Episode Notes / Video / Transcript
EPISODE NOTES
In this special episode, The Retired Mindset host, Bob Preston, goes solo to share a heartfelt reflection on the concept of Trail Angels—the kindhearted individuals who have profoundly impacted his life and hiking adventures. Bob discusses how he came to his decision to retire and highlights the importance of the inspiring people he met along the way on his retirement journey, emphasizing how their kindness propelled him forward.
Key Takeaways:
- What Are Trail Angels? Originally a term used by long-distance hikers, Trail Angels are those generous people who provide water, food, guidance, or simply a comforting smile when hikers and backpackers on long treks need it most. They exemplify pure kindness and selflessness in the wilderness.
- The Power of Kindness in Hiking and Life. The real motivation to keep going on challenging trails like the John Muir Trail isn’t just the scenery—it’s the people. Trail Angels can appear at just the right moment to offer support and encouragement, reminding us of the importance of compassion and community.
- Metaphorical Trail Angels. Beyond the trails, Bob explains his metaphor: that Trail Angels are not just on the trail, but everywhere, providing the everyday acts of kindness that help us navigate life’s journey. These are friends, strangers, or mentors who show up just when we need them most, guiding us forward, in Bob’s case, on his road into retirement.
- A Personal Reflection. This episode is a personal tribute to those who have been Bob’s Trail Angels—both in the wilderness and in life—and the profound impact their kindness has had on his retired mindset.
Closing Thoughts:
No matter where we are, we can all be Trail Angels for others, offering support, guidance, and kindness that can change a life. So whether you’re climbing switchbacks in the High Sierra or navigating the winding trail of retirement, keep your eyes open for Trail Angels. Learn from them. Appreciate them. And when you can, be one yourself. Because that’s where the real trail magic is.
If you’ve met a Trail Angel—out in the wilderness or in life—we would love to hear your story. Please share it with us, and perhaps it will inspire someone else to follow their own path. You can email us or, better yet, join the community on our website or one of our social media pages and share your story with a post.
Until our next episode, keep moving, keep noticing, and remember—there’s always a little trail magic just around the bend, Where Soul, Meets Body.
Join us as we post new episodes weekly!
Connect with Bob: BobbyP@theretiredmindset.com, LinkedIn, Facebook, YouTube.
Listen on: Apple Podcasts, Spotify, iHeart, TheRetiredMindset.com.
VIDEO
TRANSCRIPT
Bob (flying solo for this episode):: 0:00
Welcome to the Retired Mindset Podcast, where soul meets body. Hosted by me, BobPreston. Embrace the retirement journey of transformative insights, inspiring conversations, with new episodes produced weekly.Bob (flying solo for this episode):: 0:48
Wow, look at where I am today. This is pretty cool, eh? For those listening on audio only, I’m actually hanging out and broadcasting today from my backyard. In fact, moving forward, I’m hoping to record all my episodes on location, including in many cases from the location where my guest is. So how fun will that be, right? It will spice things up a bit because I’ll be popping up in all these kooky crazy different places every single week. And it’s going to be a complete surprise where I pop up. Today it’s my backyard, but it may be at the beach, on a mountaintop, or maybe even in a coffee shop. Who knows? Each episode location will be a surprise. And that’s what makes this so special.Bob (flying solo for this episode):: 1:33
Now, I’m not really sure yet; there may be an occasional studio or Zoom session. But if that’s the only way I can connect with my guests, then I’m going to do it that way. Someday, you know, we’ll do it over Zoom and split the screen, and we’ll at least be in locations somewhere. That’d be pretty cool too.Bob (flying solo for this episode):: 1:48
I’m also going to start posting this Friday some bonus shorts. They’re sort of mini episodes, if you will, called Five Minute Fridays. I’ll be broadcasting from all kinds of spots to capture my adventure spirit. This is more about fun and energy, kind of a quick watch, but it’ll all be within five minutes or less, so it won’t take up a lot of your time. More on that this Friday, when the first FMF is published. So hey, stay tuned for It ‘sgoingtobeathat. lot of fun.Bob (flying solo for this episode):: 2:18
Now, today I’m going to be flying solo again, like I did in episode one. And we will start bringing guests on the show next week for episode three in all my full-length episodes. FMF will still be flying solo, just myself. And why did I want to do another solo episode?Well, today I’m talking about something very special to me. And I call this episode Trail Angels. And my decision to make another solo episode is really to provide you with more details about my decision to retire and the inspirational people I’ve met along the way who have helped me to get where I am today.Bob (flying solo for this episode):: 2:58
I feel like honestly, I’m the only one who can explain this and tell this story and communicate properly what this is all about. So here we go again. Today you get me. Next week I’ll have a guest, I promise.Bob (flying solo for this episode):: 3:11
Now, if you’ve ever hiked or backpacked a long distance trail, take the John Muir Trail, you’ve probably heard the term before – trail angels. I’ve hiked many segments of the JMT, but not its entirety. That whole thing is still on my bucket list. But you know, the JMT is about 211 miles of rugged beauty. So you got to have a lot of time and a lot of stamina and a lot of patience. There are granite peaks, turquoise lakes, meadows that look like paintings. Oh my God, it’s so beautiful, and most of it’s above the tree line. But anyone who’s hiked it will tell you what really keeps you going out there isn’t necessarily the scenery. It’s the people that you meet along the way, the kindness, the connection over what you were both experiencing.Bob (flying solo for this episode):: 3:57
Trail angels are the kind-hearted people who offer their last drop of water, they give you food, or maybe it’s just a smile at the right moment. When you are the most vulnerable on your trek, sometimes they pop up out of nowhere when you’re tired, sore, wondering if you should have ever laced up your boots in the first place. But without a thought, they may pull out their map and compass, share some insights and guidance on the trail ahead, offer you, like I said, water or a granola bar or something, you know, without even a clue about the impact they are making on your journey.Bob (flying solo for this episode):: 4:31
But here’s the thing: trail angels aren’t just found in the wilderness. They’re everywhere and in our daily lives, in unexpected acts of kindness and in the people who show up just when you need them the most. I’ve adopted the term trail angel now as a metaphor for the friends, strangers, and mentors who suddenly came into my life, people who arrived at just the right time with just the right kindness or words of encouragement to keep me moving forward towards retirement. So today we’re going to explore trail angels in two different ways. All right. The literal trail angels that hikers meet on the trail, and also the metaphorical trail angels who show up along our journey in life. This is a very personal and heartwarming episode for me. Like I said, I may get a little emotional for parts of this. So I hope you enjoy it. I hope I make it through it.Bob (flying solo for this episode):: 5:28
Okay, part one, the literal trail angels. Let’s start with the trails themselves. Okay? So picture this. You’ve been hiking for days. Your pack might be a little lighter now than it was when you started, but your spirit is heavy. You’ve just come down a steep pass, your legs are jelly from climbing the other side, and you’re dreaming of anything other than freeze-dried food, you’re taking it out of your backpack and boiling in hot water. Your water bottle is bone dry, and you’re down to the last crumbs in your food bag.Bob (flying solo for this episode):: 6:00
Then suddenly you come around a corner, around a bend, and there is a smiling person randomly pulled off to the side, cheering for you, waving at you. They know that the slightest kindness, like a cold drink or warm smile, can make a miracle when you’re struggling. I once heard a hiker say, trail angels restore your faith in humanity. And I think that’s kind of true. On long trails where you’re stripped of comfort and convenience, maybe you know you’re getting a little ripe, who knows? It’s these moments of generosity that remind you, hey, we’re all in this together.Bob (flying solo for this episode):: 6:37
Part two. Here we go. The metaphorical trail angels. This part’s gonna be really, really fun. Now, we’re gonna step off the trail, off the dirt path, and onto the trails of our everyday lives. Okay? In my case, my everyday life is a journey into retirement. I wasn’t sure at first, but I was stressed out and it seemed exciting. You know, freedom, time to do what I wanted to do, but there were also moments of extreme uncertainty and self-doubt. Who am I without the identity and structure of my work? What’s my purpose going to be now? These are all questions I ask myself every day while I was struggling with making this decision.Bob (flying solo for this episode):: 7:17
So, who are the trail angels here in this metaphorical sense? Well, great question, right? I’m sure you’re dying to find out. They, in many cases, were friends who encouraged me to embrace new projects and move forward in some new direction. In some cases, they were family members who reminded me that slowing down isn’t the same as stepping away. In some cases, colleagues who inspired me to share my voice through things like this podcast. And it could be even books, mentors, or conversations that I had with strangers, but it all felt like trail magic. Nudges, it came at just the right moment, helping me navigate this new stretch of the journey.Bob (flying solo for this episode):: 8:00
Now, let me be clear, trail angels are rare. There have only been a few, for me, a handful of amazing people who have appeared in my life to help me gain clarity. I’ve learned that trail angels in retirement don’t always look like people handing you food. Sometimes they can be moments of clarity, maybe a sunrise, reminding you that you’re alive, a child’s laughter that recenters your priorities, or it could be a conversation that you have with somebody that sparks a new idea or encouragement to take a new direction. So, in many ways, just like on the JMT, they appear when you need them the most.Bob (flying solo for this episode):: 8:38
Maybe your trail angel was a teacher who saw potential in you when no one else did. Or maybe your trail angel was a mentor who guided you through a tough career decision. Maybe it was a stranger who planted the seed of an idea during a random conversation. Offered a smile, said exactly what you needed to hear at precisely the right time. Trail angels aren’t always apparent in the moment either. Sometimes you may not realize you spoke to one of your trail angels until later that someone nudged you in the right direction and you’re now starting to recognize that this could be days, weeks later. Or gave you enough encouragement to take that next step.Bob (flying solo for this episode):: 9:22
And here’s a twist. Not all trail angels look like angels either. They may show up as obstacles or bad influences in your life. And I refer to these types metaphorically as trail demons. Not that these are bad or mean people, you know what I’m saying here, but you know that direction that they’re going is not right for you. Nope. You know, if you’re going that way, then I’m going this way. In your career, maybe it’s the interviewer who didn’t give you that job, who turned you off and the job you know you didn’t get. Or maybe a relationship that ended, or a failure that felt crushing in the moment. But looking back, those challenges are what shaped you, nudging you onto a different path, one you might never have chosen otherwise. But today, it’s the right one and you know it. And it was all because of that incident.Bob (flying solo for this episode):: 10:15
So again, I’m sharing some very personal stuff here, but in 2020 through 2023, things were pretty tough for me, I’m not gonna lie. It was not the best version of myself. It was during the pandemic. I was working long ass days, struggling to keep my business afloat and surviving, right, during the COVID-19 outbreak, carrying the burden of keeping my staff employed and retaining clients. I felt like Atlas at times, honestly. I was stressed out under a lot of pressure all the time. I put on, you know, the quintessential quarantine 15 pounds, that is, and probably then some. Now, coming out of the pandemic, my business was thriving and was stronger than ever. The pressure from getting through it, however, had taken its toll. There was also a noticeable shift occurring in the property management industry in which I had my business. Kind of like the show Survivor, there were alliances starting to form, and several private equity-backed companies started popping up and consolidating regional property management companies like mine in San Diego.Bob (flying solo for this episode):: 11:19
One such company, Pure Property Management, was cherry-picking the best companies throughout all of California. I kind of knew that this was going on. I’m kind of like, well, what’s wrong with my company? Maybe I should take a look at that. Well, eventually, you know what? Pure and I connected and we worked out a deal. My company at the time, North County Property Group, was a perfect match for Pure, and they offered me a great valuation along with the opportunity for a liquidity event with the business. And while the prospect of selling the company was exhilarating for six months, it was like jumping out of the frying pan, the stress of the pandemic, into the fire, the exhaustive M&A due diligence process that incurred doing this transition. The acquisition was completed flawlessly. The outcome was amazing, a mid-seven-figure transaction for me, but not until after an intense period of transition for me and my team. And again, this had kind of taken its toll.Bob (flying solo for this episode):: 12:17
So I actually got to stay on with Pure in a senior management position for about a year, maybe a little longer, but something was just not right with me. I was missing some of the life purpose, didn’t feel like an entrepreneur anymore. And I kind of felt like I was back, you know, working for the man instead of running my own enterprise. So after about a year at Pure, I realized that I had to retire. I mean, I’m telling you, I had to. I needed to press the restart button on my life, make significant changes in my daily routine, and establish some atomic habits that would bring me new clarity to get healthier and find myself again, honestly. So in June of 2023, after a long and painful thought process, I took the leap of faith into retirement.Bob (flying solo for this episode):: 13:06
It was at that point, though, that the magic started to happen. I began to be more open to new experiences and events. I put myself out there again socially, working harder to connect and make new friends along the way. As I manifested positivity, more positive things started to happen. The change was subtle, but almost immediate. And to be honest, I wasn’t even sure at the time that it had started. But that’s when I met my first trail angel, my first metaphorical trail angel, that is. Now, this person knows who they are, so I’m not going to mention any names. Don’t worry if you’re watching. That is between the two of us. However, I will tell you that over the next two years, there were several more. And the cool part, I’ve been able to reconnect with most of the amazing people I’ve identified as trail angels during my retirement journey, and express my gratitude for what they meant to me during this transition. Almost every time they’ve been surprised, genuinely surprised that what felt to them like a small conversation or a normal day, you know, just a simple suggestion or even a passing moment had played such a significant role in shaping my two-year journey. And then once the surprise faded, sometimes there was this look of wonder on their face, almost amazement, that they had unknowingly been a part of my trail magic.Bob (flying solo for this episode):: 14:34
Now, I’ve discovered another thing about trail angels. They often don’t know they’re angels at all. They’re just people being themselves. That’s part of their daily life, showing others kindness. Now, as I’ve walked this retirement trail, these angels have helped me learn some powerful lessons. So here we go. I’m going to rattle them off one at a time. Okay, so it’s kind of a list. I apologize for that. But it’s really important stuff. Number one, the trail provides. Just like the JMT, where you turn a corner and suddenly find water or food, retirement has a way of offering up exactly what you need. This is at least in my case, if you stay open to it. A conversation. Maybe it’s a new opportunity, a new idea that you have, a fresh perspective, the ability to help on something perhaps that you’re passionate about that you’d never considered before. You get these nudges to go in a different direction.Bob (flying solo for this episode):: 15:29
Okay, number two, travel light, baby, because out on the trail, carrying too much in your pack weighs you down. In retirement, it’s the same way. Worries, regrets, old expectations. Letting go of that mental baggage creates room for your joy and discovery in retirement. Number three, pay it forward. Okay, don’t just take it, you gotta continue it. Every trail angel I’ve met on the trail doesn’t expect repayment. They just know kindness, and that keeps the trail alive. In retirement, I’ve learned the same thing. Sharing time, wisdom, and encouragement can be its own kind of trail magic to other people that maybe you meet in random situations.Bob (flying solo for this episode):: 16:13
Number four, say thank you while you can. I found that taking the time to tell someone they mattered, to show them they were a trail angel, or I guess to tell them in my story, is as meaningful to them as it is to me. Gratitude creates a kind of trail magic all of its own. And I’m going to say from experience that doing so is not easy, especially for men, right? But, you know, one of the best parts of my trail angel experience was having the courage to feel vulnerable and risk expressing gratitude to these amazing people, some of whom I know weren’t expecting it. This was really, really hard. A couple of times it just kind of happened randomly, spontaneously, just kind of hanging out with a person. And then, you know, some switch flipped in me, and I decided it was worth taking the risk to express my gratitude. Just like communication on the trail, it’s one of the joys of making new friends and expressing how much you appreciate them.Bob (flying solo for this episode):: 17:16
Okay, we’re headed into the final chapter of this episode, and it’s called Becoming a Trail Angel Yourself. Here’s the best part. Any one of us can be a trail angel. You don’t need to live near a trailhead or carry a cooler full of water. You just need to notice when someone’s struggling, maybe curious, be curious, and then offer what you can. It might be a smile, a kind word, a small act of service, maybe just, you know, take time to listen. It doesn’t take much because life and retirement in many ways is a trail, right? It’s sometimes rocky. Sometimes it can be breathtakingly beautiful. And while each one of us walks it in our own two shoes, none of us are walking it alone.Bob (flying solo for this episode):: 18:00
So whether you’re climbing switchbacks on the JMT in the high Sierra or navigating the winding trail of retirement, keep your eyes open for trail angels. Learn from them, appreciate them, and when you can, be one yourself. Because when you’re one yourself, that’s where the real trail magic is.Bob (flying solo for this episode):: 18:23
Thanks for joining me today on the Retired Mindset. Gosh, I made it through that without getting too emotional. If you’ve met a trail angel out in the wilderness or in life, I’d love to hear your story. And maybe that will inspire someone else to keep walking their own path. You can email me, BobbyP at the retiredmindset.com, or better yet, join the community on our website and social media and tell the story yourself with a post. Until next time, keep moving forward on that trail, keep noticing, and remember there’s always a little trail magic just around the bend where soul meets body. Hey, thanks so much for joining me today. It’s been a great episode.