The Unexpected Business Travel Cheat Sheet

Business momentum is fickle. What you spent months, even years building towards evaporates in a single indecisive moment while swift and decisive action taken imperfectly is rewarded with opportunity.

What started as a simple week-long trip to New York became a dizzying month and a half journey in a flash. The adventure spanned seven states, six major cities, four climates, and three coasts. By the end of it, I changed flights 12 times, had to hire new people, buy new equipment and figure out how to keep normal business operations flowing.

When momentum kicks in, your only viable option is to go. As a business owner that means making arrangements at the last minute without the cushion of a travel stipend. Maintaining flexibility, cost efficiency and workflow becomes a daunting puzzle.

This is how you capture lightning in a bottle to make it happen. Even if you’re a small company just like us.

Keeping costs efficient starts with choosing the right airline because you’re walking into situations where uncertainty is king, flexibility is a requirement and unexpected interruptions to your plans are guaranteed.

Pick an airline that allows you to change flights without fees and gives full flight credits when canceled. This isn’t the time to choose a premium airline, but it also isn’t the time to use the cheapest possible option. The cheapest carriers typically fly to alternative and out-of-the-way airports and aren’t very comfortable to ride in. You’re running a marathon and ease of access to the airport and basic comfort while flying is important to keep up your stamina.

We had situations where we had to rebook flights as close as an hour before take off. Stick to one carrier because it’s easier to navigate changes with one carrier than a third party or multiple carriers on the fly.

Rental cars and hotel stays are expensive. Don’t be shy about tapping into friends, family, or clients for a place to stay. A superpower advantage of owning a small company that works with other small companies is that clients value the relationship as much as you do and are happy to help you out. Just make sure your clients don’t feel obligated to give you a place to stay. That means making it extremely easy for them to say no.

If you have to move locations frequently, it’s best to go with a rental car. If you’re mostly going to be sticking to one area of town or going short distances, stick with rideshares. Being strategic about transportation and where we stayed meant that we only had to rent a car for 7 days and stay in a hotel for 6 days.

Too much baggage means getting exhausted from lugging it around as you change locations. If you’re going to be gone for a week, pack for three days. If you’re gone for a month, pack for a week.

We knew we’d be in four different climates that ranged from super hot to chilly at night and ranged from formal engagements to casual. That meant we packed five shirts, three pairs of pants, two pairs of long-sleeved shirts, two pairs of shoes, two formal outfits, and a jacket plus a week’s worth of socks and underwear.

Communicate twice as much as you’d normally communicate with clients and let them know that you’ll be traveling while also keeping workflow going because it isn’t a vacation. Tell them to expect flexibility and a little bit of uncertainty with schedules moving around and a little unpredictable.

You may fall behind on something and you’re guaranteed to have to reschedule meetings at least half a dozen times. Clients don’t get frustrated by reasonable delays or reschedules. They get frustrated when they don’t feel taken care of, last-minute, meeting changes, and confusion. Proactive communication prevents that from happening.