Traveling Salesman

Whoa whoa whoa…Look out everybody! This blog has made it past two entries and survived a gap in writing! Nothing can stop it now!

But seriously.

I wanted to take a moment to chat about writing/productivity/work and how it used to get slayed by leisure travel (at least for me). One thing that many people ask me is: “How do you manage to work from home? It would be impossible for me!”. The answer to this question, naturally, is that I’m some freak of nature that gets his jollies off of working. There are few things I enjoy more than a really productive day; and few things I loathe more than lounging about for extending periods of time. That doesn’t mean I’ve never procrastinated (more on that in a later post), it just means that my neutral state is one of seeking out work. I don’t have to ‘force’ myself, which makes the whole prospect of entrepreneurship/self-employment/remote-employment/alternative-employment WAY easier.

The same conditions apply when traveling for work: there are things to be done and anything on top of that is gravy. However, when it comes to leisure travel that’s not a strict vacation, I’ve historically transformed into an excuse-filled alter-ego. Typical excuses include:

  • ‘It so nice here’
  • ‘I just want to explore the city for a bit’
  • ‘I don’t get to see these friends/family often’

These all populate my conscious instead of the usual ‘Get X done, then Y, then Z’. I’m not saying it’s wrong to take a vacation or detach for a while. The problem lies during trips that are supposed to be ‘working vacations’. E.g. I’m spending two weeks visiting my parents for the holidays: it’s okay if I spend a decent amount of time getting things done. But instead of following the plan, life sometimes gets in the way.

So why write all this? First, the mere fact that you’re reading this means that I was productive during a ‘vacation’. Second, it’s a celebration of overcoming a gap day while working. Many folks (myself included) have let tasks/projects die because there was a bit of a gap. “I’ll write a blog post every day!” is a tall order to live up to. It’s also totally unnecessary. Although consistent time to any initiative is important it’s okay (either intentionally or accidentally) to build-in gaps/miss days. Remember, anything worthwhile is often closer to an ion engine than a rocket booster.

Most pertinently, however, I wanted to share how I overcame this gap in the travel lull. For this trip, I didn’t have to contend with family or friends; however, it is a new city that I want to explore and I do have strong urges to sit by the riverfront with a coffee/beer all day and watch the ducks swim pass. My success, therefore, has stemmed from a shifted perspective. Rather than try to ‘discipline’ myself to sitting in the hotel room getting the usual things done, I altered my game plan to let my Instant Gratification Monkey have his way. I put iPad-capable tasks (blog post writing, long-tailed brainstorming, light administrative work) on the top of my list so I could do it from the riverfront. I also shot location-flexible tasks to the top of my list. Oh I have to ship a small package? They have Post Offices and UPS stores where I’m going, I can walk there as part of exploring the city. Most critically, however, was the shift away from ‘missing out’ to one of helping out future me. Future me will appreciate that I took time to isolate myself in the hotel room while my significant other was at her conference. I’ve already spent some time by the river, so I’m not missing out on the experience while I zero-in on other tasks.

In short: Even notorious workaholics like Casey Neistat have admitted that traveling shoots the hell out of productivity (he specifically referenced travel days). But that doesn’t mean that you can’t be a productive rock star, even as you live like an actual rock star.

Originally published at on February 21, 2017.