The Evolution of One Entrepreneur’s Vacations


I know your first question.  Do entrepreneurs take vacations?  Absolutely.  I just got a chance to spend four days in a beautiful Hawaiian beach town and it made me reflect on the evolution of my vacations as a founder/ceo.  The vacation-eschewing, Jolt-cola-drinking, 24-hour-hacking founder culture is primarily the stuff of urban legend.  Entrepreneurs are like everyone else.  They burn out.  And without vacations, they burn out faster.  Any entrepreneur that believes in never taking vacations is either lying or the leader of a company that simply won’t be around very long.  Vacations are as important to the success of an entrepreneurial venture as work ethic.  In fact, if you can’t check out, you can’t be productive when you’re checked in – and that ultimately impacts your start-up’s success massively.  You certainly can’t connect with family the way you need to – and that impacts your start-up’s success massively too.

But taking a vacation as a founder is REALLY difficult.  You have an emotional connection to the company you started and can’t imagine it surviving even a day without you there.  If you’re like me, you’re typically a workaholic – and get a rush out of working a little harder.  And you live in an ultra-connected world, which means vacationing isn’t as simple as going someplace else.

I took my first vacation as a founder at least about a year and half after we started BloomReach.  We were really small then (fewer than 6 people) and the idea of one of us not being around for a week was impossible to imagine. The likely loss in velocity was just too disconcerting to contemplate.  Things got interesting when I took my first vacation.  I ended up heading to the beach, where I pretty much worked like I was at home.  The early-stage start-up vacation is simply an exercise in transplanting and pretend-vacationing.  The root problem with my early vacation was that I was too much in the flow of critical path items.  Customers needed to be signed. People needed to be recruited.  Products needed to be released. I was a bottleneck to progress in all of them. Whenever I opened my inbox, it had more emails to respond to than I had minutes to type.

As we cross the 225-person threshold at BloomReach, my vacations feel pretty different.  Sure, in Hawaii there were the one or two phone calls I absolutely had to take and re-orient my day around.  There was the occasional mind-wandering from the family back to work.  But for the most part, I checked email about twice a day and didn’t do a whole lot beyond that.  As I was on the plane ride back home – I opened my email and found that I could get through it pretty quickly. It wasn’t that there weren’t critical items for me to tackle – it’s just that none of them could be tackled via an email task list. I had about 5 big problems to think about – like an under-performing team or the long term strategy for one of our product lines or ways to continue to drive incremental growth.  All of them required a lot of thinking, significant in-person communication with key folks, some data gathering and multi-dimensional action.  Most were urgent topics, just not ones that could be tackled at a vacation in Hawaii.  The vacations changed because the role has changed.  We now have a terrific team to tackle the extremely important day-to-day challenges of the Company.  But as the team has grown, structural challenges like the topics mentioned above become more thorny and less easy to address.  Given the nature of how vacations evolve as one’s role evolves, I think an Entrepreneur should also change the way he or she takes them.  In the earlier days – take them a bit more frequently but for short bursts (a long weekend here or there).  The days are long so you need to constantly re-charge but you can’t be away very long.  As the Company grows, take them less frequently but for longer periods of time (perhaps a week or 10 days).  That might enable more of an ability to “disconnect” and greater clarity of thinking to tackle the thorny challenges.

One of my investors, Scott Sandell from NEA, advocated to me that I take a three-week complete check-out vacation every year.  I’m not enlightened enough to be there.  After four or five days, I’m pretty excited to come back to work.  But I do see his point.  As you grow in role and responsibility, the quality of your decisions become a lot more important than the quantity of actions you take.  And that quality requires a clear mind – one that comes from genuine vacations.

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