The Founder’s Paradox: How to Work on Vacation and Still Have Fun

founder's paradox: work vacation

The idea of a “vacation” has always somewhat bothered me. Not because I do not like to travel. (I love exploring new places. I am actually writing this post while in the San Diego airport.) And not because I do not think people deserve a break. We all need time to focus on other obligations and hobbies. Mostly because the way we talk about vacations infers that you need to escape your regular occupation — completely.

Yes, I love to travel and take time with my family. But I also love my work. Is it possible to do both?

Not only is it possible to work on vacation and still have fun, I think most founders would say it is a requirement of the job. It can be tempting to think you cannot step away, but you should.  Often. This is true no matter the size or age of the company. And it is particularly important for founders with families. You only have so many years to travel with your kids.

When Dr. Chris Waters and I first founded Aha! in 2013, we made it a priority to carve out trips and holidays from the beginning. Now, six years later, Aha! is nearly 100 people strong and continuing to grow quickly. Even as the demands of the business have increased, I still take time off to enjoy my family and friends. And I still end up working.

Leading a company is a special responsibility — it is important to stay connected to the work and the team.

I am speaking directly to founders and senior leaders in a company. But all leaders likely need to stay connected in a meaningful way while they are away. For me, being able to help when I am needed and relax at the same time is entirely possible and also entirely necessary.

Here is how I approach this paradox:

Love what you do
This one is a requirement. You have to enjoy what you do to be successful. When you do, you will want to take time during a vacation to check in and get some work done. It is invigorating and revives you.

Plan in advance
You cannot predict the future. But you can try to choose a time that is generally not so busy. You are in a unique position to look out across the organization and see what is happening. This will help you plan in advance and be prepared for what will need your attention.

Communicate clearly
Tell both your family and the team exactly when you will be working and what to expect in terms of responsiveness. For example, when I am on vacation, I typically spend a few hours a day working in the evening. Be clear and no one will be annoyed if you are working or not working. They might not always like it — but they will not be surprised.

Explain priorities
Know what your priorities are. Then explain what you will not do and be explicit about what projects will need to wait until you get back. For me, hiring exceptional people continues to be everything as Aha! continues to grow. I will always make candidate interviews a priority while I am away.

Name go-to people
Hopefully you have strong leaders within the organization who can be responsible for some decisions that typically go to you. This is an opportunity for them to grow and shine. Think about people’s strengths and name go-to folks for key work. Trust that they will do well and ask if they need your help.

Leading a team and building a lasting business requires real effort — you cannot turn it off and on.

Life is an adventure and work is a part of it. For founders, the responsibilities of the job are omnipresent. And while some might still think they need to totally “disconnect,” I believe it is possible to be present on vacation and continue to support the team. Because the only way to achieve sustainable happiness is to give your whole self to everything you do.

Read more of The Founder’s Paradox.

About Brian and Aha!

Brian seeks business and wilderness adventure. He is the co-founder and CEO of Aha! — the world’s #1 roadmap software — and the author of the bestseller Lovability. Brian writes and speaks about product and company growth and the adventure of living a meaningful life.

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