Why do so many people leave corporate… only to end up going back?

In this solo episode, Brett breaks down the two core reasons most corporate escapees fail—and more importantly, how to avoid them.

Failure here doesn’t mean experimenting and choosing corporate again. It means wanting out, trying to go solo, and giving up before momentum ever takes hold.

If you’re thinking about leaving corporate—or you’ve already made the leap—this episode will help you understand what really trips people up and how to build a path that actually sticks.

Resources Mentioned

The Escapee Collective – A milestone-based community designed to help corporate escapees get out and stay out: Link: https://escapee-collective.circle.so/checkout/the-escapee-collective

What You’ll Learn in This Episode

• Why not getting an early win is the fastest way to lose confidence

• How long gaps without income create doubt, panic, and backtracking

• Why most escapees don’t lack skills—they lack momentum

• The hidden cost of isolation and loneliness when you go solo

• Why “doing it alone” dramatically increases emotional swings

• How peer support and feedback shorten the learning curve

• Why community works better when people are at similar stages

• The difference between education, theory, and applied learning

• What successful long-term escapees all have in common

Key Takeaway

Going solo doesn’t fail because you’re not smart enough or experienced enough.

It fails when:

• You don’t get a win early

• You try to figure everything out alone

Momentum and connection matter more than perfection.

Resources Mentioned

The Escapee Collective – A milestone-based community designed to help corporate escapees get out and stay out: Link: https://escapee-collective.circle.so/checkout/the-escapee-collective

You can also reach out directly to Brett on LinkedIn with questions about the community or your escape path.

Welcome back to the Corporate Escapee Podcast. I'm your host, Brett Trainer. And today I'm going guest free doing another solo episode. Like I told you at the end of last year, I'm planning on doing a few more with some frequency to address topics that I hear all the time. Not only experienced escapees, but folks thinking about escaping. And what I wanted to talk about today is why most escapees fail. And there's two, I would say core reasons.

And let me first say what I mean by fail isn't that you had to go back to corporate. It's that you gave up on going solo, went back to corporate with no intention of ever escaping. To me that that's not a failure because maybe that's really what you want to do. But the folks that did want to get out, stay out and end up not staying out. That's how I'm defining it. So thought a little context was important there, but the two reasons are, and I'm going to go into what they are.

then more importantly, how to address this issue I'm gonna talk about here a little bit later. the first one is not getting wins soon enough, right? So how do you get that first client, that first dollar to build a momentum? And the second one, which may be a surprise to folks is isolation and loneliness. And even though you're going solo, you don't have to do this alone. So let's dig into both these. First one is.

not getting that win soon enough. think most people when they leave corporate have grand plans. We're going to get that first client in the week. You're in a perfect positioning and it's going to go and but like most clients goes by or most escapees go my months can go by before you end up with that first client. You start to doubt yourself. You start to panic a little bit and maybe you start looking again for that corporate job again.

And I think the longer that that goes on, the more the risk is that you're going to go back. And where I find the biggest challenge with this, and again, I was in that position, is you're doing it alone, right? You don't, and this isn't talking about the loneliness aspect. It's really about the education and awareness. One advantage I had when I left, I left corporate consulting and went into solo consulting to start my escapee journey.

So I kind of knew, right? I was responsible for doing some selling delivery. So I had a pretty good idea how everything worked, but I didn't have anybody to talk to, to bounce ideas off of, right? I know a lot of escapees will use chat GPT or the other AIs to have those discussions and maybe that's a different episode, but it's really who do you learn from, right? Do you have the right mentor, right? If you're, you're funding a company, there's a plenty of folks that have built, um,

startups, right, raise funds, et cetera, et cetera. But when you go solo, a lot of the time we just figure it out on our own. And what I will tell you is if you've had any success in corporate, whether they get, I've talked about four years or four decades, you absolutely have the intelligence, the smarts, the experience to do this on your own. Cause what we're talking about here is not rocket science, but there's a learning curve if you do it all on your own. And some people will tell you that, Hey, you just need to figure it out.

And I guarantee you that you would figure it out if you have enough time. But what I've learned over the past five years is you don't have to figure it out on your own, right? There's plenty of folks that have gone before you that have learned a lot of lessons, me being one of them, of things that I would have done differently. And I just, think not having that feedback loop, that area to bounce ideas off of, somebody that might be slightly ahead of you.

Um, can share some of those insights. So don't have to start over. I can kind of think of it as right. If you, if you are completely out of shape, want to get in shape and the person you hired was, you know, an Olympic bodybuilder or a sprinter, right. From you doing nothing to getting in shape. mean, that, that person is just far ahead. Maybe they've got some good frameworks and a process to help you.

you know, achieve your goals. But if somebody is just slightly ahead of you, it's going to be more relevant and more on time for what you're doing. So I think that was one of the biggest thing is not having someone or a group of someones to provide that feedback back to you. And like I said, one of the things I found with this escape the world

is people really do want to help each other succeed, right? In corporate, it's every person for themselves. You're fighting for the promotions. You're fighting for the 2 % raise, right? Because HR gives you a band that you have to give people. All those types of things here, there's enough for everybody. There's 400 million small businesses, right, worldwide that need help. So this isn't a zero sum game. There's plenty for everybody. And I do find folks willing to help each other. Now, the challenge is finding where those folks are. Again, I did this on my own for

two years not telling anybody biggest mistake I ever made at least through this process because there are folks out there that are willing to help and as time goes by rapidly there's more and more escapees finding this life that are again willing to help so I think you know finding folks and not just theory right you can you can take a class

join a mastermind, those types of things. And I think it's there, but I think there's a bigger opportunity, which I'll get to here in a little bit around how do we learn and how do we apply it? Because again, a lot of this is a work in progress, right? The solo world is growing and evolving as we go and being able to share those experiences, I think are going to be critical because again, this isn't like somebody's teaching you a brand new skill.

you have the skills and the experience. It's just a reframe of how to use what you already know in order to succeed solo. Now there's some of that with the areas such as finance and accounting, but there's specialists that can absolutely help you do that. So, all right, so that's one. The second one that which I touched on is the isolation and the loneliness, right? Is if you've been in corporate for any amount of time, even remote, you have access to people.

Right. You may not like them. You can't choose your coworkers, but there are folks that you can connect with, share stories with, gossip with, you know, the water cooler, where the layoffs are coming, those types of things. And usually you have, a little bit of a support network. Again, I found over the course of my career, I probably worked for what seven different larger organizations and only a couple of them had coworkers that I truly enjoyed.

on the macro level, right? We always had folks we worked with that we enjoyed working with, but as a broader team where you enjoyed the day to day and working with folks, you know, it's kind of few and far between. You can't pick and choose, like I said, those, those, those coworkers. So when you're going solo, the first step is like, this is awesome. I have complete control. I have complete freedom. Then you realize, my God, I've got complete control. I got complete freedom. How do I do some of

what I need to do and who do I talk to and who can I bounce decisions off of. And I think that's where it's important to have that support group that understands what you're going through, right? Because if you go with your family and you've been in corporate the whole time, they're going to think, what are you doing, right? Corporate's the safe world. Again, separate conversation. But there is that somebody can understand what you're going through. I

I all the time because I've seen it happen. know, folks in our community, when they left corporate and go solo that first week, it goes back to Ron Burgundy and Anchorman. It's the glass case of emotion. Right. They go through, this is the greatest thing I've ever done. And then 10 minutes later, like, my God, what have I done? This is super easy. This is hard. Right. All within that first week. And what I can tell you is if you do this on your own, it makes it even worse because

everything's amplified. You don't have anybody to talk you off the ledge, right? If you're having a bad day or have different ideas that, that you can test. And again, I'm all for experimentation learning. mean, I do think that's how you build, but there's definitely, again, going solo doesn't mean doing this alone. And I definitely find the folks that are successful and do this for the longterm have that support network. Either they found a small group that they work with.

or found the right community, right, to be able to ask questions and which kind of takes me to what do do about this, right, because I'm living the experience and I think a community is the right answer and again you're going to get a non-salesy plug from me but I want to share

how I'm approaching this. And again, if you can go find others, like if you're 100 % focused on fractional, there's fractional communities that can share this. If you're 100 % consulting, there's consulting folks. What I wanted to do is provide really two things within the community. And the first one is education. How do we get more and more people out of corporate and stay out of corporate? So the tagline that I've picked up for 2026 here.

is we are a for-profit but a mission-based organization. When I say organization, there's one plus of us right now, but I'm anticipating this growing this year. But I want to help 1 million people get out of corporate and stay out of corporate, take control, live the life. I've been very fortunate over the last five years to find this freedom. I've worked my way through

Uh, like I the different opportunities and the different ways to make money and then started teaching people how to make money. But really where the passion comes down from is coming to is, is addressing those two issues is the education piece and not doing it alone. And what the kind of the commitment I've made for the collective, which is my community, which I don't talk a lot about. shame on me. know the marketers are out there and say, I need to talk about this more, but

And I think the education is important. And one of the biggest things I learned last year, because the community and the collective has been up and running for a year now. And I think over 120, maybe we're closing in on 130 members at this point. And what I learned is not everybody's at the same point in their journey. And so when you get groups of folks together that are in very different places, you got somebody that's still in corporate, but planning their exit to somebody that's been out for five years.

They have very different needs. I finally took me a little bit to learn. But what I ended up doing is transitioning this to more of a milestone, milestone based groups, peer groups or sessions. And what I finding in the early returns is this just makes a lot more sense. Right? So we've added a new one for folks that are still in corporate that on a monthly basis, we're going to get together and talk about what are the challenges? What are you seeing? What is the feedback that you need?

And you're going to be with others that are in the exact same position as you, right? They want out, not quite ready yet, building the plan, whatever that's keeping you in there. Maybe you are going to, you know, waiting for the layoffs to come. they, pay you for some runway, whatever that is. The second group, milestone group we've got is the three K and this is focused on two things. One, just people just getting started looking for those first dollars, selling those first deals, starting to sell maybe some repeat deals.

They're a combination of, like I said, education, but it's also conversation. So it's not one way we get feedback. We provide feedback to each other as we go through the process. then quickly, we've got the 10K group, which is folks really looking to replace their corporate income. They've had some success. They're already making at least 3K per month, but now they want to go to the next level. How do I expand, maybe land that one larger anchor client that gives me

uh, the stability or how do I go find a bunch of smaller deals? So we're more focused. They've got a different set of challenges. And then the last group is the 25 K plus per month. And that's shooting for that. And the, what I call that group to go big or go home because they do want to make a ton of money. So by having these sessions broken out by milestones, it just puts people in a compere groups, right? You're in the same place. They can share the same.

journeys, provide feedback, understanding, etc. But part two of that education piece, what I found was it was really important to have outside voices also share their experiences, right? Because people get tired of hearing from me all the time. And so what now we've opened up is what I'm calling member sessions. And you do have to be a member of the collective, but you can host a session on a monthly basis.

where you talk about the things that you learn, things that are important to you, and open that up to our other members. Eventually we'll open up to non-members, but for now we're gonna focus on members. And what this allows us to do is provide basically mini workshops. My goal is at least a dozen per month outside of our core sessions. So I talked about those core sessions.

These are going to be right. What's working on LinkedIn. We've got John arms coming in next month and he's going to talk about the future of work and what that means for solo. I've got somebody that's coming in talking about outreach and leveraging LinkedIn and what are those processes look like. So we're going to have the one commitment that I'm going to make to all these sessions is it's going to tie back to that escapee journey. And again, I don't care if you're in corporate looking to get out all the way to Hey, I've been out for 10 years.

Those are the experiences that I want to provide and it starts with conversations, right? It's gonna be conversations connection and then support is what I want out of this group And I think by doing this it's gonna create that sense of connection and again if there's other areas and other networking groups and other things that you want to do You know, it's gonna give you the flexibility to do this. I just want to put these escapees together and cover those two core

challenges that make sure that we address those and one last little plug on this is If you are interested, which I highly encourage you the first month is a dollar right? So you get unlimited sessions ones I've talked about You can attend as many or as few as you want And then after that it's $20 per month. So no one's getting rich off this

But what I do see is the power and the value of this community has provided me so much just in the last year having people to talk to building this doing what I'm doing with some of my other business Solo businesses on the side. It's just been a again. I kind of built it for me originally, but now we're expanding it to you know, call it built by escapees for escapees and I think this is just the the next evolution of this thing so

Those are the two things, right? We want to provide that community, the connection. So you're not doing this alone and more importantly, continue to provide the education. And by doing this, it's just not static, right? You're just not one course or one mastermind that when it's ends, it's over. This is going to be living and breathing. So we start to learn new techniques, new networking ways, whatever it is, we're going to host sessions on it. And again, it's completely up to you to attend the ones that you want to attend. And you're only going to get what you put into it.

But I think opening up, because I really, really want to start creating awareness for those folks still in corporate. And I think this is a good low friction, low risk way of folks to start to get comfortable, start to learn, start to plan before they make that exit. So I will include the link to the collective in the show notes, but you can also DM me on LinkedIn. You can send email. You can talk to anybody else that's in the collective.

And folks do have a path out of this. And I also want to make sure we keep people out. So that's why, again, no matter where you are in your journey, we've got a group for you and we've got the different education. And quite honestly, once you're established and you want to host your own sessions at 100%, I think it's a great way for you to get comfortable and share the knowledge that you have and give back to others. And if you want to become a speaker, it again, it just, creates another opportunity for you. So anyway, those are the two things.

If you can find it elsewhere, absolutely go do that. But you know, as you're starting your journey, think through those two things, get that first win, whatever you can do to get that first dollar, build the confidence and then two, you don't have to do it alone. Even if it's a small group of folks you can bounce ideas off of, that's absolutely critical. So I appreciate you tuning in. Thank you for listening and make sure you do like and subscribe if you get value out of this podcast. Thanks.