It is summer vacation season, and for many leaders, this period reveals an uncomfortable truth: how much do you really trust your team when you step away?
Do you leave for vacation with a sense of confidence, knowing “the shop” will run smoothly in your absence? Or do you pack your laptop, plan to check your emails daily, and brace yourself for texts about accounts, crises, or issues you feel only you can resolve?
I’ve lived both versions. For years, vacations as an entrepreneur were never truly restful. I would “leave,” but my mind stayed tethered to work. I checked emails compulsively, monitored client conversations, and intervened when I felt something was drifting. I told myself it was my responsibility, but in reality, it reflected something deeper: a gap in trust and systems that prevented me from fully letting go.
The turning point: linking rest to leadership
It took me years to realize that the quality of my rest during vacations was directly correlated to the quality of my team, our processes, and the principles we operated by. Delegation, clear escalation protocols for true emergencies, and trust in my team’s judgment were not just nice-to-haves. They were essential if I wanted to truly recharge and return with renewed energy.
“Deciding what not to do is as important as deciding what to do.” – Steve Jobs
When I fully embraced this, my focus shifted. Instead of obsessively controlling every detail, I invested in enabling my team. I coached them on thinking on their feet, empowered them to make decisions within their scope, and created clarity around when to escalate issues versus when to simply act.
The first vacation after making these changes was a test. I still checked my emails daily, but I refrained from intervening unless something was truly urgent. And to my surprise, while things weren’t perfect, they were good enough. Customers were satisfied, the business was stable, and I returned to find minimal “damage control” required. That was a powerful moment.
The following year, I went one step further. I told my team I’d only be reachable by text in case of an emergency. I muted email. And you know what? No emergencies came up. It was my first truly relaxing vacation in over a decade. I was present with my family, and I returned energized. From then on, I made this the norm.
Your job is not to be indispensable
Leaders often fall into the trap of believing they must always be “in the loop” because they are indispensable. But true leadership is about building a team and a culture where you are not needed for every decision.
“If you want to do a few small things right, do them yourself. If you want to do great things and make a big impact, learn to delegate.” – John C. Maxwell
If you are micromanaging while on vacation or unable to disconnect from work, it is often a sign of one (or both) of the following:
- A lack of trust in your team’s ability to deliver
- Gaps in your systems and processes that make performance overly dependent on you
Both of these are solvable—but they require conscious effort.
First, you need to be brutally honest about performance. If your team cannot do the job without you, you must address non-performance. That may mean clearer expectations, better training, or even restructuring.
Second, you need to develop and reinforce systems:
- Delegation frameworks so responsibilities are clear
- Escalation protocols for emergencies
- Shared principles that guide decision-making in your absence
When these are in place, your leadership shifts from being reactive to proactive. You stop replacing value that should be created by your team and instead focus on building value that only you can provide: vision, strategy, and alignment.
Good enough is often good enough
One of the hardest challenges for driven leaders is accepting “good enough.” We hold high standards, and it is tempting to judge every task by how we would have done it. But leadership is not about cloning yourself.
Your team’s “good enough” is often more than enough for customers, and if you create a culture of excellence, your “good enough” will likely exceed your customers’ expectations.
Perfection is not the goal. Progress, autonomy, and sustainable excellence are.
What your vacation says about your leadership
If you cannot take a vacation without anxiety or daily check-ins, it is worth reflecting: what does that say about your leadership?
- Do you lack confidence in your team’s abilities?
- Are your processes too dependent on your constant oversight?
- Have you built a culture where autonomy is encouraged and mistakes are treated as learning opportunities?
Vacations are not just a luxury. They are a litmus test for how well you’ve built your team and structured your leadership. When you can step away and truly rest, it is not because everything is perfect. It is because you have laid the groundwork for things to keep running well enough without you.
And when you return? You bring back energy, clarity, and perspective that benefit everyone—yourself, your team, and your organization.
An invitation to reflect
So here’s my question to you:
When you take your next vacation, will you feel the urge to check in daily and keep a finger on the pulse? Or will you feel the quiet confidence that your team “has this”?
If it’s the former, don’t see it as a failure. See it as feedback. Use it to ask yourself: what would need to change—people, processes, trust—to turn your next vacation into a true break?
Because leadership is not about being irreplaceable. It’s about building something that can thrive even when you’re not there.
