Why Wait?

Do you ever experience regret? Unless you are not human, of course you do. And so do I…

Regret often occurs from the failure to do something that you intend to do. It is obviously much deeper than this, but in the context of “social distancing,” it feels timely to think of regret in this way. In fact, thinking about regret this way got Sarah and I thinking about the things we have done the last two years that we do NOT regret. Here is our list:

  • We began financially supporting a surgeon in Africa through PAACS, which is something we talked about for a while.

  • I attended the Masters golf tournament with my best-man in April 2019.

  • Last October Sarah and I traveled to San Francisco for my friend's wedding. The power went out because of the fires in the area. Not only was it one of the most memorable weddings we have ever attended, it was also one of the best!

  • Sarah’s birthday celebration was about to get “fired out” because of the fire threat in Napa, but we pivoted to Mexico. We almost waited to the spring but did not because we just did know what spring would look like for schedules. Thank goodness we did not wait (COVID-19).

  • Last October I gave our company Blackhawks tickets to a friend of mine whose husband had just been diagnosed with Cancer. He died in March this year.

  • Over Christmas we booked a hotel in Chicago and took the kids for a sleep over. We went to the “lights at the zoo” despite the weather being frigid. We went to dinner with the kids and to the Museum of Science and Industry the next day.

  • Sarah and the kids joined me in Florida for my bench-marking meeting in February of this year. We then had a mini-vacation. We almost did not do this because we also had spring break plans, but we said “what the heck.” Our Spring Break plans were later cancelled because of COVID-19.

  • Sarah’s parents came up to Chicago and met us in another hotel overnight. On day one we went to the Museum of Science and Industry and then to Joe’s Stone Crab. Day two we went to the Chicago Auto Show before going back home. It was Valentine’s Day so Sarah and I were able to go out to dinner that night with babysitter’s already staying at our house. This was 4 weeks prior to COVID-19.

  • Two weeks prior to things getting crazy our sales team had a strategic planning dinner. We broke bread, had a few drinks, and laughed together. Thank God we did this because I have not been in the same room with many of them since.

Please hear me, I am not advocating being foolish or going into debt to live life. I am only advocating not waiting for a “rainy day.” Or, as what has become an unofficial “mantra” in our house: “why wait?”

I share this because it is tempting as a leader of business to feel “too busy” to do most of the above.


It takes a little intentionality and a little planning, but do not wait to make a memory. You simply do not know how much time you have.

embrace bald, stay bold

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