One of the many stupid things I did in my first year as a consultant was booking the cheapest everything and paying out-of-pocket when traveling for business.

My first business trip to San Francisco, in 2014, was to meet with Scalyr, and it included a cheap room in someone’s home near the airport, the cheapest cross-country flights (including an overnight return), and a compact rental car.

Cartoon about ending up somewhere you didn't think you would.

Despite providing immense value to the company—among other things, we came up with a pricing strategy they used for the next several years as they reached millions in annual revenue—I thought I was doing the right thing by being frugal and paying for myself.

Upon realizing I had no intention of billing them for travel expenses, Steve—the CEO and a serial founder with multiple exits and too nice a disposition to tell me I was being stupid—offered to reimburse me for the trip. “Oh, that’s not necessary,” I parried, explaining I’m happy to be there and that I’m taking advantage of the trip by meeting with friends and prospects.

“Can we reimburse you for the flights, at least?” he said, after processing my idiotic answer.

To this I replied with the confidence of someone declaring checkmate: “No, no, it’s not necessary… And anyway, there’s nothing to reimburse because I booked the flights with points.”

Steve smiled, strained to process the stupidity he was hearing, then let it go.

The following year I was having lunch with a friend—another consultant—and the topic of business travel came up. I was surprised to learn he stays at hotels, chooses flights by convenience and not price, gets around town by Uber or Lyft, and bills the client for all of it.

When he heard how I was traveling he laughed and shook his head in a way that made me embarrassed at first and then relieved; his figurative slap in the face meant I no longer had to travel like a broke backpacker when visiting clients.

Since then, I’ve made an effort to form relationships with friends and clients in which they feel comfortable telling me I’m doing something stupid, and I can do the same in return when they, for instance, waste money on bad marketing campaigns. (And yes, I’ve since set standards for my flights and accommodations, always billable.)

What stupid things are you doing? Do you have someone around to tell you?

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