Winning, Losing, and the Importance of Staying in the Game

Stay in the Game” is a true story about a hopelessly lost teenager, salvation through dog ownership, and the kindness of strangers. It will take only take you a few minutes to read. Go ahead and click the link, I’ll wait.


Winning is great. No one hates victory, but losing itself doesn’t always have to be so bad if we get to take another shot. The problem with life is that we don’t always get another shot. Sometimes it’s because things just aren’t fair, sometimes it’s because we sabotage ourselves, and sometimes it’s just because. 


To complicate life further, winning itself is completely subjective. Tell a kid they can stay up a little later tonight and give them a bowl of ice cream. That look on their face? Winning. A promotion, a marriage, a surprise party – these are all subjectively interpretable as wins and any other number of complex emotions. We won’t even touch on how the adult who stays up past their bedtime to eat ice cream feels. Winning is subjective.


Winning can also be objectively right and subjectively wrong. “They won the game…by cheating.” “He made partner…and is divorced and miserable.” “She sacrificed everything to make her millions…and died before she really spent a penny.” There are those complex emotions again. 


For ourselves and our clients, there’s value to be unlocked whenever we see complications and subjective meanings. Struggles are the part of life where we learn who we are and who has our back. Professionally, it’s our job to help provide subjective context. It’s our job to take winning and losing and frame them in the broader context of what they mean as players of the game. The act of playing is the opportunity, even if we’re not always getting the immediate rewards we think we want. When we help our clients maintain a “stay in the game” mindset, we’re doing our best work.


Drew Dickson is a very successful investor and admirable entrepreneur in his own right. By taking the time to share this story, he’s shared a piece of his soul with all of us. It’s a special gift. Pass his post on.  

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