May 4, 2018
Bill Flagg

Making Tough Decisions

Over the years, I’ve made and have helped many others make important decisions… decisions like who do I marry, where do I live, do I start a company, do I take funding, do I buy or invest in a company, or do I sell my company. What I’ve found is that our natural instinct on making important decisions is mostly flawed. And if left to our own instincts, can have major negative impacts on our lives.

I got really lucky early on when a mentor gave me the best decision making tool of my life. I was just two years out of college, working for Harris Bank in Chicago, when I was having lunch with a banker/mentor named Cedric Thurman. We were talking about Ben Franklin (one of my heroes) and his approach to decision making. Cedric pointed out that Ben was WRONG. That decisions shouldn’t be WEIGHED by the pros and cons, but decided by what single thing is most important to us (and our happiness).

As Cedric & I continued eating the most incredible cajun food in Chicago at Heaven on Seven, I played through Cedric’s theory on an important decision I was making on whether to stay in Chicago or go try living somewhere else. On my Ben Franklin list was:

Pros: great city, great food, lots of young singles, lots of friends, close to family in Michigan, great career path at Harris Bank,

Cons: didn’t like midwest weather, not entrepreneurial enough – big business bureaucracy dominated jobs and conversation, uninspiring natural environment

As we weighed these lists, Cedric agreed it APPEARED to be a tough decision. He then asked me the question, what single item on the list trumps EVERYTHING else? What can you NOT live without? What’s the ONE thing you pick first (as if you got first pick of players for a dodgeball team)?

Then it just blurted out of me… “Living in a place that INSPIRES me!”.  Cedric laughed and said, “Ok then, are you sure that comes first over everything else?” And as I ran down the list I realized I WAS willing to risk everything else in order to have that. Now, I had to better define what I meant by an “inspiring place”. But ultimately it was and still is (after 22 years) Boulder, Colorado… close to the mountains, lots of outdoor activities, entrepreneurial, small enough to bump into people I know everyday, large enough to have a lot of cool things going on, within an hour of a major airport.  And eventually everything else on my Ben Franklin list came to be as well. Even being close to family as they came and still come to visit often!

I have applied Cedric’s decision making tool to getting married, NOT raising money for businesses, and decisions to NOT sell businesses. And I have also made lots of mistakes along the way by forgetting to apply this tool.

What breaks my heart is to see people making decisions that check the boxes but doesn’t ultimately serve them and what fulfills them.

A common one that people come to me about is whether to sell their company (because they know I’m usually the lone dissenter). The Ben Franklin list usually looks something like this:

Pros: will provide liquidity/diversification to themselves and others, will reduce risk of failure, will give more growth opportunities to themselves and their team to be a part of a larger platform, will make them more competitive, will take the weight off of their shoulders/remove stress, enable them to pursue other hobbies, businesses, and learn how to invest

Cons: could hurt the company culture, may not be as good for customers, won’t be in charge anymore, may not stay involved longer term, may need to figure out what’s next, need to figure out how to reinvest cash from sale.

What they usually DON’T know is what trumps everything on this list. The most common retrospective trump-card item (that doesn’t usually even make the list) is having a CREATIVE PLATFORM.  A creative platform to create increasingly more value in the world with. A creative platform to continue to enjoy creating with the team that they’ve culled and pulled together over the years. A creative platform to create a great culture and great place to work. A creative platform to be a voice and impact in the community with. And economically speaking, a creative platform to maximize long-term wealth with (as Warren Buffet and Albert Einstein can attest to the greatest force in the universe – compounded growth!).

Humans are horrible at prioritizing. Which inherently makes us really bad at making tough/important decisions because we DON’T have the natural instinct to prioritize the ONE above the rest of the pros and cons, instead we weigh all the pros against all the cons and then decide and wonder why it seemed right on paper but didn’t feel right in our guts and in our lives in the end.

Instead, fight the urge to use a Ben Franklin list. Discover your trump card. Take massive action in that direction. Subjugate everything else.

Making Tough Decisions
Published on
May 4, 2018
Bill Flagg

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