Mixing Work with Pleasure – Tips for “making fun” of work trips


Last week I enjoyed a 5-day trip to Houston, Texas where I mixed equal parts of work and play. A client afforded me the opportunity to fly from a hot and humid Pennsylvania to a VERY hot and VERY humid Houston. (Houstonians, you have us beat hands-down!)

Humidity Index aside, this trip was unique for a few reasons. Foremost, the travel served the specific purpose of strategic planning and team building for my longest-standing and fastest-growing client – a global nonprofit focusing on cancer research and patient care. Outside of the important work we accomplished as part of this retreat, I found myself in a new and interesting city with a desire to explore.

Here’s what I learned about mixing work with pleasure, and seizing the opportunity to make professional travel personally fulfilling.

Set expectations for when work must take place.

If work is the real reason you’re headed to this new location for a while, be sure to set clear expectations for when you’ll need to work! Whether you’re attending a retreat, conference, or some other type of work event, you should mark work-related commitments clearly on your calendar. And once you’ve done so, the rest of the time is yours to spend freely! For this trip, I was traveling with my husband who though he didn’t have any work obligations in Houston as I did, still had work that needed to get done remotely. We both carved out time upon waking to check in on emails, move the ball forward on projects, and then we could sign off for a few hours and enjoy other activities not at all related to work. This theme occurs many times throughout my blog, but I’ll say it again – it all comes down to organization, delegation, and balance.

My core purpose of traveling to Houston was for a strategic planning retreat for my client, the Kidney Cancer Association. All other travel/fun plans revolved around my commitment to them.

Intentionally seek non-monetary fun.

Back in our early work-play traveling days, my husband and I had to be very frugal with transportation, lodging, and activities. It’s easy to blow hundreds if not thousands of dollars enjoying a new city, but it’s simply not necessary! We fully embrace non-monetary fun and actually find it to often be the best kind of fun there is. We will sightsee in a city by taking a long run or walk. This doubles as exercise and allows us to see a city on foot, which is so different than in a car or tourist bus. We’ll seek no-cost or low-cost attractions like parks and museums, or simply enjoy walking down Mainstreet. For food, we intentionally (and fully) enjoy one large meal a day, often dinner. Breakfast and lunch are light and often are snacks we’ve purchased from a local grocery store and keep in our room. This allows us to spend our money on experiences that are meaningful, not haphazard, and easily forgotten.

Our 7-mile along Buffalo Bayou Park afforded us free entertainment, exercise, and beautiful views.

Make where you stay part of the experience.

On work trips, the host client often arranges for my lodging which I graciously accept and make the most of, wherever it tends to be. Thus far it’s all be exceptional locations and because it’s almost always paid in full – I have no complaints! My husband is able to stay with me (also for free) so on this particular work trip, two of our four nights were at no cost to us. For the other two nights, I wanted to experience something different in a space that would better immerse us in the Houstonian culture than just a hotel room, so I turned to airbnb. And for about the same cost (possibly even less than) of a nice hotel room, I found this guest house bungalow in Montrose, an eclectic neighborhood bordering the Houston Museum District and near downtown.

It gave us far more space and amenities, plus put us without walking distance to anything we could want. We’ve been using airbnb and Hotel Tonight often on our work-play travels and have always been pleasantly surprised by really unique choices at amazing prices that we would have never found on our own!

Do your research in advance, but remain flexible. 

On one of my very first work-play trips with my (now) husband, we coined the phrase “When you don’t plan everything, everything goes as planned.” And we continue to embrace this on our travels. Knowing what’s available in the city in which you plan to stay is important, so doing some research in advance is smart. This is how I found out it just happened to be Houston’s Restaurant Week which was such a fantastic find! All of our foodie dreams came true with excellent restaurant recommendations all with clear pricing, menus, and locations mapped out for us. We also decided in advance that we wanted to catch an Astro’s game while we were there. We purchased ticket’s to their game against the Minnesota Twins for a great price in advance, which gave us structure to our tourist time. Beyond that, we left our schedule wide open to explore and flow with wherever the day and our mood took us. This is important because some days you might wake up needing a few extra hours of sleep – take it! Come dinner you might decide I want Mexican not Italian, and you have complete freedom to switch that up. Planning out too much in advance takes away the fun and freedom of traveling on your own schedule.

Sunday’s Astros vs. Twins game added the perfect amount of structure to our day while leaving us flexibility to enjoy many other impromptu stops, like Houston’s “best” tacos at Taco a Go Go!

Don’t overthink it!

And finally, don’t overthink travel. Easier said than done, right? It takes practice. When I travel with my husband, there is certainly a level of comfort there. I don’t stress over the unknown of airports, parking, or Ubers. But he’s also my security blanket through it all. So I embrace this when he’s along for the ride! It’s why I keep inviting him on my work travels after all (kidding, kind of). But on a more serious note, don’t let travel stress you out more than what’s helpful or necessary. That robs you of the joy you will experience when you’re not overthinking. Prepare for your trip by being clear about work expectations, your needs to adhere to such work expectations (proper attire, transportation, technology), and allow the rest to ebb and flow. When you set out on your travels with minimal expectations and an open heart and mind, all experiences can be good experiences.

This photo captures the fun and carefree nature we kept at heart when exploring the City of Houston.

Happy traveling!

Have you had a similar experience, or do you have a tip to add to this list? I’d love to learn from your insights! Join the conversation by leaving a comment below.