How to Turn Business Trips into Vacations for $0

by Will Lipovsky · 2 comments

wing of plane
I worked as an analyst for a Fortune 500 company years ago. My job was basically to help banks become as profitable as possible. We used proprietary software (best of its kind, thank you) to maximize the profitability of each customer. Part of my job was to travel around the United States training bankers how to use the product.

Travel was part of the reason I took the job. Though, of course, the job comes first, but why can’t a person enjoy both work and travel? This post will tell you what I did to turn business trips into vacations. And I’m not writing this post merely for a catchy headline either, because the strategies are clever (if I may say so myself!).

Note: Business ALWAYS comes first, but traveling for work is largely about building relationships. And what better way to bond with clients than doing fun things with them? Let’s get started:

Do As Much As Possible Before Arrival

There’s a reason I love planning. In this case, planning will help you get a vacation instead of a stressful business trip. What you need to do is take care of as much business as possible before you land. In reality, you get as much done off-site even if you don’t want time for sightseeing anyway, because meeting clients in-person should be more about strengthening relationships than be sweating over spreadsheets.

I would always prepare for the on-site visit as early as possible. I would make sure everyone on the other end knew they could always contact me with questions. We did teleconferences, video conferences, everything necessary so that when we get on-site, we have as much bonding time as possible.

Have a Fixer

You may not be Anthony Bourdain but you can still have someone to connect you with the city.

Find out who you’ll be working with who knows the city the best. This will become obvious simply by asking a few questions about their city during the end of a conference call. Find the city cheerleader. Ask them what you can do for fun while you are there.

Plan Your Meals

Meals are the perfect way to bond with clients. And trying the local cuisine is a great way to bond with the city. Before leaving for your trip, ask for suggestions on where to eat.

Make sure you know how long it will take to travel and eat at these places. If you won’t have time to do lunch there, go for dinner. You must plan your meals or else you wouldn’t be able to eat at all the best places. Trust me.

Leave Time for Sightseeing

Unless you have a horrible boss, he/she will want you to leave time for sightseeing. Honestly, it’s some of the best money a company can spend on you. When you get back to the office, you’ll have tons of cool stories to share. The stories will make other people want to hit the road. You’ll also have fun stories to share when interviewing new employees. And you will have bonded with colleagues/clients.

Or… Don’t Work at All

Okay, at this point in the article you may be peeved that I’m still suggesting you work during your work trip. Yes, it’s true. You must still do some work during the day. Or do you? Here’s how you can get the company to pay for an honest-to-goodness-no-work vacation. If Americans still take those…

This is done by using your personal credit cards at every chance you get. The company will reimburse you and you get to keep your credit card rewards, hotel points, rental car points, etc. Pretty sweet.

I booked flights, rental cars, food, everything on my personal credit card. That meant I would get free nights at hotels, cashback rewards, etc. I only traveled about once every 1.5 months but that was still enough to pay for a (theoretical) annual mini-vacation. Not bad.

Because Business Travel Should Be Fun

I had a blast while traveling for work. You can as well. Simply follow the guidelines in this post and you’ll have a blast while getting work done.

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  • Investment Hunting says:

    I love traveling on the company dime. I always turn business trips into mini vacations. I agree with you, planning it out in advance allows for a lot of personal time. I catch red-eye flights on Sundays, arrive early in the morning and have the entire day to explore before heading to work on Monday.

    • David @ says:

      Good for you. I’m always afraid red eye flights will tire me out too much so I often skip those. Still, traveling on the company’s dime is awesome! ????

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