Boundaries, PTO, and the Myth of the Always-On Founder: A Holiday Survival Guide for Startups

In a lot of startups, the holidays can feel a bit like a competition: Who can remain the most “productive” over break? Even when they don’t set out to stay online, it happens. Founders tell their teams to rest, then sneak glances at Slack from the ski lift. PTO gets approved, but laptops make the trip. Phones get silenced, but every day, team members tune in for “just one quick check.”

It’s a familiar cycle, and one that costs more than it saves.

According to the American Psychological Association, vacation time genuinely works. After taking time off, 68% of those surveyed report a more positive mood, 66% feel more energetic, 57% feel less stressed, and 58% say their productivity improves. Yet only 41% of workers surveyed felt their workplace culture encourages taking time off. And just 38% feel that encouragement from their direct supervisor.

That gap between knowing rest is good for us and actually taking it is where most startup teams live. The culture rewards constant availability and applauds the “grind,” even as creativity, motivation, and quality suffer.

The good news? It doesn’t have to be that way. Boundaries can coexist with ambition (and success). PTO can fuel (not derail) momentum. And the founders who model that balance often end up leading the most sustainable, innovative teams.

Here’s how to make the holidays a real reset. For yourself and your team.

The Always-On Myth (and Why It’s Dangerous)

The “always-on” founder persona has been popularized in startup mythology. Somewhere along the line, we equated availability with leadership and exhaustion with commitment. But being always available isn’t the same as being effective. Honestly, a lot of the time, it’s just being tired in public.

A lack of rest shows up where it hurts most: in your decision-making. Studies have shown that fatigue lowers creativity and increases risk-taking. In other words, that “quick, just one more email” approach so many revere can actually lead to worse outcomes and a foggier vision for the company you’re trying to grow.

Another point of consideration? Founders set the tone for everyone else. If you never disconnect, your team assumes they shouldn’t either. In that way, modeling balance is an important leadership skill.

Here’s how to do it well.

Set the Rules Before You Log Off

Start by making your boundaries explicit. Nominate a point person for emergencies (and define what actually counts as an emergency). Write a clear out-of-office message that says when you’ll be away, when you’ll be back, and who’s covering in your absence. Then, set your Slack status to “away” and silence notifications on your phone. 

This shows your team that time away is actually time AWAY and it demonstrates how to communicate clearly and confidently about time off.

If you truly can’t resist checking email, build guardrails for yourself. Schedule one short window to glance at messages every couple days, and then go back offline. And whatever you do, don’t respond to anything that isn’t actually an emergency. If you feel compelled to, type up the message and save it as a draft or schedule the send in the new year. That way, you maintain the appearance of being offline (and encourage your team to actually stay offline) even if you falter at resisting the inbox yourself.

Redefine What PTO Looks Like

In most startups, the lines between “on” and “off” can easily blur. When everyone’s juggling multiple roles, time off can feel impossible, even irresponsible. But a truly healthy culture makes rest part of the system.

Encourage your team to plan ahead and document key workflows before they log off. Create shared checklists and quick handoff notes so everyone knows what’s covered. When people see the business really does keep humming without them, it builds confidence in both the team and the systems you’ve built.

And for yourself? Let go of the guilt. You built your business to grow, not to consume you. The version of you that comes back rested will lead with sharper perspective and steadier energy than the one who never stopped.

Plan the Re-Entry Before the Exit

The key to stress-free time off is pre-planning what happens when you come back.

Before you log off, block a little time in January for your re-entry. Think of it as your buffer zone—a day (or even just a few morning hours) to catch up on messages, review priorities, and reset before diving back into full-scale execution and back-to-back meetings. Make a short list of what’ll need your attention first, what can wait a week, and who you’ll need to reconnect with right away.

If you want a deeper dive on how to set yourself (and your team) up for a smooth start, check out New Year, No Chaos: How to Plan Now for a Smooth Start to 2026. It walks through a few light-touch planning steps you can take now that’ll make those first weeks back feel intentional instead of overwhelming.

Leadership Lessons from the Pause

Time away has a funny way of clarifying what matters. When you step back, you can see which parts of your business run fine without you—and which don’t. Those insights are priceless. They show you where to delegate more, automate better, or finally hire that person you’ve been holding out for.

Rest often reveals friction you’ve been ignoring. Every founder I know who’s truly stepped away comes back with one of two realizations: either “Wow, things ran great without me,” or “Wow, we really need better systems.” Both are useful.

Rest Is the Real ROI

At Wheels Up, we work with founders who move fast, pivot often, and think deeply. But the ones who sustain that pace long-term share one thing in common: They know when to stop.

Time off is infrastructure. It keeps your creativity sharp, your judgment clear, and your culture resilient. So this year, trade availability for trust, and busyness for balance. Because the best founders model what sustainable success actually looks like.