Episode 03: Deal Friends vs. Real Friends—The Midlife Sort

In this conversation, Rob and Brent discuss Brent's upcoming triathlon and the challenges of training for it. They then transition into a deeper discussion about friendships, particularly the differences between 'deal friends' and 'real friends' as Brent reflects on his experiences after leaving his last company. The conversation highlights the loneliness that can accompany such transitions and offers insights on rekindling connections and the importance of maintaining relationships beyond work.

Links, resources, books mentioned:

• From Strength to Strength — Arthur C. Brooks

 (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:

• Training for a triathlon can be both challenging and enjoyable.

• Active recovery is essential for athletes during training.

• Friendships often change after leaving a work environment.

• 'Deal friends' are often transactional, while 'real friends' are supportive without dependency.

• Loneliness can set in after retirement due to lack of daily interactions.

• Reaching out to old friends can rekindle valuable relationships.

• It's important to take inventory of your friendships as you transition in life.

• People are often more open to reconnecting than you might expect.

• Making an effort to connect can lead to rewarding relationships.

• Embrace the transition and be open to new friendships.

Transcript:

Transcript Disclaimer - May contain the occasional confusing, inaccurate, or unintentionally funny transcription moment. It’s all part of the show.

Lena: Remember the colleagues who filled your calendar then vanished when the meetings did? Today on Midlife Circus, Brent and Rob unpack the friendship shuffle, deal friends versus real friends. They explore how to handle the quiet after you leave the grind, take inventory of your circle, and make that awkward first call that rekindles the good stuff. It's not rejection. It's a resort.

Let's dive into deal friends versus real friends, the midlife sort.

Rob: So, Brent, you're in the middle of training right now. I know you got a big triathlon coming up here in, like, three weeks. Right? Two and a half, three weeks. You're doing an Xterra down in New Mexico. How's training coming?

Brent: Training has been good. What I realized is I haven't done an Olympic distance triathlon in probably twenty years. So putting all the elements together has been fun for me because I've done so many running events in the last, let's say, ten or fifteen years to bring in those three disciplines, you know, the swimming, the biking, the running has been really fun from a cross training. But I have to say, today was awesome for me because it's my off day.

Rob: So are you focused on recovery then today? Are you doing anything proactively on recovery or just sitting on the couch?

Brent: I am going to chill out. That's my goal. And I'm curious because you've done a lot of big events. So the reason why I'm totally chilling out today is because yesterday, I did a really long swim and I was just dragging. And the day before I trained really hard, I did like this combo bike and run.

And so yesterday, I'm like, oh, the swim will be easy. You know, I'll do it. I knew I was doing a long distance stay, but I was just dragging. So what have you done to overcome that where I just wasn't into it?

Rob: Yeah. So suffer through it is one thing I would tell you that I've done. And then on this recovery day, truly take it easy. I'd use the NormaTec boots. Maybe do a cold plunge.

If you have access to a cold plunge, do something. I know you do have access to a cold plunge, maybe do a little bit of that, but focus on active recovery versus passive recovery. That'll help you when you go back to getting back in the pool or back out on the bike again. It'll just help you be a little bit more present versus just sitting around. But your body's telling you, you need to take a break.

That's truly what it is. And I'd say take a break. Take in good calories today, good clean calories, lots of water, lots of fluid, and you'll feel great tomorrow.

Brent: Yeah. I I'm hopeful. I was just really tired last night. Yeah. And so I was like, this is really strange, but I also know I'm kind of at the peak level being about three weeks out.

So I've done some really hard, long distances over the past two weeks. And so my body is just trying to catch up saying, wow, this is a lot of exertion you're putting on here. So I feel good. That's the benefit. It's going to take me probably four and a half hours.

Mean, pretty big one just because with the Xterra, you know, you're swimming in a reservoir, but then you're on the mountain bike for like 16 miles, but it's all single track. And then the running is a 10 K’s, you know, 6.2 miles, but all single track as well. So a lot of elevation gain ups and downs. So I started putting it together and I was like, this is going to take me a while. So

Rob: Yeah. A good day out in the woods.

Brent: It will be a good day in the woods, but I'm really excited for it.

Rob: So I've never done an Olympic distance triathlon. What are the distances? You just mentioned the bike and the run, but you start with the swim. What's the distance of the swim?

Brent: The swim is 1,500 meters. So that will take me forty-five minutes. I'm not an efficient swimmer. I will say this go around for training has been really enjoyable on swimming side because I took my wife's advice and actually watched some YouTube videos on techniques. So that's actually been really productive for me to learn some simple techniques to make it a little bit easier.

I wouldn't say I'm getting faster, I'm just getting more efficient. And so I'm enjoying that. And then the bike, you know, every Xterra, because they're all on trails and so forth, the distances are always going to be a little bit different. Just based on the course and elevation gain and drops and so forth.

Then- So the bike again is, so you

Rob: have 1,500 meter swim. What's the bike again?

Brent: The bike is just under 16 miles. Okay. And that elevation gain on that is about 2,000 feet.

Rob: That's decent gain.

Brent: Yeah. Yeah. So I'll feel that one for sure. And I've been training because where we live at 7,000 feet and this triathlon or Xterra is at 7,000 feet roughly. So it's pretty high up.

So luckily my training's kind of coinciding with that elevation. Right. That's a pretty short distance for that much gain on a bike. Yeah. Absolutely.

Rob: That'll be then 10 K’s, how much gain is in the 10 K’s? Is 10 K-ish you said, right?

Brent: Yeah. It's not bad. It's like six or 700 feet.

Rob: That's not bad.

Brent: I feel really good about that. But it's just different. When you think about putting all those disciplines together, you know, I'm not going after this to set any world records. Just, I'm excited. No, definitely not.

I'm excited for it because all the big events that you and I have done together, I feel really confident that I can get through it all. My goal with any of these type events, especially in the stage of life that I'm in, is I just want to enjoy it. Don't want it to be torture. I don't want to regret it right in the middle when I'm like, I just should have trained more. So I feel really confident that I will get through it with the right level of comfort.

It'll be discomfort at times, right, just because it's a long day. I'm just excited for it, but I have to say, like, today, I was so psyched when I woke up because I didn't have anything on my calendar to train.

Rob: Yeah, you'll be back at

Brent: it tomorrow. I will. You know what's fun? As I alluded earlier, it's been so fun to do combo days. Like I've really enjoyed that where I'll swim and bike one day or I'll run and bike one day or run and swim.

And I really like that because a lot of times I'm just so used to running and I just go out and do long runs. I'll go run for three hours. I like running eight miles and then biking for ten. Like, it's a fun, like, mixing it up. And I don't feel I don't feel as destroyed when I do a combo day of those distances.

But when I do a really long run day, for example, the rest of the day is out, like I'm not. So it's nice to go out. I I've just enjoyed that aspect, and it's especially where we live. I mean, I'm exploring new terrain this season, which I typically don't do. I usually stay in our local community to train.

So I've been going into Vale, which is for listeners, that's about a half an hour from where we live. So there's a lot of great trails there. So I'm just really enjoying their trail system and getting to do something new. And then, you know, the swimming is just the swimming.

Rob: Nice. Nice. Well, we'll definitely do a recap at some point. Tell us how your event went.

Brent: Absolutely.

Rob: Today, we're talking about friendships, Brent. And I know you and I are become have become really close friends, but we're going to talk about friendships in a broad level, friendships that last and friendships that quietly just end up slipping away, and why it can feel so unsettling when you finally start to see the difference. Brent, you left. You retired or semi-retired about two years ago. I'm going to take a step back.

We're going to go back a couple of years, and let's talk about relationships as you were working And working your last few years, or maybe go back last ten years of work, what were your relationships like? What was your social circle like during that period of life?

Brent: For me, my social circles have been very tied up in work, and it has a lot to do with the intensity of work that I have chosen. So as an example, in my last company, which I ran was a private equity firm, we were fast growing, so we were hiring a lot of people. We raised a lot of capital to invest into companies. And I spent a lot of time evaluating companies, but also once we made the investment, I would be often on the board of directors for those companies. So my waking hours were very integrated with my work.

And it was intense because we had really high expectations of what we were looking to achieve. So I was just all in. So I didn't have a lot of room for friends outside of the office just because we were building something new and we really wanted to exceed the expectations for our investors. And so I was just all in, which just required a lot of intensity. So it was just my relationships were so tied to my work, which is something that is a pattern for me.

Whenever I start something, I just go all in. And that's usually the circles that I run with.

Rob: So you I know you and I were friends during that period of time and we did interact. How would you categorize the difference in terms of the work relationship or what you how your interaction was with work people versus your friends outside of work? The handful of people you did stay in touch with?

Brent: Well, it's a good question because what's interesting is the work relationships were always really fluid, meaning we had a dependency on each other to get something done. So it's that transactional in nature. So they need something from me, I need something from them. And so it's fluid in the sense of there's daily interactions with your work colleagues, you know? And that's something that I just became accustomed to, but also I was leading the team.

So it was also those employee boss relationship. So it's, you know, you have a lot of relationships that are just centered around your work and they have different characteristics based on the type of relationship and work. On the friend side of things outside of work, I would say I'd always maintained a handful of friends that I did things with. So I had like you and I, we would go skiing or we would go fishing or we would do some sort of running event. So I always maintain those type of relationships.

I have a couple buddies that I go fly fishing with, but that was about the extent of it because I just didn't have the bandwidth to maintain a lot of relationships outside of work. I also, raising kids and a family and just trying to maintain all these different relationships, I always prioritize things to say, you know, I got to keep the household healthy. And those relationships

Rob: Like going camping in a van, camping for the weekend with friends or hanging out with your kids.

Brent: A 100%. I mean, that's just that's just the way That's

Rob: this weekend. That's this weekend. You bailed on a camping trip to hang out with kids, which I get.

Brent: We started to see the clock ticking on that because my older son is going off to his third year of college. And so he leaves in a week. And then my younger son's going on this trip with another local family. And he leaves in a couple of days. And we're like, we got to squeeze it all in before.

And then right when he gets back, the younger son, he starts a senior in high school. So we're like, we need to take advantage of this time with our kids because we only got, like, ten days left till they go back

Rob: to school. Of summer left with

Brent: them. Yeah.

Rob: Yeah. You must like the boys.

Brent: I like my kids. Yeah. Yeah. Yeah. I'm very fortunate.

They're good kids.

Rob: Yeah. So let's go back to the work relationship piece and the interactions that you had at work. Something you and I've talked a little about is the depth of that relationship and doing, you know, doing commonly doing activities or doing events with people you worked with. I know you and I had a similar experience. I had interactions with people at work, and we were friendly at work, but I didn't do a lot of stuff with people at work.

I personally felt uncomfortable doing a lot of things with people that worked for me. I didn't want to do anything like put my foot in my mouth when I wasn't paying attention or wasn't on. I didn't want to say something inappropriate or something that might come back to haunt me at work. Tell me a little bit about those interactions you had, the kind of that social network with work interactions back before you semi-retired.

Brent: For me, it was always because, you know, I mean, I was in the later stages of my career, so I always had direct reports and I was leading a team. And so I was just careful about the relationships with my coworkers. And the private equity firm that I led, we were investing in companies that are improving human health through nutrition. And so a lot of food companies and so forth. So naturally we had a lot of common interests.

So people like to hike and people like to ski and go to huts and do all sorts of activities that way. We would do work related functions, but I was very careful about extending it beyond that. A lot of those were centered around team building, which I've always been a big advocate for. And I got to design a lot of those. It's nice to pull people outside of the day-to-day desk job and get to know them in a kind of an outdoor environment.

And we put a lot of value into that. But beyond that, I was very careful because also knowing that you've got that relationship with your employees, you got to maintain that in a healthy way. But also I do want to maintain my relationships with the people I mentioned earlier, like my family and a few of my friends. And so I just had to find that right balance, but I was also To me, I probably was overly protective of the relationships and try not to extend them too far.

Rob: Yeah. That makes sense. And one of the things that you shared, naturally, the title of our podcast today is deal friends and real friends. And it was a phrase you shared with me back when I was getting ready to retire. I think you shared it with me a couple months in advance of my retirement.

You shared the phrase deal friends versus real friends. Could you define those little those terms a little bit

Brent: for us, Brent? I learned about it through my brother recommended this book when I was considering retiring. And the name of the book is From Strength to Strength by Arthur C. Brooks. And the book is about finding happiness and success in purpose in the second half of your life.

So as I'm reading this, he introduced this term of deal friends and real friends. And I didn't think much of it until I really started to experience it myself. The best way to describe it is that you have a deal friend is those coworkers, those business partners, those relationships with vendors, that it's transactional in nature because we're dependent on each other for something. And that's a deal friend. But once that dependency is removed, the connection is actually weaker because we no longer need each other for something.

And then your real friends are the ones that do not have a dependency. Those are your day-to-day friends that you can call upon for anything, but you're not dependent on them outside of just being a great friend. And they're with you no matter what situation you are experiencing in your life, the good and the bad. And so it's less transactional, it's just more of a healthy relationship. And I learned about that.

It was interesting when I was reading the book, I'm like, Oh, well, I was trying to be immune to it. Because I had all these great work-related friends. And I'm like, Yeah, it'll just continue on. Well, I learned differently.

Rob: Yeah. Work related relationships. Right? It wasn't necessarily friendships. It was more relationships.

Brent: Yeah. You know what? I would say that you're I was friends with them. Like, I had a lot of coworkers that I would talk to every single day. And we got to know each other.

Like we know who what our kids up to and, you know, what vacations are we going on and things outside of, you know, in the normal work relationship. But the core of our relationship was work. Yeah. And so that's why we came together. So once you remove that core, then it's you put a challenge on that relationship.

Do we want to continue?

Rob: Well, I started thinking about in preparation for both this podcast and this recording as well as when I made the transition away from work. It's those commonalities are the conversations that I had with those individuals. So as you know, we talk about what we're doing for the weekend and what adventures are happening or runs that I was going on or what's going on with their family. Those conversations were never the purpose of the call or never the purpose of the meeting. Right?

We talked about it. It was opening chitchat almost in every call that I had was finding out what was going on in somebody's life, but the purpose of the conversation was based on a work transaction that needed to happen. I needed something from them or they needed something from me. It was almost like the warm up, or the closing part of a conversation that was the friendship part, but the core conversation was about a work issue or a work thing that needed to be done.

Brent: Yeah. It and it because that's the core. That's like why you came together. But I what I want to emphasize is they're definitely friends, like, because that's the human experience. So when you're when you're in the office and you're hanging out with people, you get a laugh, you grab a lunch together.

Our culture at my last company is we actually built a gym in our office. And so we would have an instructor come in a couple days a week. And so we were hanging out in that way as well because that was part of our ethos. So you get to know people on different levels, but you still are coming together for a specific reason is to do really good work for your customers. And that was our intent.

So it's just a strange thing that I experienced because there was just so much tied up in those relationships. But then when you're not there anymore, it changes and it changes pretty rapidly.

Rob: Let's talk about that rapid change. So you retired or you semi-retired from that work environment. What happened?

Brent: It was really a surreal strange experience for me. First, think about your calendar. So my calendar every single day was full of meetings. That was the nature of my work. So I was interacting with internal team members.

I was working, interacting with investors, some of the companies that we invested into, some companies that we're looking for. So starting out, my calendar was really full. The day I was no longer with my last company, my calendar was empty. So no longer had meetings with the people I would meet with on a regular basis. But then what I quickly learned is all those relationships just dried up.

Like, they were just Gone. Almost like gone. Yeah. And it was bizarre because I thought like, gosh. Like, there was one person that I work with as an example.

She and I would exchange, like, what music bands we're interested in, and we were both kind of more nostalgic. And so we were going back into the nineties and, you know, talking about which bands, you know, Pearl Jam and Dave Matthews, and we would just share tracks. That just disappeared. Gone. Yeah.

Gone. And I was so like, oh my, what is happening here? I actually learned this lesson. Right out of college, I worked for General Electric. And I worked there for four years.

And I had this amazing opportunity to leave General Electric to work for PricewaterhouseCoopers for their management consulting group. And I remember at the time I was so excited to tell my coworkers and my boss and all the people around me that I got this great opportunity. And my boss at the time, she and I had a great relationship. She pulled me aside and said, Hey, this is probably the first time that you've gone through a transition like this. And she goes, I just want to give you a heads up.

There are going to be some people that are going to be incredibly warm to your transition. They're going to be excited for you. They're going to ask a lot about it. Then you're going to find people that could care less. And then you're going to have some people that are, you're dead to me.

And that's what she said. Like, you moved on and now you're leaving me with the work. Or now I got to go figure out a replacement or I'm adding a hindrance to them. And she said, so every human's going to react in a different way and try not to be surprised. Just go along with the journey.

Because some people, they'll go completely dark on you no matter what. They may not even return your email. And then some people are going to be warm and open and some people are going to be frankly upset at you. And you just have to accept that because you're the one who made the decision to leave. So I kind of been holding onto that, but I never really embraced it.

And what was really different, Rob, about this time. So sometimes when you make a in kind of career transition, you may go to a competitor as an example, you're still going to have some common relationships. But when I actually left my last company, I wasn't in that industry anymore. So our common interest actually even dropped further.

Rob: So you didn't replace those individuals that you had interactions with, with a new population of coworkers. It just that portion of your life disappeared.

Brent: Absolutely. What was really strange for me is I, of course, I reached out to a few of my colleagues and I was just like, Hey, you know, I'm moving on and I'm exploring a few opportunities. And almost it just was crickets on the other end because they didn't know how to interact with me at that point in time because our common intersection dropped. So it was a strange thing. I said, wow, those lunches are kind of boring because we weren't doing a deal together.

Right. We weren't working on something together. So then it's kind of like crickets. You just look at each other and you're like, how the kids? Do anything fun?

But it wasn't like the energy that we used to have in our conversations to talk about the deal or to talk about growing a company or what's happening in the industry. That's gone. So I have to own that side of it, but I will tell you, it took me a while to own that side of it because I was just like, what changed? A lot changed.

Rob: It's funny you're sharing that. So when you when you share the phrase, deal friends versus real friends, so we'll post in our show notes a link to the book from Arthur c Brooks from Strength to Strength. So I'll add that to the show notes. But you share with this with me about three or four months before I retired or semi-retired as you and I are both kind of leaping and jumping into this foray. And I said, thank you for the feedback or thank you for the concept, but I was thinking, oh, yeah.

Right. These people like me more than Brent more than they like Brent at his old job. These are really good relationships that I have. These will carry forward. At least a handful of ones that I want to carry forward are going to carry forward because I'm better than Brent.

People like me more than they like you. That's what was going through my head. I didn't share that with you, but that was exactly what I was thinking of. I'm like, thanks for the thanks for the insight, but my life will be different. And it was the same.

It was like, you know, my phone need to be charged in the middle of the day just to be able to get through the day to I might get two phone calls in a week, the first couple weeks of my retirement. And it wasn't people I normally talk to. Those were spam phone calls that I was, having come in. Now if I get two phone calls in a day, it's a busy day for me. And it was it was interesting trying to get used to that as well.

Even though I had the warning that it was coming, I thought for sure a lot of those would transfer or I could push them to transfer a little bit. So have you so have you connected with anybody that you used to work with or used to have those transactional relationships in the last, I don't know, six, eight months? Have you had any interaction with those individuals?

Brent: Well, first off, I'm glad you think you're special. So

Rob: I think I'm special. My spouse doesn't. Tara doesn't initially think I'm special, but I do.

Brent: Well, what's interesting about your scenario before I answer your question is, I would think that yours would be a little different than mine because you worked at your company much longer than I was at my last company as an example. I was in it for five or so years, a little more than five years. How long were you at your last company?

Rob: Fifteen, at the last Fifteen.

Brent: Yeah. So you think like those relationships would just carry on, but you learned that they necessarily don't.

Rob: And I had a couple that did, a couple that that did and have surprised me a little bit, but the vast majority just it was it was instantly. You talked about crickets. It was next week, they were gone. And I think back to when I was working, I had I worked with people that retired, and I didn't reach out to them after they retired. I I'm guilty of being that person at work that had those relationships that somebody retires, I said, well, good luck to you.

Because all we had in common really was work. We had a lot of friendly interaction, but all we had in common was work. Dan, for you, I mean, you were

Brent: in a senior leadership position. So when you've got direct reports and so forth, well, they have a new boss. Right. So they may reach out to you for advice from time to time, because you had that type of relationship, but they now have somebody else that they report to that they now have to manage that new relationship.

Rob: And it's They just had my replacement really is what you're I telling was replaced pretty quickly.

Brent: Yeah. Yeah. Darn. So your question, did some of the relationships carry over?

Rob: Have you reconnected with anybody that you hadn't talked to in a while that you had a working relationship with?

Brent: Yeah. You know, it's interesting. Just a few weeks ago, one of my colleagues that I was actually on the board of directors with for one of the companies that we invested into, he was one of the founders. And he actually reached out to me out of the blue and said, hey, I'm going to be in your neck of the woods. Would you like to do something?

And we ended up playing golf together for the day, and we had a fantastic day. And it was because we didn't talk about work. We talked about life. We talked about, know, we of course, there's some commonality with their works. It was more of a catchup side of things, but we were just talking about his kids are a little bit younger than mine, so we're just talking about the stages that they're at.

But we're talking about being active and how fun it was that we both play golf at about the same level. He beat me by one stroke, so now we're going to play again so I can try to beat him by one stroke. But it was just a lot of fun, and I didn't necessarily anticipate that. He was actually one of the individuals when I left, he actually reached out to me and said, I want to make sure we stay connected. So some people do that.

And then there's a few other people that I've done the same thing with, but I would say the vast majority have kind of slipped away.

Rob: Okay. So he reached out to you. What happens? So you see the phone call come in or you see the voicemail from a gentleman you hadn't talked to in a year. What was your reaction to that emotionally when you saw when, you know, when you pick up your phone, you see who's calling.

How are you feeling?

Brent: I was really excited to say hello. So it was like this pent up energy, you know, is that work related energy? But I have to admit, when I first got the message from him, I think he might have sent me an email or he might have called, I can't remember. But I was also nervous, like, uh-oh, what happened? You know, like, is there something going on with that company?

But it wasn't that at all. He was reaching out just being friendly. And actually, it was so rewarding to know that, you know, those relationships can cross over from a deal friend to a real friend. And it was cool. We played golf.

We had lunch together. And then we left. We're like, hey. Let's play one more time in the in the fall. We had a good time.

So it's kind of like one of those early friendship come you know, like, hey. You like me? I like you. Let's hang out a little bit more.

Rob: Like, you're five at the playground meeting someone for the first time. You want to be best friends?

Brent: Yeah. Totally. Totally. So it was it was a lot of fun.

Rob: Nice. And you said you reached out to some people as well that you had lost contact with. How did that go for you?

Brent: You know what is really strange is there's a few relationships that I thought would weather the change really well, and some of them didn't even respond back. And that's like heartbreaking to me. It's just because there was such a tight connection of our work. And I think it was a lot of the work that we did was just really intense. I just think that they're incredibly busy and I'm just no longer needed.

I I was a tool in their toolbox to help them solve a problem or whatever they're trying to accomplish. When I no longer had that, then I was just not needed. Those are the really surprising ones that come up, but there was a few of those. And then there was a couple that I reached out because I I believed that they would just continue and possibly crossover. And I could tell quickly that they were more doing it as a favor to connect.

Meaning like, yeah, let's catch up. But it was like thirty minutes. You know, that's like when the meeting invite came. And I wasn't expecting much more in that because that was how our relationship was in the past, so it was pretty quick. But it was strange to me because how quickly they just moved on.

It was just like that connection was no longer valid or just needed. And that was really surprising. So it was kind of like three categories. The first category is people that really just went dark. And that was probably the most surprising to me.

Then there's a few that I reached out to because I thought the relationship would move forward and just we'd continue to connect. And then there was a few like the friend that we play golf together that were completely open. And there's a handful of actually ones that were proactive in reaching out to me that actually have just turned into a really nice healthy relationship that I actually didn't anticipate. So that was actually really fun. Like, there's a few people in particular that are just staying connected on a regular basis.

Some surprised me and some didn't. But I also realized, like, I have a role to play in this. And there's some people that given the role that they have in their career is they're just crazy busy. And I couldn't make time for somebody who had left their career when I was still in it. And so it's kind of like, I have to understand this process.

I got to own the whole thing. And just because my life has changed, their life hasn't, I can't expect them to bend over backwards and be like, yeah. Let's totally go do stuff because I know that they don't have time to do that.

Rob: Yeah. We go from working eight to eight, right, to not working throughout the entire day. So you have plenty of time to reach out to people and talk to people and not talk to people or be alone, and I did the same thing. You know? So I was working, people retired or people left.

I, you know, I didn't purposely lose connection, but it happened. And I was busy with work, and I did not stay in touch, which I feel bad about now given the experience that I had after transitioning out of work and not having those daily interactions with people that I had. And that was maybe the most surprising thing. And you and I've talked a little bit about this was that first couple of months after retiring, the, the solitude or loneliness that sets in a little bit because you had daily interactions with other adults beyond your spouse, and now not having any of those interactions. What was that first couple months like for you?

Brent: Hard, you know? I mean, it was difficult for me. So I always look at solitude as a choice. And solitude is something that as an example for me is I crave solitude periodically to reset, kind of just get out into the wilderness. So my solitude usually comes with like trail running as an example.

I like to go by myself for the most part, unless I'm doing an event with like you or some of our other friends. But I like to trail run by myself just because it's that solitude that I need to recharge or just to not like think about anything, just go out in the wilderness. I've always done that, but the difference this time around when I moved into semi retirement is I found myself with a lot more solitude, which then some of that actually translated or transitioned to loneliness. It's hard for me to describe the experience for anyone that goes through this because when you have such a completely packed day, every single day of the week and sometimes even on the weekends, and then that goes away, that human connection just drops off. And so I just think as humans, it's really important to have connections.

And for me, you and I caught up a handful of times and I would just share with you what I'm going through because I was really lonely. And I was lonely in the sense of I didn't have that common bond with people on work. I kind of was a bit directional some of actually what I wanted to do next. And there was just like all these unanswered questions, but it was really, really hard because the reality of when you make a transition like I did and what you've done and what others will go through, you can expect other people to now adapt to the new you. And so what I had thought was I've got a group of friends like these two guys that are a couple hours away that I used to go fishing with.

I thought we would just start fishing more. But, no, they're deep in their careers. You know? So I can't just also be like, hey. Let's start fishing once a month.

No. We go once a year. And it was funny. There was an email from one of them to the other two of us, and it says, guys, I just miss you guys. Let's find some time on the calendar to get together.

And all I do is just respond to them. I'm open whenever.

Rob: You name it, I could be there.

Brent: And the other guy responded and said, oh, I'm so busy. I got a lot going on. And, you know, it just it was just this broken record. Right? It's like, I got so many things going on.

And then my response was like, I'm open when you're open because I know I can't force them to alter their schedules. But guess what? I was in that exact same schedule just a couple years ago Yeah. Trying to squeeze it all in. So it's a really strange feeling.

So the loneliness is absolutely real. I don't know how to avoid what I went through because I went from crazy active to work to not at all. And it's hard to explain to somebody, I don't know, how did how did you experience that? Because I know you had you had time leading up to it where you started to prepare, But what was your personal experience when you, a year ago, decided to go semi retired?

Rob: It was I would say it was similar, Brent, with the exception of I had you in town that had had also retired, so I could always pick up the phone and just call you, and you were available to do stuff. People are surprised when you talk about going for a trail run is where you find solitude. You and I have done a bunch of events together, but we rarely do trail running here in town together. We live half a mile apart, but you and I don't go on trail runs. That's my time.

That's me time. That's me out in the woods. I find great joy in doing that on my own, but I was able to run into you from time to time because we had a similar schedule, which was empty. Right? The calendar was full.

Now it's empty. You're like, oh, I'm going to run at ten. I'm going to run at eleven. And we'd pass each other on the trail and talk for a couple minutes and wave and disappear. Right?

We'd go off on our own directions. But it was I would say it was similar. The only difference that and maybe you did this as well as I tried to be a little more purposeful in trying to stay connected, not necessarily with people I had worked with. I had a couple relationships that have continued from work, but I try to be a little more purposeful on other people outside of work that I had let relationships slide a little bit, a good group of friends that were personal friends and close friends, non-work related that, you know, every time we got together, it was great, but we never got together very often. So your two friends down in Denver, as you mentioned.

The only difference maybe I spent more time trying to be purposeful and just pick up the phone and give them a call and leave a message. And I have messages out there that have never been returned, and I'm okay with that. I'm still showing up as a good friend for them, and sometime they'll call me back. I'm not losing that friendship. But I was I think I was a little more purposeful in trying to stay connected with the people that really meant a lot to me and I wanted to stay connected with.

Brent: You know, what's interesting about that, like, what I experienced through that is let's look at the real friends category. And so I've got a really strong network of college buddies, and we've stayed active since the day we've graduated. So we used to do trips and then everybody, you know, wants to start having families and stuff, it kind of altered, but we stay connected. What was unique, and it was a weird feeling for me is also I'm more active reaching out to him, calling him in. And think about it on the other side.

They're like, oh, now Brent is just now calling me more. That's a weird transition as well. Yeah. We're always be good friends, but now I'm calling them more frequently when they're like, dude, you used to call me, like, once a year.

Rob: What's the deal? What's going on? Like, what's wrong? Why are calling me? What's wrong?

Brent: Yeah. So I've had to navigate that. All of this is new to me. Like, this was really strange, like, all these things because my career was nearly thirty years. I've invested a lot into my work.

I've founded a handful of companies, and so that was usually just hard charging just to build and make something special. And I put a lot of emphasis there. So now transitioning away from work first to relationship first is just different. I'm learning a new skill and I'm excited about it, but I'm also learning different types of rejection through the process and just learning to be realistic about expectation of my real friends because most of them are still mean, you and I are pretty young, you know? And a lot of our friends are probably not even looking at their retirement window for the next maybe five to ten years from now.

It's just acknowledging that, recognizing that, and just being honest with myself, like people are in different stages of life, and I've got to be respectful of that.

Rob: Yeah. So let's talk about that awkwardness a little bit. And let's spend some time there as I think back to, know, I mentioned this just a couple minutes ago when we were five, six, seven years old. You had the neighborhood friends, and you go to the playground, you go to the park, and that stranger, that stranger kid that you've never talked to before, you start running around the park, and you go introduce him to your mom or dad as, this is my new best friend, Billy, and he's going to come over. I want to come over to the house.

And it was pretty easy as we were kids to build good friendships or at least what we thought were good friendships at the time. And you just mentioned it's been a little awkward trying to reach back out to some people. How are you avoiding the awkwardness? What tips or suggestions would you give to someone that is trying to rekindle relationships that may have fizzled out a

Brent: little bit? Definitely awkward. Yeah. I mean, it's definitely strange. What I would say when people hit midlife, and so if we just say, let's just center around 50, just something about, you know, a timeline like that, is I think what I've seen is more people are more interested in relationships, less interested in all their materialistic things that they've acquired maybe in their thirties and forties.

And there's more of an emphasis on relationships. So what I find is if you actually make the effort, people are really open to connecting and you just have to try and be first. A really cool example of this is a friend of mine from college who we hadn't connected much in, let's say, the last fifteen, twenty years because we both had been busy. He sold his company last year. So we connected once last year.

And then he and I decided we were talking about doing something in the fall, and he and I are going to go on a road trip together. I have a van. He's going to rent a van. He moved to Jackson Hole. So we're going to do this road trip from Colorado to Jackson Hole, we're going to fly fish along the way.

So I'm going to design the trip because I know a lot of the rivers in between here and there. And he was so excited. And we both agreed and said, let's not overcomplicate this because we first started out, hey. Let's reach out to him, and let's see if they're interested in doing this trip with us. And then we both just decided, let's just do you and I, and let's go have fun.

So it's rekindling an old relationship, bringing it current to what we both enjoy doing now, and it just took the ask. Like, hey, do you want to do this? And he was so excited, and I'm so excited. So it's super fun. But knowing that he's in a time of his life that he can do that, because he did he had a major transition just take place within the last year.

And so now he's got some time, and he wants to explore the world the way I like exploring the world too. So we had that common interest. So super fun. And I actually talked to his wife as well. They were in the car one day and they had on speakerphone, and she was so excited for him to go hang out with a friend.

Rob: Like, get out of here. Out. Get

Brent: out of the house. You're driving me crazy. So she was super excited, and I'm super excited. He's super excited. So where I go with this is just make the effort, ask a friend to do something or simply grab a call.

I have another friend I haven't talked to in quite a while and he retired in May, so just a few months ago. And he and I are going to try to get together in the next six months. That's all we said, is six months. I said, why don't you take some time, do stuff with your family and so forth? And he and I were like he's my oldest friend, meaning we met when we were really young.

And he and I just talked about doing some fun stuff together. So, you know, we'll see. So it's all about asking, leaning in.

Rob: And even especially after COVID. Right? I mean, we all leave COVID. We're a few years removed now, but I think people are still starving for that connection. I think that it was lost for so long.

People still want and need that. And so that reach out, while it might feel weird to look at the name on your phone, and that's what I'm going to suggest is our listeners are listening right now or when we finished when they finished listening to this call is scroll through your phone and look for that person that you haven't talked to in six months, eight months, a year, and just make a quick call. I know it's the toughest thing is going to hit dial. That's the toughest part of the call, and then as the phone's ringing, the pounding that you got, what are we going to talk about? Hopefully, they answer, hopefully, they don't, but make the phone call.

Try to make the connection. I would say do it now before you step into retirement. If, retirement's three years out, start thinking about those real friends. Who do you have? Take an inventory now of who are the real friends?

Who are the people that you can just pick up the phone and have a great conversation with, you grab a cup of coffee where there's no transaction needed, where you're not talking about a deal or a project or something business related. You're talking about something in your personal life and you can leave without ever having beta transaction with each other. And take an inventory now. Think through your list and you have a list on our phones of all the contacts in our lives. Who is a real friend and who's a deal friend?

And can you start cultivating some of those people now so you may not suffer from some of the loneliness that both Brent and I experienced as we made the transition. And not everyone's going to be able to follow you through that transition given what's going on in their life, But start making those connections now. And if you have already retired, pick up the phone. You have plenty of time on your hands. Call someone during the middle of the day.

I like to leave voice mails right now, Brenda. I haven't told you this, but I call, like, some old coworker. I said, good. You're not picking up my phone call. You're still working.

You should be working. Darn it. I just want to make you smile and laugh that I'm leaving you some ridiculous message while you're in a conference call or you're in a meeting right now. So I'm doing those types of messages to people from time to time. I'm making it a voice mail so they have to listen to it, not just a quick text.

So I'm having fun with some of that, but I'm trying to stay connected to rekindle some of those, which the initial step is awkward. So as we wrap up, any other suggestions or thoughts you have for our listeners today?

Brent: I just want to leave people with is it is a transition. There's reality set in deal friends versus real friends. So you just have to be honest with yourself. I like how you said, look through your contacts list. And what I learned is that it is good to take inventory.

And once you take inventory, you've got plenty of people in there that you can reach out and have a laugh with and, you know, see where it goes. Be open to where the relationship can take you, but also be open to forging new relationships, which takes effort, but a lot of times you can find rewards in that as well.

Rob: Nice. Well, thanks, Brent. Thanks for this conversation, and we'll talk later.

Brent: Thank you. Have a good one.

Lena: That's it for this episode of Midlife Circus. Visit midlifecircus.fm for show notes, transcripts, and all the latest happenings. And while you're there, be sure to sign up for our newsletter so you never miss an update. Don't forget to subscribe wherever you get your podcasts so you never miss your next great act. Before we go, a quick reminder.

The opinions and stories shared here are just that, personal reflections and perspectives. We're not legal experts, medical professionals, or therapists. This show is for entertainment and inspiration only, so please seek the right professionals when you need guidance. Thanks for listening, and we'll see you under the big top next time. Midlife Circus is a Burning Matches Media production.