Tailwind Talks
Tailwind Talks is a podcast for high-performing professionals who want to build serious real estate portfolios without leaving their careers. Hosted by an airline and military pilot turned investor, it dives into actionable strategies for scaling your real estate portfolio while balancing the demands of a full-time job.
Tailwind Talks
The Paradox of Playing It Safe: Why Inaction Is Riskier Than Failure
Mortality is the great equalizer—and realizing this simple truth can transform how we approach life's challenges and opportunities.
Have you ever found yourself paralyzed by fear when considering a new venture? Whether it's investing in real estate, applying to flight school, or starting a YouTube channel, many of us get trapped in endless "what if" scenarios. We worry about failure, judgment, or disappointment until we've talked ourselves out of even trying. But there's something profoundly liberating about acknowledging our finite time: nobody survives this experience.
This realization flips traditional risk assessment on its head. The greatest danger isn't in taking action and potentially failing—it's in taking no action at all. When we truly internalize that our time is limited, the temporary discomfort of trying something new pales in comparison to the permanent regret of wondering what might have been. As a military flight instructor, I've seen countless people express interest in pursuing their dreams but remain frozen by fear, unable to take those first crucial steps.
What would you do differently if you embraced the perspective that the risk of inaction outweighs the risk of failure? How might your approach to your goals change? I hope this message reaches someone who needs it and provides the gentle push to move toward whatever matters to you. After all, we're all headed to the same destination—the only meaningful difference is what we choose to do along the journey. Take that first step. The clock is ticking for all of us, so you might as well make your limited time count.
I'm going to die, you're going to die. Anybody that ever views this video is going to die. And the weirdest way, I find that empowering and it's just now kind of struck me. I just made a video about what I would do if I need to buy a rental property in 2025 with having no experience in $5,000. That was the premise, and then I thought to myself how many people would potentially watch that and take no action because of fear of what would this person think of me? What happens if it doesn't go well? What if? What if, what if? And they don't take any action. And I know a lot of those people. I talk to a lot of those people. I really enjoy those conversations trying to get them to take action. But there's so many people that are so afraid of what will happen that they don't do anything at all. And to me, I've just started to think of it, as nobody survives this, and nobody that you know survived, like nobody within your sphere of influence. Whatever that, however big that may be, is going to survive this experience. So the risk of not taking action is greater than the risk of taking action, in my opinion, and I know it's easier said than done and it's a scary world out there. But it's something that I've been thinking about a lot, because I think the things I'm talking about with the real estate stuff or at large, are things that you could learn in five minutes or 10 minutes on Google searches or chat, gpt or maybe a YouTube video.
Speaker 0:But there's this inherent thing in some people or a lot of people, really, everybody which prohibits them from actually taking the steps necessary to push closer to their goals because they're so afraid. I see this a lot with people that want to go to military flight school. As an instructor in the unit, I've been around a little bit now. People come to me and ask questions about what would it be like to go to flight school? How can I get there, this and that. But there's a lot of people that don't even take that first step to go, do the first couple things necessary to get there, and it's not because they don't want to do it, but it's because they're so afraid of taking those steps. And what would happen if they fail? And what would happen if it doesn't go well, and what would happen if their family doesn't support it, and the list goes on and on. But at the end of the day and I tell them this, I tell this to people in my own circle literally nobody survives this, and I try to remember this myself too, with varying degrees of success.
Speaker 0:So the risk of not doing anything is so much greater than actually doing something, because at the end of the day, it all kind of doesn't matter anyways. So you might as well take those chances. You might as well try that new job or go to that, go to back to school or start a YouTube channel. I mean, that's kind of exactly what I'm doing right now is I'm trying to remember that every time that I'm going to make a video and I'm like, oh, I don't know if I should, who would even care? I'm trying to remember that.
Speaker 0:And so I'm no great philosopher or anything.
Speaker 0:It's just something that was on my mind after that last video I made and I didn't really say anything about that.
Speaker 0:But it's come to me now and I think it's something that's important, and if it even pushes one person to take a step closer to whatever the thing is that they want, I hope that it reaches that person and it can make some difference in some small way.
Speaker 0:So that's pretty much all I have to say about any of this. I just wanted to get it out there, see if it resonates with anybody and hopefully help somebody get closer to whatever goal it is, whether it's real estate, whether it's going to flight school, whether it's starting a YouTube channel, maybe having a family who knows what the thing could be but it was something that was on my mind and it felt pertinent to bring up, so I hope everyone's having a good night. If you happen to watch this and you found it interesting or valuable or resonated with you in some way like comment, whatever don't do anything, I guess, but I really appreciate you just taking the time to even get to this point in the video and I hope you have a great night. I hope you have a great 2025 and hopefully I'll talk to you soon, see ya.