Ep 483 | 5 Questions That Changed My Approach to Life and Business

Brian Gubernick shares five questions that reshaped his decisions on business, health, wealth, and relationships. They include Charlie Munger's inversion technique (what would make me fail?), a tomorrow-feeling check, a eulogy exercise to clarify values, a CEO-replacement scenario to spot blind spots, and a future-reconnection vision to picture your best life.
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Thank you for joining me today. It's Brian Gubernick, and welcome to the No Days Off podcast, where we believe that every single day brings a new opportunity to get better. Just recently, a few episodes ago, episode 480, we talked about a really powerful question that— and that question, simply put, was If you only had 5 hours to spend on your business this week, where would you spend that time? Really big question and one that apparently struck a nerve with many listeners here at No Days Off because I got a lot of messages from, from our listeners telling me that that question really challenged them. It got them thinking. It got them rearranging even their calendar. What I like to do, just based on, you know, some of the feedback that we had with that one question, that one episode, Episode 480, I want to actually give you 5 questions. Now, I have— there's lots of other questions beyond these 5, but I'm gonna give you the 5 questions when I think to myself, what are the biggest questions or most important questions I've asked myself specifically over the past 12 months or so? That have impacted my business and/or my life? What are the 5 questions— is actually what I asked— what are the 5 questions that have most impacted my business and impacted my life? I think these 5 questions are pretty powerful. Like I said, they've got me thinking. They prompted me to take certain actions. And my hope is that maybe one, if not all, of these questions makes a difference in your world as well. The first question, and it's based on my favorite mental model, you hear me talk about it all the time. The model is known as inversion, as taught by Charlie Munger. The question is, if I were to fail in achieving this goal or this objective, what would be the most likely reasons why? So if I set a goal or some sort of objective, or I have a plan to do something I like to ask the question, if I were to fail in achieving this, this goal, or fail in achieving this objective, or fail in, in pushing this project forward, what would be the most likely reasons why? I love asking this question because when I do it, what I'm really doing is identifying the obstacles that may stand in my way. And if I'm clear on the obstacles that may stand in my way, Well, then I could strategize proactively before those obstacles even come about. I think about this question, obviously, in business. I think about it in health. I think about it in wealth. I think about it just in my relationships and my life as a whole. It's made a substantial difference to me in terms of how I operate and the decisions I make in both business and life. The next question I've been asking this one a lot more the past year or so than ever before. And it's a real simple question. It's not one I necessarily have to ask every single day, but it is one I do ask whenever I have to make an important decision. And the question is, how will I feel about this decision tomorrow? How will I feel about this tomorrow? So, whenever I make a decision, maybe it's an emotional one, or maybe it's even an objective one. But usually when there's a little bit more emotion, this is a bit more effective. I ask myself, how am I going to feel about this tomorrow? Where this tends to show up for me is, is in different endurance events that I'm participating in. And at some moment in pretty much every event I do, I ask myself, why the heck am I doing this? I should just take a break, or I should even quit. The quitting doesn't come up too often for me, but it certainly comes up now and again. But at the very least, it's like, I should take a break, I deserve a break, or I, I could pull back, I don't have to push myself that hard. And I start having those thoughts in my head, but then I ask myself, how am I going to feel about this tomorrow? You know, tomorrow, 24 hours later, when the emotion subsides. When I'm not in that, call it pain cave moment, where, where I've rested a bit or, or I've eaten something and my attitude and my mindset are different? How am I going to feel about this decision tomorrow? Usually when I ask that question, it impacts the decision I'm about to make right now. Because in a lot of, a lot of cases, and by the way, this isn't just going to apply in like the endurance world. You know, when you, when you get in an argument or a debate, or you feel like, hey, I don't want to be in business with so-and-so anymore, whatever it may be, you're usually doing that no matter how skilled you are in managing emotion, there is still an emotional component to it. So this question prompts you to take a step back and really ask, gosh, how am I going to feel about this later? And maybe tomorrow is not the, not, not what you should use when you ask the question. Maybe you say a week from now or a month from now or a year from now, how am I going to feel about this a year from now? Now? Will it even matter? Great question. Next question, uh, very different than the first two, but it is one I've been asking myself for a very long time. Uh, when I started going through a lot more of the life planning process, uh, the book Living Forward is actually what prompted me to start asking this question. And the question is, if my family wrote my eulogy today, what would they say? What would I want that eulogy? No, I'm sorry. What would they say in that eulogy? Then that kind of part 2 of this question, what would I want them to say instead? What's the difference between these 2 things? So my family were to write my eulogy today, what would they say? And what do I want them to say instead? I love this question. And for some of us, maybe it's a little too heavy. Maybe it's too morbid. I don't know. But I really think that every one of us should think around, what would I like for my family or those most important to me to be saying at my celebration of life? What would I like for them to be saying? Now, what might they say if it had to be written today? And then assess the disconnect that may exist. What I'd love for them to be saying versus what they might be saying today. I won't dig too deep there, but I think that this one is such a— this question brings about so much awareness. It really forces us to take a look in the mirror and decide, gosh, what kind of life do we want to live? Right? Like, what kind of impact do we want to make? What sort of relationships do I want to have? Next question. If I were fired from being the CEO of my business or my life and a new CEO was hired to take over, what are the first 3 decisions or moves that he or she would make? If I were fired from being the CEO of my business or life and a new CEO was hired to take over, What are the first 3 decisions or moves that he or she would make? Think around that one for a little while. That might be one to write on the whiteboard, sit in a room for an hour and just stare at, you know, on that board and see what you come up with. If you were fired right now and someone took over, what would they go and do right now? Like if it wasn't you, they took over and they had to go make some moves. Especially moves that make an impact because they want to make a splash when they take over that CEO role, what would they go do? It's a really fascinating one. And the very last question that I love to ask, and I— this is actually one I ask in a lot of interviews, but I like to ask it of myself. And I, I think the past 6 months I've been really thinking around this, this question, really the past 3 months as I've You know, every year I kind of go through my own personal planning. And the question is, if we didn't see each other, let's say myself and someone else, if we didn't see each other for 3 years and then we suddenly reconnected, what would have needed to happen for me to say to you that my business and my life are absolutely amazing, the best they've ever been? Again, if we didn't see each other for 3 years or, you know, pick a timeframe, 5 years, 1 year, and then we suddenly reconnected. So we chatted one day and then we fell off, you know, our relationship fell off for whatever reason. And a few years later we reconnected and you said to me, gosh, how you been? And I say, my life and my business are so amazing. The best they've ever been. What would have needed to happen for me to make such a statement? Another write on the whiteboard and stare at it for a while type of question, right? Because what you're really, what you're really saying is, you know, I want to live an amazing life and I'm going to close my eyes and employ all 5 senses. You know, what am I seeing? What am I hearing? And I'm going to kind of really think through what that is. And then I'm going to walk it back to today. What would have to happen for me to be saying, my relationships are so amazing. And here's what that means. And, or my travel experiences have been so amazing. Where did I go? Or my business is so amazing. Well, what did the business accomplish? You know, you start really thinking through those things and then you get clarity around where you want to go and you can walk it all the way back to where you're at right now. And again, address the delta between what your current reality and where you want to go. So just 5 really big questions I think that have made a substantial impact on me over the past year or beyond. And I think 1 or 2 or maybe all of these questions are things that you want to work through just as an exercise. And the answers that you come away and, you know, come away with and asking these questions will be so powerful My belief, I fully believe that if you study or really think through these questions, come up with some clarity, and then take action steps to achieve whatever that, you know, that clarity brought about, your life and your business will be even better than it is today. 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.
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