Tailwind Talks

I Lost My Job as a Pilot — Here’s How I Survived (and What I’d Do Differently)

• Cole Baltz • Season 1 • Episode 24

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Imagine going from the cockpit of a commercial jet to facing unemployment overnight. That's exactly what happened when COVID-19 devastated the aviation industry and left me questioning everything I'd built. This raw, honest conversation explores the harsh reality of career vulnerability and the steps I took to rebuild financial security.

The panic I felt during those first days of unemployment was real. Despite years of specialized training and experience as an airline pilot, I suddenly found myself competing with thousands of other displaced aviation professionals for vanishingly few opportunities. Had it not been for my part-time military flying position, I might have found myself back delivering mail in Milwaukee—a sobering thought that fundamentally changed my approach to financial planning.

Today's job market faces threats beyond pandemics. Artificial intelligence, automation, and technological disruption pose existential risks to careers across industries. Whether it's a pilot losing their medical certification or an office worker being replaced by AI, the message remains the same: having all your income dependent on a single source is increasingly dangerous. Through my journey into real estate investing—starting small with single properties and gradually building a self-sustaining portfolio—I've created a financial safety net that gives me peace of mind regardless of what happens with my flying career.

Whether you already feel the anxiety of potential job displacement or simply want to strengthen your financial position, now is the time to act. Start learning, saving, and planning for your first investment property while you still have stable employment. The security of knowing you can weather career disruptions is invaluable, and the autonomy of building something that's entirely yours brings satisfaction beyond just financial returns. What steps will you take today to protect your financial future?

Speaker 1:

What's up everybody. My name is Cole. I'm a part-time real estate investor, full-time legacy airline pilot and a part-time military instructor pilot. Today I'm going to talk about something that hits real close to home, and that is what do you do if you lose your job. How do you prepare yourself for something like that and what did I do to get out of that situation? When Uncle COVID came and paid us a visit in 2020? I had a job. Empathize with that.

Speaker 1:

Before you knew it, I went from being a jet pilot thinking I was somebody special, thinking I was cool, to literally having no jobs. What did I learn then and what do I do now to try to adjust the implications of something like that happening in my life? The first thing I did was panic. I had left the post office delivering mail in the city of Milwaukee and I was flying jets. I was thinking like I might have to go back and do that. A lot of the guys that had been flying with at the airline told me they were getting jobs like UPS and local retail stores and things like that, and so I was looking at the prospects of going back to delivery mail and I was terrified at that. So I was a little bit like man. I took a gamble on my career to try to get things going and get myself onto the next level. Didn't really work out. Now here I am with no job. It's the middle of COVID, everything's shut down. What do I do? And so I kind of had to sit down and look at the options, and one of the great options I had was I was flying in the military part-time, so I had a unit to go to and ask you know if they would bring me in full-time.

Speaker 1:

If I didn't have that, I would have been totally screwed because all the guys that had more experience than me at the airline suddenly also didn't have jobs. So any flying jobs that were available flying cargo, doing things like that were suddenly snapped up by all those guys and I was still on the street with no job and dwindling hope. Every minute that went by I was less and less sure about this whole aviation thing. Looking back on it, I should have had a plan in place beforehand and I was doing some of the real estate stuff. I had done the single family flip house. I had the eight unit, so I had something, but it wasn't enough for me to live off of. It wasn't even enough for me to consider. Like doing part-time work Like this was not. That was not the kind of money that was on the table. So looking back on it now, I wish I would have done more to prepare myself, because I wouldn't have had that moment of panic and thankfully I had somewhere to go, but if I didn't I would have been totally screwed. So now I've set myself up in life today that I don't have to panic about that. I can rest easy, knowing that I have something else to lean back on if both my careers fail.

Speaker 1:

And for me, just like a lot of other jobs, there are little things that could happen that could actually derail your entire career. And for us it's our medical. If you can't get your medical, then you can't fly. And if you can't fly, then suddenly all your expertise and all your knowledge and everything that you've learned over all the years is suddenly worthless because you can't fly. So what are you going to do? And that's something that's always been scary for me. I'm young enough that I feel like I'm going to be healthy for a while, but you never know what could happen. I always joke that I could go get stabbed in the eye tomorrow and, if I do, my flying career goes to zero, and now I have nothing. So what do you do now? And there's a lot of people out there that are thinking the same thing, not so much because of the medical stuff or because of COVID, but because of AI. Artificial intelligence is on the horizon, it's here. I use it, I'm sure a lot of people do and there's quantum computing all these other things that are coming down the pipeline that could take people's careers and take it from a very profitable, lucrative career and destroy it.

Speaker 1:

I think some people are feeling some anxiousness about what am I going to do? Where am I going to go? And I think this is when you really want to lean into having some sort of side hustle. For me, it's real estate. That's what I'm going to talk about, that's what I'm going to focus on, but it doesn't have to be that. It could be something in the digital space. There's people that are making videos about eating burgers and like he made a whole channel out of that and that's awesome and that exists, and not everybody's going to do that. Everybody wants to do that, but there are a lot of other things that you can do? I know people that are working on motorcycles as a side hustle. I know people that have coffee shops. I mean, there's an unlimited amount of things you can do, but you have to do something and you can choose not to do anything.

Speaker 1:

But then don't complain when AI takes your job and you have nothing, and I know there's gonna be lots of people that are complaining about that when that time comes. But you have to start planning for it now, because by the time it's here, by the time that you get the notice like I did at my job to say, hey, april 1st, we're closing down and you are effectively fired. When that happens it's too late. You don't have enough time to do that, because now all the money that you would have allocated and all the time that you would have allocated towards the side hustle is not gonna be taken up by trying to pay your bills with no job, by trying to find a new job, by trying to figure out go back to school, whatever the case may be. You're gonna be doing that to try to get yourself back on your feet and at that point it may be too challenging to get your side hustle going. So I'm gonna focus on real estate, how you can implement that to try to offset the risk in your own job. Even if it's not AI, who knows what it is the company could go out of business. Those happen all the time.

Speaker 1:

This is what I do and this is what I would tell you to do. If you were my kid, I would tell you to start with a small property, whether it's a single family, duplex, four family. That's what I've been focusing on with most of these videos. You don't need a million dollars, you don't need 500 units, you don't need anything like that. You need one property and you start with one property and you learn the business with just one. Maybe that means a flip house. Maybe that means you get a rental right off the bat and you do a house hacking scheme where you're living in one, renting out the other and you're maybe breaking even, maybe paying a little bit per month. That's where you start and that's a great place to start, because now your monthly expenses are lower and you're able to use that to try to double down on this whole side hustle thing. From that point I would start.

Speaker 1:

From that point I would start looking at, okay, learning the business, obviously trying to figure out what is the actual monthly expenses on this property. I can sit here and put it in a pro forma you know an Excel spreadsheet and say this is what the expenses are going to be, but what actually happens every month? Is it more, is it less? Do it? Did I do good math? Did I buy a good deal? And start learning that and from that point then starting to use what you've learned on the first deal and implement it into the second deal. Obviously and this is a simple progression but you need to start with one and if you can get your foot in the door with one while you do have a job, then the risk of not having a job is just slightly lower, because now you already have a property. You don't have to go all that. You already have something going. You got your foot in the door, you've got a placeholder. Now when you go back to the bank and try to get a second property, they're going to see your track record with the first and you're going to be able to use that to leverage into that second building, even if you're having trouble with your job.

Speaker 1:

This may not be applicable to the majority of people, but there's a vested interest in succeeding. That's huge, because you're not beholden then to a company, to a CEO, to a manager that may not have your best interest in mind. They may not even deserve to be in the position that they're in and you're dealing with that. So you can get something that's all your own. Every decision that you make is yours. You can own it, whether it's good or bad, and you can grow from there.

Speaker 1:

So if you don't have enough money right now to try to get an FHA loan, which is usually about 3% down, or maybe a VA loan if you're a military veteran, which is 0% down, if you don't have the money and the resources to try to do that right now, then your best bet right now is to get educated, to learn as much as you can about the business, because education for the most part, is free. You can find a lot of paid education, but there's a lot of free education as well, so you can focus on that. And the other thing you can do is try to save money as fast as you can, as best you can If you can do a little bit of flipping or whatever, to try to make a little bit of money and start stashing it away. That's what I'd recommend you doing, because everyone talks about Armageddon and how the world's falling apart. All these major events in society are happening, people are talking about them, but what are you actually doing to try to hedge your bets against them? And I think there's a lot of people that are doing nothing to do that.

Speaker 1:

And if you're one of those people, I implore you to try to change your thought process with that and try to make, try to set yourself up for what may be coming. And that's exactly what I'm doing. I'm trying to get things going. Right now, I've got kind of a self-sustaining machine. One building's paying for another building. I'm to do more. I want to do it bigger, better, faster, all that stuff.

Speaker 1:

But at this point I know that if I lose my job tomorrow, I'm still going to be able to find a way to survive. I have enough properties that I can sell and refinance and trade up to other properties to try to get through that period of time until I can get back on my feet. If you're not in that situation and you're feeling anxiety about that my feet. If you're not in that situation, you're feeling anxiety about that then you're in the right channel. I'm going to continue to talk about practical advice that people can use to try to get their foot in the door with real estate. I'm not going to talk about other side hustles because I don't even know what I'm doing. If, by some miracle, you're watching this video, then it was basically pure luck. At the end of the day, I'm not quitting my job flying tomorrow. I'm not expecting to lose my job in either case, with the military or with the airline, but I am prepared, if I do and I'm very, very thankful that I did things five, 10 years ago to set myself up for today, and that's something I want you to keep in mind.

Speaker 1:

This is a long, slow game, but it's a game that's very lucrative. Once you get going, you just have to start, and starting is always the hardest thing for most people to do. It's been hard for me in my lifetime to do it as well. So I implore you to take the steps necessary to get yourself prepared for what may be coming, and this isn't fear mongering, this is just the real life. I've lost my job. I'm sure I could lose my job again. Maybe I will. So I'm ready to go. Hopefully you'll get yourself closer to that goal If you're watching this video. I truly appreciate it. Like I've said in the last couple videos, if you're watching this, you could be anywhere on the internet doing anything right now, but you're sitting here watching to me and that doesn't. I don't take that lightly. I really, really appreciate it and I'm going to continue to try to put out better and better content. I'm learning the game as I go. Let me know what you think and I'll talk to you soon, see ya.