To the Big Decisions
I have been wrestling with a large business decision, one bigger than any other decision I have made as a entrepreneur. The upside is massive, and the downside is just as scary. I was really struggling with this decision and have been going back and forth on what I wanted to do for the last 10 days.
And then my wife, during one of our many parenting + biz strategizing sessions, mentioned casually that “Well, with this big of a decision, I doubt you will ever feel 100%.”
There it was. There was the barrier that I had been struggling to get over, cleanly laid out in front of me as I was changing my kid’s diaper… I was never going to feel 100% confident in the move I made, and no matter what happens, there will always be a risk that I regret what comes next.
Marriage Counseling
Before my wife and I got married, we went to premarital counseling. We talked with our priest about finances, expectations, even how we would deal with each other’s family. And at the end of every session, we had a small homework assignment to work on before the next session.
One of those homework tasks that we had to do was to speak to other older married couples and get their advice on conflict resolution. Not the typical “Hold hands while arguing,” but the real stuff that you get after 25+ years with the same person.
One couple told us, “If one person feels off about the decision, neither should do it.” Basically, if one half of the couple was anything but 100%, then it’s a no. Not a begrudging no, not a “veto power no,” but a no that shows that you completely trust your partner and are better with them than against them.
My wife and I use this framework to this day, and it has helped us through countless discussions and decisions, both respecting each other enough to understand when to push and when to trust.
But for business… That doesn’t work.
Business Risk is Real
I had been waiting, agonizing, trying to get to the same level of certainty in this business decision as I get in my personal life. I wanted 200% certainty that I was making the right decision, and I was struggling, only being able to get to 75%-80%.
And it wasn’t until my wife pointed out the obvious that I figured out what real risk means in business. It is not some all-in poker chip moment where you throw your last 3k on Meta ads and see what happens. It is not flashy, nor is it memorable. It is making 10 decisions a year, all of them with a 40-60% chance of working out.
A good founder gets 6/10 decisions right and grows the business year after year.
A bad founder gets 4/10 decisions right and loses 10k in profit year over year.
And a terrible founder? They make zero decisions and lose the infinite game.
More on how business is an infinite game later!
By waiting for 100% certainty, I was missing the 6 potential good decisions that could change everything. The same strategy that has kept me married for 6 years was now causing my business to stale.
When in doubt, fail fast
In the end, what pushed me over the edge was not some magic change to the contract or negotiating hard for something I demanded. It was recognizing the fact that my 75% certainty was actually a massive green flag. In a world of coin flips, any chance I had to play the odds on a 75% chance is a bet I will take every single time.
And of course, what has become the motto of my budding entrepreneurship journey, when in doubt, I can always choose to fail fast. Don’t spend 6 months assessing what can be determined in two months. If you need to take 20 sales calls to validate an idea, get them done in a month, get your data, and get out.
Personally, I think I set myself, my business, and ultimately my clients up for success with my decision. And if I don’t, well, I will know in 2 months instead of 6 months, and will be on to the next decision!
P.S. I mentioned how the great founder makes 6/10 good business calls… I think the amazing founder makes 1/1 good business call, and then never lets up on their focus the rest of the year. I’ll get there… I am not there yet, but I will be.
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