In this solo episode of the No Days Off Podcast, host Brian Gubernick recounts a story from Keith Cunningham’s book The Road Less Stupid about a “double bogey” – a bad shot followed by a stupid shot – that occurred while Cunningham was playing golf with Hall‑of‑Famer Tom Kite. The anecdote illustrates how second‑order thinking can prevent a compounding mistake. Gubernick then translates the lesson to business decision‑making, proposing concrete habits to avoid “double bogey” scenarios in organizations: (1) a “pause‑and‑evaluate” policy after setbacks, (2) scheduled deep‑thinking time for leaders, (3) quick risk‑vs‑reward analyses before high‑stakes moves, (4) a habit of seeking a second opinion, and (5) systematic documentation of past mistakes and lessons. He frames each practice as a way to curb impulsive, reactionary choices, encouraging more strategic, reflective action. The episode ends with a thank‑you to Keith Cunningham and to a listener who prompted the story, reinforcing the podcast’s mantra that every day is an opportunity to improve.
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Thank you for joining me today. It's Brian Gubernick, and welcome to the No Days Off Podcast. We believe that every single day brings a new opportunity to get better. Today I'd like to tell a story. I was reminded of this story by my good friend Brett, who is an avid listener of the No Days Off Podcast. Tells me it is one of his favorites. Brett, I appreciate you following along and reminding me of this story that came from one of my favorite authors, one of my favorite books, Keith Cunningham, and the book is The Road Less Stupid. Great book if you haven't read that one, or if you're looking for something to read, check it out. But in the book, Keith has a great story, and I'm gonna read the story to you. And then we're going to talk about it. Keith says, many years ago I was playing golf with Tom Kite, a leading money winner on the PGA Tour at the time and now a member of the World Golf Hall of Fame. On the 16th hole, I hit my ball deep into the woods. After searching for several minutes, we found the ball nestled against a bush. In evaluating my next shot, it was, it was obvious my swing would be awkward and very constricted. I looked up and noticed about a 3-foot gap in the trees that was in the general direction of the hole. The gap was maybe 15 or 20 feet off the ground and probably 30 yards in front of me. As I was thinking about attempting this miracle shot, Tom was watching me very closely. Keith, do you know what a par is? he asked. Of course, I replied. It's a number of strokes a good player should normally require on a hole. This is a par 4 hole. Then he asked, do you know what a bogey is? Since I play golf, this was seemingly obvious and unnecessary question at this particular moment. One over par, I answered as I reached for the club I intended to use to pull off this incredible recovery shot. Right. Do you know what a double bogey is, Keith? Now I was getting a little irritated. I'm trying to concentrate on my swing and hitting the ball exactly right. And Tom is over there playing 20 questions with me. I mustered some degree of calm in my voice and respectfully replied, it is 2 over par, Tom. Tom's answer has stuck with me for over 25 years now. No, a double bogey is a bad shot followed by a stupid shot. Keith summarizes this story by saying that thinking about second-order consequences minimizes the probability of a double bogey. Mistakes are inevitable, but double bogeys are usually avoidable. He says he placed the original club back into his bag, selected a new club, chipped out sideways, and made a bogey and dodged the dreaded dumb tax. He then goes on to say Tom is a smart man, and he still wonders if he could have pulled that shot off, by the way. So I'm telling you that story. I think it's a great one, this idea of a bogey being bad but a double bogey being worse, not necessarily because it's one more stroke per se, but because it was a bad shot followed by a really stupid shot, a really dumb shot. It got me thinking, how do I put Keith Cunningham's double bogey lesson into action in my business? What can I do to make sure that when I make a mistake, which of course is going to happen, when I make a bad shot, how do I avoid following it up with the impulsive, I would say stupid shot? When there's a setback and I want some sort of miracle, how do I make sure I minimize avoidable mistakes by not following that impulse. I got to thinking what we could all be doing, and here's some things that came to mind. Number 1, implement some sort of pause and evaluate policy. So like a pause and evaluate policy. In other words, put some sort of policy in place for me, my business, my team, where it's mandatory we pause after encountering any sort of setback. And the idea here is evaluate options before making the next move. For example, you've got a project that hits a roadblock. Pause, hold a quick review to explore the different alternate approaches and analyze the risks before you move forward. So pause and evaluate policy. Number 2, as anyone that's followed Keith Cunningham knows, Uh, his big thing is thinking time. We've talked about thinking time here a bunch at No Days Off, but schedule regular thinking time. So what Keith teaches us is that we should set aside some sort of dedicated amount of time each day or week for more deep thinking. The idea here being to avoid, uh, rushed decisions. So if you carve out time, let's say each week for yourself, and you encourage the people around you, especially your key leaders, to do the same, but you carve out time each week to kind of take a step back and review the current challenges or the current obstacles and assess any recent decisions that could lead to unnecessary risks or double bogey situations, it would be a great benefit. Number 3, kind of along the same lines, start working some sort of risk versus reward analysis into your process. So before making any sort of high-stakes decision, Run a quick analysis of the potential risks and the potential rewards, the potential costs and the potential benefits. Ask yourself or ask your team, are we attempting a risky fix just to avoid a minor setback? In doing this, it somewhat helps ensure the decision isn't a reactionary one. And sometimes those reactionary decisions make the situation worse. Next thing that comes to mind for me, build a second opinion habit. So like Tom Kite's role in Keith's story, have someone by your side that can give you a second opinion, which aids in you avoiding those stupid shots. If you're gonna make a critical decision, especially if it's one after a big mistake, run the idea by someone else, someone that could give you an objective view. This will avoid— ideally help you avoid the stupid shot. And then lastly, one thing I think that we could all benefit from, especially as we get some years under our belt, some experience in business: document our lessons, especially specifically those lessons from past mistakes. Keep a log of the double bogey scenarios that you can review. I don't remember what chapter it is in Keith's Road Less stupid book, but he's got a chapter that's just dedicated to him writing out all of his past mistakes and his learnings from those mistakes. I think it's the most powerful chapter in the book. I loved it so much that I started vlogging my own experiences in a very similar manner. Frankly, that's part of the reason No Days Off was created, where I couldn't write quite like Keith, but I like to record. So keep a log of your double bogey scenarios so you can review them during future strategy meetings. See what kind of patterns show up. Adjust your practices. Train your people to avoid similar mistakes in the future. So in summary, my idea here is that these action state— action steps, I'm sorry, uh, help you to be a bit more thoughtful, a bit more strategic in your decision-making, and ideally in doing this and taking these steps, you're avoiding or preventing to the greatest extent these compounding errors that can potentially occur when you double down on a mistake. I think we owe Keith Cunningham, uh, a thank you for this insightful guidance of his. And I want to thank my buddy Brett one more time for just bringing the story about. It was well-timed. I needed to hear this one. That's all I have for you today. The No Days Off Podcast. Thank you so much for listening, and remember, every single day brings a new opportunity to get better. So let's get after it.
