Episode 18: Why Not Now? Your Next Great Act Is Waiting
In this episode, Rob and Brent dig into why the traditional idea of retirement no longer fits—and why waiting for “someday” often keeps us stuck. They talk candidly about their own experiences, the fear and excitement of change, and what it really takes to trust yourself enough to make a bold move. From financial clarity and sabbaticals to real-life stories of people who’ve already taken the leap, the conversation challenges listeners to rethink timing, momentum, and what’s possible next. The question at the center of it all: if you’re feeling the pull… why not now?
Links, resources, books mentioned:
Topics we are covering in this episode:
Retirement doesn’t have to mean slowing down—it can be an active and intentional next chapter.
The traditional idea of retiring at a set age no longer reflects how people want to live today.
Waiting for the “right time” often becomes the biggest obstacle to change.
Trusting yourself is essential when navigating major life transitions.
Financial clarity creates flexibility and opens more options.
Simplifying life through downsizing can free up time, energy, and experiences.
Sabbaticals can offer valuable space to explore what’s next without full commitment.
Transcript:
Transcript Disclaimer - May contain the occasional confusing, inaccurate, or unintentionally funny transcription moment. It’s all part of the show.
Lena: Ever notice how retirement is supposed to be the reward, but for a lot of us, it feels more like a slowdown? Today on Midlife Circus, Rob and Brent challenged the old script and asked a bigger question. Why not now? From outdated retirement rules and the one more year trap to bold leaps, sabbaticals, and designing an active next chapter, they explore what it really takes to start your next great act. It's not about stopping.
It's about choosing what's next. Before we begin, remember to follow Midlife Circus on Apple podcasts or wherever you listen, and join us in the Midlife Circus community on Substack. Let's dive into why not now. Your next great act is waiting.
Rob: Brent, when I say the word retirement, I want to describe the first image that comes to your mind.
Brent: The one thing that comes up most when you say that is an image of my grandparents. And my grandparents, they retired at a common age that their generation did. So let's say mid sixties. And what I remember the most, Robin, this is funny, is when we used to do family vacations with my grandparents, they used to travel with this little teeny suitcase with liquor in it. So it was like a little bit of a mobile bar.
They had the different alcohol that they liked at the time and little glasses and little pouring guides and things like that, because we'd go to places where there was a lot of grandchildren, so usually there wasn't a lot of alcohol around, but they made sure that they brought their little suitcase. But back to your question, it just reminds me of that sedentary lifestyle, that it was much more of have a cocktail in the afternoon and kind of wind things down very early, not overly active. And they would do a lot of things, they'd go to the country club and have their dinners. And it was just a very, almost like planned lifestyle once you hit a certain age. So that's the memory I have of retirement.
But to me, when you say that word, it makes me cringe a little bit because I don't want that. I don't have an interest in that lifestyle, at least at the age that I'm at right now. So it's a very interesting dynamic that I have. I just think back to my grandparents and how they retired, and I don't necessarily envision myself retiring in the way that they did.
Rob: So you're not looking forward to that life of leisure, the walking hand in hand with your wife on the beach as the sun sets? That that's not something you're that's on the radar for you right now?
Brent: It's definitely on the radar, but it's after doing, like, a triathlon that day or doing something super active along bike rides, scuba diving, whatever it may be. So there's a lot of activity. I envision if we use the word retirement, I envision a very active retirement that's filled with a lot of adventures. And yes, there might be this awesome opportunity to stroll on the beach and have a nice sunset with my wife, but it will be following a day of a lot of fun stuff.
Rob: It's kind of funny you said that the word retirement or thinking about retirement kind of almost was like a cringe moment for you, if you will. Right? It's like, don't look forward to that. That's not what I want to do. And that's really what we're going to talk about in today's episode is the construct of retirement in this next phase of life that we're all going into.
And I'm going to start today just give you a little bit of background, Brent. I did some research going through and looking at retirement and the history of what retirement is and has become. And so retirement, prior to the early twentieth century, retirement didn't exist. You worked until you were physically unable to go to work anymore, and then you died. That's pretty much what happened.
Right? You worked, you stopped working, and really quickly you died. And then in 1935, not everybody was dying. And in 1935, social security was created as a way for elderly, unemployable individuals to not be destitute, to actually give them some form of an income so they weren't a burden on the broader society. And when social security was created in 1935, what was the age they set in place for retirement benefits?
There was only one age. They said full retirement benefits. What's the age? So we're back in 1935. What was the retirement age they said then?
What do you think?
Brent: 55?
Rob: 65. So the whole retire at 65 started ninety years ago. I just want to put some context around it. That's a long time ago in terms of the modern day version of retirement. Still a lot of people thinking about retirement happens at 65.
So retirement and how it was built wasn't built around what we're seeing as population's, health span increases, which is what we talked about a little bit on our last episode was health span. It's not it's not been evolved with how people are becoming more and more active. And my grandparents like your grandparents were somewhat active, but not super active as they go into retirement. And we're seeing that our generation is approaching this quite a bit different. Many people are retiring a little bit younger.
Many people are significantly more active as they get into retirement. So that's really what we're going to talk about today is, do we have to approach our lives now as if it we were ninety years ago and that '65 was the date that everybody stops working? And could you actually do it sooner? Could you be bold and actually make that transition earlier in your life?
Brent: One thing that I think about too, Rob, is the mobility has changed quite a bit over the last ninety years. So not only the mobility of the individuals, so there's more of an emphasis on taking care of your body in a different way. But the other thing that I think about is the world has definitely shrunk in the sense of it's easier to get from one place to another today than it was years ago. I mean, air transportation is super simple. You could make a trip to say, Hey, I want to head over to Japan.
And with not a lot of effort, you can head over to Japan. Now, if you go back fifty years, it wasn't that way. So our world proximity to get to different places and explore the world has changed. And so that's part of this evolution of how people are spending their time as they get into their midlife and beyond.
Rob: And that's really what we're going to spend a lot of time on today is making that bold decision to make the leap and not get stuck in the convention of a 65 retirement. Or the place that I got stuck in was the one more year place. I'll just work one more year, one more year, one more year. And I said that for, I don't know, four or five years, I think, something like that. I kept saying one more year, one more year, and I knew I wanted to make a transition.
I was just afraid to go and do it. I was afraid to go and do it because I didn't know what was going to be next. I didn't know what my life would be like if I stopped doing that thing that gave me purpose all day long. And so I wish we did have a better phrase. I've heard somebody else say they use the word renewalment before, and they're getting, they're getting renewed and reinvigorated with energy and excitement about the next thing they get to go and do.
But I'm not looking forward to pulling back. If anything, I'm looking for more to get deeper into the things that really drive me from a passion standpoint.
Brent: Yeah. And it actually came up yesterday in this call because this individual, he was actually exploring his next great act, which we've coined, you know, as part of our podcast and, you know, Midlife Circus, what's your next great act? And he started using that phrase. I didn't bring it up. He just said, I'm really focused on my next great act.
He's in the process of selling his business and he knows that he's got to still do something, but he's like, What am I going to do? And he goes, What's my next great act? I'm like, Oh my gosh, that came out. So that's something that we use, but it's a lot to do with our struggles with the word retirement.
Rob: Because it's the next phase. It's getting excited about what that next phase is, not a retreat or a pullback, which is what I think of the, you know, the phrase retirement is. It's a pullback or a retreat or a cease. Right? It's a was started off, I think it was in a military term.
To retire was to cease and to actually pull back and to run away from the fight, and that's not what any of us want to go and do. Now as we started talking about retirement and talking about kind of the approach that we wanted to use in this discussion, just to set some context, Brent, and I'm sure you're fully aware of this is that we're all terminal.
Brent: We're not trying to be morbid in this podcast. That's not what we're about, but it's truly understanding that there is an end to this journey that we have on this planet. When I say that to you, Rob, life is terminal, there is an end. What emotion does that create for you?
Rob: A little bit of fear in terms of how soon is it going to happen and what can I get done between now and then? That's what I start thinking about is what am I able to accomplish and what am I able to do? What am I able to experience between now and then? So there's a little bit of fear, but that quickly pivots for me to excitement to go and explore and make the big jump into doing something else and to go take advantage of the time that I do have right now.
Brent: And we can't predict when the end is. That's the reality with life. So we don't know if it's tomorrow or if it's forty years or fifty years from now, but the emotion that gets created for me, similar to you, is more excitement. What can I go get done now? And that's a big part of this conversation today is really understanding if you are considering your next great act, what is holding you back?
Like what is the emotions that are holding you back? What is the material items potentially that are holding you back? What is the financial that's holding you back? And that's the piece that starts to create this curiosity that's really important to try to navigate because if you wait, you wait, you wait, or maybe you wait a little bit too long.
Rob: And your ability to extract enjoyment from the money that you've saved goes down as you age. It truly does. You're not able to extract as much enjoyment from the work and the hard work that you put in for a long period of time.
Brent: What does that mean? Can you further explain that? Because I think I understand what you're saying, but can you describe that a little bit more?
Rob: So a 85 year old that wins the lottery, what are they able to do with it besides give it away? Oh, okay. Some enjoyment. Right? They it's maybe a little less selfish.
They get to give that away and see other people enjoy it, but they're not personally able to do the things anymore that a 50 year old or a 40 year old that won a big lottery payoff would be able to go into. So to personally be able to extract enjoyment from money does go down as we all age.
Brent: Yeah. And that's something that as I navigate life, like with my in laws as an example, where I'm starting to see that they're, you know, approaching 80. And so their ability to go do a lot of the things that you and I would like to do in our 50s or 60s has just declined. But there's different expenses that come with life as well. So it's not saying go ahead and spend everything in the next ten years, knowing that you're not going to spend as much down the road.
There's different costs that start to come in at later stages in life. So you have to manage that, but it's important to understand that. And we've said it so many times, Rob, is it's really difficult if you try to delay gratification. Meaning if you've got that trip and you're able to do that trip, why aren't you doing it now versus waiting five years to do it? But I think this conversation today is a bigger picture question, right?
Is if you are considering your next great act, why not now? What is truly driving the why not now dilemma in your head? Let's talk about a few examples here because I think there's a spectrum that we could go through. And I actually want to jump to the extreme spectrum where I know your sister made a really big bold move at one point in time a little while ago, that actually was let's sell it all and go reestablish herself elsewhere. So I'll let you tell that story.
But the idea here is where we're going with this is you can make change. Don't fool yourself here. Like you can try something new and there's various degrees to doing that. So I want to take us on a journey of some of the bigger changes that we've seen people do and do it really successfully. And then we'll take it down to some of the smaller things that we've seen people do.
Cause we're trying to give pathways for people to think about their next great act, but there's a lot of things that people can do now that help them establish that.
Rob: So I'll start with, I'll point out, it's my younger sister, Brent, that did this, and she did this while I was still working. And she'll probably listen to this episode, realize that I was envious of the big bold move that she made. Yes. I was. I've never told her that directly, so this is the only way she's going to hear it is listening to the podcast because we Gen Xers can't give our siblings the benefit of the doubt while they're while they're in person with us.
Right? We can't give them that kudos in person. But my younger sister and her husband decided that they were burned out and they'd had enough of the stress in their lives. They sold everything. Literally, the couches, the house, the furniture, they sold literally everything and bought a place in Saint John in the Virgin Islands, bought a duplex.
And their plan was to move down there. They'd spent some time down there. They think they had their honeymoon down there. They've been on a couple of cruises, been on Saint John a number of times, and they really desired the island life. So they sold everything, moved to Saint John, no jobs at all.
So they had no idea what they would do, turn an income. The original plan was this duplex, they'd live in half and they would Airbnb the other half. And pretty quickly, they realized that they didn't want to Airbnb the other half because they wanted to have people come and visit on a much more frequent basis. But without jobs, they spent some time down there, got to know people in the community. My sister then became a teacher.
She was a teacher here in, in Colorado. She became a teacher down in Saint John. And her husband now, I would say, I like the phrase recreationally employed. He's a job as a boat captain. So he left being an accountant for a big oil company.
Now he's a boat captain driving people out to go snorkeling or fishing in the Virgin Islands. And that was their big leap. It was a big bold leap. I thought they were crazy for doing it in the first place. Like, what?
You're selling everything and downsizing to a tiny little place, And they're making a go of it, and they love it. And I keep asking her, does she want to move back? And she says, no way. This island thing is for us. We're never leaving this place.
Brent: I find that so fascinating. That is one. Yeah, absolutely. That's one end of the spectrum. I mean, there's a family that lives locally in the community that we're in that did a similar thing is moved to The Bahamas and they bought a small little condo.
And they lived in the condo and they realized this is the life that we now want to live. He had a small business, they sold the business, they sold their house, and now they live in The Bahamas full time. And what is he doing for work? He's a mechanic or just helps people fix boats, their boats, the engines and the small crafts around The Bahamas. It's something that he was curious about.
We live in Colorado, so it wasn't like he was working on a lot of boats in Colorado. But he went down there. I think they went down there with an open mind, similar to your sister. We have to go down and trust ourselves that this is something that we can do, we can figure it out. We removed ourselves from a lot of the attachments that we had that were drawing the expenses and so forth.
So we made some major changes in our life and we decided to do that. Now, are really extreme examples, but you can start to go back and you can kind of look at other scenarios. And I would guess all of our listeners probably could think of a handful of people in their lives that have done something like that, where they've decided to pick up and move to another location and really almost do a start over or do something that is just, I'm going to try this new adventure because I'm at this stage and I'm itchy. And some people get itchy in their thirties, forties, fifties, sixties, seventies. So it's consistent along our life cycle that it doesn't necessarily dictate when you do this, but those are extreme examples, but let's pull it back a little bit, Rob, and let's think about what does it take to do a change?
Like what does it take to actually make a decision like that? So what is your sister, if you use that as an example, what does it take to actually make a change like this?
Rob: I think the first thing it takes, Brent, is trusting yourself. And we need to be able to trust ourselves that we can figure this stuff out. That's our kind of our generational motto. Right? Is we're the generation that had to go and figure stuff out.
We were left to fend for ourselves. I know I said that before. Why would we treat this time of our life different? Why are we waiting for this set script to tell us how to do things going forward? We can go and figure this out.
So the first thing I would say is trust yourself that you will figure it out. Second thing I would say is you're more likely to regret risks that you don't take than risks that you do and fail at. And I heard that on a Mel Robbins podcast recently. If you look backwards in your life, you're more apt to be anxious or upset about things you didn't do than a risk that you took. And even if it failed, you chalk it up to I learned something, I tried something.
You give yourself the benefit of that doubt. So making that leap while it feels risky, I do sometimes think the riskier thing to do is to wait and say, well, I'll just hope that I don't look back with regret, which is one of the emotions I never want to have at different points of my life. I want to reduce the amount of regret that I have. And so I will typically try to make that leap and take that risk and make the jump. Lastly, I would say is plan and start to begin to building a plan for what does that look like and when can you feasibly pull it off.
So, you know, is it is it six months from now? Is it a year from now? Is it three years from now? And you don't have to make the big leap, but it might be, I'm going to downsize from a big house into a condo because I know that I want to travel during retirement or I know that I'm going to want to travel a lot more, And I want a little bit more simplicity of having this big house and all this clutter and stuff I have to worry about with the flowers and the lawn care and all of the things that go along with upkeeping of a house.
Brent: I think it goes back to the episode that we did quite a while ago on the two numbers and starting to understand the two numbers that it takes for your next great act. And you were really good about explaining the two numbers. So could you just recap that really quickly for people that maybe didn't listen to that episode and it's part of the financial equation? And when you say two numbers, what does that mean for people that are considering their next great act financially?
Rob: Yeah, so in real simplistic terms, two numbers that all of our listeners should be firmly aware of is how much do you want to be able to spend on an annual basis after you stop working. Just what is your spend rate going to be? And you have control over that number to a pretty large extent. So what is your spend rate going to be? And then the second number is what dollar amount needs to be set aside to create that spend rate?
And that dollar amount goes down if you have some form of income coming in. You don't need quite as much of a nest egg set aside to create that income, but those are the two numbers you should be aware of. And there's a lot more nuances in withdrawals and things like that. I don't go into detail even in the podcast. That's why I do think people should work with the professionals to get closer to retirement.
But knowing those two numbers and starting to adjust your lifestyle today to live into those two numbers will make that date come a little bit quicker for you.
Brent: And so when you have those two numbers, that to me gives you clarity. And clarity is a really important part of this process. So if you're exploring your next great act, having that clarity to say, well, currently I'm spending $5,000 a month as an example. And let's say that is your expenses. Well, okay, that equates to $60,000 a year.
And you start to see some of the taxes and stuff that you'd have to earn to actually have $60,000 Well, if you're 55 and you plan to live to 95, you can start to play the math. That is an important part of the process. But then maybe you can do a little bit of a deep dive into people that you know and maybe provide a good example of people that have downsized or changed their lifestyle to actually accommodate where they want to head and create more flexibility for them. So you'd mentioned to me, as we were preparing for this episode, you've got some friends that actually did sell their house. Why did they do that?
And what are they doing with their time? I think that'll be a fun way to describe and get us all, you know, excited for maybe this type of an opportunity.
Rob: So these friends sold their really nice big house, and they downsized, I think it was like a four or five bedroom house that they downsized into a two bedroom condo. And the biggest reason why is they want it to be turnkey, lock the door, and walk away and don't have to worry about it anymore. Now I know there was a financial component to it as well. There was equity in the house. Payments weren't as high.
The condo was a lot less expensive, gave them some asset. But the biggest reason why they did that is they want to be able to lock the door, walk away, and not worry because they live somewhere else for three and six months at a time. I think they spent all of two summers ago in Italy. They rented a Airbnb in, two different towns. I think they moved between two different locations, and they spent a month and a half in one and a month and a half in another Airbnb and just lived like Italians.
Went down the street and had cappuccino in the morning, got to know the locals, and stopped at the grocery store with all the locals in the area, took some cooking classes while they were there. They did that for an entire summer. This last year, they were in Nova Scotia doing the same thing. And so not only did downsizing provide them financial opportunity to be able to go and do these things, they also simplified a lot of their life by moving into a smaller condo to be able to walk away and not feel obligated to go back and just check on the house or check on the place on a regular basis.
Brent: So that's an example where things can start to consume valuable resources. So when I think of valuable resources, it's not always just money, it's time. No. Time.
Rob: And emotional space, Brent, I would say it's also emotional space too,
Brent: Yeah, I mean, if you have a large house and let's say you did have kids that, you know, grew up and they moved out of the house and now you're holding onto this large house for those moments in time when everybody comes back together, but then you've got the emotional connection that you're dealing with. And I understand that because I'm in the middle of it myself. And then you start to think about the time you spend on keeping up the house and then the resources, financial resources to maintain the house. And so I've seen some really interesting examples as well, where friends have sold their houses and whether it's their house and then they downsize into a smaller place or they rent. But one thing that was really unique that I see people doing is how are they spending time with their loved ones?
And when they make such a big change, there's this common thing of you want to keep your house because a lot of people will come back to your house. Your kids will come back to your house. But then as your kids grow up, maybe they decide to get married, they decide to have kids. Well, guess where you're going to travel for the holidays? You're going to go visit them because that's where the excitement is.
It's harder often for small families or young families to travel. It's just complex sometimes. So you have to put things in perspective. So I've seen couples where they now start to go where their kids are at. They might do an Airbnb in the town that their kids are in versus always trying to be back to this quote unquote mothership, you know, where it's like we all come back together.
Rob: You just said it, Brian. You want the nostalgia of having your family back at your house because that's where all the memories were created. I'm guessing your kids want to do that with their kids too. I don't have kids, Brent, but I'm assuming your boys are probably going to want to create memories with their kids some at their own home when they get there. Yeah.
Brent: But all of this ties back to the whole thing about how do you envision your next great act? And when you start to think about your next great act, there's a lot of different components to it. And it's amazing when you stop and think about some of the things that people have done and the choices that they've made. I know another couple that decided to stop. They were very, very successful in real estate, but they were hard charging.
And about 55 or 50, they decided to stop. And they really challenged themselves to think differently and what do we want to do next? And they created an amazing lifestyle of their next great act. And part of it was being incredibly creative. So they got into the woodworking side of things, they got into the art side of things, but they built communities around that.
And it was something that they did because they felt like they were on this treadmill and the treadmill is, I just need to keep making more money. I need to keep making more money and I will spend it someday. I'll spend it someday and I'll start to do these really wild trips someday, but there's a risk associated with that. But the challenge here is how do you navigate that? And so an exercise that I've done, Rob, is going back to the two numbers, is I actually build scenarios.
And I build scenarios and I'm analytical this way, I build scenarios on different expense levels. So if I want to spend this much money per month or this much annual, could I do this with the savings that I have at the age that I'm at? And then I do another scenario that says, okay, I could actually increase it by 10%. All I would need to do at that point in time is pick up some sort of employment or some sort of work that's part time or do some consulting, and we'll talk about that at a future episode. That's my next layer.
And then I might add a little bit more saying, you know, maybe I want to do a few more trips, or maybe I don't want to downsize my house or do those things, so what would it take to actually get to the next level? And I create these different scenarios, but I've also played the scenario, what if I did sell it all? Now I have zero interest in selling it all, that's not exactly where I'm at in my life. I like what I have, but I also want to understand what does that mean in our situation. What does that mean if we just sold it all and we rented a house?
I needed to do that exercise because it's not, I have zero plans in doing that, but there's a, you said earlier, there's a component of trusting yourself and trusting yourself. Let's say you pick whatever plan B is, you pick plan B to go pursue. Let's say plan B doesn't work out. Well, most likely there's a plan C, D, E, F, G that you could go pursue and it could be right in front of you. And I think that one thing, and I'd like to see how you think about it.
One of the challenges that I faced is I created this binary situation. And this binary situation is I have all of this now, And if I decide to leave that career that I have, I'll have none of this. And I have to live just on meager means. That is so not true. There's a lot of in between there.
And that's a piece that I encourage people to think about. Did you ever go through that? This binary thinking of like, I've got this great income, all the things I could do and all of sudden, woah, if I stop that, then the brakes are going to just bring me to a halt and I can't really do much of that stuff anymore.
Rob: I sometimes still feel that, Brent. That the income isn't coming in and I can't afford to go do the things that we had saved money to be able to go and do. That still comes up from time to time. So, yes, that still exists. And it goes back to the earliest part of our conversation, the retirement cliff.
And I think about that mindset being a cliff as I work, work, work, work, work, and then it stops, and it's completely done and no more work at all. We all can go back to work at some point. I can go back to work in my seventies if I wanted to. It may not be what I was doing before or at the income level that I was at, but there's this mindset that that greeter at Walmart that's in his seventies or eighties is a bad, didn't do well. I could see myself doing that just because I was bored, and I wanted to go see people on a daily basis and go wave at people and wave at little kids and greet people as they come in the door.
And so there's that I think the perception has caused us a lot of us to think that way and have that binary thought. It doesn't have to be that way. Continuing on this nonbinary thinking here, which is hopefully we're starting to help get our audience in attuned to and maybe thinking what's possible. Another way to test this is to actually do a midlife sabbatical. And Brent, you and I have a friend that's done this as a way to test out what retirement might look like.
Would you share what that experience was for our friend?
Brent: I think it's been I have multiple people that I know that have done this. And what I find is that they create space to really explore and they plan for it. There's a guy, I can't remember the book that I read about this. It's like taking sabbaticals and he takes one every single year And he takes a month, I think every year, and he's built a life around that. And what I find is when you take a sabbatical, you're allowing yourself to breathe in a different way and you're trying to test out a specific life.
Some people's careers allow for that. That's something you could possibly explore with your employer. The people that I talk to that do a sabbatical, it takes a lot of the stress and strain of, Oh, what am I going to do for the next twenty years? No, you're just planning for the next year. Right, take
Rob: one year off.
Brent: Yeah, if you take one year off, you're just planning for that one year, and there's kind of this off ramp of like, when you step away from whatever your career is for that first few weeks is probably going to be crazy uncomfortable or crazy exciting. And then you're going to have an on ramp that you have to get back to at one point in time as you ramp back up into it. But there's this fear that people have is that if I leave something, I can never go back to it. I don't buy that. It may just be a little bit different.
It could be a lot of it different, but what if it's better?
Rob: That's the biggest question, Brent. What if it's better? No matter what the outcome is, what if it's better? Because everybody gets worried about it's going to be worse. Right?
Before we go there, let me take a step back. A midlife sabbatical is stepping away, and some companies allow this. It's actually stepping away from your current employment to follow your curiosities. Have some of those big experience. Live abroad for a period of time.
So instead of doing the gap year after college, you do a gap year in the middle of your working years. And, unfortunately, for some people, this is their peak working years and peak income years, but it's probably going to be okay after that because you take that period of time, you might find something in yourself you have great passion about that becomes the next great act, and you don't end up going back. Or you realize that I got some experiences. I still need to have some income coming, and I still need to save a little bit more, but I'm better because I had those experiences. Now I take those things into that next line of work or the next job that I'm going to have or the next thing that I'm going to go and do.
Brent: I think the word sabbatical too is, I think in today's day and age, there's so much talk around jobs and careers and how things are disappearing, how AI is taking over the world and all of these things. So there's a lot of fear. I don't want people to walk away from this conversation to say, Hey, Robin Brent said I should take a sabbatical and everything will be fine. There's a planful side of this. There are certain employers that would welcome it.
There are certain employers that won't. So you have to be prepared for that. But you also have to go back to what you said, Rob. You have to trust yourself and you have to trust yourself. If you say, I'm going to take a year off, then you have to trust yourself that you're going to be successful after a year in whatever you choose to do.
Whether you go back to the same space that you're in or you decide to do something different, you have to trust yourself. It is a risk. But the last thing you want to do in a sabbatical is spend the whole time worrying about what your next thing's going to be. You want to actually take advantage of the time. So what I usually tell people is if you're trying to explore your next great act, and I shared this with you, Rob, when you were about to step away from your last job.
If you have the opportunity to take three months, take three months. No matter what you do, take three months. If you have the opportunity, and if you know you want to go do something different, completely different in your career, take three months to go figure that out, but take that pause because a lot of clarity comes with space. And when you have time to think about things, then it's going to be, you'll get stir crazy a little bit because you're going to try to figure out so much in the first five days. But then if you allow that space, I think it's important.
Because what we're trying to relay here is if you feel itchy and you know that you want to do something different, then there's an opportunity to step back a little bit and explore the optionality. And we gave you a few ideas. Your sister's example is excellent. That is one extreme where sell everything and move to a new location and do essentially a massive reset. Then you gave an example where, Hey, I had some friends that decided to downsize, which gave them greater flexibility to travel, live in other locations.
It was an important time in their life that they could do that, so they made the choice to do that. We've had other friends that have done just sabbaticals. So they're not ready to fully commit to something massively different, but they're going to take some time and space to do that. There's a lot of ranges here. And that's something that I think about is if you allow yourself to get creative with this, my guess is you're going to explore lots of ideas and it can be a ton of fun.
Rob: Key point there, Brent, was to give yourself the space. If you're going to do the sabbatical, you're going to step away, you're going to try something new, is to give yourself space before you jump in with both feet. Because you might find out that that one thing you thought of isn't the thing that you want to go and do. And don't be worried if you gave yourself a year, spend the year doing the experiences and having the learnings, taking the classes that you want to take to develop yourself because the new person that comes out of that gap and out of that period of time is vastly different. I'll tell you that from personal experience.
From my three months of not doing anything, I was vastly different after those three months, and I extended mine to more like five and six, but I was a totally different person than I was when I jumped right out of work. Right? When I left work, I was still the same work Rob, not the new Rob, which is I hope to be feels like a better version of myself.
Brent: I've been asked to our listeners, if you know of somebody that is a really good example of they've made a shift, they've really taken that leap into their next great act, or you've done it yourself, could you head over to our page on Substack and just share that example? All you have to do is just hit this episode and just drop it in the comments because that's helpful. That's helpful for the Midlife Circus community to see other examples, not just Robin Brent's examples, it's other people's examples of what they've done. Because all this is trying to give people ideas. And what we really pushed on this episode is if you're going to delay this, you're going to delay it, you're going to delay it.
You might get stuck delaying it for a long, long time. So is there a possibility to do this now, Six months from now, a year from now? Is there different alternatives? I'm going to ask you a question because this is another close friend of ours that I think you and I have been in separate conversations with him over the last year where he has clearly said, I really want to do something else. Really, really want to do something else.
Rob: I know I need to leave.
Brent: I know I need to leave. What is your coaching or advice to him?
Rob: Just do it. He knows it. He's causing himself angst and anxiety. Just do is a phrase that came out from Nike in 1988, Brent, so it fully sits into our generation. Just do it.
You're not going to look back with regret at what you lost. You're going to look back if you don't make the changes that I wish I would have. He knows he needs to. That's why he keeps bringing it up to us.
Brent: And the layer that I would add on top of this is trust yourself. You've done so much in your career to get to this point and you have this massive skill base that you've built. And it doesn't mean that you have to go explore something in your existing industry. You might be able to apply that. Think back to that episode we did with Ron, our guest, where he was exploring his next great act and he went to law school, which was a complete departure of what he was doing prior, but he just went for it.
And now he's thriving because he went for it. He took that leap of faith. The challenge I'll leave that friend of ours is if you're waiting for the perfect clarity, it's not going to come. Perfect clarity just doesn't exist. It's not like it's just going to fall into you like, Oh, this is my next great act.
I'm going to start tomorrow. You got to create some space for it. It's like, you got to be planful, you got to be thoughtful, but if you keep ruminating it year after year after year, then you're taking away from your true gift of exploration, curiosity, and just trying something new. And yes, it will be challenging, believe me. But will it be rewarding?
I absolutely think it will be. It's just a matter of trusting yourself and taking on that courage.
Rob: It's funny you said ruminate on it, Brent. That's what I did. I ruminated in the decision for a long time. I knew I needed to do something different. I was just afraid to do it because of what might happen.
And the person we're talking about would crush it at anything that he went and did. And most of our listeners would go and crush it at anything they go and do. If you're excited about it, you're going to do great at it. That's the thing.
Brent: So that is not just intended for one person of our listeners, that's intended to a lot of our listeners. There's a moment in time where if you're trying to find the perfect solution, it doesn't exist, but if you trust yourself, then I think you can go accomplish great things. Your next great act is just right around the corner.
Rob: Any final thoughts on our discussion today?
Brent: Well, I think we just summed it up pretty well right there. Let me close on my thought process as my own personal process. This was a challenging time for me of trying to figure out my next great act. And it was difficult because I had so many things that I wanted to do. And I do need to earn an income.
I've got one kid in college, another kid going to college. So there's all these expenses that are coming in, But the one thing, and you've done a great job with me over the years is, if you look back in your career, Brent, you've done a lot of amazing things. You can apply those things and just don't get too caught up on, it's not going to be identical to what you had, but maybe there's something better out there. And I just encourage people to think about it a little bit more broadly, but trust yourself, challenge yourself. And guess what?
If it doesn't work out, then you'll figure that out too. And that's an important part of the journey. But I do want to lead people, and I think this is important part of the conversation too, is you got to be thoughtful with this. This is not us saying knee jerk, just leave your job tomorrow and all of sudden you got zero income and you don't have, if you have zero savings or you're in a lot of debt. That's not a great solution.
That puts more risk and stress on yourself, but there's a process to start to think about all this. So take in your financial situation, your relationships, all the things in your life, and just start to have those inner dialogues, create space for it. We've talked in previous episodes where solo retreats, Rob, I think would be a really great way for people to explore this, where go spend some time by yourself for half an hour, hour, if you've got the opportunity, maybe it's an overnighter to really explore this and really sit in your thoughts for a little bit, you might get a lot out of that.
Rob: I leave with a couple of thoughts. One is, are you more afraid of running out of money or wasting your life? Especially at this point in our life with the limited days we have left as we talk about that we're terminal. There's a finite number of days we all get left. Unfortunately, we don't know when that ends.
Time and health are your most important assets. Start to treat them that way. Brent, you mentioned, you know, don't jump into this, and we want people to be bold, but we want people also to be planful. And so don't just jump into this on a knee jerk reaction and go into your boss's office tomorrow and say, quit. Robin Brent on midlife circus said, I'll figure it out.
We're not telling you to do that. There's probably other people in your life you want to get involved in this decision. So I would say share this pause test with your spouse or significant other. Share it with a trusted friend, and then go and have a conversation around what might be next. Why what resonated with this episode for you, and what are you thinking about you could go and move on to?
So share it with some other people to actually get their insight on you, and they might actually come back with some of the best encouragement they could have like we just did for our friends. Like, you could do this. You're going to be incredible no matter what you do and give you that sense of confidence you need to be able to make that change. I said, Brent, just do it came out in the eighties. Why wait?
Our health isn't getting any better. It's only going to get worse. We can over a longer period of time. Now is the time to enjoy what you've worked so hard for. And how much longer will you delay that gratification?
Don't sign yourself future self up for any regrets. Remember, you're the director of your next great act.
Lena: That's it for this episode of Midlife Circus. Visit midlifecircus.fm for show notes, transcripts, and all the latest happenings, and be sure to join us in the Midlife Circus community on Substack. Follow Midlife Circus on Apple podcasts, YouTube, and wherever you get your podcasts so you never miss your next great act. Quick reminder, the opinions and stories shared here are personal reflections, not professional advice. This show is for entertainment and inspiration only.
Thanks for listening, and we'll see you under the big top next time. Midlife Circus is a Burning Matches Media production.