Text 28 Dec I don’t know how to take a vacation

You know the feeling… you’ve just been on a long flight, and are about to land. Aside from being in a new place, you’ve likely been disconnected from the world for hours (except for WiFi enabled flights in the US) and are clutching your phone. The plane touches down. If you’re like me, even before it fully lands, you’re already taking it out of ‘airplane mode’ (or the non-iPhone equivalent) and now waiting for incoming voicemails, texts, and emails. You try and bang out as many as you can while the plane is taxing to the gate, knowing that it’ll reduce your burden later.

I get more emails than one person can realistically handle. Or, I should say, handle, AND have a life apart from work. Every day I wake up and declare war on my email. On really good days, I leave the office with just a few unread emails, totally doable from home before bed. On bad days, I’m hundreds of emails behind, and have employees, major customers, partners, and more, waiting. “Unread emails” has become my task list.

I’ve tried different techniques ranging from checking email once or twice a day to even having others check and return email for me. I’ve even tried weaning myself off of that metric – the # of unread emails – as a barometer for my productivity. And yet, I keep coming back to the same gut feeling. Email is important, and psychologically you need to feel like you’re getting somewhere, and getting your email load under control, every day.

At USC business school, it was drilled into our head to be “on” your business not “in” your business. Meaning, one of the tell tales of an effective CEO is to build yourself out of a job. Delegate and assign responsibility, and put systems in place for redundancy and accountability. In a startup, this is usually more theory than reality as you build up the business around you. I think I’m maybe 50% there… but my business still needs me to be on call, 24/7.

 Going back to a typical day, I get up around 630, sometimes earlier if I need to do calls with our European reps or office. I feel like a robot. I get up, look at my calendar, and start doing what it says. On “good” days there are only four or five meetings. On some days, there are more than a dozen meetings; I once did 10 meetings in a day in New York, and calls in-between. My assistant knows to arrange the calendar so that every minute can be used efficiently. The addresses and/or call in #s are clearly in the details of the calendar, so my iPhone recognizes them automatically and I can just tap to call in or get directions. I prefer taking public transportation in cities with good metros, and so my “from” and “to” stations along with the details are clearly inserted into my calendar. Time is at such a premium that I find myself not knowing what to do if I have downtime longer than a few minutes.

I’ve often wondered how healthy this is. If I’m letting myself be creative keeping such a packed schedule. If I’m too “American” about work. If I’m a workaholic. Then I look at 2010 and see the pace at which we’ve been able to grow the business, and remind myself that it must be worth it.

Unless you want to take a break. I’ve traveled a ton this year, and all for work. I’ve worked every single weekend. You see, when you’re an entrepreneur, work doesn’t feel like “work” and therefore you don’t need to take breaks as frequently as others do, because you’re not “working” as much.

I try and take a single week a year for myself – and it’s usually the week between Christmas and New Years, when the email volume dies down, when calls and meetings can’t really be scheduled at the same pace, and when I can safely – and without guilt – disconnect.

I landed in Colombia on Christmas day. When I turned my phone on, getting off the plane, I had two more emails than I had had when we took off. Even on vacations, I’ve gotten in the habit of enabling my international data services so I still get email, and taking calls that I receive to insure I’m not letting any part of the business down.

On the 26th I took a ride on the Medellin Metro – the only system of its kind in Colombia. It passes above ground so you can see the whole city, and then connects to the “metro cable” which is a Disneyland-like cable car that whisks you to incredible views of the entire city.

Except I found myself missing half of the scenery because I was checking my email, or Twitter, or whatever. And I knew that I didn’t need to – it was the day after Christmas, no one was working on that Sunday – and yet I still did, out of habit. Halfway up the mountain, I was getting upset with myself. Was I really this addicted? Was I really not able to fully relax?

We stumbled in on a small town square somewhere in a barrio (neighborhood) we probably shouldn’t have been in, and sat down and had a beer. After about 15 minutes, I felt like I was spending too much time in one place. Didn’t I have somewhere to be? Could I really just “waste” time like this?

You see, when you spend the entire year getting wound up so tight that if you lose five minutes it’s a problem, it’s then challenging to do the reverse – “waste” time, or in other words, take a break so that time doesn’t matter. Unwind. Relax. And put the wires away.

And that’s exactly what I’m determined to do. Technology has brought great things to the world; I’m building a business around the latest in mobile technology. But as smartphones proliferate it also requires us to be disciplined in a way we never had to try to be before. It requires us to be unavailable. To unplug. To not check our email. To make an effort to relax. It’s hard. Maybe it’s the equivalent of quitting smoking, or drinking. And I’m determined to do it, starting right now. 


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