How a 16 Hour Flight Changed the Course of My Career

Mike Debnam
Upside Team Blog
Published in
4 min readAug 13, 2020

Several years ago I was looking forward to going to AWS re:Invent in Las Vegas. I was super excited about it. I’d get more exposure to AWS, spend quality time with my teammates out of the office, and meet new people. Plus, Las Vegas is a fun city. If you haven’t had 8 plates of food at Caesar’s Bacchanal Buffet you’re missing out on one of the true joys of life.

At that time, I was right in the middle of getting up to speed on a new project. A development partner had built an early MVP of a new product for us. It looked great. We had some awesome feedback from early customers and we were ready to take it to the next level. I was getting our team onboarded and building out an updated technology roadmap for it.

This was a strategically important product for our company and our CTO was directly involved. About two weeks before the AWS conference he came to me and said “hey, would you be able to accompany us to Sydney to meet with our commercial partner to discuss the product launch?” Well, Las Vegas is cool but Sydney, Australia? Count me in. A few days later we decided to add on a stop in Hong Kong to meet with one of our other divisions about launching the product there also.

Not only was it an adventure halfway around the world, but a great opportunity to build a relationship with our new partners. Plus, a chance to learn directly how our CTO approached the technology strategy for this new product. Traveling with colleagues is a great way to bond. You have to solve problems together (where is the rental car counter?) and debate weighty topics (burgers or sushi for dinner?).

It is a long way from the United States to Australia.

On that trip our CTO, my product partner and I got some special bonding time. Our product launch hit a last-minute snag with some app store approvals. We were waking up at 2:00am Sydney time to talk with the review board who was on the US West Coast. Evenings we spent in the hotel lobby doing user experience and system design on the fly. Days we spent onsite at our commercial partner’s office reviewing those designs. Our commercial partner said “we are so glad you’re here onsite to work through this with us.” We finally came up with a solution that met all the requirements. We were able to launch. It was a grueling week, but a rewarding outcome.

About a year after that a new opportunity in the company came up that I was being considered for. The work I did with our CTO put me in a great position to be selected for that new opportunity. That one business trip altered the trajectory of not only my career but also my personal life. I discovered a love of traveling and have been to Munich, Berlin, Prague, Sydney again (twice!), Melbourne, and London since. In my professional life I’ve since had the opportunity to build some great products and be a leader of some amazing teams.

In this global pandemic it may read a bit odd to delve into how one business trip changed the trajectory of my career. I barely leave my house now, let alone travel across the world to meet with colleagues and business partners. But for me, it’s more relevant than ever. In this great global reset, there’s an incredible opportunity to imagine and build the future. Video conferences are great, but there’s nothing like being there in person. At Upside we believe that business travel grows companies and careers. I’ve seen that personally up-close in my career. Whether the goal is to win a new customer, learn a new skill, connect with co-workers, or secure a strategic partnership each trip has a specific business purpose and goal.

A bunch of people having the best meeting of their lives.

I lead the engineering team at Upside Business Travel and we believe the future is blindingly bright. Business travel is returning as the pandemic subsides and we are ready to support every business traveler. We’re building products that enable people to travel safely and reduce travel friction from achieving their business goals. We’re always looking for technologists, product experts, and designers to join us. You’ll have the chance to help millions of business travelers have a productive, safe, and enjoyable business trip. If you’re looking to learn and leverage cutting-edge technologies and iterate quickly on solutions — come join us. Check our open positions on our careers page.

--

--