Making Tough Decisions

By May 2, 2018blog

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, and do I sell my company. What I’ve found is that our natural instinct around making important decisions is mostly flawed and if left to our own instincts, can have major negative impacts on our lives.

I got lucky early on when a mentor taught 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 discussing Benjamin Franklin (one of my heroes) and his approach to decision making. Cedric pointed out that Ben was WRONG. Decisions should not be determined simply by the pros and cons, but rather by the single thing that is most important to us (and our happiness).

As Cedric & I continued devouring the most incredible cajun food in Chicago at Heaven on Seven, I played through Cedric’s theory on an important decision regarding whether I should 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, insufficiently entrepreneurial (big business bureaucracy dominated jobs and conversation), uninspiring natural environment

As we compared these lists, Cedric agreed my decision appeared to be a tough one. He then asked me, “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?

I  just blurted out, “Living in a place that INSPIRES me!”  Cedric laughed and said, “Ok then, are you sure that comes first over everything else?” As I ran down my list, I realized I WAS willing to risk everything else in order to surround myself with an inspiring environment. But ultimately it was and still is (after 22 years) Boulder, Colorado – close to the mountains, lots of outdoor activities, entrepreneurial, small enough to run into people I know everyday, large enough to have endless cool things going on, and within an hour of a major airport.  Eventually, everything else on my Ben Franklin pros list materialized as well. Even being close to family, as they come to visit often!

I have applied Cedric’s decision making tool to getting married, raising money for businesses, and selling companies in which I held an ownership position. And I have made plenty of mistakes along the way by forgetting to apply this tool.

What breaks my heart is seeing family, friends, and associates make decisions that check the boxes, but don’t ultimately serve or fulfill them.

A common decision that people ask me about is whether to sell their company – probably because they know I’ll be the lone dissenter. Their Ben Franklin list usually looks something like this:

Pros: Will provide liquidity/diversification to themselves and others, reduce risk of failure, give more growth opportunities to themselves and their team (to be a part of a larger platform), make the company more competitive, take weight off 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 haven’t considered/thought through is what dominates everything on this list. The most common, retrospective trump-card item (that doesn’t usually even make the list) is having a CREATIVE PLATFORM with which to create increasingly more value in the world. A creative platform to continue developing a great culture and a great place to work. A creative platform on which to have a voice and impact in the community. And economically speaking, a creative platform to maximize long-term wealth (as Warren Buffet and Albert Einstein have described as the greatest force in the universe – compounded growth!).  A creative platform to continue to enjoying what they’ve nurtured and cultivated over the years.

Humans are awful at prioritizing. This inherently makes us really bad at making tough/critical decisions because we DON’T have the natural instinct to prioritize the ONE factor that stands above the rest of the pros and cons. Instead, we weigh all the pros against all the cons, and decide, and then wonder why it seemed right on paper, but didn’t feel right in our guts – and in our lives in the aftermath.

So, fight the urge to use a Ben Franklin pros-cons list. Determine your #1 priority and then take massive action in that direction. Subjugate everything else.


  • Dustin keyes says:

    That is great advice! It is easy to over complicate decisions with things that don’t ultimately matter. I am not inspired by Melbourne Florida. I’m going to fulfill my dream of moving to Colorado that i’ve had ever since I went to the Adventure Unlimited ranches in my youth.

  • Laura McCann says:

    Bill – I love this and have come to understand this for myself, as decisions continue to pour in having a new framework for thinking about them is welcome. I also totally relate to your pros/ cons on leaving a business. I realize the creative platform business provides to me is more valuable then other choices like freedom, financial security, more free time. Once I realized this is a driver for me many other things became clearer too. Wonderful insights! Boulder is lucky to have you.

  • Casey Schorr says:

    Immediately shared this with our entire team. Excellent post! I’m slowly realizing the creative aspect of business is one of the most important things for me, personally. But it’s still so easy for me to to forget and chase what’s popular (funding, growing to grow, etc).

    When I’m in the “zone” not thinking about anything else is when I’m solving some hard creative business problem. It would be tough to sell and potentially have this taken away for good. Maybe CREATIVITY and CONTROL go together more than I thought? CONTROL ensuring the CREATIVE PLATFORM remains?

    You always make me think, Bill. Keep the posts coming!

  • Eric James says:

    Amazing article Bill. This is such good advice!

    My wife and I made this exact mistake in choosing where to live. The Ben Franklin method lead us down the wrong path. Luckily we learned the lesson, found our trump card and now live in our favorite place in the world!

  • Rich manders says:

    Great article. I have suffered when I ignored this and succeeded when I followed.

    Why is it so hard to follow. Damn human nature !!

  • Clear. Concise. Wise. Thanks for the perspective, Bill (and Cedric)!

  • Ryan Bell says:

    Love the simplicity of this! What it made me think of: pro/con lists are the beginning of compromise, which can be good between people or groups. But if you’re compromising with yourself, you’re probably compromising with your own self-doubt, self-consciousness, or other hindrance(s). “Big bureaucracy jobs” sounds like it could be “Temptation to quit the entrepreneur path and take the safe bet”; “Uninspiring natural environment” could be “I may not have the internal drive and creativity”.

    Could apply to pros as well (in the “take investment” decision example): “will reduce risk of failure” is a big one, that I think is ever-present for many entrepreneurs. Boiling the decision down to the single most important factor could remove some of that noise and prevent a compromise with your self-doubt.

    Thanks for writing!

    • Bill Flagg says:

      Great points Ryan! Compromising ourselves away from what we truly want most. Thanks for the extra insight.

  • Bill Flagg says:

    Love this scene in City Slickers with Curly’s “One thing”. Don’t get all knotted up with everyone else’s priorities, instead focus on your one thing…

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