How to Take a Successful Vacation

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Confession time: I’m not great at taking time away from work.

In April of this year, my wife and I took a vacation, our honeymoon actually. We spent two weeks in Greece eating whatever we wanted, drinking far too much, and sightseeing whenever we felt like it.

We had an absolutely amazing time, and I certainly wouldn’t trade it for anything. But, it was hard.

My initial goal was to disconnect 100%. I didn’t bring my laptop. We didn’t have a cellular signal. I turned off email on my phone. Coworkers knew that I was completely out of touch.

That’s how it started at least.

Slowly but surely, I fell back into my normal habits. Email was turned back on “just to make sure I don’t get backlogged.” I added Slack back to my phone just to see if anyone needed me. While I wasn’t working per se, I definitely was spending more time than I had anticipated paying attention to work. 1

I have a sneaking suspicion that I’m not alone.

A recent headline I noticed read “41% of American Workers Let Paid Vacation Go To Waste.” 2 In reaction, new flavors of vacation policies have started to spring up wherein employees are incentivized or forced to take vacation. FullContact, a company based in Denver, even incentivizes employees to take a vacation by offering every employee an extra $7,500 to go on vacation and fully disconnect.

While I commend these noble policy efforts, they’re just band-aids rather than solutions. They don’t address the real issue. The real issue isn’t with your company. It’s not your coworker’s fault or your manager’s fault that you feel guilty taking time off. It’s your fault.

You don’t need another revamping of workplace vacation policies. You need to set your own vacation policy and take charge of your recovery.

Admit that you need it (and so does your team).

If movies are any indicator, the first step to any addiction group is admitting you have a problem. Why should work addiction be any different?

The first step is admitting that you need time away from work to recharge. This is harder than it looks. We wear our work schedule as a badge of honor. Overtime? It’s like extra credit.

Take an introspective look at your mental state, energy levels, and work output. Can you honestly tell yourself you’re doing your best work after several 80-hour weeks? Admit it; you’re not a robot.

Here’s the kicker: You’re not just hurting yourself. You’re sabotaging your team too. If you’re not taking time for recovery, you can bring the whole team down with you. Want to benefit your team while you’re away? Focus 100% on recharging and give them the best you when you return.3

Make irreversible decisions.

My biggest mistake when I was on vacation: Relying on my willpower. I thought that if I disabled all temptations from my phone, I could keep myself accountable and avoid a relapse.


I mistakenly thought that my future self would have just as strong a resolve as my current self. That’s a losing bet every single time. Make decisions assuming your future self is gullible. You’ll set yourself up for better success.

A much better method would be to remove willpower from the equation altogether and make an irreversible decision. Leave devices at home or lock them in a safe and have someone else set the code. Add as many steps as possible between you and your vice. If you’re tempted to check your email, delete the account rather than toggling it off on your phone. You’ll have the added step of setting up your account again and entering your password, more time to think about what you’re actually doing.

Live outside the norm.

We’re creatures of habit, even bad habits.

When left to our own devices, we relapse quickly into a normal pattern of cause and effect, triggers and events. Stuck inline at a grocery store? You’re pulling out your phone. Open up your laptop? First stop is your email inbox. Stopped at a traffic light? Twitter it is!

There’s a (high) chance I’m projecting a bit, but the takeaway still applies. If you stick to your same routine, you’ll be tempted to fall back into work.

Break the cycle by living outside your normal box.

Change your environment by going somewhere special or doing something as simple as hiding your laptop in another room. Remember, future you is gullible. Switch up your routine by visiting different restaurants or shops. Read different styles of books. Catch up with old friends.

If your vacation environment and work environment are exactly the same, you’re going to fall back into your work routine.

The Take Aways

Let’s get better at taking vacations as a collective group. Let’s…

  • Take ownership. Don’t pass the buck and rely on a company-wide policy to determine how you recover.
  • Give ourselves permission. Stop idealizing 80-hour work weeks as some badge of honor. They’re not sustainable and hurt the output in the end.
  • Plan for relapse. Avoid them ahead of time by making irreversible decisions.
  • Break outside of our normal rut. Use vacations as a time to refresh and recharge with new experiences.

Field Notes

1. To be clear, this wasn’t my employer’s fault. From my coworkers to leadership, everyone is very encouraging of taking time away for recovery. I just stink at doing it.
3. I read this somewhere on Twitter previously so I can’t take full credit. I searched and searched, but I couldn’t find the original author.

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