How taking vacations can help you build businesses that scale // Notes from the Executive Director // Aug 13 2019

How taking vacations can help you build businesses that scale

vacation on the beach
Heather Wentler shares scenes from a recent vacation.

By Heather Wentler 

American entrepreneurs suck at taking vacation. 

Now, you might be thinking, entrepreneurs aren’t supposed to take vacation. I would disagree. Learning early on in your venture how to take a real vacation is a vital skill that most entrepreneurs overlook. 

American culture makes taking a vacation hard, no matter what your career. Our laws make it clear that vacation is not a priority. With no federally mandated minimum for vacation, the average amount of time American workers receive for annual paid leave lags far behind other countries. 

And worse, the average American only uses a little more than half of their available time off, according to a Glassdoor study from 2018

And when we do take vacation, we do it wrong. We check work emails, we get bugged by coworkers who need our input to make decisions, we mentally strategize new ideas for the company and plan out how to launch it, and we wake up in the middle of the night making to-do lists for deadlines that are months away.  

I’m someone who struggles not to work during vacation. I’m so connected to the work we do at Doyenne that I find it hard to disconnect. During our July break, I found myself browsing Facebook and getting pulled into pages that I monitor for work, including one page called Nonprofit AF. The author, a nonprofit blogger, sparked a lively discussion around the difficulty in unplugging during vacation. More than 500 nonprofit professionals chimed in with mostly sarcastic comments about how not to take a vacation.

Reading through the responses, I got several laughs as I related too well to the stories of waking up in the middle of the night during my vacation worrying about the next two Doyenne events, or sponsor meetings, or who-knows-what other detail. But one comment stood out as a reminder that it does not have to be this way. 

The commenter shared that they had recently moved to Australia, where people typically take off two to four weeks at a time. And when they do, they set their out-of-office email to say, “I am on vacation (on these dates), and will not be reading anything sent during this time. If you need a response from me, please resend after my return date.” Upon return, the vacationer deletes all of the emails sent during the trip without reading.

While that may be an extreme approach, it reveals how much of our attitude about vacation is influenced by our culture. And study after study has shown that taking real vacations is a vital piece of a healthy life. 

Why entrepreneurs need to take vacation 

I’m a member of a very active Facebook group for entrepreneurs in Austin. It helps me gain a sense of what entrepreneurs in other cities struggle with. And one of the most common refrains is the struggle to lead the business instead of getting stuck in the day-to-day.

One of the most effective ways to take a step back from the day-to-day of your business is to physically leave it behind for a few weeks. Take a real vacation. Empower your employees to make decisions in your absence, and then leave. 

When you come back, you’ll probably find that the business still functioned without you. Perhaps your employees will have flexed their skills and become more self-sufficient. 

At Doyenne, we take vacation seriously. We’re still developing the skill to fully disconnect, but we put measures in place to protect our vacations from interruption. This means that during our vacations, we aren’t available for our members if they need urgent advice. But I think those moments are good for our members. It gives them a chance to gain some distance from the situation while they wait for a response, and many times they find an answer on their own. 

Taking vacations forces you to prioritize your time leading up to the vacation and focus on what’s most important for the long-term success of your business. For me, it also means learning to let go. I know that I am a control freak. I’m super Type A. Seriously, when I took the Strengths Finder test, my lowest score was in “going with the flow.” But for me to go on vacation, I have to give up some control. I have to trust that I’ve done the prep work, and it’s time to let go. 

Yves Chouinard, founder of Patagonia, takes months off at a time to go adventuring. In an interview with the How I Built This podcast, he explained his attitude. “If the warehouse burns down, don’t call me. What can I do? You know what to do.”

Franklin Barbecue in Austin is another example of a business that knows how to take a vacation. They do an annual shut down the first two weeks of August. This is a restaurant that typically has people lining up at 5 a.m. to eat there. If they can take a break, so can you.

If your business cannot function without you on the day-to-day, your startup will never be able to scale. 

How to take better vacations 

At Doyenne, we decided that our entire organization would shut down for four weeks out of the year: the first two weeks of July, and the two weeks surrounding New Year’s Day. 

This was a careful decision made after evaluating the nature of our work, and the typical busy and slow times in our business. Doyenne doesn’t need to maintain banker’s hours because our work is based around events, programs, and one-on-one meetings that can be scheduled around everyone’s availability. In Wisconsin, attendance for business-related events drops in July and during the holidays, so it’s a great time of the year to take a break. And since the work each of us does is so interconnected, we found that it’s most effective if we all take off work at the same time.

Here are five tips we can share: 

  • Prep strategically.

The last month before our July break is intense. We have to make sure our contractors are equipped with what they will need to meet deadlines while they can’t reach us. I actually start my auto-responder two weeks ahead of the vacation, letting anyone who emails me know that it is coming, giving them time to ask any urgent questions.

  • Take off more than one week.

Being an entrepreneur means being deeply invested in your work. When you’re that emotionally connected to what you do, it can be hard to turn off your work brain when your vacation starts. I’ve found that it helps to take longer chunks of vacation so that I can let myself decompress for a few days and then begin my vacation. Additionally, many entrepreneurs have told us that they if they only take a week off, they come back to a mountain of work and delayed decisions. But if they take off a few weeks, their team members seem to step up to the plate and handle problems on their own. 

  • Don’t spend the whole vacation traveling.

It’s tempting to squeeze every last minute out of your vacation — especially if you want to travel to another country. You feel pressure to make the cost of the flight “worth it.” But if I don’t give myself a buffer of a few days before and after a trip, I’ll come back from vacation more worn out than I left. Traveling is exciting, and fulfilling, but it’s also work. Know yourself, and give yourself time to take care of household chores, mentally decompress, and fully enjoy a vacation, even if it has to be a shorter trip. 

  • Put an auto-responder on your text messages. 

Most smartphones have a variety of options for auto-replies under the “Do Not Disturb” function, which silences calls and notifications. On the iPhone, you can access this menu from the main Settings menu. For example, you can create an auto-reply message that sends to all of your contacts, or just your favorites, and you can schedule it just like you would an out-of-office email.

  • Ignore the haters. 

By taking an extended vacation in America, you’re actively going against the grain, so of course you’re going to face resentment. I have run into resentment from other entrepreneurs in the Madison area because Doyenne shuts down for four weeks out of the year. We get asked, “How come you get to do that?” But we know how much effort it takes to pull off these breaks. We bust our asses in June so we can take this time off, because we know it’s good for our individual health and sanity, which benefits the organization as a whole.

Be a force for change 

When you first transition from the corporate world to the startup world, it can be very difficult to plan for and follow through with vacations, because there’s so much pressure to always be working. You have to juggle an unpredictable schedule where both opportunities and raging fires can pop up out of the blue, and you’re often handling multiple full-time responsibilities at a time. 

So in the face of all of that, it’s completely counter culture to still make the decision to prioritize your health and your family, and take the long-term vision that this is best for your company. But change starts with you. It’s your company. You get to make the rules. Isn’t that why we all became entrepreneurs in the first place? 

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