What Long-Term Travel Taught Me About Project Planning

Imagine your last day of your first post-collegiate job.

For me, it was with some nerves, but mostly eager anticipation that I decided to leave my position (and benefits!) as a User Experience consultant to go on a round-the-world vision quest. With three years of professional experience, a longing for exploration, and no “real” commitments it was the right time to go. My journey has bore witness to undeniably breathtaking views and heartwarming human interactions but arguably one of the best side-effects of travel has been perspective. Of course perspective has manifested itself in a variety of ways, one of which is understanding the work I did in a new way. Long-term travel informed my perspective on managing a budget and documentation, but the most eye-opening was its impact on how I understand project planning.

Planning is a balance

My mom probably sole-handedly keeps 3M’s post-it note division in business. She has long lived by lists and notes, a trait that has been passed down to me. At work, I loved to have my whole day – realistically week – and project tasks laid out so I could not only check them off my list but know what was coming. If it were up to me, our trip would have been laid out in much the same fashion, but luckily I was traveling with a partner who does not require the same level of careful anticipation. Instead, we opted for check-marks, countries where we were meeting people along the way, to give points of reference on our trip. Knowing every minute of every day would have meant we missed out on wonderful experiences. Similarly, planning a trip prior, entirely online based on “best practices” would’ve meant we would have to neglect all of the first-hand knowledge we gained at each new spot. Putting too much effort into upfront planning means that amending your hard-and-fast plans – project, travel, or otherwise – will likely be expensive and inefficient.  Of course, going into a situation blindly can similarly be ineffectual. I found the happy medium for me was:

1. Allow for three days in a place to get acquainted to it in lieu of planning for weeks prior without any “on-the-ground” information to infuse in. Note: this requires trust on the part of those you’re traveling with.

Project Planning Translation: Allow for a chunk of time upfront to get to know the organization and people you’re working with BEFORE building out a project plan. Where do people sit? How do they communicate? Note: this requires trust and understanding on the part of your client or team.

2. No more than an hour of research can be spent on tourist attractions and food prior to arrival.

Project Planning Translation: Figuring out everything before you’ve gotten started can be dangerous and a misuse of time. Best practices are important but solutions are contextual and there are a variety of options. Plan your project as such. 

3. Understand loosely how easily things can be booked last minute. If it’s plausible to hold off on making a major decision – like where you’re going to stay – why not wait until you have more supporting information. It’s perfectly fine to have a straw-man itinerary as a jumping off point.

Project Planning Translation: Take advantage of placeholders and loose schedules. Understand if it’s feasible to flesh out a solution more once there’s more information.

Example from long-term travel:  We planned a train from Oktoberfest in Munich, Germany to Zagreb, Croatia and a month later a flight from Dubrovnik, Croatia to Rome, Italy with no plans for a month in between. One of our first nights in Zagreb we decided to book a place in Belgrade, Serbia for a few days following. Shortly after, we met up with a couple who have been digital nomads for the past few years. They invited us to a party where we met a number of other people who wanted to show us around the city. Unfortunately, since we had booked another place after that we weren’t able to stay but learned for our stay in Belgrade to keep our departure date open-ended should the same situation arise, which it did. Of course, staying longer had no impact on our leaving from Dubrovnik at the end of the month but meant that our time was used in a meaningful way and we were able to incorporate the lesson we had learned from our last stop in Zagreb.

At some point along the way, I stopped using other people’s trips from TripAdvisor as a means to determine what we should do. Not only did Bob, 57 from Tulsa, Oklahoma have wildly different expectations for dining than we did, we found meeting and talking to people as we were in the place often yielded more memorable results. Occasionally I would check if a place had horrible reviews but anything just below stellar didn’t phase me if it had been recommended by a local party. Ultimately I learned that our trip, just like your project, was unique with its own set of expectations, challenges, and joys.

To read and see more from our adventure check out our blog Same Clothes, Different Place.