In this episode of the No Days Off podcast, host Brian Gubernick shares a personal decision‑making dilemma: whether to sell his family’s second‑home cabin in Northern Arizona. He describes how the logical, financially‑driven analysis (the “head”) told him to sell, while the emotional attachment to memories and family energy (the “heart”) made him hesitate. Rather than framing the choice as a binary battle, Brian proposes treating the head‑heart tension as a conversation. He walks listeners through five reflective questions he uses to evaluate such decisions: (1) What do I want my life to look like in five years, and does this asset support that vision? (2) Is the asset fueling or draining me? (3) What is the true cost of keeping it beyond dollars—energy, focus, freedom? (4) What could I learn by pausing for a year (e.g., renting it out) instead of selling now? (5) What advice would I give a child in the same situation? He then offers a single focusing question: “If I could fully trust myself to handle whatever comes next, what decision would I make today?” Applying this framework, Brian decides to hold onto the cabin for now and explore other investment opportunities, such as commercial property. The episode blends personal storytelling with a practical decision‑making framework aimed at helping listeners navigate head‑vs‑heart conflicts in business, career, relationships, and life choices.
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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. Today we are once again talking about decision-making. It's been a hot topic for us the past few episodes or so, and I want to continue on on this path because I found that the best business people, the best entrepreneurs, the best leaders are great decision makers. And so, I'm gonna keep spending time here so that all of our No Days Off Nation could get a slight bit better today in the spirit of No Days Off, get a slight bit better with respect to our leadership and our decision making. Now, today is a pretty interesting episode because it's about something that I just recently experienced. I'm gonna paint the picture for you. Okay, I went up north to our family's vacation home in the woods. We've had it for a little while, little place up there. And it's, it's been great for us. It's been a lot of fun. However, I've recognized we are not using it at nearly the level we used to. I think that, being honest, I think my kids really don't like to drive all that much, and, and it's become a little frustrating because it's a little far, and we are so darn busy that it's just tough to, to make time. And I'm sure many of you can relate, well, with respect to going on vacation, or if you have a second home, or whatever it is you're doing in your respective world, you want to get away but your schedule, your calendar, and all different sorts of variables impact whether or not you could do that. Well, that's our cabin in Northern Arizona for me. So, I go up there to the house just a handful of days ago because I've actually concluded that math, the math doesn't make sense. The math is not mathing. It's time to sell this house. There's better ways to leverage the equity and the dollars tied up in it. And we talk about investment quite a bit here. We talk about wealth building, uh, quite a bit. And so I'm analyzing the various assets that, that we've accumulated over the years, and I'm looking at this one and I'm saying, gosh, I don't know if this math makes sense. So I head up to the house and I'm there to pack it up. It's time to prepare it for sale. As far as I had concluded at that moment, the decision had already been made. I've been thinking around it a bunch. I've been Running the numbers, I mean, financially it made perfect sense. I'm actually under contract on a new asset, and, you know, provided I can work out the sale of this house, I think I could roll the proceeds into that deal, and it ends up being a 1031 or reverse 1031 exchange, which we won't talk too much about today. But the bottom line is it's a really efficient, strategic way to be using the money. It's a smart decision. And yet, as I'm at the house or in the house, and I'm supposed to be packing up, I find myself just kind of standing there. And I'm staring at the walls that have seen, you know, summer family hangouts, and snowball fights, and, you know, cookouts, running around, friends over, all different sorts of things. And I realized that this, this house isn't just math. It's not even just real estate. It's actually, it's got a lot of memories to it. It's got a certain energy to it. It's actually a piece of my family in me. And it's in that moment, the spreadsheet that was in my head is, is kind of completely drowned out by this feeling in my stomach or even lump in my throat. That's what I want to talk to you about today. It's a very long setup, but I think that many of us can relate. You have your own version of this going on in your world. And, and that moment for me is one where your head is actually telling you one thing, but your heart is actually screaming another. In business, we're taught to make rational decisions. And in life, we're actually, actually told to follow our heart. But when those two voices are equally pretty loud, equally convincing, well, which one do you trust? So for me, yeah, this is selling a cabin, selling a second home, but it's kind of more than that. For you, it could be leaving a job, it could be ending a relationship, maybe moving your family, maybe it's investing in something new. The setting may change, but the tension is the same. There's this logic versus love, this efficiency versus emotion, this head versus heart. And so I want to, I want to give you kind of my thought process here, how I've worked through this and the conclusion I came to, because again, I was selling. I think there's a different way to look at this kind of decision, not as a battle that's to be won between, between the head and the heart, but as a conversation, maybe a negotiation between the both sides of you. I think we tend to treat this head versus heart, these head versus heart moments, as, as kind of either-or situations. We think we have to pick, pick a winner, that one has to win out over the other, has to triumph over the other. But the truth is, I think the most aligned decisions, the ones that, that bring us peace or make us feel at peace, uh, in the months or the years later, they're not made by silencing one of those voices. They're made by actually listening to both, understanding each side and what it's kind of aiming to protect and, and what each side, you know, fears and what each side hopes. And I think that's the real work. I think we have to pause really long enough to get beyond the noise and get into clarity. That's what decision-making is oftentimes about. So there's a handful of questions, really 5 questions I had asked myself. And, and these are questions that I've used in other areas of life, and even questions we've, we've covered here in the past 500 or so episodes. From, you know, from time to time, I, I asked these questions because I found myself in that moment. I was stuck between the spreadsheet and the, in the heart, in the soul. And so I, I actually sat down and, and thought around these questions, and, and they certainly did not give me an instant answer. But they actually did move me forward. They kind of got me unstuck. And let's— let me share them with you right now. Number 1, question number 1 I asked: what do I truly want my life to look like 5 years from now? And does keeping or selling this second home, this asset, fill in the blank, does it— does keeping it or selling it support that vision? So what do I truly want my life to look like 5 years from now? And does keeping or selling support that vision? I think this pulls you out of the now. It forces you to look beyond the, maybe the temporary emotion that you have, and maybe toward the direction you're trying to go. I mean, in 5 years, do, do I want more simplicity, or do I want more experiences? Do I picture my life having fewer properties and, or, and, or more legacy spaces, or, or You know, do I see myself living somewhere else altogether? I mean, how does this particular house in this example fit or not fit into that vision? So number 1, what do I truly want my life to look like in 5 years, and does keeping or selling support that vision? Number 2, is this asset fueling me or is it draining me? See, this was a tough one for me because as much as I love it, it does drain me a bit because we don't use it much, and so I get stressed Sometimes we hold on to things because they feel familiar, but not because they feel right. And I had to really kind of sit with that. Does this house still energize me, or am I clinging to an idea, an idea of maybe what it used to be? Am I keeping it because I love it, or am I keeping it because I feel guilty? Really, really interesting question. Is the asset fueling me or draining me? Number 3, What's the real cost of keeping this, this asset, this house? Not just in dollars, but in energy and focus and in freedom. This one was tough for me as well. On paper, I could afford it, but what about the, the extra mindshare, the, the management, the money I'm tying up that could go towards other priorities? What would that mental and emotional bandwidth cost me over time? So what's the real cost? Question 3: What's the real cost of keeping this, this cabin, this asset, not just in terms of dollars, but with respect to focus, freedom, energy, etc.? Question 4: If I waited a year instead of selling it right now, what might I learn? If I rented it out or just sat out for a year instead of selling it, what might I learn? This is the, the, the pause instead of eject question, because sometimes the answer isn't, isn't binary. What if I tried, you know, renting it for a season just to see how I feel with some space? That insight might be more valuable than any immediate decision. So, question 4 is the pause instead of eject question. If I rented the cabin out for a year, if I just sat on the sideline for a year instead of selling it, what might I learn? And question 5, I love this one. If one of my kids were in this exact situation, and they're likely to be one day, if one of my kids were in this exact situation, what would I tell them? This question kind of strips away the ego. When I flip the script a bit and imagine advising someone, especially someone I love like my kid, Uh, there tends to be a little bit more thought and wisdom. I mean, would I tell them to protect their memories? Would I tell them to make the smart financial move? Would I tell them to delay the decision until it's clear? I mean, whatever advice I'd give them, it's probably the advice I should consider giving myself. Uh, not so ironically, I had somebody important to me ask about a second home of theirs about a month or two ago as they were thinking about selling. And my advice, don't sell. I know the math may make sense, but you'll figure out other ways to make, to invest in and create wealth. This is something that, you know, is time with family, and that's impossible to replicate in a lot of ways. So I think there's a new way to decide. These questions didn't necessarily give me a right answer, but they gave me this degree of alignment. They kind of helped me stop thinking in terms of right and wrong and start thinking in terms of what fits with who I'm becoming or who I at least want to become. Those questions, they let, I think, both my heart and my head talk. And they showed me that the best decisions aren't made by choosing one or the other. They're made by actually listening to both of those situations, the head and the heart, listening deeply to both. So if you're facing your own version of this, if there's a decision in your life right now that's tearing you apart because you're again stuck between head and heart, I want to give you a focusing question. Obviously those 5 I just gave you, I want you to lean into, but I want to give you one specific focusing question. I want to ask you, if I could fully trust myself to handle whatever comes next, What decision would I make today? Again, if I could fully trust myself to handle whatever comes next, what decision would I make today? That's it. That's all I want to ask. Because so often we're not afraid of making the wrong choice. We're afraid we won't be able to handle the outcome. But I mean, I think if you look at your history, you have handled the outcome, you always have. And the more you trust that, the clearer everything kind of becomes. Where did I land on this one, if you care? What I thought was a for sure sale, I packed up a few things, brought them home, did some summer, you know, early summer cleaning, and came home and told the family, uh, we're gonna hold on to this thing a little while longer and figure out other ways to acquire new assets, particularly commercial property. 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.
