Episode 29: Before You Retire: 5 Things We Wish We'd Done First
What if retirement isn't really just a finance problem? Finance is the part most people plan for. It's the four others — relationships, health, purpose, and adventure — that quietly reshape everything. Rob and Brent walk through all five: test-driving your spending before the leap, inventorying the relationships that will and won't survive, building health habits while you still have structure, giving yourself room to find purpose again, and writing the adventure lists you've been putting off. The episode they wish someone had handed them before they walked out the door.
Links, resources, books mentioned:
Topics we are covering in this episode:
Test-driving your retirement lifestyle before you leave
Why work relationships disappear overnight
Building health habits before the paycheck stops
The identity shift and the case for a real break
Why adventure lists are a transition plan in disguise
Plan Z as the fallback that frees you up
Transcript:
Transcript Disclaimer - May contain the occasional confusing, inaccurate, or unintentionally funny transcription moment. It’s all part of the show.
Lena: Between them, Rob and Brent made more mistakes than they'd like to admit in their first year away from work. You don't have to make the same ones. Today on Midlife Circus, they walk through the five things they wish they'd prepared for well in advance of their last day on the job. The test drives, the inventories, the breaks, and the lists that would have made the transition land a lot clearer. Before we begin, check out the message the show feature in your podcast player. It's a simple way to reach us, share feedback, or say hello. And remember to follow Midlife Circus on Apple Podcasts or wherever you listen, and join us in the Midlife Circus community in Substack. Let's dive into Before You Retire: Five Things We Wish We'd Done First.
Rob: Before we jump into today's episode, Brent and I have a really fun and important announcement for all of our Audience members. And rather than just make the announcement, I figured I'd show you what it was. Here we go.
Jason: Hey guys, Jason here, really enjoying the show, you are doing a great job. Have you ever thought about finding a way for the audience to engage a little bit more? Whether it's sending questions in after a show that you guys can respond to and in subsequent shows, or if there's a way to even get us uh questions ahead. So if you have like an upcoming topic and you want to get listener participation, maybe even uh collecting them ahead of time and addressing them in the show, it'd be really a nice way to get plugged in. Keep up great work. Look forward to hearing your next one.
Rob: Why, Jason, yes, we have thought about this. Kind of a little tongue-in-cheek. Jason actually is a longtime friend of the show, and he made this suggestion a number of months ago, actually, as a way for us to deepen our connection with our audience. And we figured out the technology. It's taken us a while to figure out the technology to be able to do this in a really easy and simple way for our audience to actually engage really directly with us. And so to engage with us in this manner, all you have to do is open your podcast player. So on Apple, if you open up Apple Podcasts and in our episode, so the episode page, at the very top of that page, it actually says message the show. And if you click on that link, it's a hyperlink there, it'll take you to a landing page where you can either leave us a voicemail, as you heard Jason just did for us, or you can send us a text message directly. And our goal is to play some of these messages during our upcoming episodes.
Brent: It's so cool that we did this. And thanks, Jason, for giving us the opportunity and the idea a while ago. We'd love the feedback for the show. Thanks for listening to the show. But the whole idea for message the show is we want to make a deeper connection to our audience. And so how we plan to do this in future episodes, we'll probably do a call out, a call to action to saying, hey, we have this idea. Share us your thoughts and we'll integrate it into the show. Or if you ever have an idea for a show, that's another reason to message the show. Or if you have feedback for us, please do it because we're going to read every single one of them. Now, what we can't promise is that we're going to play every single recording or you know, call out every single text message because it will grow. Our audience is growing pretty significantly, and we're super excited about this. But this feature is something we've been working on. So, Jason, thanks for giving us the idea and the inspiration. We figured out the technology. So it is now available any episode. All you have to do is just message the show, and here we are. We can text us, you can leave us a voicemail, and it's instant feedback for us, but it's helping us grow our community. So thank you.
Rob: We're super excited about this feature. So thanks again, Jason. Let's jump into our normal format.
Rob: Brent, what mistake did you make early on in your transition away from formal employment?
Brent: Rob, I probably made about 50 mistakes really quickly. But as we were preparing for this episode, two that stuck out for me. One was something that I did immediately. And I actually spent a lot of time in LinkedIn just trying to follow all my former colleagues. Like I'm still in the game. I'm still playing on the field with them, but I'm not. So I'm like, what is that person doing? What is that person? And there's some people in my network that were posting a lot, and I'm like, oh, that's really great. But I wasn't in it. So I was trying to replace that day-to-day interaction that I had with people by doing it all virtual through LinkedIn. Not a healthy way to create a transition into my next great act. I learned that. So I'm sharing that for others to say, maybe tone it down on the social media because that might be a way that just wants you to get back in the game. And so that wasn't super healthy for me. But the other one, which is just a common thing that I do, is and when I think about making transitions from one thing to the next, is I instantly started building out business plans for my next business that I'm going to go build. And I'm a serial entrepreneur, so that was just this idea engine, and I'm starting to build out all these plans, and here's what I'm going to do. And that wasn't healthy either because I just didn't give myself a break. I didn't give myself a breather. And that was something that I've learned. And now when people ask that question, like, what's the one thing that I should do, you know, in making a transition from, you know, my prior employment or my prior company or whatever it might be, take a break. But what I will say, Rob, is I learned a ton in our recent episode with Sarah Hager. And she actually provided us a recommendation that I think is really relevant. So if you haven't seen that episode, Sarah or listened to that episode, Sarah did a midlife sabbatical at 52 for two years. We asked her at the end of the episode is what's one piece of advice you would give to somebody that's considering doing a sabbatical, you know, mid-career, let's say, or midlife. And she said, identify your plan Z. And your plan Z is somewhat of a fallback plan where it's an idea and it's saying, hey, maybe this doesn't work out. Here's what you could go do. And she said what it did for her, or as she looks back, is it gives you something to fall back on. So you stop thinking about all the different changes that are going on in your life. Like, I don't have a paycheck anymore. I don't have all this network that I'm used to interacting with. It was a plan Z just to say, hey, here's what I could go do if this idea of mine of transition to my next great act doesn't work out. And I could go do that and you set it and you forget it. Rob, when you heard that, I don't know if it had the same connection to you as it did for me, but what is your plan Z? You left your last company a couple of years ago. Now thinking back, what would be your plan Z or what is it?
Rob: I had actually a plan X, a plan Y, and a plan Z, Brent. So plan X was if things didn't work out either emotionally or financially, and I had to do something. I kept my licenses and I still have my licenses in a maintenance mode. So I could easily go back and actually get employed within the financial services industry in some fine type of a role. So that was plan X. Plan Y was to really build out a consulting business to replace the income. So build out a much more robust business around consulting and helping people with their businesses and business growth uh ideas and execution, really. And plan Z was a coffee shop. Um, I don't know why, but there's something just super cool about I think about being a barista at a coffee shop. You're getting people first thing in the morning. I could never be a bartender because I like going to bed too early. And so the same interaction I think that you would get as a bartender, you get at a really good coffee shop as a barista. So my plan Z was the barista serving coffee at our local coffee shop here in town and interacting with friends and neighbors that we have here in our area was my ultimate last, last ditch effort fallback if I needed to go and find something to do. What about you?
Brent: I'm like you. I actually, now that I think about it, I wish I would have had this plan Z in my head back then, but I just didn't. There's three things that I had as well. So the first one is I've served on a lot of board of directors, and I actually really like the work, but I needed to take a break from that work. I could go back to that work and maybe I will someday. I enjoy the stimulation that comes with working with leadership teams and other board members. And so I could go do that. Another plan that I've been thinking about is consulting work. I like the strategy work, and I've done some of that work since leaving my last company, and I could continue to do that. Similar to you, Rob, I could grow that practice bigger, and I feel confident that I can add value to companies in the strategic coaching or strategic consulting capacity. And the third one, which is really my plan Z, is work at a bike shop. I've always I love bike shops and I love the mechanical nature. Now I have a steep learning curve because I just don't know exactly how to fix bikes the way that guys at bike shops know how to fix bikes. But there's something about using my hands, doing something very mechanical. I know there's a lot of e-bikes today, but doing something very mechanical is very um, seems very fun to me, very rewarding, similar to your barista thing. I could go in and I could just do that. So maybe that will come into play quicker than the other ones. Maybe I'll go work at a bike shop. So that could be my plan Z.
Rob: Perfect. And today's episode is not really about what is our plan Z, but today's episode is really about how you can prepare to enter into retirement. And so, as Brent mentioned, some things that he did really well and some things he made mistakes on. So I got the benefit of learning from Brent's mistake of trying to build out 17 different business organizations. And he shared with me take a break, take a breath. And I had a great benefit in my transition away from work into a semi-retirement lifestyle that we thought this episode would be a really good way for us to share with you the five areas we believe that are really important to start considering and actually working through before you step away from employment. So it's all the things that we either did really well in our transition or we wish we could have gone back and done differently. So you can learn from some of our mistakes in our transition away from formal work. We think there's actually really five main categories that you should address prior to stepping away. The five categories are finance, relationships, health, purpose, and adventure. So we're going to cover all five of those topics today. And actually, all five of these topics have really mixed into a bunch of our previous episodes overall as well. This is really a recap of some of those previous episodes in a much more digestible format. As here's some of the things, key things to consider and take it, take care of prior to making that transition out of formal employment.
Brent: So, Rob, let's start with finances because if we look back, those are some of the episodes that people gravitate to the most. And they're really trying to understand what their finances would look like. So a couple episodes that we could call back on is episode 21, which is getting honest with your money. So you have more options. So that's trying to understand how are you spending, what do you have saved, and so forth. Then we also have episode 26, which was distribution strategies. That was a more recent episode. We got a lot of feedback from people saying, thanks for giving me that education. How am I going to pay myself in retirement or as I'm navigating my next great act? So to open up the finance category, and this is something that you and I have worked on a lot, just personally, but we talk a lot about as it relates to the show, is what financial steps should people take in advance of navigating or going into their next great act? So when you think about this, what should people do to start that process of thinking about finances?
Rob: The first one, Brent, and I think this is one that actually for both of these, you need to really start thinking about and planning around a couple of years. So not just a year before your retirement. In fact, I think all of these categories, it's ideal to start doing this three years in advance, two years, five years, right? So some time in advance in preparation. The first one I'm going to say is trying to live that financial lifestyle before you actually make the jump. And so I'm just going to use round numbers for ease for all of our listeners. If your plan in retirement is to spend $100,000 to maintain a quality of life that you have, I would suggest spending that for the couple of years prior to retiring. So live in that lifestyle, experience that lifestyle before you make the leap. A couple of big reasons for that experience is one is you can actually learn and understand is that number correct? So if your plan and the work you've been doing with an advisor is to spend $100,000 in retirement and you live that lifestyle for a couple of years before you retire, only spending $100,000 a year, you're able to actually understand, is that going to be enough? Are you able to have the life that you envision what retirement looks like on that dollar amount? So whatever that dollar amount is, can you live on that dollar amount? What does that do? And that actually provides a lot of security to say, if the math works out that that's that you have enough money to retire and you like the lifestyle, it actually provides a lot of emotional security around that decision to step away.
Brent: Really quick on that one, Rob. I think this is probably the most underestimated thinking process that people do when they think about finances. Because you could put something on paper and saying, Yeah, I'm going to spend $100,000 a year, great. So that's, you know, just under what's eight to nine thousand dollars a month, something of that nature. Well, guess what? What are you spending today? And if you're spending $20,000 a month today, then it's a really, really challenging transition because those expenses just don't go away. Like those things that you're used to or you're accustomed to. But the opposite can also happen too, is that when you're doing your financial planning, you may learn that you can spend a little bit more money. And that might be something that you want to try out as well. So I find that this step, I don't want to underestimate it, is so important to get the truth behind what are you spending, what can you spend, give it a try. And when you say one to two years, the hardest thing if somebody says I'll try it for two months, is it doesn't incorporate the cyclical nature of certain expenses. You have certain things that happen during certain times a year. So let's say real estate taxes are always due in the first quarter. Well, those will show up in the first quarter. If you run your test in the third quarter, you may not have some of those beginning of the year expenses. So that's why a year kind of helps you through it. And then you can make adjustments and so forth. So I think that's one that I really want us to hit home here. I learned a lot from it, Rob. I think you had in the previous episode, you talked a lot about how you learned a lot from just that practice.
Rob: Most of my experience has been people will step down in what they're planning on spending in retirement. So if they make $150,000 a year, they're planning on spending $100,000 a year. If they make $100,000 a year, they're planning on spending $50,000 a year. And so most people take that as a step back in overall expenses when they get to retirement. Part of the reason why is they don't need to save for retirement anymore. If they're living in retirement, right? So that's one of the major expenses. Kids are typically out of the house. So that big expense goes down as well. And so people are assuming they're going to be spending less. But living in that lifestyle for at least a year, as you mentioned, Brent, it gives you that understanding is it going to be enough? The other thing it does is it gives you an additional buffer to save more money for your retirement. So I'll keep going back to that math. If your plan is to spend $100,000 a year in retirement and you make $150, you could save that difference and actually give yourself an even bigger buffer as you go into retirement or give yourself a celebratory trip when you actually make the leap and you actually now have that asset, those dollars that you would have been spending in lifestyle, you've had the chance to save them and use them for that, for your retirement. So it actually is almost a twofold living that lifestyle gives you the security, but also might give you that buffer to make it even more fun when you get there.
Brent: Absolutely. So let's jump into your second one, Rob.
Rob: The second one is actually really go deep in working with your advisor to understand how distribution planning is going to work for you specifically. So it's understanding how are you going to be pulling out of your accounts? What does that look like? What will you likely happen to your accounts when you're in that distribution phase? And that was one of the things, even for me in the industry for a while, was hard to get my hands and mind around how I was going to feel when I saw my cash accounts going down in value, not getting replenished on a bi-weekly basis when that normal paycheck came in. And so walking through real life example with your financial advisor on how you're going to be taking distributions from your accounts, not just for the first year, but map out the first five and 10 years of your distribution plan to have an idea what that looks like. That just gives you another sense of security when you make that transition onto how you're going to be pulling out. Not what you're going to pull out, but how you're going to make distributions.
Brent: And I learned a lot from that step. We have an episode that we did recently. It was episode number 26. So if you're really curious and you haven't listened to that episode, I recommend going back to it because it talks about distribution strategies as well as the other episode of getting honest with your money and how are you spending. That's an important episode to go back to really understand the financial component. Because we've been doing this podcast for a while. And this is probably the one question that comes back the most from our listeners is around the financial component of making a transition. How do I do it? How do I think about it? And we're just trying to simplify this process. It is complex, but we're trying to simplify it to these kind of two main categories: how are you going to pay yourself and what are you going to spend?
Rob: Distribution planning is some of the most complex work a financial advisor is going to do with you. And so, Brent, you gave the phrase having a really solid relationship with your advisor is key and going through in detail the emotion around withdrawing from your accounts. And
Rob: that helps us pivot to the next category from finance to relationships, which I think actually, for me, Brent, was one of the harder transitions that I went through. And actually, this is an area I did not do very successfully. Even with your coaching, I was not successful in how I transitioned relationships after I stepped away from work. And this is somewhat of a callback to a really earlier episode that we did, episode three, about deal friends and real friends. And so, Brent, when I stepped away and when you stepped away, all of those business relationships that we had, they ended the next day. In fact, it was over the weekend, my phone completely stopped ringing. I jokingly say I went from having to charge my phone in the middle of the day because I was so busy to not hearing my phone ring for an entire week. When somebody transitions away from formal employment, Brent, or before they start their transition, what should people start to think about doing in advance of transitioning into retirement to cultivate their professional relationships into personal relationships, but also deepen some of those personal relationships they currently have?
Brent: Well, the cool thing that we have as Gen Xers is we have a term called a Rolodex. And the Rolodex, we all remember the Rolodex, it's like you could flip through it and it would have little cards of all your different contacts. So now it might be in Outlook or it might be in your contacts folder or something of that nature. There's an inventory process that we recommend doing and truly understanding. Let's use just a simple, let's say you've got a hundred contacts in your Rolodex or in your contacts list on your phone. Going through that and understanding which one of those are related to your work, which ones are related to your family, which ones are related to your friends, and so forth. That's an important, that's this inventory process that I recommend going through because as you alluded to, Rob, is there is something that will take place that will blindside you when you make a transition from your former employer or into your next great act, is majority of your network as it relates to your work will dry up overnight. It will blindside you. You will be shocked by it, you'll be surprised by it, you may be disappointed by it. It happens to all of us. And it's just something because you don't have that common thread anymore. You don't have that connection of work where you may talk with the same people every week, week in and week out, about a project you're working on, or you may have a team that you're working with. They move on, you need to learn how to move on. So that's why going back through this inventory of your network and saying, what is it? And you may need to start spending some more time with some friends. And you may need to reach out and make further connections with other people, and you'll surprise a few people. I'm sure I did. They're like, why are you now calling me all the time? Like, well, I need to call somebody. So, what was your experience? Because I gave you the heads up, Rob, and I know we've talked about this at length, but what was your experience of making that transition? And how did you start to make those connections with people from the past, let's say, or ones that maybe you just talked to infrequently and you started to pivot to a more frequent connection points?
Rob: I'm glad you started with the Rolodex phrase, Brent. So at least that does age us quite a bit, having to go back and having a Rolodex, like because it is scroll through your phone. That's really what the Rolodex is now is rolling your thumb through your phone. I uh I didn't listen to you when you gave me the advice. I've shared that before. I thought you were wrong and I would continue those relationships. And I thought I had actually done a pretty good job of staying in connection with friends. I'm the person that would randomly send a text or randomly just pick up the phone and call somebody, but it wasn't as frequent as I had thought it was in my own mind. And so my suggestion is, and this is really simple these days to actually go and do, my suggestion for our audience, and I wish I had done this, would have been to go back over the last week in my phone. And you can actually look at your phone records over the last week and scroll through your phone over the last week. And how many conversations did you have with a friend? Pick up the phone where you called the friend, not a business friend, an outside of work friend. How many conversations did you have with the somebody over the last week? You can go back as far as you want. You can go back and look at the last month, how many conversations that you had. And if reality is you've had just a couple, imagine that's the only conversation you have. That's that weird feeling that we had. So it's really easy to look back. And if you and if you haven't been in contact with those people more regularly, before you actually just blindside them by serial calling them, like Brent said he was doing with friends because he was bored, didn't know what else to do, start to cultivate those relationships a little more frequently on your own. The other area, going back to work friends, or as we referred to them as deal friends, people that were only part of your work environment, how many of those people will you call on a Saturday? I didn't have very many people that I would call on a Saturday because I didn't want to bother them. But a friend, you can pick up the phone and call at eight o'clock at night. You can call on a Saturday, you can call on a Sunday. And can you start to cultivate that relationship to carry it forward with you? And so a couple of years out from retirement, you have some people that you really enjoy interacting with from work is are you building that relationship such that whatever you were doing from work goes away, you're actually able to maintain a relationship because you built something separate from the deal that you were doing. And so looking back and how often do you talk to those people on a Saturday and how many work friends are Saturday friends is maybe a way of thinking about the deal friend to a real friend conversion.
Brent: And I also think beyond the work related is you got to take inventory of your household. And things change pretty dramatically. Let's say you're married and you've got a few kids. In my case, here's my example is my wife is probably looking at me at that moment in time like, oh, now am I your playmate? Like we're going to just now do everything that you want to do. And she's got a life of her own. So that was a transition that took place. And then my kids, I teenage kids, it's like, hey, do you guys want to go? You know, should we watch a movie tonight? Do you want to go play golf? Do you want to go camping? And they're probably like, what's wrong with dad? Like all of a sudden now he's just wanting to do all these things. So the inventory of all your relationships here from your family, your friends, your work friends. And then also thinking a little bit beyond that is how can you start to get involved with new friend groups or community type efforts? And that can be an important part of this process. So where I will leave this one, Rob, from a relationship standpoint, is I find that this one of all of them, of the five categories we're going to talk about today, I was blindsided by the most because I just was so ingrained in my work. My work was consuming me anywhere from 60 to 80 hours a week. And this was something that took place for 30 years. And so I had all those relationships and then it just stopped. So we're just trying to give you some encouragement to think a little bit beyond. I like your idea of looking back at your phone records just to say, how many people are you reaching out to? And if I did that, if I was able to go back in time and look at the month or two, you know, prior to my departure, I probably talked to one or two people, you know, outside of my work in the month.
Rob: Yeah. Yeah. And it's easy when you have good friends to be able to just pick up right where you left off. It's not about the friendship in particular, it's around the emotion of the silence. That's what I experienced. It was the emotion of the silence of the adult conversation other than my spouse. And yeah, I don't want to drive my spouse crazy by saying, what do you want to do? Like you said, Brent. I just went into a cave a little bit. We've talked about loneliness and some of those things that came out of that transition as well. This is something that is very much easy to get ahead of, but it's taking a step, and it's a little bit of an emotional step for our listeners to take a step to go and do those things they hadn't been doing before. But what'll surprise you is having been more active in doing those things now and being forcing myself to scroll through my phone every day almost, and who haven't I talked to? Who should I text? Who can I call? And it's because I'm bored and lonely. Yes, that is the case. But it's also I've gotten some feedback that some of these people really appreciate the outreach because they've been meaning to do it. They're just too busy right now to do it because they're currently working. So I'm trying to show up right now as that friend now that can be the resource when somebody else goes and steps away and they go into their own retirement.
Rob: Talking about friends, this is probably the other big one that I hear from a lot of different people, Brent, is that when they step away from retirement, they say, Oh my gosh, I can't wait till I stop working so I can work out every day. In fact, I'm going to work out twice a day. I'm going to have seven-minute abs. So I'm going to get the seven-minute ab videos and I'm going to work on my eight-pack and I'm going to be in the best health of my life. I'm going to get my diet in order. I have all this time, I'm going to fill it with being healthy. What do you say about that phrase, Brent?
Brent: Good luck. It's a hard one. I mean, there's the reality here. Now you have all this time, and I'm not saying that people are going into like this full retirement in this transition. You might go into part-time work. But if you don't have those habits built up, and right at the beginning of the new year, we had an episode on habits. And if you don't have this long history of eating well, exercising, and being very active, it's not something that you all of a sudden just flip a switch and be like, now I'm going to work out twice a day or twice a week. Now I'm going to start eating healthy. Good luck. That's hard to do. So, what I say with this one, it's very similar to the way that you were describing the finances. If you could a couple years before you actually make your transition, start to build in healthier habits. If you know this is something you want to do, and let's say you're not working out at all, what if you decided to exercise once or twice a week? That is building the habit muscle. And it's easier to add on from maybe a baseline of two days a week to add on a third day. And then the same thing with eating. If you are notoriously an unhealthy eater, you will be tortured and you will hate every bit of it because it's something so foreign to you. And so I just think that this is something we got to set realistic expectations. So if I could give a couple examples of myself, so this is habit forming, is I've always enjoyed exercise, but my career was definitely dominating my schedule for many, many years. And so I got pretty good at about doing two days a week on a regular basis. And this is probably the last 10 or 15 years. Then at one point in time, I added a third day. And that third day could be maybe on a weekend or something like that. And I did that for a handful of years. Now, fast forward to today is I'm a couple years removed from leaving my last organization. I work out five to six days a week, but I had a baseline or I had a foundation already built. And it wasn't as difficult for me to go from, I wasn't going from zero to six, I was going from three to six or three to five. And it was a much easier transition. But I can tell you, even making that change, I had all this time and I still had excuses of why not to work out five or six days a week. Like, well, why can't I make that a priority? Well, there's other things that were a priority, I guess. So it's a habit forming loop that comes in. I can tell you, we've had episodes where we've talked about healthy eating. I generally eat pretty healthy. My Achilles heel is the quantity. Just because I have more time doesn't mean that I'm going to eat less. It usually means I'm going to eat more, Rob.
Rob: Well, snacking gets easier because you have all day to go snack. So definitely increase volume of food consumption.
Brent: And all day to think about it. Right. What am I going to have this afternoon for my snack?
Rob: I'm going to go to the store and buy something that I don't have in my refrigerator right now because I can and I could just make a quick trip to buy that one thing.
Brent: So some things are going to work against you. And then here's the reality that sets in. So it's funny when you get into this stage of making a transition, you want to transform your body as an example. Guess what, people? Transforming your body in midlife is a little bit different than transforming your body when you're back in your 20s and 30s. It just takes a little bit more time.
Rob: You mean I'm not going to get the seven-minute abs? It's not going to take seven minutes to have the eight-pack Brent?
Brent: It's going to take you a little bit more than seven minutes, Rob.
Rob: It's going to never. It's going to take you never to get that.
Brent: So there's a reality that sets in, is your body is operating differently at midlife than it did 10 or 15 years ago. You've got to take that into consideration. So when we get into the health component of this, we're trying to just share some realities, but also some huge encouragement. And you have this opportunity to maybe, because you might have a little bit more time, is to start doing more active type things, get out in nature more. We've talked a ton about that. There's huge value in that. Maybe one of your workout days is just going for a longer walk. Maybe it's going for a short hike. Those are things that help you start to build habits. So I'm not trying to be doom and gloom on this topic. I'm just trying to set a reality. Just because you have more time doesn't mean you're going to use that time to really, you'll probably build an amazing workout routine, but to actually fulfill it and execute on it is a little bit more challenging. Rob, you probably could talk about this one because I know you've played some. I'm going to start lifting weights more and I'm going to start doing some more strength training because you've always been great at doing the endurance type things or really the cardio type. But how has it been for you and doing strength training as an example?
Rob: It's funny you're asking the way you asked that question. So I mentally I think about doing two-a-days, right? I think back to when I was in high school, getting ready for sports, especially in the fall. I played soccer growing up. And, you know, right before the season started, you were jumping into two-a-day workouts, daily doubles, we called them back then. I don't know the kids still call them that these days or even do these activities, but one was in the morning, one was in the heat of the afternoon, just a miserable workout to get in really good shape. And mentally, I keep thinking about doing doubles. I think doing a two-a-day workout regime. Think about it. I've yet to execute really on it. And I've stayed pretty active. And one of the things I did differently, because I don't have good workout habits, Brent. Now, it's just funny because I've done some big events, but my habit around working out is not that solid. I sign up for scary things to force me to work out. So it's not painful when I actually go and do it. And so when I left, I had a big scary event, the Cocodona 250, a 250-mile race across Arizona that I signed up for, that I knew I had to start training for. And I built out a schedule. And I just followed that schedule. So I had something to look forward to accomplishing as an outcome of doing these workouts. And so that's my only saving grace. Now, once that race ended, my training was not a habit, even though I've been doing it every day because I've been doing it for a singular purpose. I fell off the wagon. I've gained 20 pounds since finishing that race. I can tell you, running 20 pounds heavier hurts a little bit more. I went to a chiropractor yesterday and did cupping for the first time. My back looks like a ladybug. Really a fun experience getting back into shape after having been in shape. Everyone of our audience probably knows that. And so starting with just simple habits while you're at work that you can transfer after work are going to be key. I didn't have those except for signing up for some big crazy stupid event.
Brent: And I think the key here, Rob, on health is really trying to keep it simple, not overthinking this one. When you try to, anything in life, if you say I'm just going to go from zero to a hundred overnight, is so hard to do. It just doesn't happen. So if you can be additive and you can add a few things, maybe if you're really struggling with your diet, maybe start out with one simple meal. Get your breakfast figured out or get your lunch figured out or get healthier snacks in the house. Or if it's the exercise, I was just talking to my wife this morning about exercise and she was sharing how a friend of hers was a bit resistant to doing strength training. And she actually signed up to go with a few of other friends and go to a trainer on a couple days a week. So it was something that you're doing it as socially, but also you're getting the expertise. There's things that are out there. We talked this in previous episodes about health span and some of the important things. So we know it's out there, but there's a reality that sets in. But wow, take advantage of it because you'll feel great. Rob, you got to give yourself some credit because you have made some changes and you're starting to lift weights a little bit more and you're starting to do some things that you normally didn't do consistently. So give yourself a little bit of grace here. But now the goal is how long are you going to stick with it and um get the benefits from doing it?
Rob: So, all right, we're almost coming home now. We're now uh four deep into our list as we start into the
Rob: next category. So we've talked about finance, we've talked about relationships, we've talked about health. The next area is purpose. And I don't know necessarily that this is something you can have completely figured out before you leave, but I think it's something you can start preparing for before you make the transition. And so when it comes to purpose, the conversation here is, and it's both for Brent and I, and I know it's been for a lot of our audience, it's the loss of the sense of identity. It's we had this identity as workers. And once we leave that work, and I've even heard people say is my identity isn't my work, but they don't have anything beyond that going on either, that significantly drives them. It's how are you going to ask the question, what do you do with your time? So, Brent, for a lot of people that might be looking at their retirement coming up on the really immediate horizon, how would you approach them before they go into retirement, trying to find what their purpose is, trying to identify a purpose, or like you did for me, what would you suggest they do the day they retire to actually go in and find what their purpose truly is?
Brent: This is a tough one, Rob. I mean, it was this is one where I probably of all of these I struggled the most. And this is how we opened up the conversation today, because I went from, like all of us, really active in our work, and it's been an identity, and I would have these lofty titles and all these fun accomplishments, and all of a sudden you put the brakes on and you're like, well, who am I? I think having the honest conversation with yourself about the identity. And for me, is I've always been like, I don't want to be defined by my work. Let's be real here. I was certainly defined in a major way by my work. So, what the idea here is when you think about purpose, what I caution people is it's a very lofty word, and it can mean so many things to so many different people. And what's my purpose? And you get into this zen state. I need to go see Yoda to talk about my purpose. I don't recommend that. I recommend, and if I did this, I think it would have been a much easier on-ramp into the next great act for me, off-ramp from what I was doing, on-ramp to what I want to do, is take time. We mentioned this earlier. Step back, give yourself some space. And if that space is three months, great. You did five or six months, right?
Rob: I did, yeah. It ended up being five months after a planned three-month break. I did five months before I started anything.
Brent: So if you do that, you get clarity in doing that. And it's not five months of just sitting on your couch binging Netflix. It's breathing. It's getting outside, it's reconnecting with some of those relationships that we talked about, getting yourself healthier, like all the things that we've just talked about. That's what you should do in the first few months is get yourself re-engaged with who you are. I think Sarah, in the episode that we recently had about her midlife sabbatical, said it really well. Get in touch with yourself. What she described, and I loved the way she talked about this, she had a 30-year backpack that was so heavy that she needed to set down for a little bit. In that backpack, she had her career, she had raising kids, she had a lot of different traumatic experiences that were taking place more recently when she was going into her sabbatical. She set it down and she just breathed and she just took some space. If you do that, you will get clarity. Then you'll start to understand like, do I want to get involved in nonprofits? Do I want to start another business? Do I want to write a book? Do I want to take on some new hobbies? There's so many things that you can do. And I think, Rob, one thing that you did, and we talked about in a previous episode, and I know we'll talk about this when we get to the last category, but I want to dive into this a little bit because I think you taught me something really well is you established a list of 50 things that you want to do in your 50s. And I think that's a great way to transition into understanding purpose without actually saying, I want to launch five companies and I want to go back to work and I got to go earn this income. You actually picked a lot of skills that you wanted to learn. And it's a way to help you pick up maybe a few new hobbies or do a few things to not be so work-centric. So maybe talk a little bit about that because I think it helped you navigate the anxiety that comes with as I should be busy, really busy today, because I've always been busy for the last 20 to 30 years.
Rob: Well, if you're not busy, you feel guilty. And when people ask you the question, what are you doing with your time? And you don't have a good answer for that, it just feels weird. And so I did create a list of things I wanted to learn how to do, some random things, some fun things, some crazy things, but they all had to do with learning to stimulate a portion of my mind. And it took me a while to build the list. So I didn't have this list built before I retired. I wish I did. I took the entire year after I retired to go build out this list to be able to then start to execute. So I took my time in building that. But Brent, this is the area that I think I did really well in when I made my transition. And I have to thank you for the suggestion here was to give myself space and give myself time. It would have been really easy to step in and jump in and do something, which probably wouldn't have been the right thing. And the my original plan was to take three months off. That's what you said I think was the minimum. That's what I would suggest is the minimum for anybody. And it's not taking three months off to sit on the couch. It's it is taking three months off to find yourself because a lot of things coincide with the transition of retirement that may not have caught up to you. So the kids are out of the house. That usually happens right around the same time or just before somebody steps into retirement. So the identity was a worker and a parent. And for you, it was a I worked and I was a father. Now it's the, well, I'm a worker and I that's all that's my identity. And then both are gone when you step away from work. And that may have taken some time to actually come into play to actually where you realize that. So at a minimum, my recommendation is taking that three-month gap and just sit with yourself and learn who you are, or start to define who you want to be. What are all those things you want to become? What do you want to learn? Who do you want to know? What are the things you want to see and do? But let that time be that breath that you need. And three months might become six months because you don't have an answer. Six months might become a year. If you go back to the first thing we talked about, the finances, the finances are okay. You don't have to find that next thing right away. Take the time, but also understand you might make a mistake. You might jump into something a little bit too early and give yourself the opportunity to unwind that as well. Don't just sit on the first thing. Well, I started this, I got to finish it. That's I know what mindset my mindset is. That's what your mindset was. I started this thing, I need to finish it. And I know, Brent, you had to unwind a couple of things you got started as well. You started a couple of businesses that you realized weren't really your purpose. How did it feel to unwind those things now that you're actually because that's a different thing for you? Is you start and built successful businesses, you start and built something, you got it going. You said, wait a second, I don't want to do this. Let me unwind that. What was that experience like for you?
Brent: It was really hard. I mean, it was something that I was really unfamiliar with because I was used to taking things into fruition. Like, let's see how this plays out. And I launched a few businesses where I'm like, I don't have the energy for this, I don't have the excitement for this. What I had was the capability, but capability sometimes doesn't pair well with excitement or desire or purpose. And so it was something that it was part of, it was a healthy part of my transition because I was trying a few things. And you have to give yourself a license to try and maybe pull back and stop worrying about what other people think. Here's the one thing that I think if I would have done would have been really helpful for me is if I would have given my title in my first three months of my transition, my own title. I'm the CEO of me. I'm the head of strategy for my next great act. I'm the project manager of cleaning this act up. Like that to me would have given me something to tell people that could create a funny conversation. I had none of that. And if somebody hears you say, Hey, I'm the head of strategy for my next great act, they're going to be like, What's that? Versus, I have no idea what I'm doing. I'm just kind of sitting around, people kind of looking. Like, you're just a lost cause right now. I did that. So, speaking from experience, that's an embarrassing moment when you're around people and you have nothing to say to them. I just pause and be like, um, I don't know. I'm just kind of hanging out. Or then you talk about all the great things you used to do. But if you tell somebody, just like I'm the head of strategy for my next great act, and stop right there, they will ask you a question. What is that? I love that. So maybe that's maybe that's purpose that'll help.
Rob: I love that. I was thinking of saying as you were sharing that, Brent, I was thinking, like, ah, I'm taking a gap year. That's something I never was able to do when I left from college. I went straight from college into work. I'm taking a gap year and I'm figuring it out. That's a great answer. In fact, probably whoever you're telling that to is going to be jealous that you're taking a gap year at 50, not at a gap year at 25. Because that's a totally different experience of a from a financial standpoint to take a gap year when you actually have money.
Brent: I'm taking a sabbatical. I'm taking a gap year. And it just says, or I'm just taking the next three months as a break. I've been working hard in my career. Have a simple answer, but don't over-answer it. That's something that I learned that I tried to over-answer it of all the things because I felt like me sharing with people that I'm launching five different companies, because literally I was trying to do that, was a way to say I'm still productive and to get people to think like I'm really important and I'm doing all these things. Guess what? Most people really don't care. So if you just give them something really simple of just saying, I'm taking a gap year. I'm taking the next few months as just a break. You know, I've just wound up my last opportunity or my last job and it was awesome. And now I'm just going to take some time to think about what's next. Most people will be so excited for you. They may be a little jealous, which we've talked about in previous episodes with people that have done this. But if you get caught up on trying to be so precise right out of the gates, it's a recipe for disappointment for yourself because you're going to try to do too much. So that's a lot of learning and purpose. I mean, there's something there. And I think I learned a lot. I just encourage people to take the two things I recommend you do is take three months or more to not do anything outside of taking care of yourself. Be the head of strategy for yourself, which is the second thing. Give yourself a simple title that creates a conversation in case anybody asks. And then you can just flat out tell them what you're up to. So, Rob, next one here, last topic for our five categories is adventure.
Brent: You and I have talked so much about adventure on so many of our episodes. We can go back to, I mentioned the list of 50 things. That was episode five. So that goes pretty early on in the podcast. We've talked about micro adventures, we've talked about macro adventures. But let's just let's ground this conversation on why we put this as one of our top five categories of things that you should do in your transition, especially leading up to your transition. And so, how should people think about activities or adventures when they're planning to step away? And how should they start to think about this?
Rob: I'm going to start with the why it's important, Brent. And I think that gives us context to the how, how to start approaching this. So the why it's important is we had identities as we were working and as we were parents, as you were a parent. You had an identity you were trying to replace. And we just finished up the last step, the last conversation around finding purpose and what is your new identity. I think adventures and learning and experiences can actually truly help define what those things are for yourself. And it the purpose you have to has to find you, you have to find it, and it takes some time. Adventures and experiences and things of that nature can help influence that for you, can actually help find it for you, can help you find that version that you want to go and create, or find the areas that you don't. So that's why I think it's important is they put you in a place of sometimes discomfort, sometimes of being, you know, a beginner at doing something again to actually find that purpose. So I think this is the follow-up to purpose. If you're going to take the time off, I do think this category helps fulfill finding that purpose over time. And it might take a number of adventures or a number of experiences to go and do it. So that's the first thing is to answer your question as to the why it's important as it goes back into our last topic. The how is really before you go into this retirement, start building your lists. And I think of lists in a couple of things. One, it's adventures you want to have. And these are experiences that you want to go and do. And so it could be a big trip that has something really foreign or different than the norm for you. So if trip typically a vacation for you is going to the beach, it might be going completely different and going to a developing country and volunteering. That might be the adventure you're going to go and have. So it's building up that list of things that are just interesting to you. You don't have to decide what they are right away, but building up a list of interests. And there's so many places you can go to find interests. I know I've shared this with you before. I'm a serial YouTube watcher. I have all sorts of people that I watch on YouTube. And they're always posting incredible videos of adventures. That's probably the algorithm that I'm in. But almost every morning I start with watching a YouTube video because it just sets me up in a great tone and a great place because it's always something fun and exciting that I may or may not add to that list. So adventures is one. And I put experiences and adventures together. The other area that we've talked about is the learning list. And this is really to help me push myself to go to another place of discomfort, but to be a beginner again at doing something. And in our midlife, a lot of times we built skills that are very comfortable for us and we live within that skill world. Being a beginner at something rebuilds a muscle that many of us haven't had to use since we were in our 20s entering the workforce. And rebuilding that muscle is so much fun. It's scary and it's downright embarrassing at times. If you want to see an embarrassing video, I posted something of me trying to ride a unicycle. That is definitely embarrassing. I've not mastered that. That's on my 50 list, is to ride a unicycle. It's way tougher than it looks. I thought it looked pretty simple, just hold on to something and figure it out. But even holding on to a fence, I fall down on my butt. And so I think the learning piece pushes your comfort zone to be a beginner again, which again helps you find yourself and might help you find more of that purpose you're looking for.
Brent: With all this, Rob, I think it's really important for us to ground reality for people with adventures, trying new things. Guess what? You earned it. Like you've worked so hard up until this point, and you may have not had the time to go, as Rob alluded to, learn how to ride a unicycle, travel to a destination that you've wanted to do or you're curious about, but you haven't had the time. You now have some space to go do that. You earned it. So reward yourself. And that's where we look at adventure. Sometimes adventure is to grow, sometimes it's to explore. But part of it is you've earned the right to go do it. And so it also is great from a transitionary standpoint because you may have a little bit more time. So use your time wisely and pick a few things that might take a little bit of time to plan. It could be exciting. It could be a lot of logistics involved. Use your skills that you've gained throughout your career to go do something that's active related and reward yourself. And that's a piece that I find it's uncomfortable for people because they're not used to saying, I'm going to go on a two-week vacation. They may have never done that. It's no different than what we talked about on the health side. Like if you haven't been working out, it's difficult to just start working out a lot. Same thing here. If you're not used to doing long vacations or going on adventures or trying new things, or it's been a few minutes since you actually learned something new that's unrelated to work. It's going to be a habit-forming thing that you got to get used to. But the rewards are just endless. And we just highly encourage it. Rob, when you think about adventures, you do some really cool things and some areas that you visited throughout the world, and you and I laugh about some of the funny things that you do. How do you get somebody to just step into an adventurous lifestyle or challenge themselves to learn something new? Because I know that's something that you take a lot of pride in is encouraging people to get outside, to do different things. How do you get them from a status quo of I'm a great worker to, hey, I'm actually curious and I'm an explorer?
Rob: I would say, Brent, start with just building the list, no matter what it is. Just start building a list. And that's something you can do before you leave work. If you don't have the time to take that two-week trip, build a list of things that are interesting to you, the places to go, write it down. We've all heard the Harvard Business Review that came out about written down goals and written down lists are more likely to happen, write them down. You don't have to do everything on the list, but if it's interesting to you, put it on the list. And then the first step is a micro step. So if you've never done a two-week vacation and that sounds difficult or foreign to you, you don't think you ever could handle a two-week trip, don't schedule a two-week trip. Schedule a 10-day trip. Meet in the middle. If you've taken a week-long vacation, now take a week and a half in a different country and go see what that life is like and go spend that the 10 days, not 14 days. What you'll find is while you're doing that, in the middle of it, you're going to go, wow, I could have actually done two weeks here. This actually feels really good. I don't have to go back and answer a hundred emails. I don't have a thousand emails in my inbox. I could go back and I don't have to go back. I could just stay here. And you might even be able to change your trip. That's the cool thing, is you don't have that, you may not have that pull to come back and do something. So it's build a list. And then what are some of the micro steps you can start to take short term to expand your comfort zone to maybe go and do something that is on that list?
Brent: That's a great way to start because we're all capable of doing that. The list is not the hard part of some of these things. It's just an initial nudge to actually try something of saying, hey, what are 10 places I want to visit in the world? What are 10 trips that I've been avoiding doing because I'm so busy with work or my kids or things like that? Or what are five things that I want to learn? Not 50, but five things that I'm curious about. Or the adventure might just be something close to home. What's something that I've heard about that's pretty cool that I haven't done because I haven't given myself the space to do it.
Brent: As we bring the conversation home today, I'm going to give us a quick recap. The whole idea of this episode is planning for a transition to your next great act. And we talk about it a lot. So we referenced to a tremendous amount of our past episodes because it's a buildup to this episode, but it's probably one of the bigger conversations that we have with people is, you know, and our listeners is like, how do I do this? So we said, hey, there's five main categories that will help you navigate your transition. We started out with finance. We think it's a great grounding exercise. There's a reality that you need to identify is, you know, how are you spending? How much are you going to spend in retirement? What's your distribution planning look like, working with a professional? So we talked about finance. Then we dove into relationships. This is the one that's been really hard for me. Not as hard today, but at right out of the gates of leaving my last company is your relationships are going to change. So take inventory of your relationships, understand who are your real friends, who are your deal friends, and work on all those. It takes time, it takes patience, but it's very doable. The next one is we went into health. Health is about building habits and habits around if I want to exercise two days a week, but start building that habit now. If I envision myself exercising four or five days a week, what would that look like? How could I achieve that? And what are the tools that you're using to help you with that? You don't have to do all of this with self-will. Then we talked about purpose. This is a meaty one. Super meaty. There's a lot in it. I would call it an identity shock because you're used to having a specific identity and now your identity has changed. So maybe start out with just giving yourself a simple title as I'm the chief strategy officer of my next great act. And I'm going to spend three months working on my strategy of doing nothing. That's what we're asking you to do or recommending you do. Then we moved into an adventure, and adventure is a way to help bridge the gap. But also, as Rob alluded to, it's something that you're building lists and you're starting to understand what are the things I want to do. You now have the license, so why don't you go do it? But there's ways to start to make it a process that's enjoyable and something that you can start to take advantage of. So this was us walking you through the transition. Rob, did I miss anything on that that we want to highlight before we close out? You hit all the key points. Great. All right, so we like to close out every episode with a gratitude share. And I think this is a really important Rob for us to circle back and say thanks again to Jason because he did give us that feedback a couple of months ago about ways to create engagement with the show and how can we, you know, get listeners to provide episode ideas or feedback. So we took a little bit of time, we built the technology, we have it. It's accessible to everybody who listens to the show, message the show. It's really easy to do, but we just have to say thank you, Jason, for not only giving us the idea a few months ago, but actually testing it out with us. And thank you for um giving us that little push. So we appreciate it, Jason, and uh we're excited to see what feedback other people give us. So go ahead and try it out. The tools available to you. And thanks for spending time with us today. We'll talk to you soon.
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.