - not to present myself as someone who always gets it right.