How to Take a Vacation as a Founder

How to Take a Vacation as a Founder

As founders, we don’t always give ourselves permission to take vacations. We feel like we have to grind it out to reach our goals. We feel like we’re running on a treadmill, and if we stop… CRASH. We fear that we’ll ruin our streak of productivity, the delicate flow that we’ve created through day-in-day-out nose-to-the-pavement work.

In his book, Flow: The Psychology of Optimal Experience, Mihaly Csikszentmihalyi defines flow as:

“a state in which people are so involved in an activity that nothing else seems to matter; the experience is so enjoyable that people will continue to do it even at great cost, for the sheer sake of doing it.”

Founders build their flow state over time. It begins with a small streak. One great day turns into two, two days into a whole week, a week into a month, and so on. You get into a rhythm and fear that you won’t be able to find it again. But when we’re so focused on working in the business, grinding, and not giving ourselves the time to rest our bodies and minds, we actually limit our potential for making stepwise transformations—new innovations, pivots, strategies, pathways toward a bigger picture.

My first vacation away from the grind…

During my first three years at my start-up, my partner was always traveling to amazing places all over the world for work, and I consistently passed on travel opportunities with her because I didn’t think I could manage that kind of break from the momentum of the startup. There was always a major project underway, and I was usually the focal point of the operations.

Finally, while the company was in the midst of building a brand new roastery (one of our largest capital-intensive projects ever), I decided to go to Colombia for two weeks with my partner. At the time, we were installing hundreds of thousands of dollars worth of equipment, handling tight project timelines, setting up terms, wiring payment, and communicating and negotiating with landlords, architects, consultants, workflow designers, and other suppliers. And, I was spearheading this effort having never handled this level of coordination in my life. Good time to go on vacation, right?

After committing to the trip, I needed to find someone to take over the responsibilities that I was just beginning to familiarize myself with in the first place. Luckily, our head of production stepped up. We had several phone calls filled to the brim with information, files, briefs on what had happened so far, and plans for what would happen in the next two weeks.

The biggest stressor of my two-week absence was the receipt and installation of the roastery equipment. It was the foundation of the company’s next chapter, and we had little room for error.

This was a huge exercise of trust, but I was determined to find a way to enjoy my vacation, so I set up a daily 15-minute check-in call and a weekly equipment installation project check-in with our head of production where we aligned the team and clarified the step-by-step project plan. Other than those check-ins, I just had to let it ride.

Fast forward to my return to work, and I was astonished to find everything in place. Our head of production and the team executed everything to perfection. I was so impressed; she and the team did an excellent job.

This was big for me too. It was proof that great results didn’t depend on me, and it sparked my journey of uprooting my insecurities as a leader. Why couldn’t I have delegated something like this earlier? What has stopped me from taking time off before? What part of myself had made me feel like I couldn’t do that? I didn’t have to hold every important task and project close to my chest. I could delegate and actually take some time to smell the roses.

And you can do it, too. Here’s how.

Set expectations.

When attempting to take some time off, it might feel like a massive amount of to-dos and responsibilities need to get done prior. Additionally, it might also feel like your work is waiting for you upon your return. So, with this sense of time pressure, it can be really easy to drop work on someone else’s plate quickly without setting expectations.

We might say, “Please take care of this while I’m out” or “Could you run with this and we can resync when I’m back?” without providing any context.

You have to teach others what success looks like in your mind, give them proper training, and guide them. If you don’t set expectations appropriately, you’re essentially rigging the mission for failure.

What happens without expectations?

If you fail to set proper expectations, you’ll create a negative death spiral, returning from vacation with proof of your worst fears: nothing got done, or the work was poor quality. You may even focus on all the flaws as opposed to all of the progress, which means succumbing to your own confirmation bias. You might think to yourself:

  • I knew I shouldn’t have gone on vacation.
  • I knew I shouldn’t have trusted that person.
  • I’ll just take it back and do it myself.

Now that you’ve come back with lots to fix and rework, you have perfect reasoning for why you “can’t take a vacation.”

What happens with expectations?

But it doesn’t have to be that way. Ask yourself, What has to happen in this period of time while I’m gone? Have I provided adequate resources to my team to successfully run with their new responsibilities?

With these questions answered, your team will be ready to cover for you. And this could potentially spark a permanent transition of responsibilities moving forward.

Delegate authority.

Vacation can be a catalyst for change. To be able to take one, you have to set up your operation to run without you. Set up a checklist, process, manual, or anything else for the person who will be running your projects while you’re away. Set clear expectations and guide them with your wisdom. If you want to take it a step further, delegate authority to decide. You can be really clear on what they can and cannot decide on as the arbiter of this project.

For example, when my head of production stepped up to handle our capital-intensive project, I gave her the authority to cancel and change our meeting times, answer emails on my behalf, coordinate deliveries, and decide where and how the equipment would be placed. She didn’t have the authority to proactively change the project schedule without new information, and she couldn’t just say, “Hey, actually, for the next two weeks, we’re just not going to work on this project.” But giving her as much flexibility as possible to make decisions was the key to her success.

If I hadn’t focused on realizing outcomes and instead expected her to run everything by me and do everything by some hyper-specific process, I would have been a bottleneck to our success all the way from Colombia, I would have been on the phone with her multiple times per day, and I would have worked throughout the whole vacation.

Think: How much authority can you delegate to help this person move the ball forward? Set expectations about what they can and can’t do accordingly.

When operations run without any hiccups, these short-term delegations can turn into permanent ones. And when that happens, you’ll have more time to focus on creating value from a higher level.

Focus on vacation.

Once you’ve set expectations and delegated, it’s time for vacation. Don’t let emails and notifications hijack your time off. I’m a huge believer in uninstalling apps and snoozing notifications, especially badges. That little red bubble at the corner of your messaging app is designed to trigger you to open the app, but constantly opening these apps defeats the purpose of your vacation. You aren’t actually clearing your mind. You’re still concerning yourself with what’s happening inside the business. Ideally, you’ll have set the right expectations and boundaries with your team so that you won’t have to check your email or Slack channels at all, and you’ll have to fight the urge to break your commitment.

But sometimes, you can’t completely escape work. In these cases, you should limit your work responsibilities as much as possible. One way I’ve done this is by asking my partner to check my email for me. I don’t have her explain a play-by-play to me. My only request is that she tell me if there’s anything that seems urgent—emergencies only. Most of the time, there’s nothing. When a trusted person checks your messages for you on vacation, they can help you push the boundary of what really matters. They won’t make excuses for why you need to check an unimportant email. They’re biased to enjoying vacation with you—whether that’s by relaxing, sightseeing, experiencing something new, etc.

And if you really don’t trust yourself to keep your distance from Slack or any other app related to work, uninstall it. If you set your team up for success and set the boundary that you’d be away, hold yourself accountable to those expectations. If you’ve communicated to your team that you’re taking a vacation, but they notice that you’re checking email and sending messages, you’re unconsciously and unintentionally communicating to them that vacation isn’t important. This will:

  1. Make them think you’re readily accessible on your vacation.
  2. Make them infer that vacations aren’t valued or valuable in the company culture.

Does this sound like you? On your vacations, are you sneaking an occasional Slack message? Are you checking email a little bit just to keep a pulse on the business? Are you not truly disconnecting and self-sabotaging?

Vacationing is an act of self-discipline and trust.

Vacationing is an act of trust in your team and yourself. It’s a time to refresh your mind. For so long, I didn’t believe in taking time off. Thanks, in a large part, to social media, I was indoctrinated into the culture of hustling to the finish line. But stepping away from those beliefs, challenging them, and seeing evidence that it doesn’t have to be that way gave me the confidence to ask, What else can I delegate? What else can I systemize? Do I really have to limit my next vacation to two weeks?

If your value to a company is big picture strategic thinking and driving growth, then you should be excavating time to think. In your role, you can’t say, “I got X amount of thinking done today,” which can make it hard to feel valuable because it isn’t exactly tangible. But, if you get really clear on what the value is that you provide for your business, then you’ll start to see avenues for growth and prosperity in your role and the company.

You’ll have an easier time trusting those around you to take on new responsibilities, and you’ll be able to take a much-needed break.

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