Take a Strategic Vacation

This is yet another story that I’ve told dozens of time to individual and groups, and now finally written down. Here is a short video talk:

Back in 2004 I co-founded Mobile Workforce Management, a vertical market SaaS firm. For the first 6+ months, I was the entire development team, while my co-founder was the entire analysis, support, and customer happiness department. Over the course of a few years, we hired developers, a very-senior developer / leader / general manager, support staff, and more. In spite of these hires, as of 2007 I was still in the loop for numerous critical processes that had to happen every day or week to keep the doors open – not a great situation.

Around that time I was inspired to take a month-long family vacation, far longer than any past vacation. My family made arrangements to spend 3 weeks in a house by the beach, 1000 miles away, in the summer of 2008; these arrangements must be made far in advance, as such houses tend to fill up. I’d be away for approximately an entire month, allowing for travel time and stops along the way.

With that hard date in hand, my notions of ironing out the business processes “someday” were swept aside, and I set about tracking, automating, documenting, and delegating any of the work that involved me and had to happen at least monthly.

• accounting / bookkeeping / payroll
• production sysadmin
• development sysadmin
• system monitoring
• management processes
• customer relationship processes
• vendor relationships
• design and code reviews
• much more

It took months of hard work (by myself and others) to build up our company ability to handle all of these things well in my absence. As of the vacation date, all of this was set up to run smoothly either entirely without me, or with a tiny bit of remote input from me.

This worked, in fact it worked so well that our customers didn’t even notice my absence.

Though I didn’t know it at the time, the work I did then to increase our organizational process maturity was a turning point in the life if the business, enabling its eventual sale. Before that work, I’d have been a bit embarrassed to say “organizational process maturity” in public. Afterward, I have lived (rather than just learned about and talked about) the notions of working on-rather-than-in a business, of building a business with a life separate from that of its owners.

In retrospect I’m calling that trip a Strategic Vacation – a vacation taken both for its own value, and to drive the accomplishment other critical goals. If your business needs you every single day, that’s a problem. Create some pressure on yourself to solve it, by scheduling a strategic vacation, then go make it happen.