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Alive But Not Well…A 2019 Travel Recap

Things have been quiet around here. My bad. There’s been a lot going on. New job. New apartment. New book. And with a new year comes a new resolution. One blog post a day for 365 days. Promise I won’t be that MIA again, folks.

I’m not at all where I thought I’d be on New Years Day 2020. In all the best ways possible. Considering the fact that I started 2019 driving a rickshaw through India, I should have expected a wilder year.

Best way to have described the year? Alive…But Not Well…

Seven Years in Solopreneurship

As I entered my 7th year working for myself I had an “ah ha moment”. It was while on said rickshaw that it happened. Here I was in the middle of nowhere India with WiFi thanks to a hot spot enabled rickshaw. And as I’m bouncing in the back, I’m going back and forth with a prospective client who is nickel and diming me to death. What…was….I….doing?

I’m so grateful to be my own boss, and not just because it has allowed me to travel as I do. That said, a lot has changed in the seven years I’ve been doing my own thing. For the first time in a while I found myself starting to consider taking a J-O-B.

This past November I did, and while it took longer than I thought it would, I’m grateful it even happened. Seven years ago not only would this job not have existed, but the concept of a fully remote team working within this Fortune 200 company would have been unheard of.

2019 Travel Recap

It wasn’t my “busiest” travel year, but 2019 involved plenty of hotels and flights. But it did include two trips to India. I spent most of the first half of this year commuting between Cancun and Chicago. By the time summer came around, I’d given up my apartment in Chicago and was planning to spend some time in Madison, WI. Well, as they say, “The best laid plans of mice and men…”

In the end I flew on 80 flights for a total of 119,475 miles and spent 278 nights in hotels/coliving spaces/on the road (READ: not in my own bed).

a graph of different colored bars

By Plane

I started the year with Executive Platinum on American Airlines and as Platinum on United. I never thought it would happen, but thanks in part to the new job (and a quick mileage run to Hong Kong ) I hit Premier 1k. Can’t wait to begin learning all about PlusPoints. 🙄

I never fell in love with American Airlines (except for the fact that they upgrade award flights). Add in their maintenance strike issues and I am glad to have gone running back to United. I earned ExPlat on a challenge and I really won’t miss it when it expires Jan 2020.

While I didn’t do a ton of international travel, I did get a chance to check out plenty of new airports and cities!

New Airports

  • Belgrade, Serbia (BEG)
  • Bombay, India (BOM)
  • Cleveland, OH (CLE)
  • Goa, India (GOI)
  • Incheon, Korea (ICN)
  • Istanbul, Turkey (IST)
  • London Gatwick (LGW)
  • Montreal, Canada (YUL)
  • Oslo, Norway (OSL)
  • Sarasota, FL (SRQ)
  • Tampa, FL (TPA)
  • Trivandrum, India (TRV)

United States

  • Atlanta, GA
  • Baltimore, MD
  • Dallas, TX
  • Los Angeles, CA
  • Madison, WI
  • New York, NY
  • Orlando, FL
  • Philadelphia, PA
  • Portland, OR
  • San Francisco, CA
  • Sarasota, FL
  • Tampa, FL
  • Washington, DC


  • Canada
  • Hong Kong
  • India
  • Mexico
  • Poland
  • Serbia
  • Taipei
  • Thailand

By Car

I had 43 rentals with Hertz. Three with Avis. My roll with Hertz continued as I earned a ton of bonus United MileagePlus miles with each rental car. 80,500 in fact. I totally stopped keeping count, but I know I did more than 20 RTs from Chicago to Madison. That’s 6,000 miles alone.


I missed my chance to match my ExPlat with AA to get Globalist with Hyatt, le sigh. So, I retained my Platinum status with Marriott and have my eyes set on Globalist in 2019. A lot of my time was spent at Selina. As it relates to Hilton, their points don’t really buy a lot, but I enjoyed minimal Hilton Diamond benefits.

All in All

So, 2019 was crazy. Less travel, but more new airports. More hotels. More rental car miles. Highlights included being invited to check out the new United Polaris lounge at LAX, Coworkaholic joining BoardingArea, trying out Norwegian Air and enjoying starting to earn and burn Chase Ultimate Rewards and getting creative with new “dynamic pricing” award charts.

The post Alive But Not Well…A 2019 Travel Recap was first published on Coworkaholic.

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