Episode 20: The 10-Year Letter to Yourself: Relationships, Health, and What Matters Most
What would your future-self want you to hear right now? In this episode, Rob and Brent write letters to themselves from ten years in the future—and then read them out loud. What follows is an honest, emotional conversation about relationships, health, risk, and the quiet shifts that happen in midlife. From evolving family dynamics to staying physically resilient and letting go of the need to control outcomes, this episode blends vulnerability, laughter, and practical insight into a simple reminder: while we can’t control the future, we can influence it by how we show up today.
Links, resources, books mentioned:
The Let Them Theory - Mel Robbins
(This post includes affiliate links. As an Amazon Associate, we may earn a small commission if you purchase through these links—at no extra cost to you.)
Topics we are covering in this episode:
Writing a letter from your future self is a powerful way to get clear on what actually matters now.
Midlife isn’t a crisis—it’s a transition, and how you show up determines what the next decade looks like.
Health works best as a filter for decisions, not a short-term goal or catchphrase.
Strong relationships evolve when you stay present, let go of control, and make room for change.
You don’t need to eliminate risk—just approach it with intention and preparation.
Vulnerability, especially when shared with someone you trust, deepens connection and self-awareness.
While we can’t control the future, the choices we make today have more influence than we think.
Transcript:
Transcript Disclaimer - May contain the occasional confusing, inaccurate, or unintentionally funny transcription moment. It’s all part of the show.
Lena: What if your future self could sit down and talk to you today? Not to give you answers, but to help you ask better questions. Today on Midlife Circus, Rob and Brent do something a little uncomfortable and surprisingly powerful. They read letters written from ten years in the future to themselves right now. From relationships and health to risk, change, and what really matters, this conversation is honest, emotional, and deeply human.
Before we begin, remember to follow Midlife Circus on Apple podcasts or wherever you listen, and join us in the Midlife Circus community on Substack. Let's dive into the ten year letter to yourself, relationships, health, and what matters most.
Rob: In advance of our session today, Brent, I ask you to come prepared by having gone back in your photo album and what were you doing roughly ten years ago at this time? Tell me what your life was like and what were some of the things you're doing around this time?
Brent: This was such a fun reflection backwards, Rob. My kids were probably going crazy and my wife, because I started sending them a bunch of pictures of ten years ago. Because at the time my kids were seven and 10, and there were three themes that kind of came about. The first one was lots and lots of skiing with family and friends. And so there was a period of time where we did a cat trip up in this high area near Vail that was super fun.
And then tons of trips with my kids jumping and doing all sorts of stuff. It was so cool. And we had a lot of snow that year, very different than the snow in 2026, but in 2016, there's a ton of snow. So skiing was one theme. The next theme was Spelling Bee.
So one of my kids was really active and they made it pretty far along in the competition for the Spelling Bee. So that was a big highlight. And then the third thing, Rob, which is really fun, and I forgot that this was ten years ago, is at the time there was a TEDx event in my community, and I actually coached 16 people to prepare for their TED Talks. And I also did a TED Talk of myself. So it was fun to go back down memory lane to see the TED Talks and how I was preparing.
So that was a big part of the activity that I was doing at that point in time. And then to add one more layer of fun, I actually jumped over to my music. What was the most played song that I had in 2016 that I listened to? And it was unsteady by the ex ambassadors. So the curiosity question for me was high unsteady that year.
And I just that was resonating with me, but it was so fun to go through the pictures and just seeing all the skiing that we're doing and all the family time and time with friends and then Spelling Bee and then doing my TED Talk and then listen to little music. So that was fun for me.
Rob: It's so interesting. I would have thought your TED Talk or the TEDx Talk that you did up here in the mountains was more recent than ten years ago. It's crazy how fast some of those things get behind us. And that age you were talking about skiing with your kids, I think that has to be, like, the best age range to ski with kids. Now I don't have any, but it's almost a favorite time when we go out with friends that have kids when they're that age because they literally jump off of everything.
They're laughing. They don't want to hang out if it's super cold, which I don't want to either. So they end up wanting to go inside, get some hot chocolate. You know, you got all that activity, but they're fearless. They're so close to the ground.
They jump off of everything. They ski in the trees all the time, and you just hear laughing as they're going up and down the mountain. I love that period of time skiing with kids.
Brent: That's like the first time when you're really experiencing the fun that they just want to go for it. And it seemed like every picture I took of my kids was them jumping off something. So it was super fun to go back through that. Did you go back and look at pictures from ten years ago?
Rob: I did, and it was interesting. This week, ten years ago, I was hosting a pretty significant corporate event. We lived in Portland, Oregon at the time, and we were hosting a pretty significant annual event, and it had a theme around it. It was a great Gatsby theme, so there's pictures of my wife and I dressed in nineteen twenties and thirties type of attire with a bunch of people that I worked with in that geography all dressed up for this big event. And then we left going into kind of the same vein you were in at that time of year.
We actually took a road trip and went skiing in both Grand Targhee and in Jackson, Wyoming, two places we had never been before, but jumped out in the van, took off, went skiing in a couple of new locations. And it as I look back, it was blue sky, not a not a cloud out there, cold days. But based on the clothing I was wearing, it had to have been really cold and, and just gorgeous weather for those couple of days of skiing in, in a totally new area for us.
Brent: So that was cool to see the pictures of a themed party, and it shows that you can have fun. But you guys do that a lot. You guys are always dressing up for different themes as you go to Oktoberfest over in Germany and all the things that you've done. So it's probably hard for you to think that you actually lived in Portland ten years ago. Now you live in Colorado.
Rob: Yeah. Very happy to be back in Colorado, but that time in Portland was perfect for us at that time in our lives as well. It gave us that city lifestyle we were looking for, so we moved from a suburban community into the city in Portland. Absolutely. Alright.
So my next question for you, and it's really going to pivot us into the theme of today's topic, Brent, is Back to the Future two. Do you remember what some of the premise was of Back to the Future two?
Brent: You know what? I'm probably blending all of them. I I remember there was some casino stuff in one of them where the betting side of things, they predict the future because he had, like, a a betting odds book or something from the future.
Rob: That's it. Back to the Future two was the movie that had Marty McFly had the sports almanac, And he was going to give it to himself in the past, but ended up that Biff found it. And Biff started betting on all of those sporting events impacting the future. So it was a future almanac that landed in the past that then was used to change and impact the future. And that is really what we're going to talk about today, Brent, and something that you and I have hinted about in a couple of our episodes, specifically is what would your future self tell you today?
How would your future self react to the decisions you're making? What would your future self recommend that you go and do? And you and I just did an exercise over the last couple of weeks, and it's given us a couple of weeks to actually go and do this exercise, is we actually wrote letters to ourselves as if we're ten years in the future writing to our current self today. So while we're not giving ourselves the sports almanac to forecast out future gambling, we are giving ourselves an insight into some of the things that may have happened over the next ten years of our lives or that we want to have happen in the next ten years of our lives. Brent, you call it forward, back, forward.
It's, let's go forward and actually give ourselves back some information from the future, and then we're going to finish conversation today as what things we're going to be doing going forward to help impact that future. We approach this completely independently. And so, I have no idea, Brent, what your letter says. You have no idea what my letter says. We actually didn't even talk about how we were going to approach writing these letters.
So this is going to be a lot of fun. I'm going to get to learn a lot about you today, I think, and you're going to definitely learn some things about me. I think it might be a little scary as I'm just thinking about what I'm going to be sharing today, a little bit scary as we read these out loud. Yes. We're going to read our letters out loud and actually have a discussion around each one of our letters.
So that's really what today's episode is, forward, back, forward. And let's, let's think about in the future, giving ourselves some advice and recommendations and insight into what things we need to be doing today. Sound good, Brent?
Brent: It absolutely sounds good. And it is a bit terrifying writing this and also reading it. So as I read mine, Rob, just know that I might get a little cracked up because it is sensitive topics, but actually very healthy topics. So it may take me a little bit to get through it. So mine is a couple of minutes just to give you a heads up.
Okay, here we go. Hey buddy, I'm writing you from ten years down the road. I'm 63 now and you're 53 as you're reading this. It may not feel dramatic, but you're standing at the front edge of a meaningful shift in life. When I look back, what stands out most is how much you stayed focused on relationships even as things were changing around you.
The boys grew up fast. Moving from being dad to something more like a guide, a sounding board, and eventually appear wasn't easy. You didn't always know what the right move was, and that bothered you at times, but you stayed present. You listened, you didn't force things. And because of that, the relationship you have with them are strong today, honest, and still evolving.
That matters more than you probably realize right now. You and Carolyn also stepped into the empty nest chapter without trying to rush through it or pretend it wasn't happening. You stayed curious together. You talked more, you let the relationship change instead of holding on to what it used to be. That openness created space for new rhythms, new conversations, and a different kind of closeness.
Beyond your core family, you stayed connected. You didn't let relationships with siblings, relatives, and longtime friends slide just because life was busy. You kept showing up. You made time, you shared experiences. Looking back that consistency played a big role in what a healthy life actually looks like.
That word healthy turned out to be more than a theme. Back in 2026, you chose it as your word for the year. And without realizing it, you set the tone for the next 10. It became a filter for decisions, not a catchphrase. Over time, you stopped measuring everything by outcomes and results.
You became less critical of yourself and of others, more present, less rushed. That shift didn't happen all at once, but you kept working at it and it changed how you experienced day to day life. Physically, you leaned into instead of pulling back. You respected your body, adjusted when setbacks showed up and trusted its resilience. Because of that, you're still doing the things you love.
Fly fishing, skiing, biking, golfing, exploring, and chasing adventures. You didn't step away from movement or risk, you just got smarter about how you took care of yourself along the way. There's one more thing worth calling out. Back in your mid fifties, you and Rob committed to building Midlife Circus. You didn't know exactly what it would become.
That uncertainty was a part of what made it work. The community kept growing, changing and surprising you. It stayed alive because you stayed curious. Even now it's still evolving, still connecting people who are trying to figure out what midlife really looks like. So here's what I want you to remember and what I'd tell myself again if I could.
Stay present, take care of the body you want to keep using, invest in relationships and stay open to what's next. You're doing better than you think. I love you.
Speaker 2: Wow,
Rob: you made it through it.
Brent: Oh, barely, man. I'm just holding on. I'm just holding on. There's a few catchy points. Got like, I know for those of you that are on YouTube, you can see I got tears in my eyes that I'm just rubbing out right now.
Definitely, yeah. Thank you for putting this out there. It was actually really fun to do.
Rob: It's going to be interesting when I read my letter, how the similarities exist in some of the topics while specificity is different. I think a lot of the similarity and approach, which I get the benefit of being second person to read this, I think.
Brent: Do have like two versions of yours, Rob? Like No. One
Rob: No, I don't. I didn't want to show off
Brent: and one to one to be like, oh, I'm going to one up him, and the other one is like, no. I'm just going to say it how it was.
Rob: No. I couldn't one up you, first off. And then the second thing is I don't want to work that hard. Why would I do two versions of something? I barely got one done in this time.
Brent: Yeah. It's a tough one.
Rob: So I have some questions for you. Let's start with the healthy one. So I I you used the phrase healthy became a filter, not a catchphrase. Can you share more about the filter you're thinking about with healthy?
Brent: Well, as I was writing this, it's obviously really important for me today. And I started out 2026, the year that we're in right now that we're recording this podcast, and that was the theme of the year was healthy. And that's my word of the year. But what I started to think about this word is, if I want to do and keep doing the things that I want to do in life, I have to use the word healthy a little bit broader. And so when I say filter, it's part of my decision making framework.
And let's say for instance, we've talked a lot about diet. And if I don't really have a consistent hold on my diet, meaning a grasp on it, and I'm eating healthy and I'm eating the right quantities and so forth, I believe it's going to impact me long term. So what I think about from a filter is it's an easy question to ask myself is to say, is this healthy? And then it's the activities that I'm doing. And it's the preparation for those activities.
And I was talking to my brother over the weekend and we were talking about skiing in particular, we said, there's some simple things you can do to warm up to go skiing as an example. And he goes, When we were younger, we would just go out, do moguls, we'd be doing all sorts of stuff. But now you could just do some things in the morning before your ski days, just stretching, flexibility, mobility, not complex, but it shouldn't be something that is optional. It should just be part of the routine. It's healthy to allow you to do the things because we're no spring chickens here, Rob.
I mean, we've where our bodies are adapting and changing. And so healthy for me can be a filter for a lot of things in my life. It can be healthy relationships, it can be healthy relationship with myself, it can be healthy food, it can be healthy activities, things like that. So I just felt like it was a filter for better decision making by simply asking that question, is this healthy or not? And I think we all have good radars for that.
You know, we can kid ourselves, but now I just need to take it more serious.
Rob: So when next time we go skiing together, I get to watch you doing some warm up exercises beforehand in the lift line. Is that what I'm hearing from you? Or I should at least make you do those standing in the lift line. Alright, Brent, let's see your stretches.
Brent: I might be doing that and I'm going to make you really uncomfortable or you'll probably just start doing them with me.
Rob: No. I'll probably tell everybody else in line to look at you.
Brent: Yeah. That's right.
Rob: Look at this guy. He must be old. Yes.
Brent: And old and proud of it.
Rob: Yeah. We Tara and I went skiing just this past weekend, even though we don't have a lot of snow, and I we got on the chairlift with an 85 year old man and great conversation with him. He wasn't moving as fluidly as you would, as you would wish somebody would move, but he was still out there. And so I know that's something you have in your radars to try and keep doing. I know I do as well.
Alright. Relationship is where you started the conversation, Brent. I want to talk about the you talked about embracing empty nesting. And so rather than, you know, rush through it as you embrace it, can you share more about what your thoughts are there and why it's important for you to embrace the empty nesting versus just try and work through that that experience?
Brent: I'm not quite there yet in the sense of I've got about six more months till my youngest goes off to college, but I've already experienced with my oldest and it's just such a transition in life. And when you embrace it, it means that you're allowing, for me, myself to go through the emotions. It's something different, it's changed, but let's look at the bright side of this. It doesn't have to be this doom and gloom scenario, it is they're going off to grow up and prosper and live their lives, so let's celebrate that. And then also there's a celebration for both Carol and I too, that our kids are at that stage in life.
So embracing it for what it is, but also allowing myself to go through the emotions of what it is. Because my past, especially when I lost both my parents at a pretty young age, was I just bottled that one up and stuck it so deep inside that I never really dealt with it. And particular, my father, I didn't deal with it for fifteen years later. Then I started to realize how I navigated that was just not talking about it, not expressing my emotions. And I think this one is just embracing it.
And hopefully I've evolved since, I mean, I was 29 when my dad passed away. That's pretty young in my book, and so hopefully I've learned from that experience. I wouldn't say it's the same as death, but it's the same as change. And so if I embrace that change, I just think it'll be healthier for me and then healthier for others around me.
Rob: You and Carolyn should definitely celebrate the two young men that you have raised. And so I know the second one's going to be going off to college coming up this fall. Do you have on the radar then a celebrate celebration event? I know you I know you're planning on a, like, a high school graduation party, but that's more for him. Have you and Carolyn thought about hosting or having your own little celebration of that transition?
Brent: We haven't. That's something that we should take into consideration. Like, we haven't even talked about that. I think right now we're just trying to live in the moment with him being in the house and not trying to project ourselves, six to nine months from now, I'm just saying, wow, life is going to change. But that will be something that we'll start to think about as we get closer to that.
But that's a really good idea, like have a little celebration for ourselves just to say, good job. I mean, two boys and getting them into college and watching them thrive in the broader universe is an important reason to celebrate.
Rob: You should definitely celebrate. Maybe not even just a little celebration. It could be like A blowout. A trip to Hawaii. You and Carolyn just do a nice long week at a really fancy resort in Hawaii or something like that.
Brent: Now you're talking. Maybe I should get Pearl Jam to come have a party at our house. Let's go big here, Rob.
Rob: Yes. Now you're getting that. I love it. Love it. I'll be the first one in line.
Alright. I'm going to stay on the same piece with relationships. We talked about kind of the transition for you and your wife as you become empty nesters. You also talked about the change in your relationship with the boys being from a, you know, that that fatherly guidance figure to more of a sounding board. Have you started experiencing any of that thus far as they're getting closer to being out of the house and being on their own?
Brent: Absolutely. I mean, part of it is the stage of life that they're in, so they're flexing a bit. And that's what we've all done when we were at that age, late teens, early 20s, it's like, hey, I got this. And that's a different stage because as a dad, you're sitting there trying to help them throughout the day to day, but now you have to let them go experience life. And that's been a challenge for me.
I'm getting more and more open to it. There's a book out there that I highly recommend is Let Them by Mel Robbins. And it's a really important process that she describes as letting people do what they do. Now, a parent, and she's very clear in the book, as a parent, you also should know that you do have responsibilities until they're somewhat fully developed. So let's say mid twenties, but there are also things that you got to let go of.
And that's a big part of my journey is letting go, but also understanding that they'll reach out to me when they want advice. They'll reach out to me and also being comfortable when they don't reach out to me. Because I feel like I have all these experiences I could share, but I'm also still dad and that's kind of boring to them, that they need to go make their mistakes and they need to try things and they'll have their successes and their failures and we all went through it. It's something that I'm working on, but I have to say it's challenging because it's something that I'm so used to for the last twenty years, but now it's trying to make that transition to be more of a guide. And a good friend of mine gave me a really good recommendation years ago, because his kids are older than mine.
He said, You're like going down the highway, you're just the guardrails on the highway. You're letting them swerve a little bit, you're letting them speed a little bit, slow down a little bit, take exits when they want to take exits. But your job is to keep them on the highway, but not necessarily tell them what to do while they're on the highway. It's just the guardrails. You're keeping them in the boundaries.
That resonated really well with me when he shared that. I didn't understand it at the time, but now I'm in that stage where I just need to be guardrails and just let's hope for safety here, and other than that, just let them roll.
Rob: And they both make really good decisions, so I don't think, know, they're not crashing into the guardrails regularly, at least that you've shared with me. But, Mel Robbins book, Let Them. And so, Brent, you're letting them sleep until 02:00 in the afternoon if that's what they truly want to do. Right? That's absolutely okay.
Brent: If it doesn't impact other parts of their life, if they don't have other commitments, then that's it. Even if they do have other commitments and they miss it, they're the ones who have to deal with the consequences, not me. I can recall back when I was 20 years old and came home from college for the holidays and I'd stay all till two and I'd wake up at noon. I mean, that's just part of this rhythm that I got to be aware of, that's the stage of life that they're in. It's challenging for me, but I'm learning and I'm learning sometimes the hard way, but it's also fun to see my kids grow up.
The experiences that they have, the friends that they have, the things that they're exploring are so fun to be on the sidelines and watch and just see where they take this.
Rob: The next question I have actually, I probably should have asked more when we were talking about health, but and this one kind of surprised me a little bit, Brent, because I don't see you as someone that jumps in and does things that are highly risky, but you said you don't step away from risk was the phrase you used in your letter. And sometimes risk can actually impact the healthy part of life. Tell me more about not stepping away from risk. What are you thinking about there?
Brent: I find that, and I see it with other people where they stop skiing, they stop mountain biking, they stop doing thing that they once loved because for the fear of injury, the fear of falling, stop doing that intense event because they're just worried about the outcome or something may happen. And I just believe life will happen. You may get an injury, you may step into a space that you're not overly comfortable with, but that's part of growing, evolving. For me, it's just the exploration is so much fun. I don't want to take that away.
So I need to be smart about how I approach it in the sense of, am I physically and mentally prepared versus just jumping in? But I don't want to take those things away from my life. I still want to go fly fishing very far up places that may be uncomfortable for me, but that's part of me growing and evolving. I still want to ski, I still want to mountain bike, I still want to trail run. And each one of those, as you know, because you do all of those brings their own level of risk.
I don't want to take those away. But I do know there's certain things like you and I've talked in previous episodes like hucking cliffs skiing. That's something of the past for me because I know the probability of injury is much higher because my body just doesn't flex and move that it did maybe ten or fifteen years ago. So I know there's certain things that I want to eliminate, but the bigger picture, I still want to ski till I'm in my mid-80s. I'm going to be that guy on a chairlift that you just experienced last weekend.
That's me at 85. That's what I want to do. And I want to make sure I'm allowing myself to take the necessary risks to get to that stage.
Rob: So risk was definitely aligned with you staying healthy physically, right? The ability to assume some level of risk, not an increased level of risk is what I'm hearing from you. And that today, you need to be doing things physically to allow you to continue to do those things down the road.
Brent: Definitely. I mean, I just think it's so easy to stop doing things. That's like the easy button. I want to continue doing them. I just know I need to step up my game to continuously do those in a healthy way, so I'm not adding the unnecessary risks like, yeah, I didn't prepare for it.
So if I know that I'm going to go on a five day ski trip as an example, then I need to be physically prepared for five days in a row of skiing. That's not something that I do on a regular basis. So I have to be ready for that. Because I used to be able to just wing it, I just know those days are gone. I could wing it, but it's not going to be enjoyable.
And the likelihood of injury just elevates a little bit when they're not prepared physically for something like that.
Rob: You say a five day ski trip this last spring, almost a year ago, coming up on a year ago, I met a group of friends from high school and they were doing a golf outing and five days of golf in a row. And I don't golf, so they were out golfing, but they were all really sore after five consecutive days of golf. They were, you know, hobbling around the hotel a little bit more, measuring their aches and pains and discussing them. So your goal is to actually to be able to stay healthy, to be able to continue to do those things in that type of frequency.
Brent: Yeah, and just enjoy it. Like that can be so fun, but I don't want to wing it. I enjoy getting ready for five days of skiing or multiple days of golf or a mountain biking trip to Moab. Like I enjoy that. I just know that there's certain things I can do to make it enjoyable when I'm there leading up to it.
Rob: And that really is kind of that second forward thing. So forward, back, forward. So forward self, writing a letter back to yourself, and then what are the things forward you can do to impact that letter, Brent? So as you think about the ability to be able to continue to pursue some of those things, what must you do today to make the risk component of your life to be able to keep skiing, to be able to keep trail running, and keep mountain biking? What are just a couple of the key things that were either epiphanies or that you already knew need to happen now to allow those to continue to happen?
Brent: Well, let me even take it one step further. Even like with the relationships, like let them evolve, be patient. Don't try to control all the outcomes of life. I mean, that is my business mindset that my professional life taught me that you got to just be in it and you got to keep pushing, pushing, pushing, but there's certain things you just have to let evolve. And once I breathe a little bit, I pause a little bit, let things happen, I think it'll be a healthier outcome.
As it relates to activity, the things that I'm doing right now are so important and I just have to continuously do them. Like we've talked about in previous episodes, yoga, core workout, strength. I think the number one thing that I just have to stick to because I've read about it so many times is strength training. Like if I stopped doing that, then I think I'll eliminate some of those activities because there's too much literature on it and I've proven it to myself. So there's certain things that I need to own and not make optional.
And I think I'm doing a pretty good job of that today, but I have to make it always a priority. And I think it's adapting my life to accommodate that. If I know I'm really good in the morning, just block my calendars and just don't plan to do a whole lot of things early morning so I can get those workouts in and just start the day off on the right step.
Rob: But it it's interesting, though. You talked about not trying to control things, which I think a lot of us have a tendency to do is try to control the outcome of a lot of things. And given your previous controlling nature, I'm guessing it's taken some work for you to be at the place where you can just let it evolve and let it be very fluid.
Brent: I think controlling I've got a healthy dose of perfectionism, trying to control all the outcomes and make them all look pretty and perfect. I think part of me is the key, and I mentioned it probably a few times in the letter is being present and just being present and not trying to control what does six months look like from now, what does twelve months look like from now? It's being present and enjoying the moment.
Rob: Well, benefited you in the business world to anticipate all the possible scenarios and then build contingencies around those so that the plan kept moving forward. Yeah. And life isn't like that. And you have to let it evolve and you have to step back and let things unfold naturally or let people evolve as they're going to evolve and become who they are.
Brent: Yep, yep. And mentioned this that as I think through this overall process, it's just going with the flow here, like not getting too caught up on the little things in life. The relationships are really important to me on all aspects of my life. My friends, my siblings, my relatives, my kids, my wife, like that is top of mind to me and keep evolving those and keep exploring those. That just is a fun part of life.
Rob: Are you ready for my letter?
Brent: I am, Rob. Let me just switch gears here really quick and get over to my ability to take some notes.
Rob: I know we're going to get into our approach to writing the letter and kind of the experience, but mine actually I put in a journal. And one of the things I hope is an outcome of this exercise is I actually begin to start journaling on a much more frequent basis. So I have a new journal that this actually kicks off this decade of my life to start capturing ideas and thoughts and insights that I have. Something I've tried to do on a for the last number of years, and it's anything but consistent. I think as I look through old things, was a year, year and a half apart between some of the entries in prior journals.
I'm hoping, this new approach will help me be a little bit more consistent. So I'm not going to be reading off of a screen. I'm going to be reading actually out of the journal and, and hopefully I can read my handwriting still. It's been a long time since I've just written much by hand and I got cramps in my hand trying to write all this down. It was surprising.
Alright. Dear Rob, I want to start this letter by thanking you. Everything you have done up until this point and what you will do in the next ten years has given me an incredible life. You should look back and be incredibly proud of what you have done. You should look forward with excitement for the next decade.
You won't believe me if I told you everything that happens, but here are some of the things that I am benefiting from today. You and Tara continue to travel, but the experiences will become more diverse and distinctly unique from prior trips. Your small trips will be bigger than they were before, and your big trips will be significantly more diverse. While all of your travel has shaped you in some way, this next decade of travel is going to be through a totally different lens. You enter it wiser and more open to growth than ever before.
You know that list of 50 things to learn? Well, you finished it. It took the whole decade, but you did complete all of the items. While some were goofy, some were one and done, there are a number that I'm still enjoying today. Spanish was really helpful on that big motorcycle trip through South America.
I wish I could tell you that I'm a male swimsuit model, but sad to say I'm not. I am, however, one of the healthiest and fittest 60 year olds in our community. You will continue to do endurance events and yes, you finally buckle at Western State's endurance run. FYI, we don't get any faster, but we're still out there doing it. I take the most pride in the stability of our healthy lifestyle and the fact that we don't need any medication.
Keep up the strength training and get more consistent with yoga. I need these in order to be active for the next twenty years. Speaking of health, the greatest has come in your mental health. What started that morning during Coca Cola has continued to change you for the best. It isn't lip service anymore.
I love myself. Thank you for putting in the work to get us here today. The conversations in my head are mostly positive now. I know, hard to believe, but it's true. We have also mellowed out quite a bit, though I wish that that had started earlier.
While I still have that fuse, it is so much longer now that I rarely ever get angry. The podcast is still going strong and you have a huge ten year anniversary celebration. This is what you're meant to do. Be patient and keep going. Not only is it changing you, it is helping a generation live their best midlife.
I can't wait for you to read some of the letters the audience sends you. You can finally say you found your calling and you get to do it with one of your closest friends. Now I've been saving the best for last. I have the best relationships. We have friends located all over the world, some people you don't even know yet.
Please don't change the path you're on today. You're developing deeper, more connected relationships with your existing group. We laugh. Oh, do we laugh. Have fun, travel, and still and do crazy beep together still to this day.
Some of them will join you on your big adventures in the next few years, and you will get to experience things through their eyes. Make sure to tell them how much they mean to you while you can. You also have increased the quantity and quality of time spent with family. Those relationships have grown and been transformed. Keep helping your parents take those big trips.
The change of pace is good for you and for them. Finally, Tara. Yes, she's still with you. Yes, you deserve her, but barely. Your relationship will see the most change over the next ten years compared to everything else in this letter.
You don't fall into a rut. You carve an entirely new path going forward. She continues to be our best friend, our closest confidant, and biggest cheerleader. She needs to hear how much she means to you so much more often than you currently communicate. Start to tell her and show her this more often, please.
Rob, thank you for giving me this life that I have had and that I get to have. I love you.
Brent: Whew. Hang bro. Tough letter. Yeah. Those again, if you're on YouTube, you're seeing us wipe tears from our eyes.
That's exactly what middle aged men do. We put it out there. Hey, thank you. That was incredible. I'm so happy for you, Rob, that you wrote that.
I just feel like you put it out there and we'll talk in a little bit about how we went through this process, but it was so thoughtful, so meaningful, and you highlighted some really important things. So I'm going to jump into a few of my questions and I'm going to start in a place that I want to understand what was really driving the emotions. So we were about half to two thirds of the way into your letter and you really got choked up and you were talking about being patient, relationships, mental health. What was it in that section that just really triggered you, probably as you're writing it, but even as you're reading out loud?
Rob: It was interesting. Reading it out loud with you brought on more emotion because it was actually public now. I mean, I did this in in the office by myself. Tara hasn't heard any of this letter at all. So that brought out more of the emotion than it did even writing it because it now became real and something that I haven't necessarily put much voice behind before, let alone tell anybody else about, you know, the conversations I typically have in my head, you know, where I where I naturally gravitate towards.
And I did glance back at some of the journal entries for multiple years of journaling. I think I had maybe 30 entries over a seven year period of time, so very sporadic. And a lot of them had the same theme about me being able to take care of myself and actually not get into the place of bigger, better, like, could be better. I need to be better. I need to do more.
And we've talked in previous episodes about impostor syndrome and things like that, just high level. It's kind of how my mind has worked. And Cocodona and the run at Cocodona and the experience I had there started to shift in me, and it and it really has continued to grow. I think some of this podcast is actually helping me continue to grow as well by just putting a voice to it and actually putting it out there in the world.
Brent: What's interesting is we both came from different perspectives of the podcast, but we both believe in what we're doing. And it showed up in both of our letters that this is work that we both believe in, that we're both going to continue, but it's building this community. And when you, there's a few fun parts of this that I'm going to go from kind of near the beginning that I want to talk about because it is part community for you, where you said, you you're going to do lots of smaller trips, you're going to do a lot of big trips, but you also partway through, you talked about doing it with people. What does that mean to you, by doing it with others?
Rob: We've talked about on these episodes, Brent, the amount of adventure things that I have done and that my wife and I have done together. And a lot of it is just the two of us off doing something kind of crazy and then telling stories with friends about it. And one of the things I do want to start to do more often is bringing friends along or and people along to have those experiences with us for a couple of reasons. One is it makes the stories that much better that we're now reminiscing not just Tara and I telling people about it, but it's a group people having that story around it. So I'm really hopeful that the surfing camp in Costa Rica will create that type of an environment.
But a very specific example is we've been to the continent of Africa three times in different countries and traveled around Africa a little bit. And while we were there on this last trip, Tara and I started talking about our next trips to Africa because it's not about if we will come back, it's when we're going to come back. It's one of those places that is so magical. It just draws people back on a regular basis. And the next trip back, I want to do with other people, not just the two of us.
And each one of our trips have just been the two of us, and there's been other people around us, but not that we know. And so the next time we go to the continent, I want to go with other people so I can actually experience that first time scenario through their eyes. The first time they see an elephant. The first time they see a lion. And it sounds bad because we've done those so many times, you almost become numb to that experience and how incredible the experience is.
It's very selfish by having other people there. It gives me a different level of experience to see stuff through their eyes that I've seen before.
Brent: I am the same way with some of these adventures. It's cool if you go with the same friend or the spouse every time, and I love that. So I don't want to take away from that, but it's really interesting when you expand the group a little bit. But part of that to me that I need to keep growing and continuing is not trying to control the outcome when I do it with others, because that's the risk that I've taken on. So when we're doing Costa Rica, we've got, I think we have over 35 people that are all part of our friend network going to this.
And we have to be open to letting it flow, letting it go because we can't control the outcome. I can't control if one person's going to have a blast and another person's not going to like it. I got to let go of that emotion. And part of me is just that living in the present and just letting it go and then letting it be. And I think one of the things that I wanted to also get your perspective on is because you'd said, one of the things that you want to keep working on is mellowing out, being patient and how your mental health, you're already seeing an improvement.
What does that mean to you? So when we think about going forward, what are you doing to allow yourself to mellow out? How are you allowing yourself to be more patient? Because this is, you and I both have this etched inside of us, this controlling nature, this perfectionism of trying to control the outcomes, because a lot of that is part of our careers, but let's not have a career hangover here. We don't need to bring this into the rest of our lives.
So what are you doing as you look forward into the future? How are you addressing that one?
Rob: As I shared journaling, and one of the things I've My goal is to start journaling more frequently and just sit in my own thoughts and sit in my own emotion. Last couple of weeks as we started this exercise, I started putting notes down around some of the topics I was going to be sharing, you know, going backwards ten years for myself. I started thinking about every day and setting intention for the day and just being very mindful to start the day in a certain way, those things will help. Likely, Brent, it'll involve some form of therapy that I'll be working with someone to help with that because it is so ingrained and the confirmation bias that I've had for, you know, twenty five years of a professional career that by being controlling, being really driven, being really focused, all of those things and being intense served me really well. Because of the positive outcome of that, it recirculates and that that that gets more ingrained in who I was.
Right? So, look, if I because I did it this way, I became successful, so I'll keep doing it that way and it kept fostering more success. And so it became more and more intense. And so to break that cycle, it's going to take some professional work, I'm sure, with someone to help me move into the better version of myself now at this point in my life.
Brent: And we've talked about it a few times that being present and just letting it go, you know, and it's just, it's hard to do. So if it's been a part of you and who you are as you've, you know, in your professional life and now you're in 50s and you're saying, I don't really want some of those traits anymore, Celebrate what you have and what you had, but also recognize the importance of if you want relationships to evolve. And I love how you said that you've got the best relationships. And part of that to me and the encouragement that I have in listening to you is having the best relationships is also being open to how relationships need to evolve and not trying to control the outcome of this relationship or that relationship. It's really understanding that to have a healthy relationship, it's a two way street.
And recognizing that some of those relationships just may not last the test of time, but some of them are just going to keep growing and evolving. It's super special. I love how you said the best relationships. And then you also incorporated laughter. One of the things that I talk about with Carolyn is, you, Tara, Carolyn, I, and probably three or four other couples, get together periodically and go camping or we'll go on a ski trip.
And I often say that group is the funnest group because we laugh so much. And we're not worried about what the other person is going to say. We're not trying to hold back. Just who we are, a bunch of humans show up as individuals and we just laugh our way through the experience, the goods and the bads and the funnies and the sillies and all of that. That is so special when you have that.
And I'm just so excited to hear that laughter was added to that as well as the best relationships. That's so cool.
Rob: Yeah, we leave those events having done like a thousand sit ups is what it feels like, because our stomach hurts so much because we're laughing so hard.
Brent: They're just so much fun. So the way I want to close out my comments to you or just my questions is, I really love how you ended this with talking about your relationship with Tara. And I find that there's so much commonality that I have with you is, I don't say it enough to Carolyn how much I love her. I don't express it enough, but she means so much to me. Sometimes we just get stubborn as males and just how we're going to operate and how we see the world, but there's others that are on the journey and our spouses are the ones that are closest to us.
So thank you for that. It gave me the opportunity to say that to Carolyn, but also you said it so eloquently. And I just really appreciate that. And I know Tara means the world to you. And for you to say that and express it, our wives always say that their biggest fear for this podcast is are we going to be cringeworthy?
Hopefully, they'll take these as positive cringes.
Rob: Yeah. Tara's going to listen to this out on a walk, which is how she typically listens to these things. I'll probably hear about it when she gets back. And I know I'm very confident, Brent, based upon our relationships, we're not going to be the individuals that have the midlife crisis. And I think part of it is just putting the intention out there with these letters to help us do it.
I'm a little disappointed though that you didn't argue with me about the male swimsuit model opportunity that I still might have available to me.
Brent: Man, that ship has sailed, brother. I know you well way too well. You and I, before we started re recording this, you're talking about going to diners and having French toast and eggs and hash browns and stuff. If you want that swimsuit model body, you're going to have to change a lot. I don't know if you're up for that challenge.
I'm not definitely.
Rob: I don't think I'll stop liking eating as much as I do. I don't think that's going to change.
Brent: Yeah, yeah. No, that is great. I thank you again for doing your letter the way you did it, it was beautiful. And I'm super proud of you that you put the work into it and the outcome was just exceptional. So awesome.
Just a super cool experience.
Rob: Thanks for your letter as well. And as you can't tell listeners, Brent and I obviously didn't talk about these letters in advance, so we're both seeing it and hearing from each other very raw. This is something I know, Brent, I've heard for the last, I couldn't tell you, ten or fifteen years. I've read books. I've listened to podcasts.
I've heard commentary around write a letter to yourself. Write a letter to yourself from the future and just have never done it before. So it was nice to be able to go through this exercise and actually approach it with you. And I think I'm guessing you and I may have had different approaches to how we went about writing the letter. And so before we go into the approach, let's maybe talk about the experience, Brent, that you had in in going through the letter.
So what was your experience in writing the letter and then sharing it now publicly? How would you how would you describe the experience?
Brent: I would say that it wasn't difficult to do, which was a fun part of this. I was nervous about doing it because I'm like you, I've heard about this, people have told me the benefit of doing it, but it really flowed and it was flowed in a really special way for me because I started with my kids and my wife, and then the relationships with my friends and then my relatives and so forth. So it flowed really easy for me and it wasn't hard to do. What the challenge was for me is when I read it for the first time, I couldn't get through it because once I assembled it, because I did it all little parts. Okay, let's relationships.
Okay, let's talk about your physical and your mental well-being. And okay, let's talk about midlife circus. And so I knew all those, the pieces of the puzzle, but boy, that first few times reading it was really hard for me to do because it was hearing me talk about myself. And that's an uncomfortable place, but it was amazing. And I got a lot out of it and I'm glad that I did it.
When you did it, how did you do it? Because you actually hand wrote this and that's a different, I did mine on my iPad, but I was curious, how did you go about doing it handwritten? Was it multiple drafts or was this just like a one and done?
Rob: A couple of drafts. And so we started this process a couple weeks ago as we came up with this as a topic of discussion that we wanted to record an episode about. And so I think I did the same thing that you did, Brent, as I started just writing down quick notes. And it was just started off, know, as I had a thought, I write a quick note down. I might have been on my phone just typing in because I was out doing something.
I'm like, oh, I should probably reference this or I should reference that. And then I took those notes and I sat and actually wrote an entire letter. And from start to finish, I sat down and you shared it. It just started flowing pretty quickly. So I just sat down and I hand wrote the letter and then I let it sit for a couple days.
And more thoughts came to my head. I was, oh, you should have referenced this or that's not quite how you felt and maybe this is how you're feeling. And so I kind of bounced back and forth with different ideas and so and different ways of voicing it. I then started writing again and then my notes, I started getting up in my head. I'm crossing stuff off and all over the place.
I had an old journal that I started writing in to keep this letter and then I was like four letters in where I got like a paragraph and I said, oh, that's not good enough. I'm going to change it. So then I pivoted to electronic. So I had all the thoughts down just to be able to keep it clean and be able to move forward easier in the content. Then I went into typing it.
So I typed the letter, and then I wanted to capture in handwritten form and just do one final version of it with me writing because I think different with a pen in my hand and working with a pen that I do typing in front of the computer. And so I then took the took the typed version and I reworked it into the final version that I read today, which is written in the letter folder.
Brent: As you said that something came up. I said something specifically in my letter, and I'm just going back to it, which was a part of me moving on from my letter was over time, you stopped measuring everything by outcome and results. You became less critical of yourself and others. I had to embrace that part of the letter really by writing this letter because I could have rewritten it a 100 times. Did I say enough about my kids?
Did I say enough about my wife? Did I say enough about my relationship with my own health? I mean, did I order it right? The perfectionist was starting to come in and I said, I've got to own this and move forward. And I could rewrite this letter.
Is it going to be better? Sure, maybe, I don't know. But I feel I had to be confident myself. And that was a part of this journey that was really important to me. I think a side benefit was, it's okay to say this is the version I'm going to put out to the universe today.
And it may evolve in the future. Maybe you forgot to say something you wanted to say, well, find another medium to do that. Write it down again, write it down another time, do this exercise once a year, once a month. I just had to allow myself to put it out there. Rob, I was really nervous about doing this even on the podcast, I'll admit, because it's not something that I've been overly comfortable with in my past life, because I was trying to be so perfect about things.
And it shows some of my flaws and some of my weaknesses, areas I'm working on, my vulnerabilities, but I'm so glad I did it. Like that's the fun part of this, but it was definitely hard for me to do because it wasn't hard to write, but it was hard to speak it and know that I'm putting this out to a broader universe. That is something that was making me nervous, but I'm glad that we're doing it.
Rob: The part that caused me to rewrite it a couple of times were the tenses or I versus we versus you and the timing and wait a second. I'm writing back, but it's about it's like that was where I got like, started getting confusing as I read it. I'm like, I read it again. I'm like, that am I talking backwards, or am I asking me to think forward on this too? And so I got in my head a little bit, but once it started flowing, I will say it flowed really smoothly, which was actually really fun.
And if I was to compare the letter that I read with the first letter, they are really, really close in terms of what my outcome was. I enjoyed the overall experience. I was a little anxious coming into today knowing I was going to read it, but also excited because I don't know that there's any downside of sharing this only upside. And so I started thinking about, you know, that the rational side of my brain says is I don't think anybody's going to send me an email or send me a message saying you're an idiot for what you wrote. I don't think that's going to happen.
And so I was able to get in my own head and get into the excited phase of, I'm just going to share this publicly and hopefully someone will want to go and learn from it and do it themselves.
Brent: And one thing that I was really glad that you and I did is we did it together. And I find if I would've just done this just for myself, I don't think it would've turned out the way it did. I wouldn't be as proud of the work because I would've just done it and folded up the notebook and I wouldn't have gotten as much out of it. And so thank you for being my friend to do this with. Like, I felt really safe with you and I know we're doing this in a public space right now on a podcast, but I never intentionally wrote it that way.
Like it wasn't about the podcast, was about doing it, sharing it with you, and then I felt safe and you reflecting back to me. So people are considering doing this, highly recommend it, but grab a friend. I mean, it's really cool. It's a neat way to explore it. And I got a lot out of it, but I just want to thank you for allowing me to be vulnerable to you, knowing that you wouldn't be overly critical back to me.
You were very thoughtful in your responses and things, so thanks for making this a safe place for me because I enjoyed the process and that made it just that much better doing it with a friend.
Rob: I'm really glad you shared it that way, Brent. If I was as I think through my approach, if I had just written this for myself, I wouldn't have put in the effort that I now get to benefit from having really put in the effort to read. It would have been letter to myself with not necessarily a lot of truth or a lot of challenge. I would have been able to cheat it. And having to share it with you directly, I know you would have asked me some follow-up questions as a good friend would and really challenged me on some areas.
If I was skirting something and didn't want to discuss something, you would have challenged me a little bit. And so for our audience, doing this for yourself is the first and foremost first step to take is just take a step to write down this letter. We've, a lot of us have heard this approach and something you can do to write a letter from the future to yourself and then areas of your life that you may want need to change is starting to take action in doing it. But I think the bigger benefit is going to be sharing it with somebody and doing this exercise with a friend. So I recommend sending this share this episode with a friend that you think you'd want to do this exercise with.
Ask them if they're open to doing the exercise with you. Odds are you're not going to get turned down because I'm betting the person you're going to ask to do this with you has heard this type of discussion before and likely if you're choosing them, they would probably choose you for that same experience. So share the episode, ask them to go through the exercise with you.
Brent: And one thing that we want to take this one step further is Rob and I are going to share our specific letters out in our Substack community. So the Midlife Circus on Substack. And those of you that are not familiar with Substack, you just have to go to substack.com, search Midlife Circus, subscribe to our publication or our space. And what Substack is, it's a place for a lot of podcasters, creators, where they're interested in creating a community and they want to build a community together. So millions of people use the Substack platform.
Rob and I worked really hard to build out our platform and we're continuously evolving it. And so it's a space for you to actually get to know us even further, but also get to know other listeners further. It's a place that you can share your own stories. You can ask real questions. You can talk honestly about what you're going through.
And so this is a space that we want to create for the broader Midlife Circus community. And if it resonates with you, head over there, you'll see our letters. All you have to do is go to the episode for this release and you'll just see it in the comments and we'll have our letters posted there and you'll get to see what we did and hopefully it'll inspire you to do something similar.
Rob: And if you're so inclined, please feel free to share your letters with us and share those letters with other individuals. I think there's incredible power of making some of these things very public and it, it might just help hold you accountable to doing some of those big things that, that you say you want to do or you know you should do. And so if you're willing to, please share your letters with us. Those of you that do share your letters, we may reach out to you and ask if you'd be open to letting us share those more publicly in our podcast going forward. And that really takes us to kind of the final components of today's discussion, Brent.
This came as a suggestion from one of our listeners and a friend of mine actually made the suggestion trying to bring our audience more into these episodes. And so as we go to wrap up, one of the things we hope to incorporate going forward is questions or comments or letters or thoughts and ideas from our audience, even experiences that our audience is having. And so thank you, Jason, for that suggestion. We'll start adding that in to our episodes going forward as bring our listener stories and questions to the table more frequently. If not in every episode, at least most of our episodes bringing listener interaction into the end of them.
So as we wrap up, thank you for listening to both Brett and I ramble on a little bit and get a little bit emotional here publicly. It definitely was uncomfortable for me, but I want to thank all of you for at least listening to it and letting us put a voice behind the future versions of ourself that we want to have. While I don't think we have complete control over what the future will hold, we do, I think, Brent, have some influence on our future, and we can influence our future by the decisions that we make today. That letter back to yourself from ten years, ideally, is going to come from a place of love and hope and positivity of the things that you get to have because of the choices that you make today. And so I just implore all of you on this episode today that are listening to this episode to at least jot some notes down and write a letter to yourself, share it with a friend, go through that exercise, and you're the director of your next great act.
Lena: That's it for this episode of Midlife Circus. Visit midlifecircus.fm for show notes, transcripts, and all the latest happenings. And be sure to join us in the Midlife Circus community on Substack. Follow Midlife Circus on Apple Podcasts, YouTube, and wherever you get your podcasts so you never miss your next great act. Quick reminder, the opinions and stories shared here are personal reflections, not professional advice.
This show is for entertainment and inspiration only. Thanks for listening, and we'll see you under the big top next time. Midlife Circus is a Burning Matches Media production.