Sailing with Phoenix: Lessons on Non-Traditional Retirement Paths

The traditional path is not for everyone. That's where planning comes in.

Planning is not about, as we're going to talk now, about being perfect, but it's about knowing possible outcomes so you can make the best decision for you. The traditional path is not for everyone. Welcome to the Healthy and Wealthy Retirement, where your certified retirement counselor, Mark Struthers, takes a holistic approach to retirement. Going beyond finances and embracing holistic well-being, this YouTube channel. Music.

Will address not just the financial part of retirement, but also the social, the physical, and the emotional parts of retirement. Everything you need for healthier, a wealthier, and a happier retirement. Welcome to the Healthy and Wealthy Retirement. My name is Mark Struthers, and I appreciate you joining us today. We are recording over Memorial Day weekend, a beautiful weekend here in Minnesota. Some just gorgeous weather, cool mornings, warm afternoons, a lot of sun. Simply wonderful.

Our topic today is a bit unusual. We're talking retirement, but we're talking about retirement as it relates to an Instagram sensation called Sailing with Phoenix. And it's something that a lot of financial planners are probably not going to go near. I don't blame them. In case you don't know, Sailing with Phoenix is about the gentleman, Oliver Widger. Oliver Widger is a gentleman who embarked from the West Coast. He liquidated his 401k, quit his job.

I think he had some neck issues, some health concerns, but decided to do what a lot of us dream about, thumb the nose at corporate America, at the system, at the man. I don't know if they still use that term. And he set off to Hawaii with his cat, Phoenix. That's where sailing with Phoenix comes from. And just a couple of days ago, he arrived at Oahu. After his very entertaining voyage, it's really cool to see his little videos, a lot of challenges.

And believe it or not, I think retirees can take something from his journey. Now, before I continue, I'm going to get to what's probably the elephant in the room is, Mark, would you ever recommend, I have two boys, one is 17, one just turned 20 the past couple months, somewhat recently. Would you ever recommend they do something like this? And as you might guess, I would have trouble as an advisor and a father.

It's tough to deny the magic that time has on compounding of not just your 401k, not just your wage income, anything, anything that you stick to. That being said, I understand where Oliver is coming from and why he has resonated. I think he has close to 2 million followers on Instagram, which is a lot, from what little I know. It's because he, one, the risk he took on. Two, I think many people feel trapped. They feel trapped in a bad system.

And most Gen Xers like me, or especially if you're a baby boomer, you might greatly disagree with that, say we all had to suffer through it. And to a certain degree, that's probably true. I, for one, got into my 20s with a lot of aviation debt. Aviation, for pilots in the 90s, jobs were hard to come by. You made very little to next to nothing while you built hours, flight instructing, commuters. And it was really a job where the parents could afford to pay easily $100,000 for flight training.

Now, college back then wasn't as expensive, but I was one who worked more than full time through college to come out and decide I couldn't continue. I just couldn't afford the debt payments of what was easily $100,000 in today's dollars. And I didn't really have a marketable degree. It was something where I was lucky to make $40,000, $50,000.

Grand, you know, you could, because you don't have that true professional degree, you're starting off like a normal businessman, just a very general business major, or you're piecing together jobs, you know, and as we talked about, when we talked about college planning, once you get beyond that one-to-one ratio, meaning if you come out with a hundred thousand dollars in debt, you should be making at least a hundred thousand dollars.

Well, I came out at two to one, and I know at the cost of college, a lot of people who aren't aviation majors go through something similar. And a little side note, the reason for that is once you get up to two to one ratio, that means at least probably at least 30% or close to it of your gross income is going towards debt. For those of you that have kids, keep that in mind. But I understand where is he coming from? I felt trapped. My 20s were awful.

I had to work so much harder to find that career path and to service that debt. And I think a lot of just people, a lot of his generation, I think he's about 30, are going through the same thing because college has cost so much. You don't have the anomaly. You know, most of the time, if you had, for my generation, if you had $100,000 in today's dollars in debt, you had a job that paid pretty well. Probably a lawyer or a doctor or something.

But I think a lot of kids are coming out because the cost of college is sold. They're going through what I went through, only it's more universal. So the cost of college, thanks to Gen Xers and baby boomers, we're the ones that are in charge. So college has gone up two to three times inflation. and housing prices relative to wages and housing prices as well and interest rates. And so you could understand where they feel trapped in a system that is not set up for them to succeed.

You know, it seems like younger men, especially. So I understand where they're coming from. And as many of you know, I preach that in our financial plans, we need to factor on not just return on investment, not just longevity risk, but also the risk that you don't have those return on memories. It's why financial planning is about coaching and counseling, and it's about looking at all these factors so you have as few regrets as possible.

So when I think about my 20-year-old in 10 years came to me and said, Dad, I'm going to do this. If he had no kids and he was very aware or what these risks look like, I can't say I'd be pounding at the table for it. I can't say I'd be pounding the table against it. At least with Oliver, he is young enough that he can't start over. Now, if my boys were in their early 20s and the impact to their career potential was less, I might be a little more for it. It depends on the visual.

One of the takeaways is the traditional path is not for everyone. That's where planning comes in. Planning is not about, as we're going to talk now, about being perfect, but it's about knowing possible outcomes so you can make the best decision for you. The traditional path is not for everyone. So I hope that, I know Oliver is not asking for my advice, and in this case, he's probably going to make a lot more money and has a lot more career potential going forward.

If you're relying on social media to do that, that's a little bit like a lottery ticket, but give the guy credit. He's... Probably got a much brighter future, took on a lot of risk to do it, which is why he's been rewarded. But on to retirees.

So what can retirees learn from Oliver? And we'll call him sailing with Phoenix. Don't let the perfect be the enemy good. If you always wait till things are perfect, you're probably not going to act, not act in time or act till late.

And this isn't just for financial plans this goes for other not just financial plans and retiring but also for other things learning a new skill volunteering reconnecting with people i have several clients who in their late 40s early 40s started planning early they weren't happy where they were they too felt stuck like sailing with phoenix like oliver did and they they made a well-thought-out plan decision really nothing realizing nothing's perfect we don't know what's on the horizon

but they made a move to careers where they didn't mind working well into their 60s. Often when they had a good chance of doing it, they had control. And even in some cases where they could work part-time for a decent wage, it's something that if they didn't like or love, they at least could tolerate. And even from a financial plan standpoint, there are folks who want to wait until their asset size is so large that there is nothing that could go wrong.

We run what's called Monte Carlo simulations, where we take historical stock, bond, inflations, we take all their goals in spending and cash flow, and it comes up with a probability of success. The mistake, and it's not the perfect measure of if you can retire, but the mistake many people make is thinking, well, this is like school. I want to get 100 to 100%. That perfection is far from perfect. One, if you do that, you're most likely going to pass with a lot more money than you probably want.

And you might have to delay retirement, delay some of those return on memories, So when we do these things, we talk about what is an ideal, the perfect probability of success is not perfect. It's not 100%. We take a look at everything and say, you know, usually for most clients, it's somewhere between 65 and 80%. You can see a dispersion of returns.

And you can take a look at the most likely scenario. But as you move forward through time, when you're talking 30 years, again, we're taking educated guesses. Here, we put as much education as we can and experience behind these guesses. But the idea that you're assuming the worst and also that there's no adjustments along the way. But you can see there's some bad scenarios, but there's also many, many good scenarios. So the lesson from Oliver from Sailing with Phoenix is just do it.

He was able to sort things out along the way. So whether it is starting that part-time job, the work, comforting the job, volunteering, meeting new people, traveling, it's not that you just don't, I wouldn't do anything reckless and same with your picking retirement date and all these things. A good analogy is my son's like anyone else when they're doing something that makes them feel uncomfortable, especially for one is very much an introvert.

For him to go into a job and ask them if they're hiring, ask to try to speak to a manager or sell himself is very uncomfortable. He will use trying to have making sure the scenario is perfect before he acts. It keeps him from acting to where he's, and this has happened, where he's often too late, where he doesn't have the pick of the best jobs for the summer. Now, does that mean he goes and walks in after he's been working in the yard with me or landscaping when he's dirty and smelly?

And doesn't know anything about the company, doesn't practice. No. But you don't have to wait till things are perfect. You're going to be able to figure some things out along the way. You know, he takes a shower. He gets on a reason, has a reasonable clothes, look nice, does some practicing and realize, you know, that part of that's the journey. Just like with Oliver, that he figured things out. Oliver did not have a sailing background. He learned from YouTube.

He did not have a large bankroll. Now, in my opinion, did he probably take on too much risk?

Maybe could have been paired a little bit more yes but there's an old saying i think it's by, apple's the regional founder or current ceo entrepreneurs have to ship that if you wait till things are perfect it's going to be too late so my number one takeaway for retirees is, don't wait for perfect conditions you're going to be able to source some things out along the way and overall it's going to be a much better outcome it's going

to be closer than perfect than you thought perfect was, if that makes sense. Number two, be resilient. Make resiliency your North Star. Keep at it. You're going to be able to problem solve along the way, as we talked about. So this goes especially for retirees. Be prepared to adapt and adjust when it comes to mental, emotional, and provide some resistance for yourself. You should be exposing yourself to new things.

The new retirement paradigm, I don't like using fancy words, because we're living so much longer, the idea that you have no adversity along the way, when you're going to, but you should try to continue to grow. Put some resistance in front of you. Meet new people. Do new workouts. Do new volunteer work. And financially, try to make yourself as resilient as possible. This is where the financial planning comes in.

Have a large emergency fund. The idea that you're going into retirement to where you do nothing might have worked when we lived 10 or 15 years, but it's probably not going to work going forward. I also think you're going to have more challenges than you realize. And if you haven't had that resistance, you're going to be less prepared for them. And that includes your portfolio, your financial plan.

That's where you have an emergency fund. And knowing that you have a plan, you have a withdrawal strategy, that you can handle risk to balance what might come up. What if your son decides to do what Oliver does and you need to backstop him? I know a lot of Gen Xers and baby boomers would say, nope, not going to do it.

But if you have a spouse you might not be the only voice in the room, so part of that's having a good portfolio strategy also a resilient withdrawal strategy that's why we use guardrails a lot guardrails bases your distribution amount on portfolio performance when things are good you take more out when things are bad you take less out it also allows for a larger distribution initially and with having but still having the same probability of success still dealing with longevity so when

you when you when you do this combined with spending in emergency funds and other asset classes it does make for a more resilient portfolio so oliver was very resilient in how he handled some of this stuff i i think at one point he accidentally locked himself in his engine compartment still by himself because lord knows the cat's not going to do anything no i think a dog probably would have been able to figure out how to get them out.

I'm just a dog person. But being resilient, and also I think trying to grow and create some resistance for yourself in retirement. When you're going from 40 years of resistance of work, family, to where the kids are out of the house, to you have no adversity whatsoever, I think there's an idea that you have a healthy resistance, it's a healthy adversity.

Number three, redefine success. So for Oliver, his success no longer was the corporate world, but also many simple things. Now, his sunsets were beautiful. Of course, it wasn't all sunsets, as we talked about, but enjoying that sunset was a very simple free thing. Now, getting out into the ocean, all that costs some money. But I think also redefining what success means for you for retirement.

In all likelihood, the old way of success, which means doing nothing or just playing golf five days a week, for most people, it's probably not going to be their true version of happiness. It's not going to be the journey that's best for them. So start putting some thought into this early. If it's pickleball, do you need to start playing a little bit early? If it's golf, what does that look like? If you're, you know, and you could even throw work in here.

Again, if there's a part-time job that you would like that, maybe take some prep work for some certifications. Several clients have gone through this. Now, in many cases, they're working full-time for a while, but they all chose jobs where they can work part-time. So put some, redefine what success is, and that might be working part-time. I mean, I think about myself, even if I was going to play golf every day, that's only six hours.

Once my boys are truly out of the house and we're not as involved in their lives anymore, you know, the idea that I work four hours a day, that's not, for me, that's actually ideal. We're all different. But I think one of the takeaways from Oliver in Sailing with Phoenix is, one, success does not have to be expensive, and two, redefining what that is for you.

Just because those, just like Oliver didn't want the traditional path as he's in or going into it, I guess in adulthood, most people do not want the traditional retirement that my parents had. Where they did very little and their life expectancy was also for older baby boomers, for middle to older baby boomers, their life expectancy was also much less. Number four.

Consider your companion. I know the Instagram folks seem to love Oliver. He seems like a very nice cat. But I strongly, as a dog person, I strongly encourage you to think about your companion along the way. I think a dog could offer so much more. They're more interactive. They can go explore. If you're doing what Oliver does, he can go explore shores. He can go walk along beaches. He can do a lot. He's much more of a, of a companion.

He is there for you. They just, they want to be with you. They have a lot more energy. It's actually a little security for the boat maybe. Also, when we think about interacting with people, there are few things that allow you to talk to strangers and where you have a common bond than a dog.

I have met so many people so many of my neighbors because i have a dog and we'll we put out we put a picture of oliver on our newsletter up at the top from his instagram post and a really cool page and he actually has one of one of my favorite songs frank sinatra my way he is playing in in his one of his videos so we have the song up there it's just an image from instagram we also have a picture of my oldest son and our dog so my fourth takeaway is strongly consider those sorry,

consider your companion. I think for many people, especially with our more active retirements, a dog might be a better choice than a cat. No offense to Phoenix, to Oliver and Phoenix. I also related to this is, As I've worked with so many couples, starting early as far as reconnecting with your spouse, because quite often for 20, 25, even 30 years, depending on how many kids you have, most of your world has been wrapped up in raising kids.

And, you know, and even quite often you both had work, you both had kids. So the idea that all of a sudden, after all these decades, that you are going to be perfect companions might be the case. But it'll also be something that you might want to address early on. So consider a dog over a cat, strongly consider.

Also, just like as you try to reconnect with old friends or find new hobbies or more rewarding work as you kind of work comfortably or part-time in retirement, also just consider reconnecting with your spouse, maybe trying to find a common activity. My old pickleball has been a big one. And in my pickleball group, there are lots of couples that are in their early to mid-60s that are taking it up for the first time.

So as you're thinking about retirement, certainly take some time to draw some lessons from Sailing with Phoenix, from Phoenix to Cat and Oliver, as far as how you can approach retirement in a healthier and a wealthier way. And don't forget to subscribe. Thank you. Thanks for tuning in. If you enjoyed this episode, make sure to hit subscribe, leave a review, and share with your friends. Share the love. Make sure they have a healthier, a wealthier, and a happier retirement as well.

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