How to go on vacation without worrying about work (3-step process)

Ever found yourself stressing about work while TRYING to enjoy a vacation?

Worrying about clients or wondering if your team can manage without you? (What if there's a big problem?)

I've been there. 

It's not easy being a business owner, but with the right building blocks, you can create a firm that runs smoothly without you.

As someone who's built multiple businesses over the past decade—including eCommerce businesses, a bookkeeping firm, and now a recruiting agency—I've learned, through trial and (mostly) error, about successfully stepping away from work. 

I want to share my 3-step process I use to go on vacation, completely unplug (no email), and never worry about work ever again while I’m away.

A recent family trip to South Korea was special for me

In July, I took my wife and daughter to South Korea for two and a half weeks. And here’s the thing—I didn’t even check my email while I was away.

It was the longest I’ve been completely disconnected from work in my ten years of entrepreneurship.

In years past, I’ve been an anxious vacationer, not because of the travel, but because I was afraid there would be a blowup at work and I’d be dragged into sorting it out.

This time, however, I was at peace. I was present with my girls walking around the serene Gyeongbok Palace in Seoul because I knew everything would be fine.

My wife Lauren, daughter Lily, and I at Gyeongbok Palace. This was the king's stunning banquet pavilion.

But this peaceful vacation didn't happen by accident. 

It was the result of careful planning and a test run I did a few months prior.  

In March, my wife and I celebrated our 18.5-year anniversary with a week in Jamaica, where I truly disconnected, for the first time—ever. (Ask me sometime why 18.5 years specifically.)

After that trip, I knew my fulfillment team could handle anything in my absence.  

But there was something missing: Sales

Being away for only a week, I didn’t bother having someone step in to take sales calls for me. New prospects just scheduled around my vacation time. No big deal.

But, if I was to be gone for more than half a month, that extended period without any sales calls would impact the business more than I was willing to accept.

So, I spent some time training someone on my fulfillment team to handle sales calls. I assumed our revenue would dip some, but I was confident that she could reasonably land a few sales.

What happened?

Not only did we continue to get positive feedback from clients while I was away, but we also continued bringing on new clients without my involvement.  

And it ended up being a great month!

That's the dream.

How do you build a business that keeps running (and growing) while you're away? 

It's actually pretty simple, but it's not easy.

🤝 1. Build a team of people who are better than you

Here's something you might find surprising: I built a bookkeeping business even though I'm not a bookkeeper or accountant. 

Now I have a growing recruiting agency without being a professional recruiter.

There's tremendous self-doubt that comes with doing something so crazy (I can't even tell you the emotional challenges here), but there is an upside. 

And that is that it's impossible for me to get sucked into client work. Because I can't do it. Truly. 

This forced me to hire top talent from the very beginning. I had no choice if I wanted to succeed.

As Michael Gerber explains in ‘The E-Myth’, the biggest barrier to a thriving business is often the owner's involvement in fulfillment.

If you're a bookkeeper or an accountant, it might be harder for you because you know how to do the work. 

But if you want to be able to go on vacation and actually forget about work, it's what you’ll have to do.

I'm exaggerating my story slightly because I do understand (some) accounting concepts and I can recruit well for my own team, but I can't do either of these things well (or profitably) for other people.

🎯 2. Delegate outcomes and don't meddle

When I hired Lala Paiton, my first hire at TeamUp and now a key member of our recruiting team, I gave her a clear objective: 

Implement a professional recruiting process and deliver excellent results for our clients. 

I didn't tell her how to do it, because obviously I didn't know how.

Now, if you're checking in with your team, answering questions, or providing guidance, it'll be hard to remove yourself (and hard to take that vacation).

As our team is growing (adding two more recruiters this month!), we're focusing on maintaining consistent results. 

To do that, we're going to allow a lot of independence, managing them by outcomes and KPIs.

But wait.

Let's address the elephant in the room here. This assumes you have people who can do the work without you.

I said this was simple, not easy. 

If you don't have people at that level, you have two choices:

1. Train your current team

2. Hire new people

Training will take time and intention.

It'll also take a lot of self-restraint to avoid taking over when they're struggling.

🧩 3. Remove yourself strategically

As a business owner, there's a lot on your plate. You need to work ON your business, not IN it. 

So, remove yourself strategically from each segment.

A great question from ‘The One Thing’ by Gary Keller is: 

"What's the one thing I can do, such that by doing it, will make everything else easier or unnecessary?"

In my eCommerce business (before the bookkeeping firm), the answer was hiring someone for customer service so I could focus on marketing.

For you, it might mean delegating fulfillment or administrative tasks first.

Hire people who are the best in one area. Then, once those things are off your plate, you can spend more time on marketing and sales.

As I mentioned, this vacation was the first time I let someone else be involved in the sales process. 

With just a little training, Lala stepped in while I was away, and amazingly, we had a pretty good sales month despite my absence for most of it!

I believe you can do this too. 

If you have a consultative sales approach like we do, where there's no pressure to sell, and you're just trying to help, a technician (accountant) should be able to do sales.

And that's it. 

Build that momentum

To recap:

1. Hire people better than you

2. Delegate outcomes and don't meddle

3. Remove yourself strategically

It's really thrilling to have a business with this much momentum after less than a year and a half!

But who knows, this all could come crashing down around me (that familiar self-doubt), but I think we're on the right track.

I hope you can learn something from my experience. If you have any questions, I'd be happy to answer them. 

By the way, if you’d like help hiring talented people in the Philippines, we're here to help. 

At TeamUp, we help bookkeeping and accounting firms like yours hire top talent in the Philippines directly, without ongoing fees.  

Essentially, you can hire a person rather than a company, putting you in control of team culture, training, and retention while eliminating middleman fees and paying your teammates more. It’s a win-win.

Feel free to schedule a call with me, and I'd be happy to chat.