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What Happens When Our Strategic Director Plans a Trip to Italy
What Happens When Our Strategic Director Plans a Trip to Italy

Last spring, my wife Megan and I finally took the trip to Italy that we had always talked about. In January, we booked a 10-day trip that would take us around to Rome, Florence, Cinque Terre, and Venice. We were leaving in March, so we had plenty of time to figure out exactly what we wanted to do.

But to be perfectly honest, we had already started planning months before. We had already read travel blogs, magazines, talked to family and friends who had gone before. Megan had also lived in Florence for a few months on a work-study program, so I was lucky to have her to say, “Oh, I’ve done that. We should definitely do that together,” or vice versa.

When I came back from the trip, I launched into my new role at Pivot as Strategic Director. And I started noticing a lot of parallels between planning for a trip, and planning for a marketing strategy.

Get an idea of what is possible.
We started out reading everything we could get our hands on. I read so many blogs about “10 Things You Shouldn’t Miss Out on in Italy” and “You Didn’t Go to Italy if You Didn’t Visit These 5 Places.” We listened to everyone’s stories of their times in Italy. We talked to each other about all the things we could do while we were there. We compiled a list. And then a list of lists. It got a little overwhelming.


I think a lot of business owners fall into that trap when they start thinking about their company and all the things that are possible. Entrepreneurs are naturally enamored by possibility, and sometimes they can get lost in that—always chasing the things they feel they’re missing out on, but not taking a moment every now and then to just be where they are and reflect on what got them there, and simply being there. Which brings me to my next point.

Decide what you want out of the experience.
Before we could take all of that information and really put a plan together, we had to figure out what we wanted out of the trip. While we wanted to experience all these things, at a certain point, we decided that it was important to us to make sure we had time to relax and just enjoy being in another country and culture.


I think the turning point for us was when we truly realized that we couldn’t do everything. We only had 10 days, and we didn’t have a Visa Black Card in our pocket.

The main reason you make a plan is to make sure you get the most out of the time you have, whether that’s 10 days in Italy, or one year in business. And it’s important to understand that “getting the most” doesn’t mean cramming your schedule with every possible thing.

Developing a strategy or plan is more about figuring out what’s important to you, what you want to accomplish, and removing all the extra stuff—the stuff that will just add stress and force you to run from place to place without actually enjoying the ride. Or, even worse, because you’re so stressed and spread thin, it causes you to miss your train entirely and miss out on that thing you really wanted to do.

Realize the value in making the plan, and the value in flexibility.
We spent at least six months planning for our trip, and in the last couple of weeks, I worked night-and-day designing an itinerary that would make Rick Steves jealous. And once we actually got to Italy, we may have actually looked at it a handful of times.

On one hand, it was because while making the itinerary, we absorbed all the information. Once we got there, we knew the 2-3 things we wanted to do on any given day or in any given city. We found that we only really needed to refer to the itinerary as a resource for smaller details, like when a certain museum opens or the address of a restaurant we wanted to visit.


On the other hand, we knew that no matter how much we planned, we couldn’t account for the unknown. We intentionally built flexibility into our plan because of this. We wanted and needed that plan so we knew where we were going, but we didn’t want to feel bound by it if something great and unexpected came along.

Because if you to are too rigid and too buried in your plans, you can miss out on exploring. You can miss out on those unexpected things that really make a trip worth taking.

If you’re taking a trip to Italy yourself, or you’re merely curious, you can click here to download the final version of our Italy itinerary.