How to Not Suck at Vacations As a Freelancer - 7 Practices

For most of my so-called “career” as an entrepreneur, I have sucked at “vacationing.” Not working seems like most people’s idea of a good time, but after tearing myself away from my computer, I’d be in a funk for several days. I couldn’t snap myself out of it.

A once-in-a-lifetime trip to Greece in 2016 is the perfect example. The trip would have cost over $30,000 if we’d paid retail price for everything. I offset most of the costs by using frequent flyer miles and reward points to book the best flights and hotels, and we’d saved up plenty of cash for food and incidentals. Our two kids were staying with my mother-in-law. I shouldn’t have had a care in the world.

My wife and I flew through the night and arrived in Athens dead tired. We walked around to stay awake, and the sights, sounds, and experiences were all muted, as though they were coming through water. I could appreciate the unobstructed view of thousands of years of history from the rooftop of our hotel. As the sun set, lights came on around the Acropolis and painted the Parthenon gold. The view was epic in every respect, and I wanted to go to bed early.

Maybe the problem was jet lag.

The next day, we flew to Mykonos and drove our tiny rental car to Kivotos, a boutique beachfront hotel with a panoramic view of Ornos Bay. You’ve seen the color palette in Condé Nast: curvy, whitewashed walls, volcanic rock in every shade of blonde and brown, and blues so deep and pure your eye bounces right off them.

There I was, with no to-do list, gazing out at the sparkling Aegean, and feeling uneasy. I’d been looking forward to the trip for months, and once I was finally on it, I was acting like Eeyore, not Tigger: pensive, anxious, brooding. I’d already picked several fights with my wife.

I knew I was spoiling the precious time for both of us. Thankfully, by the time we reached Santorini, light had pierced the gloom, and I settled in to something resembling enjoyment.

Still, what explained my mental state those first two to three days? Why couldn’t I relax and enjoy myself?

Human beings are strange creatures who can manufacture misery while visiting the most beautiful, awe-inspiring places the world has to offer. We can have the best of everything and feel a gnawing discontentment.

I won’t bother to pick apart my circumstances at the time because those circumstances have changed. What you need to know is that pattern kept repeating. Mr. Grumpypants would show up and ruin the first two to three days of any vacation.

What broke that pattern was understanding three things:

1. Why I wasn’t good at vacationing
2. How someone like me even defines “vacation”
3. 7 practices that help me enjoy myself while I’m out of office

Why wasn’t I good at vacationing?

For most of my so-called career, I thought I could and should vacation like certain family members and friends.

By all appearances, they found it easy to disconnect. When they left the office or left town, work ceased to exist. They could weekend like it was a verb, and they could devote themselves fully to vacation with a childlike disregard for what might be happening in their absence.

I wanted this compartmentalization. I wanted to be Keeper of the Fun. Surely, I could figure it out?!

I never figured it out.

Or rather, I identified one key difference between these expert vacationers and myself: Most of them were employees. They took paid vacation while members of teams kept the bus moving.

My situation and disposition were different. In 2016 I didn’t have a team. I didn’t have anything resembling a transmission. I struggled to sit still (Park) and do nothing (Neutral). I saw the benefit of going backward (Reverse) but only to try a different approach. That left Drive. Ambition. Doing.

For me, not working meant not getting paid.

I wasn’t good at vacationing until I recognized that I must vacation differently from my employed friends.

Those of us who own businesses have a distinct set of responsibilities and concerns. I do have to plan for my absence. I do have to save up to “pay” myself while I’m out of office. I do have to deliberately substitute one set of motivations, such as making money, for a different set, such as making memories.

What is a vacation?

I’ve also spoiled vacations because I lacked a clear definition for what a vacation is.

For me, a vacation never involves doing nothing. Inactivity holds no appeal for me. Sitting around on a beach? Not interested. This is a faux vacation because it doesn’t satisfy my curiosity, bring a sense of adventure, teach me anything, stoke awe and wonder, feed my gratitude, connect me with God, or create long-lasting memories with people I love.

A true vacation doubles down on those things that I love, wakes up the parts of myself I most cherish, and energizes me because I’m spending more time on what I enjoy most. Feeling fully alive is more important to me than sleeping in.

Through trial and error, I arrived at a routine at home that enables me to consistently show up at my best. Throwing out the reliable and beneficial structure, practices, and self-restraint would be unwise and counterproductive.

I don’t want a diversion or departure from my work or “real life.” I want to appreciate the best things in life. I also want to show up at my best.

So how do I do that? I prepare.

The best vacations put literal and metaphorical distance between my body and mind and my business and life. Those vacations have one common attribute: preparation.

I’ll share the seven practices that help me ensure Mr. Grumpypants doesn’t make an appearance.

1. Ask the question.

Here it is: “What must be true for me to leave the business in good shape?”

The question reveals loose ends I need to tie up. My assistant and I will also set her priorities so that the business can move forward in my absence. If you don’t have an assistant, tap a freelance friend whom you trust. Your vacation buddy can be on call, perhaps even check your inbox, while you’re unavailable.

You can return the favor next time your buddy goes on vacation.

2. Make a to-do list.

Being a recovering perfectionist Type A entrepreneur, I like to reach Business Zero, the distant cousin of Inbox Zero, before I’m out of office.

I also like to have gotten to the end of the Business Zero to-do list 48 hours before I’m supposed to leave. If I’m hustling to grind through tasks in the car or airport, that preoccupation bleeds over into the vacation. I don’t want that.

I do better when I have more buffer, and my mindset can reset.

Here are some of the things I’ll do to clear my mind and desk:

• Email all active clients and set expectations about my availability.
• Catch up on all communications in Slack, text, etc.
• Reschedule any appointments that might still be in my calendar.
• Get a jump on any emails and get to Inbox Zero.
• Clear out responsibilities, both large and small.
• Optional: Set up autoresponder that tells people who to email instead, either my assistant or vacation buddy.

3. Adopt my persona.

When I’m on vacation now, I am not Strategist Advisor, Scholar Author, or Ambitious Entrepreneur. Certainly, not Mr. Grumpypants!

I am Keeper of the Fun.

Keeper of the Fun has different motivations than those other aspects of my identity. Keeper of the Fun seeks out joy, new experiences, and sweet memories, not productivity, achievement, or money. Keeper of the Fun isn’t interested in saving money, running lean, or finding efficiency—all black coffee and focus.

Instead, Keeper of the Fun orders the fancy latte. He encourages the kids to buy candy in the gas station. He plays a few pranks.

I gave that part of my identity a name so that I can more easily act in ways that align with it. Cognitive psychology calls this “identity priming.” If it worked for the Black Mamba (Kobe Bryant) and Sasha Fierce (Beyoncé), then it will work for Keeper of the Fun (Austin L. Church).

4. Make my substitute to-do list.

Instead of finishing projects or sticking to my Friday Zero practice, I choose other achievements.

Maybe I set a goal to have one-on-one time with my kids. Maybe I explore a new corner of the place we’re visiting each day. Maybe I go out of my way to make my wife feel special.

Meanwhile, my drive to achieve is a source of energy that needs an outlet. It’s an arrow looking for a target. I don’t enjoy being sedentary. I don’t enjoy doing nothing. I often set a quota of pages to read each day, often in two or three books, and look for a way to exercise or sweat.

Rather than risk slipping back into my default mode of achieving business objectives, I proactively substitute business objectives for family and enjoyment objectives.

5. Make a Don’t Do list.

I get the itch and cheat on my vacation. I’ll crack open my inbox just to see what’s going on, and just like that, I’m preoccupied again with the very needs and problems I wanted a break from.

The best way I’ve found to counteract the itch is to set rules around what I won’t do.

That way, when I’m tempted to take a coaching call—”I was planning to go on a walk anyway”—or do something for a client—”It will only take thirty minutes”—I can fall back on the rules. “Nope. I don’t have permission.”

A Don’t Do list enables me to treat my vacations as sacred and not let business interests intrude.

6. Pick a vacation “project.”

As crazy as it sounds, I’ll often “save” a problem, idea, or question I’ve been wrestling with for my vacation. This may seem to contradict the Don’t Do list, but hear me out.

The problems, ideas, and questions don’t stop simply because I change my environment. Instead of trying to ignore them, I’ll write them all down in my journal.

The extra journaling accomplishes two things:

1. Once I’ve captured my thoughts, they stop being dried seeds rattling around in my gourd.
2. I have more breakthroughs, thanks to the spaciousness of vacation that nourishes my imagination and creativity and the distance from regular life that brings clarity.

I do enjoy entrepreneurship. I do need rest and replenishment. A little vacation “project” actually seems to help, not hinder. It channels the free flow of ideas and gives the problem-solving part of my mind a direction to go.

7. Stick to routine.

Certain habits and practices enable me to show up at my best. I arrived at them through trial and error, and no one benefits when I throw them out the window, even when vacation offers an excuse.

So why wouldn’t I still have sacred beginnings, centered on scripture, prayer, and gratitude? Why wouldn’t I move my body? Why wouldn’t I stay hydrated and get some exercise?

Freedom, novelty, and variety I love, but mindless pursuit of them would trample the best parts of my routine. That doesn’t help me show up at my best or enjoy myself more.

My best vacations don’t involve “getting away from it all.” Whether I’m at home or on vacation, I thrive when I still have some structure, routine, and habits.

Closing Thoughts

We sometimes need to leave the office to remember why we chose the entrepreneurship path. That’s why going on vacation, or resting at a distance, is one of the most strategic things that freelancers and other entrepreneurs can do.

Because that’s true, the last thing any of us wants is the regret that comes from not fully enjoying your vacation.

How do you avoid that regret? How do you return to your business and life with fresh vision, renewed passion, and clarity around what we need to do or say no to?

It’s taken me sixteen years to learn that I need to put the same creativity and preparation into a vacation that I would put into a dream client’s project. Preparation, structure, and rules—ironic, I know—make it possible for me to rest well and capture the many benefits of distance.

When you’re ready, here are ways I can help you:

1. Free Money. A pricing and money mindset guide for freelance creatives. If you’re unsure about your freelance pricing, this is the book for you.
2. Morning Marketing Habit. This course will help you build an “always be marketing” practice, become less dependent on referrals, and proactively build the business you want with the clients you want. My own morning marketing habit has enabled me to consistently make 6 figures as a freelancer.
3. 1:1 Coaching. Gain clarity, confidence, and momentum in your freelance or consulting business.
4. Freelance Cake Community. Build the business you really want with people who really get it.
5. Clarity Session. It’s hard to read the label when you’re inside the bottle. I've done well over 100 of these 1:1 sessions with founders, solopreneurs, and freelancers who wanted guidance, a second opinion, or help creating a plan.