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Published on:

15th Aug 2025

Portfolio Life: Building Purpose and Freedom After Corporate with Joy Levin

What does “retirement” really look like for Gen Xers—and why do so many struggle with it?

In this episode, I sit down with Joy Levin, market research consultant turned retirement coach, who helps Gen X professionals design their encore years with purpose, connection, and freedom.

We dive into:

  • Why retirement is no longer a five-year chapter but a 30-year journey—and what that means for planning.
  • How our latchkey kid upbringing shaped Gen X resilience, adaptability, and desire for freedom.
  • The social side of retirement—why isolation is one of the biggest post-corporate risks and how to avoid it.
  • Common mistakes people make when transitioning out of corporate life.
  • How to create your own “portfolio life” built on purpose, flexibility, and joy.
  • Why couples need to plan their next chapter together—before one person books the world trip and the other says, “But what about the grandkids?”

Whether you’re years away from leaving corporate or already in your next chapter, Joy’s insights will help you think bigger, plan smarter, and make the most of the decades ahead.

Connect with Joy Levin:

• LinkedIn: Joy Levin

• Website: Gen X Exec Encore

Transcript
Brett Trainor (:

Hi, Joy. Welcome to the Corporate Escapee Podcast.

Joy Levin (:

Hey Brett, I'm so excited to be here.

Brett Trainor (:

No, no, my pleasure. Anytime we've got folks that work with Gen Xers and improving our lives and I think you call it the encore, which I love. I'm super excited to have you on. I know we were talking offline and we should hit record. the challenge is up to us to make sure we bring that same conversation now that we've hit record. I think there's actually a whole series for me. That's going to be before we hit record that I've got to figure out how to, how to capture.

Anyway, that's on me. So welcome and maybe to get us started, just share a little bit about what you do. Now, would you say you have a dual path? Are you still doing some consulting with small businesses and the coaching with General? Okay.

Joy Levin (:

Yeah, yeah. actually, yeah, so I started out, I've been a market research consultant for like 30 years. And so it's not really small businesses that I work with, kind of mid market and large companies, everything from Fortune 50 to, you know, really large companies. And so over all those years, I was working with executives at these companies to understand what strategies are going to work for marketing and looking at the data and all that kind of stuff.

And so I love that I still do it. But in the last few years, there were a couple of things that happened. For one, I started to think, you know, I've been doing this for 30 years and I've always been this kind of naturally curious person wondering, gee, I wonder what it's like to be a lawyer or whatever it is. And so I started thinking about what else is it that I would like to do? And then the other part of it is,

you know, just talking to my clients, we would get beyond the business and strategy conversations and they would talk about their own personal lives and how they, some of them were starting to think about retirement. But just saying, I have no idea what I would do. Like this is so much part of my identity and that's such a common theme for a lot of people. And so putting all that together, I went on my own personal journey and found retirement coaching and was really excited about it and enjoying it. So yeah, I still do both.

I love both. Yeah.

Brett Trainor (:

Yeah, no, it's that's often so we've kind of similar path. You just found it much earlier than than I did. And, you know, I think it's it's interesting because we both, you know, kind of hit that curiosity stage again. And I'm not sure if that's just a Gen X or that we hit 45 or what if there's a magic age number if we were burned out, I don't know what triggers it. But there's a lot of folks that have either rediscovered the curiosity and creative I know, maybe not mutually exclusive, but

Yeah, it's interesting that you found that as well. So how did you, go ahead, sorry.

Joy Levin (:

Yeah. no, I was going to say, there, think there are some things that are unique to Gen X that are making us curious. And I mean, for one thing, you know, if we roll back the tape way back when people, know, when retirement was first a concept and social security was kind of a concept that had been implemented, people were living on average, maybe two to five years into retirement. So now it's like 30.

And so that's been, had a huge impact because people think I've got to find something to do for 30 years, you rather than just five. And I think something else that's different is, you know, our generation is so resilient and adaptable because of what we've been through. You know, you think about everything from the energy crisis to, you know, 9-11 and then going back again to the challenger. We've seen so many times where we've had to recover from a crisis.

And so I think that also makes us very resilient and adaptable. And so because of that, we start thinking, okay, what else could I do? It's kind of a mindset that I think is kind of unique. Yeah.

Brett Trainor (:

Yeah, no, I think that's such a good point. didn't even think about it that way. Cause I always go back to the childhood, the latchkey kids and it's over generalized sometimes, but it's true, right? We didn't have the cell phones. We didn't have any of the digital. You did have to go figure out how to get things. We didn't have helicopter parents, right? None of that was there. So in our youth, we did have to figure out how to take care of ourselves, get things done, and then we get put us in that corporate box. I think even doing what you're doing, even though it wasn't in corporate, you kind of put yourself into a box, maybe a little bit.

Joy Levin (:

Yeah.

Joy Levin (:

Yes.

Joy Levin (:

Right?

Joy Levin (:

Mm-hmm.

Brett Trainor (:

started doing the same things. And in corporate, you're rewarded for not rocking the boat and you're not taking chances and being a good soldier and doing all these things. I think at some point we all just hit that breaking point of where it's going. I think one of the things that, again, my uneducated or no research theory is the pandemic kind of opened eyes, right? That holy.

Joy Levin (:

Mm-hmm.

Joy Levin (:

yeah.

Brett Trainor (:

crap, we built our lives around these corporate jobs. What the hell are we doing? Because we got a taste of a little freedom and control. So I think it's kind of the perfect storm. And I hadn't thought about that, the adversity part of it, but you're absolutely right.

Joy Levin (:

Bye.

Joy Levin (:

Mm-hmm.

Joy Levin (:

Yeah, and I think the point you bring up about Latchkey kids, you we became independent very early. You know, it was like, this never happens now, but it was, okay, it's after breakfast, I'm going out on my bike, see you at dinner time. And it's just so scheduled now and just, you know, it was so different. And I think our minds got conditioned to think about freedom differently and, you know, a lot of opportunity to have that freedom again. So I think that that plays into it as well.

Brett Trainor (:

Yeah. Or we stopped thinking about it, right? Because it was just life. We didn't know it was freedom. was the way you grew up. And then you went into, you did what you're supposed to do by going to corporate and different paths. And you just kind of forgot. I mean, cause I think about some of the things we did, it must've been second or third grade. We didn't live too far from a golf course. And, this golf course was over a canal and it literally was a canal. So this isn't a river stream. It was a canal. so

Joy Levin (:

Right, right.

Joy Levin (:

Mm-hmm.

Joy Levin (:

Yeah.

Brett Trainor (:

there's rats and everything down there. But what we would be able to do is go fish, find golf balls, and then turn them into the halfway house there for food. I mean, this second and third grade, I'm like, I'm thinking, I wouldn't let my high school. But it was just the world that we lived in, I guess, right?

Joy Levin (:

Yeah.

Joy Levin (:

It is so different, yes.

Brett Trainor (:

All right, so again, it's always good to go back in time. let's talk about kind of what you're seeing with clients that are coming to you. What are some of the big challenges? I think you maybe mentioned a couple of them. Then after a bit, we'll get into kind of how you recommend folks thinking about retirement or maybe retirement's not the right word anymore.

Joy Levin (:

Mm-hmm.

Brett Trainor (:

I'll pause that thought, but I'd like to hear, you know, the folks that come to you, what are some of the challenges you're seeing?

Joy Levin (:

Yeah.

Joy Levin (:

Yeah, you know, I mean, first of all, there's research that's been done that shows that like three quarters of retirees have seen others struggle with transition. And so that impacts how they're going to perceive their own, you know, they think, that going to be me? And then also there's a good proportion, like four in 10 report that it's harder to adjust to retirement than they expected.

and a similar percentage say it's taking longer than they expected. So all of that really, you know, they end up kind of having these visions of what retirement will look like, like I'm gonna travel, but you can't travel 365 days a year, or you're gonna do these different activities. And so I think that's one part that's a challenge is having certain beliefs about it and then realizing those beliefs are not really born out in reality and struggling with that part of it.

So that's one thing. And I think also socially, know, we kind of retire, a lot of people do, and they find that, you know, either their friends are still working or they've moved and they have to build a whole new social network. And that is a real challenge for a lot of people, especially, you know, when you think of people in corporate America, they've kind of had a social life delivered to them through their work, right? You know, there's the water cooler conversations, there are people they make friends with.

And now they're kind of on their own and haven't really had to work to make friends since like high school or college. So they've forgotten those skills and they are skills and how to do it and you know, kind of what different friendship roles fulfill for you. So there's that piece as well, that social part and that really has an impact because what happens to a lot of people is they find themselves isolated.

And that isolation is so bad. I mean, we are social beings and to kind of be isolated all the time really leads to a lot of depression. So we definitely see a lot of that where people are just like out of sorts and they feel like kind of the rug was pulled out from under them. They didn't plan for that. So one of the things I find that's helpful in a lot of these cases is to kind of have these conversations before you retire, like three to five years before two to five years to kind of say, okay, this is

Joy Levin (:

kind of what I'm thinking, and then this is the reality. So how do I set myself up now so I don't have this longer period of adjustment, so I don't go through this isolation? Because there are a good number that report feeling very lonely and isolated when they do retire. So a lot of it is kind of recognizing that that could be a path and then doing things now to prevent that from really happening. So that's a lot of what I see is.

those kinds of issues. And then there are issues that couples have, like one person, the couple says, we're gonna travel. And the other person's like, I'm not sure, you know, we have grandkids now and I don't think I wanna travel as much. So, and that can cause conflict. there's a whole host of issues we see that, you know, I find that people come to me with that, you know, or need to have a conversation about.

Brett Trainor (:

Yeah, so true. And so many things to unpack there. And I think maybe the first one, going back to the social aspect, because one of the things I thought when I started the collective was more strategies and tactics, right? How to make money and do these things. But one of the biggest things I'm finding is the value is the connection, right? That

Joy Levin (:

Absolutely, yeah.

Brett Trainor (:

people and it was funny because by the end of the career, my career, it was, it was different, right? I wasn't choosing my coworkers anymore. It's just who I, who was working there and you like some, you didn't like some. So when I read, but people tell me that, well,

Joy Levin (:

Right.

Brett Trainor (:

Right. You had coworkers, you got to replace it. I'm like, most of them I didn't like or not. didn't like, but I'm not going to go hang out with them. So you have the ability to choose, but I did find a lot of folks that joined the collective came from really good teams or people they really enjoyed working with. And they really are going through the, as you mentioned, the tougher transition from a social that. Right. They are isolated in doing it. And, um, it takes time to get there, but yeah, it's a big piece of it.

Joy Levin (:

Yeah.

Joy Levin (:

Mm-hmm.

Joy Levin (:

Definitely. And it can take longer than people think it will. And that's when they start to feel like, oh my God, this is not going to happen. they just need a little coaching on how to get there a little faster. And that can make a big difference. Yeah. Yeah.

Brett Trainor (:

they're not alone, right? I think that's one of the bigger things. And it's funny, you mentioned, right, couples 100 % we went that was your last point, we went through and we're still working through it. Because one of the things my wife's like, well, we had to make sure we've got enough money for retirement. I'm like, what is retirement, right? I'm not going back corporate. So in the traditional sense, I'm retired from corporate America. And, you know, putting those definitions around X is right, if you live another 30 years, hopefully healthy.

Joy Levin (:

Yeah.

Joy Levin (:

Right.

Brett Trainor (:

Right. That's a long time. And unlike previous generations that did have pensions, right. Which lifetime paychecks we don't have that. And I don't know about you, but we're not going to be comfortable living on a monthly draw off of a 401 K which with the things that we want to do and those types of things. so, you know, the other thing that I found was a big transition that I did not appreciate. So folks out there listening that are still in corporate think through this is

Joy Levin (:

No.

Joy Levin (:

Mm-hmm.

Brett Trainor (:

My wife really didn't necessarily know what my job was, right? But what she did know is I was getting a paycheck every two weeks and we had benefits that were covered on everything. Now when I went solo five years ago, all of that's gone. Still doesn't really know what I'm doing, right? Hitting my little radio show and she doesn't joke with it anymore. in the early days, right?

Joy Levin (:

Mm-mm.

Right.

Joy Levin (:

Yeah.

Brett Trainor (:

She had no idea, right? The uncertainty she faced was so much worse than me because I could at least see and control where it was going. But until I brought her in and I shared on the podcast before, we do a quarterly business review where we kind of reset life and the business. I bring her up to date. I say, what are we looking at going forward? What expenses do we have that we need to think through? As you talked about, one wants to travel. Do you want to travel? Our original plan was before...

Joy Levin (:

Mm-hmm.

Joy Levin (:

Mm-hmm.

Joy Levin (:

Thank you.

Brett Trainor (:

When we got older, we spent half the time down in Florida because that's traditionally what you do. But guess what? We've got a granddaughter up here now. That's completely off the table. Both of us realize that we're not going to do that. I think it comes even to a bigger conversation that in corporate, you just really don't ever decide what you want. There's things you can do based on what you're getting. But yeah, where do you want to live? What is the type of work you want to do? How much do you want to work?

Joy Levin (:

Mm-hmm.

Brett Trainor (:

I, again, if you, you would have had this conversation with me five years ago, you probably would have helped me accelerate that because right. was a couple of years of plotting and figuring out. again, we're still figuring it out, but you know, it's, sounds simple, but it's so important.

Joy Levin (:

Bye

Joy Levin (:

Yeah.

Joy Levin (:

Yeah, and I think, one thing you said about still figuring it out, I think that that is actually a positive and that's kind of reality is that things change. You know, what if one of your kids moves away and they have a grandchild over here or well, what if, you know, we decide that we want to invest in something and it's over here. So there's, you know, it requires, it's not just a one and done thing. It's something you revisit.

over the years. mean, so many changes, your health changes, you know, all kinds of things. And so you, you know, it's something that you want to constantly kind of re re-evaluate just like you're doing. I love that idea. I that's great. Yeah.

Brett Trainor (:

Yeah. And we've, we've started to make it a little bit more fun. We broke it into two, so we'll go out and do something again, you know, but then we will review the numbers at home when it's just the two of us, but then we'll go out to movie dinner, something to, to celebrate it. So yeah. So I highly encourage folks to, I know some people do it on a monthly basis, but we would just find a quarterlies gives it enough time, gives us enough time to reset everything and talk through. And, again,

Joy Levin (:

Yeah, you gotta make it fun. Yeah.

Joy Levin (:

Exactly. Yeah.

Joy Levin (:

Right.

Brett Trainor (:

Probably should have been doing this through my corporate career. would have been a hell of a lot easier, right, are some of the discussions that we had after the fact. But hey, better late than never. So, all right, so let's go through kind of, you've been doing this for a while. Now what is, what's kind of your approach though? If somebody's news coming to you, how do you, I mean think we got a little bit of a sense of how you work with folks, but what's your approach to this? How do you help people get through this transition?

Joy Levin (:

Yeah.

Joy Levin (:

Exactly. Yeah.

Joy Levin (:

Mm-hmm. Yeah, you know, like I said, I have like tools and exercises that I will take them through and it varies, you know, we'll find that some people want to, need to spend more time on like making sure that they're still relevant to others, you know, and so that's one thing we can work on or it could be.

Brett Trainor (:

interesting.

Joy Levin (:

you know, their health or it could be their social network or it could be what's going to be their passion project or their legacy. So that one of the first things we do is we sit down and we look at kind of we call it like a wheel where we say, okay, here are the different segments of the wheel. What's your satisfaction level in those different areas? How much time do you spend in each area? How much time do you want to spend in those areas? So it creates kind of this map where you can say, okay, here are the areas that need the most attention. So we'll work on those.

And usually we end up hitting a lot of different areas, but it helps to kind of focus initially on one because then you can start to see, okay, these are solvable problems. I'm getting a lot more clarity and I'm feeling a lot more confident. And so that helps you to kind of say, all right, now let's move on to this other area. So if we attack the social network first.

then we can attack, okay, well, we're thinking of moving. So what's that gonna look like in this new place? How are we gonna create that social network there? So, you know, it's just kind of a set of tools and worksheets that we go through that are customized to deal with each of these different areas and make sure that we develop this holistic kind of picture. And I call it like a portfolio life because, you know, a lot of people say, well, I've got my hobbies I wanna do, but I wanna travel, but I also want...

you know, to create something of a legacy. And so we kind of put it all together. And then at the end, it can be a spreadsheet, it can be a vision board, whatever it is, but I designed something that they can take away with them. And so it's concrete and they can look at it and then reassess it over time if they want to. So that's kind of how it works on just an overall level. Yeah.

Brett Trainor (:

Yeah, it makes sense. And again, I take that holistic approach. In hindsight, a lot of the things you would have saved me, you know, a couple years of the journey, because when I left, it was purely to make more money. He was financially driven. But as soon as I got a little bit taste of the freedom and the control of it, again, once I figured out how to get my schedule under control, those things, I'm like, Whoa, this is way more important than the money. Money is still important. It's always going to be important.

Joy Levin (:

Mm-hmm. Mm-hmm.

Joy Levin (:

Yeah.

Brett Trainor (:

It's a tool to get you to the other things that you need. But I didn't realize that how much what I was driving for wasn't the financial. It was the purpose. was, you know, what do I want to do? Again, it's going to sound super simple, but, you know, the way I've kind of looked at it, what's giving me more energy than it gave me the day before? And...

Joy Levin (:

Absolutely.

Joy Levin (:

Right?

Joy Levin (:

Exactly. Yeah.

Brett Trainor (:

When I started solo consulting, was definitely more energized. This is my own thing compared to what I was doing in corporate. Then over time I discovered, you know, fractional leadership. like, all right, this is giving me more, I don't like project plans and stakeholders. And over time I just kind of figured out how to monetize my corporate experience in different ways. But it wasn't until the corporate escapee kind of, I started as a passion project, but again, for six months people heard the story.

Joy Levin (:

Mm-hmm.

Joy Levin (:

Mm-hmm.

Brett Trainor (:

It was crickets and then bright place, right time on tick tock. And, I've got 10 X the energy from doing all of this versus what I was doing before. And I think, you know, I don't want to put words in your mouth, but it sounds like some of the coaching you're doing energizes you more than maybe what you're doing with the research portion of it. think you need to have more than one.

Joy Levin (:

Yeah.

Joy Levin (:

Mm-hmm.

Joy Levin (:

Yeah, I mean, I think they energize me in different ways. And that's kind of like what I see the benefit of is like this portfolio life kind of thing, because each thing can kind of give you different energy. But you're right. I mean, a lot of it is finding purpose. there are like, there is the small things that give you purpose, like, OK, today I'm going to do X, Y, Z. I'm going to work on this today. And then there are the bigger things that give you purpose, like, what's a nonprofit board I want to work on? Or what's a

a thing I want to do that will have an impact on the world. And it could be a different career. Like a lot of people find, you know what, I want to do this. I never thought about it. But when I look at my values, which is another hugely important part of this, to make sure that what you do aligns with your values. And when they look at that and they look at what their values are and what they enjoy and how they want to spend their time and who and all those questions, it can really create new opportunities they hadn't thought of.

So, yeah, that's like, think a hidden benefit to a lot of this.

Brett Trainor (:

Yeah, for sure. Yeah, again that we don't realize coming back out of corporate that you don't realize what you're missing until you actually start to see it again. And kind of curious too from your work with folks, it, do they realize that there's a big beautiful world out there? they kind of siloed in their thinking and they just kind of open it up?

Joy Levin (:

Yeah.

Joy Levin (:

Yeah, I think it's different for different people. Like some people are siloed and or they'll think I know exactly what I'm going to do. But then they realize, but I don't know how to get there. And so we work through that for other people. It's it is a just an eye opening thing where I never realized this. You know, like I worked with an attorney who decided she wanted to write a book and had never thought about that, but realized

some of the things she valued and some of the ways she liked spending her time aligned with that. So it can kind of swing a couple of different ways. It varies from person to person. Yeah, I mean, that's been my experience.

Brett Trainor (:

Yeah, it's kind of interesting too because I do view different projects now as things, right, that I want to do like the book. I'm in the process of finalizing a book, but my wife will say, well, is that going to make any money? I'm like, no.

Joy Levin (:

Yeah

Brett Trainor (:

Unless the rare instance, but so, part of it is still, even though she's on board with a lot of the business stuff that we still have to communicate, right? That there are certain things that I want to do that, that aren't going to push the business forward, even though it will indirectly, but it's kind of finding those projects and paths that, um, portfolio. love that. That's a great way of thinking of it. Not because I was thinking portfolio career. can make money different ways, but it's really about.

Joy Levin (:

Mm-hmm.

Yeah.

Brett Trainor (:

your portfolio of life and where you're focused. I think that's, we don't focus on a lot of the other areas nearly as much as we should.

Joy Levin (:

No. Yeah, I mean, because it's like these are conversations that we just don't typically have, you know, and we've been wired to think of retirement in a certain way as we grew up and watched our parents retire. And, you know, we just didn't didn't see this side of it. Nobody talked about it. So the positive is that people are talking about it now, but it can be very overwhelming to figure it all out.

So, you know, there's that part of it too. It kind of depends on the person and how they're approaching it and what their experience has been, you know, and how they've been shaped a lot of it too. So, yeah.

Brett Trainor (:

Yeah.

Do you find a lot of folks actually had a plan? Right? Cause I don't know, just give you my, I didn't have necessarily a plan. I'd never thought through of what, when I'm done working, right? What's the number I have to have in retirement in order to do this. It just never crossed my mind. But when I hit 50, all of a sudden it hit me. like, I'm not going to get to the C-suite, right? So there's not going to be a huge payout. That's going to allow me just to do whatever I want her to do nothing.

Joy Levin (:

Mm-hmm.

Joy Levin (:

Mm-hmm. Mm-hmm.

Brett Trainor (:

And I'm finding again, just overgeneralized, lot of millennials are getting to this point now in their right mid thirties, early forties of what's the end game with this, right? Because we don't have those pensions. And I still talk to a lot of Gen X that are still in corporate that they don't have a plan. Right. And so again, not just the financial, but to your point, that that whole portfolio we don't think through. So I'm curious is a lot.

Joy Levin (:

Yeah.

Joy Levin (:

yeah, yeah.

Joy Levin (:

Right. Right.

Brett Trainor (:

Do a lot of the folks that come to you have a plan or do they know what the exit strategy looks like?

Joy Levin (:

Yeah, I mean, sometimes it's kind of vague. Like it's, okay, I know I don't want to be doing this in X more years. I'm not sure how I'm going to replace it. And I'm not sure what my life is going to look like. So what happens on a lot of times is they'll go beyond that time and continue to work because they don't have a plan or they it's too big for them to think about too unmanageable. So they just keep working to kind of

you know, avoid dealing with all that. Cause it's easier. There's a known quantity. I know I'm going to, whatever, I'm going to get up, do this, do that. Whereas this is like, I don't know what the heck I'm going be doing with all that time. So, you know, and you're right, the financial end of it is clearly important. you know, not to take away from that, but I just think people are realizing that it's so much beyond numbers that we really need to think about. And you can't, you know, you can,

Brett Trainor (:

Yeah.

Joy Levin (:

procrastinate it or avoid it, but at a certain point you just get so frustrated. Like, this is not what I wanted to be doing. And then there's also like people who think, I want to do this and this and this. And then it's like, they can't figure it out. And so it's that paralysis by analysis kind of thing where they just are like, you know, like there's a million directions I could go in. I can't figure it out. So I'll just keep doing this. Yeah.

Brett Trainor (:

Right and get more and more unhappy because that's the other thing I found I've yet to find a person That's left corporate that

Joy Levin (:

Yeah.

Brett Trainor (:

that wants to go back, right? I I use Lainey all the time and she appreciates because she was on the podcast maybe six, eight months ago and she has been out like seven or eight years she got out and I just throw him like, Lainey, would you ever go back to corporate? And she's like, Brett, I'd rather be homeless than go back to corporate, right? And so I think that's the way we all feel. And I know some people have had to go back to corporate to reset, get some financial runway, redo some things. So I completely get it, but they know they're heading out so that I can't find a single person that wants to continue.

Joy Levin (:

Right.

Joy Levin (:

Yeah.

Joy Levin (:

Yeah. Yes, right. I mean, I do find people who want to try something different, but don't want to do it full time or be in a certain environment. So there are so many opportunities, especially now with technology and everything to do your own thing and or find something part-time or fractional or whatever it is to continue to, you know, have relevance in that way while also doing other things. Yeah.

Brett Trainor (:

down that path right?

Brett Trainor (:

Right. Yeah. Yeah. Yeah. Cause one of the things to hindsight, I get just the mental state because, and I've written about this before too, but when I was, cause I went into management, consulting after corporate, which is just corporate and steroids and some instances. And it was about a year and a half or two years out. Maybe it was our first quarterly review I did with my wife. She just, she's like, what the hell was the matter with you? Right. And that was when I was still in, in consult.

Joy Levin (:

Mm-hmm.

Joy Levin (:

Mm-hmm.

Brett Trainor (:

Good job, right? Work I generally liked. The family was doing great, but it just, something was off. I wasn't happy. Um, it was just all that what we kind of talk about when you get to 50 or 45, didn't have the energy anymore. And now I buggered the other way being too optimistic and you know, it's my nature to be more that way, but, but she'll say she'd rather have me this way than the other way. But, but yeah, I mean, do you find,

I don't know again the science behind that or if it's just I was in a bad situation with work. I just think I got to a point where I needed something else and I just didn't know what that was.

Joy Levin (:

Yeah, I mean, that's very common. You like I said, you're so tied to an identity for so long. I've been a doctor. When you go to anywhere, you introduce yourself. What do you do? I'm a doctor. I'm a lawyer. do, I'm a firefighter, whatever it is. And then all of a sudden that's gone. And it can be very freeing. just, we have to find things to replace it that are fulfilling. And it just, so what I do is I kind of short circuit that.

that thing that can take such a long time to figure that out. Yeah.

Brett Trainor (:

Yeah, it's so helpful. And again, just talking to somebody else, getting it out and understanding. I think part of it is we all think we're on our own. We're the only person that's going through this. And one of the mistakes that I made was for the first two years really didn't tell anybody that I was out on my own. I'm like, that's the dumbest thing I've ever done in my life because there's no reason not to tell my network. They could have helped and they found people to be super supportive and helpful.

Joy Levin (:

yeah.

Joy Levin (:

Right. absolutely.

Joy Levin (:

Mm-hmm.

Brett Trainor (:

You know, it was more targeted and selective networking and I'm like, what was I thinking? And I don't know. I can't, maybe it was again, my identity, it was now different and I don't know. I wish I did know, but I'm super fascinated by this. And that's why I have guests that talk about this to help me think through some of my old, so we can save some folks going forward.

Joy Levin (:

Yeah.

Joy Levin (:

Right, because you're right, think they're alone. Nobody talks about this stuff, you know. It just, we have this vision, I'm retiring. Life is gonna be perfect and ideal. And then, you you retire. And for a lot of people, there's a honeymoon phase where, you know, my gosh, I can do this. can, you know, do this in the middle of the day. couldn't do that before. I can see my grandkids. can, but,

then there comes for a lot of people, for most people, a certain point where they're like, I'm needing something else. I don't know what it is, but this is not what I thought it would be. I cannot spend 30 years on a golf course.

Brett Trainor (:

No, no, I'm with you. I'd like to play golf. I like to work out I like to but these days are long to not do it. met somebody in my network who's I think he's just either 76 or 77. He's starting another company now. And because he year ago or 18 months ago sold off an agency that he created built it successfully. He's like, right, I need to do I'm figuring out something that's gonna be more part time, but I

Joy Levin (:

Yeah, exactly. Yeah.

Joy Levin (:

Mm-hmm.

Brett Trainor (:

leveraging the skills I have that I need it. I'm like, that's, that's what I'm going to do. Right. At 77, I want to start something new and figure it out again. But I think the differences and what you talk about is it's on your terms. It's what you want to do, not what you have to do, which I think is the biggest thing that we're fighting, right? If it would be super simplified or that you have to go back into corporate, do these jobs to pay your bills, to do it, or do you get to, or do the things that you want to do? Right. It's just, um,

Joy Levin (:

Yep.

Joy Levin (:

Right.

Brett Trainor (:

curious to see because one of the things that again really surprised me over the last 18 months working with probably a close to a thousand conversations now with folks and the key difference and success is in the eye of the beholder but it gets success quicker in their mind is they take action right it's I don't know if we're wired and not take action or we're just in corporate

Joy Levin (:

Mm-hmm.

Joy Levin (:

Mm-hmm.

Brett Trainor (:

tells us to analyze analysis paralysis, right? Same type of thing that, you know, people with limited skills or experience are doing to by just going to have conversations and going and doing it. They're winning businesses. They're doing different things where there's folks that I need the perfect website or I need the perfect pitch, the perfect proposal. And it just can't get them to take action. And I'm finding it's two camps, different degrees in there, but there's folks that are willing to just go.

Joy Levin (:

Right, right.

Joy Levin (:

Mm-hmm. Mm-hmm.

Joy Levin (:

Yes.

Brett Trainor (:

than others that are like, it needs to be perfect. So any suggestions on how to help people drive? Because I have not cracked the code on that one yet.

Joy Levin (:

Exactly. Yeah.

Yeah, I mean, you're right. think that there is a group of people who are perfectionists who say, can't do it until it's perfect. So part of that is realizing, because a lot of people don't even realize they're doing that. It's OK if it's not perfect. So it's kind of getting to where you feel like, you know what, it's OK enough the way it is. And that's very hard for a lot of people.

Brett Trainor (:

All right.

Joy Levin (:

But I think the other thing is when you say taking action, it can be very small actions, but that will get you started and will increase your momentum. So if, I don't know, it could be something like, you know what? I've wanted to, you know, be on the board of a nonprofit. Okay, so the first thing to do is just to take the action of just looking for those nonprofits out there. You know, who's working in that space?

What are the kinds of things they're doing? What are the different nonprofits? And then volunteering for it. And then maybe leading a committee. But kind of at least taking those smaller actions just to do some searching or whatever it is can create that forward movement so that you get out of that sort of has to be perfect. I have to find the perfect organization on day one. And that's just, you know, it can create like, well, that's not it. And that's not it. And so you're never getting there, but

by sort of saying, okay, I'm gonna find one and then I'm gonna see there are things I like about it and things I don't. So now I know when I look for the next one, what to avoid, what to look for. And so taking the small action steps can be a big way to overcome some of that sort of indecision or inability to take action, yeah.

Brett Trainor (:

No, it's such a good point. And I was at like, setting and consulting. I had a colleague that used to remind me all the time, he's like, Brett done is better than perfect. And so when I went into the world, it still sticks with me and I still get stuck sometimes doing that. yeah.

Joy Levin (:

Right?

Joy Levin (:

It's hard. It's hard. Yeah. Especially for people who, you know, expect a lot of themselves who are very driven, very ambitious. You know, it's really hard to, what is that expression? Great is the enemy of good or something like that. And so to say, okay, this is good. Let me just start here. Yeah.

Brett Trainor (:

Yeah.

Brett Trainor (:

Yeah, I'm curious about another, again, I've had a lot of self-reflection over the five years and it's trying to figure out again, hindsight's easier than looking forward. But I think one of the things that I found, I don't know if this is age or just the freedom is I really don't care what other people think anymore. I mean, I do, we all do to a certain extent, but nowhere near what I did when I was in corporate. I don't know if that was just my livelihood was dependent on what other people thought, but

Joy Levin (:

Yeah, sure.

Joy Levin (:

Mm-hmm.

Brett Trainor (:

I really don't care what others think and it's been so freeing. again, I haven't figured out how to bottle that and share that with other folks, but that's, and maybe that was just part of the journey to get out and have the control that you realize that you are your best asset, you bet on yourself and it really doesn't matter what other people think. And it's easier said than done. I get it.

Joy Levin (:

Very freeing.

Joy Levin (:

Yeah.

Joy Levin (:

Yeah.

Brett Trainor (:

But it's really been a huge change for me once I was able to, one, identify it then two, just avoid it, if that makes sense.

Joy Levin (:

Yeah, it's so great. And I think it is part of the journey because it's like when you take those first steps and you realize that there are things you can do that you feel good about, there's so much intrinsic pleasure that you get out of that, that kind of over tends to override that worrying about what other people think of it. You know, like in both of like, when I started with my market research consulting, I was nervous, you know, and this was like,

30 years ago. So was way before the economy and thinking, what are people going to think? You know, but, it made sense for me. And then once I started having some success in it, even if it was small, was like mine, right? Like you were saying, it was mine. I did it. And then that whole kind of thought process tends to overwhelm those other voices that are, you know, worried about what others perceive because you realize how unimportant it is.

Brett Trainor (:

Yeah.

Joy Levin (:

You know, and I think you also realize that the vast majority of people are worried about what others think. you know, it's just part of the human experience. And so that makes you realize, OK, if they're worried about what I'm thinking, why am I worried about it? It's just this funny kind of dynamic that works out. Yeah.

Brett Trainor (:

Yeah, yeah.

Brett Trainor (:

Yeah, I know it's, you can see it, but it's harder to get people to stop doing it. And again, I think maybe as part of that's just confidence as you get out and again, your identity is no longer corporate. It's what you're building. And, you know, we've been thrown around some of those sayings, but right comparison is the thief of joy or something like that, which is so true, right? Don't what you see on social media is not the real story. Right. And so you got to do what makes you happy and what works.

Joy Levin (:

Mm-hmm.

Joy Levin (:

Yeah, it's part of the journey.

Yep.

Joy Levin (:

Yeah.

god.

Absolutely. Yeah. mean, you think about before, so like when we were growing up, right, they didn't have phones and social media and it was just, you know, I just don't think it was as prevalent then to worry about this that much, you know, or the whole FOMO stuff. I mean, you know, there were times I know that I was left out, you know, of, of social things and, I feel bad, but now it's like in your face. So it's much worse now.

Brett Trainor (:

Yeah.

Joy Levin (:

it kind of amplifies that whole feeling. And that's why I think, yeah, getting off and doing something on your own can be very freeing. Yeah.

Brett Trainor (:

I think it comes back right because I do believe that the times have changed right back in the day. But you know, I went to a high school that had 500 and some people per class right so 2000 over the 500. There was a bunch of things like the breakfast club right you had the the job. But everybody got along right there was still the script but you had your tight little group and then there was the next layer next layer and pretty soon you had a whole bunch of different people but could all be at the same party.

Joy Levin (:

Mm-hmm.

Joy Levin (:

Right?

huh.

Joy Levin (:

Yep.

Joy Levin (:

Yeah.

Brett Trainor (:

With no issue, right? And now I just, it just, you're right. There's social media presents a different picture of it. And again, I think a lot of it is we're just coming back to where the way we grow up and it feels a lot better than, you know, the box that we've been in for 20 or 30 years. So, you know, time will tell. So, well, Joy, I want to be respectful of your time. there anything the audience should, we'll get to contact in for a minute, but anything else that some folks still incorporate?

Joy Levin (:

Mm-hmm. Mm-hmm.

Yes.

Brett Trainor (:

Advice for them or anything we didn't talk about you think we should before we wrap up

Joy Levin (:

A lot of the main points, I think, for people in corporate, it's to just start thinking, what else could there be, you know, to take, to harness that curiosity and start thinking about it and, you know, having conversations with other people that you trust, you know, finding a coach, whatever it is, to be able to start exploring.

can really make things a lot more clear for you and give you that confidence to say, okay, here's how I'm gonna make the switch. Here's what I'm gonna do. Here are the steps I'm gonna take. Because having that plan can kind of overcome a lot of that hesitation, I think, if they're wanting to leave, yeah.

Brett Trainor (:

Yeah. Yeah, that's awesome. Again, yeah, plan for the worst hope for the best, right? But again, we're all heading to see eventually corporates not going to take you back. So you're gonna have to figure out something. So you might as well do it now.

Joy Levin (:

Yeah, exactly. Yeah.

Joy Levin (:

That's right. Yeah, that's right. I mean, because we haven't even talked about ageism and that whole situation, right? So yeah, and it's real. It is happening there. I know there are some companies working on overcoming that, but they're far and few between. So for the most of most people, it's, you know, we're going to come up against that stuff. So yeah.

Brett Trainor (:

Yeah, don't get me started on that.

Brett Trainor (:

Yeah. And the good news is, as I tell people all the time, there's businesses, small business nonprofits, they're hungry for your experience and love your age. So that's why there's a big, beautiful world out there that isn't full of ageism. It's just, you just got to re-prioritize what we're doing. So, all right, Joey. So if people want to connect with you, what's the best way, can they find you and chat with you?

Joy Levin (:

yeah. Yes. Yes.

Joy Levin (:

That's right. Yeah.

Joy Levin (:

Yep. Yep. Yeah, I'm on LinkedIn. So Joy Levin, L-E-V-I-N. And my email address is J-L-E-V-I-N at GenXEncoreLife.com. My website is GenXExecEncore. So I think one of those ways they'll find me, and I love it when people reach out. I love to talk to them.

you know, and hear their stories because really everybody has their unique story to tell. So it's not like I think, I've heard this before. I mean, there might be some pieces of it, but there's always an interesting little twist. And I love that. Yeah. Yeah.

Brett Trainor (:

Everything's unique. That's for sure. So we'll make sure we put all this in the show notes as well. So if you're on the podcast and didn't have a pan handy, we can go look it for it. But yeah, no, I'm always happy to connect with others that are helping Gen X. So I'm glad we could make this happen and look forward to future conversation. I'm have to maybe put a panel together of some other Gen X focus people. Because I had Shelly not on too long ago and...

Joy Levin (:

All right.

Brett Trainor (:

on a blank of a few others. appreciate everything that you're doing. yeah, we'll definitely more stay connected. But like I said, we'll touch base back on the podcast before too long as well.

Joy Levin (:

Yeah, I look forward to that. I'd love to be part of a panel. Whatever you're doing, Brett, I think is so valuable to be out there talking about this stuff, about Gen X, and for them to realize all the different opportunities there are out there for them. I I love that you're bringing that to this group. So great job you're doing too. Yeah, exactly.

Brett Trainor (:

one Gen Xer at a time. If we keep one person out of corporate and living the life they want, it's successful. anyway. All right, thanks, Joy. Have a great rest of your day.

Joy Levin (:

YouTube Red, thanks a lot.

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About the Podcast

The Corporate Escapee
Helping GenXers Escape the 9-5 and Find Freedom. Real stories. Real advice. Your new playbook for life after corporate.
You followed the rules. You climbed the ladder. But now you’re wondering… what if there’s more?

Welcome to The Corporate Escapee Podcast—a show for GenX professionals who are done living a life around work and ready to start living life on their terms. Whether you’ve just started questioning your 9-5, got caught in a layoff, or are already out and building your own thing—this podcast is your roadmap to freedom.

Hosted by Brett Trainor, a former corporate exec who escaped and never looked back, each episode features real conversations with real escapees, subject matter experts, and authors. You’ll hear the highs, the lows, and the practical strategies that help GenXers leave corporate—and stay out.

🎯 Inside each episode:
• How to turn your corporate experience into income
• Ways to land your first customer (without a website)
• What’s working with consulting, fractional roles, and coaching
• Mindset shifts to break free from fear and perfectionism
• How to optimize for freedom, fulfillment, and flexibility

If you’re feeling stuck, burned out, or just ready for something more—you’re not alone. Join thousands of others who are building the next chapter their way.

✨ It’s not just about leaving corporate.
It’s about taking back control of your time, your money, and your future.

It’s time to Get Busy Living.

About your host

Profile picture for Brett Trainor

Brett Trainor