You booked the trip.
You set the out-of-office.
You gave your team a heads-up and told everyone, “I’ll be offline.”

So why’s your laptop still tucked into your bag  –  you know, “just in case”? Why are you sneaking peeks at Slack in the hotel lobby before dinner, right after breakfast, on the beach, even in the bathroom? Why does this still feel… well, not exactly restful?

Here’s the truth:

You’re not broken.
You’re just a business owner who hasn’t quite built your business to run without you.

And you know what? You’re not alone.

“I Thought I Had Everything Covered…”

One of my clients – let’s call her Jordan – runs a growing consulting firm. She’s smart, prepared, and had delegated everything she could before taking her first real vacation in two years.

We even built a checklist: client handoffs, a “who owns what” chart, and a custom out-of-office system.

But on Day 3 of her trip, she got this text:
 “Hey, can you approve the revised scope doc real quick? The client just pushed back.”

That one little ping snowballed into three hours of Slack threads, emails, and decisions.

Not because her team wasn’t capable – but because she was still at the center of it all.

Why Delegation Alone Doesn’t Equal Freedom

1. You’re still the default decider.

Even with great people, if you’re the only one who can say “yes” to a proposal or “no” to scope creep, your business still depends on you.

This isn’t about trust – it’s about structure.
 Until decision-making authority is clearly delegated, your team will default to asking you – which means you never get to fully step away.

2. You’ve delegated tasks, not outcomes.

When delegation is vague (“take care of this” or “send it when it’s done”), your team ends up hesitating, double-checking, or holding things until you’re back.

What works better:
 – Spell out what success means for the task.
 – Make it crystal clear what they can decide solo.
 – Set guidelines for when to keep moving and when to loop you in.

That’s how you move from feeling “covered” to feeling genuinely confident.

Two Other Reasons You Still Can’t Fully Unplug

Even if you’ve delegated well and aren’t the bottleneck anymore, two other things might still be tripping you up.

3. You’re cramming a month of work into two weeks.

Here’s what most business owners do before vacation:
 – Say they’ll take off 10-14 days
 – Then try to do 3-4 weeks of work in the two weeks before they leave
 – And return to a full calendar, inbox avalanche, and zero transition time

No wonder you’re worn out before you even go.

Want it to feel different?

Try actually working two weeks of work in two weeks. That’s it. Stop pushing for superhero hours. Your inbox and projects will wait.

And while you’re at it, build in a Reset Day for when you return.

Block out the first day after your vacation as a buffer – no meetings, no deliverables, no expectations. Just space to catch up, triage emails, close loops, and ease back into a rhythm.

Without this, the return feels harder than the break was worth – and that pattern quietly reinforces the idea that stepping away is risky.

4. You don’t know what will break until it does.

Taking a real vacation is like stress-testing your business systems. If you’ve never stepped away for more than a day, you don’t actually know what’s going to fall through the cracks.

That’s why I recommend something simple but powerful before any real time away:

Take a Midweek Test Drive

Instead of waiting until your next vacation to see where things fall apart, take two weekdays off.
Not a weekend. Not a holiday. Just two regular days where you don’t check in, respond, or hover in the background.

Then when you come back, ask:
 – What came to me anyway?
 – Where did things stall?
 – What decisions waited for my return?
 – What did my team handle better than I expected?

Plug the gaps now – before you’re on a plane or a beach.

This Isn’t About a Trip. It’s About Taking Back Your Time.

You didn’t start your business so you could work 24/7 or spend vacations juggling “just one thing.”

If you’re delegating but still feel tethered…
 If your team is capable but hesitant…
 If you’ve built a business but it still runs on you…

Then it’s time to rework the way your business operates.

This is exactly what we do in 1:1 coaching:
 – Redesign your team’s decision-making structure
 – Clarify ownership so delegation actually sticks
 – Build systems that protect your energy
 – Create space – real space – for time off, thinking time, and time to be a human again

New private coaching spots open in August. If you want your next vacation to feel actually restful, let’s talk now.

Book a 15-minute clarity call and we’ll figure out what’s keeping you tethered – and how to fix it.

You deserve to lead and live. Let’s make space for both.

 

 

*Header image created in Canva