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Breaking Corporate Dependency: Why Going Solo Alone Keeps You Stuck w/Brett Trainor
17th February 2026 • The Corporate Escapee • Brett Trainor
00:00:00 00:17:22

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Jon the Escapee Collective!

What keeps 79% of corporate professionals stuck isn't lack of skills or opportunity—it's something deeper. In this solo episode, Brett shares the story of landing his first client, making good money, and then doing something that still makes him cringe: convincing that company to hire him full-time. Nobody forced him back. He walked himself in.

This mistake cost him 18 months and taught him the hard truth: leaving corporate is tactical, but breaking your dependency on it is psychological. Brett breaks down what corporate dependency actually is (hint: it's not just the paycheck), why going solo alone reinforces that dependency, and the two critical milestones that finally sever the tie.

If you're still in corporate and thinking about making a move—or you've already left but still feel the pull—this episode will help you understand what you're really up against and how to break free for good.

What You'll Learn:

  1. Why corporate dependency is psychological, not financial
  2. The three things you're actually dependent on (and it's not what you think)
  3. Why isolation amplifies doubt and keeps you stuck
  4. The two milestones that break corporate reliance
  5. How to avoid the mistake that sent Brett back 18 months
  6. Why community matters more than tactics when going solo

Key Quotes:

  1. "I hadn't really thought about why I did it, but it was really my dependence and my reliance on corporate."
  2. "What I really broke it down into three areas: I wanted control of my future, control of my money, and control of my time."
  3. "When you go alone, you have nothing else except yourself to talk you in or out of what you're doing."
  4. "Once you get to the point where you're confident that you can bring in that next deal, you know you're never going back."
  5. "I wasn't escaping corporate per se. I didn't have to stay there. I had options."

Resources Mentioned:

The Escapee Collective: Join Brett's community

Subscribe & Connect: If this episode resonated with you, please subscribe to The Corporate Escapee Podcast on your favorite platform. New episodes drop multiple times per week featuring guest interviews and solo deep-dives like this one.

Looking to break your corporate dependency? Visit TheEscapeeCollective.com to connect with others on the same journey.

Transcripts

Brett Trainor (:

Welcome back to the corporate escapee podcast. I'm your host Brett trainer. And today we are doing a another solo episode. And personally, I believe this is one of the most important variables. This topic is on determining your success or at least time to success, right? Or you can overcome just about any challenges and it's the dependency and reliance on corporate. You know, it really didn't dawn on me until I've been out of corporate for five years, four, I've been out six years.

But I really started thinking about what it was about corporate and what was I really running from? it the, the job? No, I actually kind of liked the job. Did it pay paid pretty well. it was just corporate in general. What it really came down to is my reliance and dependency on corporate. And I think that is one of the biggest reasons why 79 % of folks are stuck in corporate that are burned out.

and not looking to make a change or if the change they're looking to make is just to look for another corporate job. So I do want to talk about my journey a little bit because I think lessons learned from what I did could help a number of you folks and also what you can do about this throughout the process because again escaping corporate and going solo in and itself is a very isolating process or it can be especially when you're in corporate because who else do you have to talk to?

If you're thinking about making a change, not your coworkers, definitely not your boss, maybe, maybe not your spouse until you actually get a little bit further in the process or educate yourself. So it can be really lonely because there's just not a lot of folks that you probably connected to that you can have this conversation with. So I want to get into that. But first, you know, let's get into the dependency and the reliance on corporate. And, you know, my story, the first time I escaped,

corporate, I literally did escape, right? I was done with, you know, it was actually a true corporate job. This is before I went into consulting and I knew I was done. needed to change. wanted to do something else. the company I was leaving, we left on good terms. And after I'd been out for a bit, you know, one of the things I was considering, was consulting. really hadn't thought super deep about the solo aspect and it was before.

Brett Trainor (:

Fractional was the thing there's definitely solo consultants and freelancers and contractors, etc But I hadn't completely made up my mind what the path was that I was gonna head down Because these terms didn't really exist. I had been in corporate for 25 years I was kind of figuring it out as I went along. Well, I ended up getting a Contract work for a manager consulting firm really good gig It was a right in my wheelhouse of the type of work. I was doing back then paid me well

And in hindsight, it really would have built a good foundation for my solo business, right? It would have opened the doors. This would have been cornerstone and I could have started adding and supplementing and bringing on or at least booking, you know, future customers. But what did I do? And instead of building off of that, I went out of my way to convince this company to hire me full time, you know, bring me on as an employee. I can build out this practice within the organization and

In hindsight, I'm like, what the hell was I doing talking about? What an idiot, right? At least that's as I'm looking back, what was I doing? But as it turns out, I hadn't really thought about why I did it, but it was really my dependence and my reliance on corporate. And it was easy. It was safe. I may have been really unhappy with everything that I was doing or the way it was going, but it was the path that I knew. instead of continuing,

down the scarier path of going solo and building something for myself, I went down the path that was more traveled, more comfortable. And it was the biggest mistake, right? I mean, I learned some things. Sure. You can always pull lessons, but it sent me back probably a year and a half in my, uh, my solo journey. And when they ended up quitting on me after I had kind of quit, was, it was mutual. I started over again.

and took those lessons. like I said, had I stuck out that process and maybe I needed that learning, but it really opened up my eyes to, what was I running from or more importantly, what I was running towards. And I really broke it down into three areas and it came to, I wanted control. Number one, first and foremost, I needed and wanted control.

Brett Trainor (:

Mostly of my future right because in corporate I was completely reliant on that organization and how long they were gonna keep me I wanted control of my money right they're paying me a salary but unless you're in a sales role it's gonna be capped or you may get a Small bonus or a cost of living increase if you're going through it But you're not in control of that money and they can decide when it ends When they want it to end and most importantly or I shouldn't say most importantly another big factor was control of my time

Right in corporate, they tell you what to do, when to do it, what are the projects that you're working on? And it just, it, that was just again, what I knew until I got out and actually had control and manage my time. I didn't realize how much freedom that actually gave me. So that was one of the eye-opers. So if you're still in corporate and thinking, you know, I can't do this because I know what's comfortable. I'm to keep fighting the corporate fight, finding a different job. And as long as they keep having me back.

Just think about it from a mental standpoint, is it just because it's what you know or is there something else that that's keeping you from it? Because at the end of the day, the three things that I, again, I find almost every escapees after is those three pieces of control, time, money and future. Obviously you got fitness and some other things, but I usually roll that down out of what am I doing with my time? Right. I can decide if I want to spend some time working out, work four hours a day.

Whatever it is. I'm in control of that process And so if you're thinking yes, that could be me that is the reason why I'm stuck the next thing I want to talk about kind of part two is Why going alone is probably the worst thing that you can do for this and again speaking from my experience and then now getting an interviewing by a thousand different escapees and definitely working with a number of escapees

It's when you go alone, you have nothing else except yourself to talk you in or out of what you're doing. Um, again, cause you can't talk to Bosch, you can't talk to coworkers and it's left to your own mind, right? And if it's an unknown, that's even, even more difficult to overcome mentally to go after that process. I guarantee you, if I would have had the community that I'm in now, back when I was thinking about

Brett Trainor (:

trying to convince this consulting firm to bring me on full time. I you know, I would have had a sounding board to talk it through and realize that probably wasn't wasn't going to hurt me. Again, it's stunted how long it took me to get out and get finally get control. But I would have had somebody to talk through, especially if somebody had been slightly ahead of where I was or a year ahead of where I was. And once I finally got out into that world after they quit on me the second time.

I realized that there's a lot of people that have done this for a lot longer time than I have. Nobody talks about it. It wasn't a movement. People weren't talking about fraction on all those types of things. But again, having that, it doesn't even have to community. You could have a few good folks that you can talk to. I just think is so helpful. One of the biggest mistakes I made when I left both times was not telling anybody, right? I was very opportunistic about the deals I got.

Especially the second time when I knew I wasn't going back to corporate, but yet I didn't broadcast it that I was starting my own thing. And that's a whole, whole separate act episode. But, you know, I think that's the one that's things having somebody, a group, a team, a community, even if you don't work with us or work with my group, find some people that you can have these conversations with. It's critical. I've heard John arms, right? The, the Godfather of fractional, same thing. He's like, you got to surround yourself with five other fractional, at least five.

that you guys can work on this together, right? Be that sounding board, be the strategy, be the vent, be the, you know, the support as you, as you go through this process. Um, all right. So with that being said, don't do this alone is the number one thing there. found there's two real milestones. So if you're thinking about this, you're still in corporate thinking about, I'm going to go solo. Here's the two milestones that I want you to think about. The first one is getting that first win. It is critical.

and if you can do this while you're still in corporate and there's a host of ways you can do this, you know, every day I'm finding more ways to, create revenue or generate revenue, even while you're still in corporate, to get started, right? Because it's such a confidence builder. If you've never sold anything outside of, of what maybe it had been sold in corporate, it's, it's just a confidence builder. And you realize, you know, pretty quickly.

Brett Trainor (:

that you absolutely can do this. is in a sales hard, intense sales position. It's really about building relationships, connecting with folks, solving problems and getting paid to solve those problems, right? In the simplest form, that's what you're doing. And again, to have another pose or another episode where I talk about how this is similar to looking for a job. If you're looking for the job, it's almost the same process as looking for customers, but I'm going to dig in. want to, so this one I'm focusing on those milestones. First one is

earn that first dollar, do what you can to find that first dollar outside of corporate, gain that confidence, realize you can start stacking them. The second milestone, and this is the big one, again, this is why I don't think you should do this alone, is that consistency. Once you get to the point where you're confident that you can bring in that next deal, you know you're never going back. And for me, that was about a year two-ish somewhere in that area.

where I now had enough experience. I had transitioned from consulting into fractional and was starting to pick up some smaller deals like on the advisory side, doing some business development. I was really starting to figure out how to monetize my corporate experience. And at that point, I knew that I wasn't going to go back. I could figure out how to make enough money to pay my bills. Would it be ideal and optimal all the time? No, but I knew I didn't need that. And that goes back to that dependency on corporate.

I didn't need it anymore, right? There was no crutch. There was no easy way to get the salary and benefits. And that comes at different times for different folks. Again, if you have some success super early, you can start to build on that. But it's really the consistency. And then once you get the idea of, I know I can do this, it's just so freeing. Again, that's when you know you're not going back to corporate, unless you choose to. Maybe somebody wants to pay you a boatload of money.

to come in and run something for a bit and you know you're going in eyes wide open saying, yeah, I can charge X, Y, and Z to do this, but here's my conditions, right? I need to do this. again, so as long as you're going in under your terms and it's towards your grand goal, then it makes sense to go back into corporate. And I think the last, I would call it milestone that I see folks

Brett Trainor (:

And not everybody gets to this point or even wants to get to this point, right? A lot of people when they leave corporate just want to replace their corporate income and work for you hours, right? Give them time, work remote, we're working on their project. They want to work, but there's a good portion of folks that want to go big. They want to make money. They want to make 25,000 plus a month. And that milestone is you're going to flip the switch. At some point you're going to want to go from trading time for money to

You know, so basically one-to-one consulting for actual advisory where you're changing, you're charging money for your time to one to many, where you start to develop revenue streams. Maybe it's a service, these different areas. So even though I said, I alluded to in the beginning that there's two milestones, that's really the third one. And third one's optional, right? Because some folks just want to make enough money to pay their bills, live their best life and, and move on. again, I find those to be,

Again, the key milestones and again, breaking that reliance on corporate. So again, I wanted to share this because it's crazy that I've been doing this for almost six years now. And it really just hit me that I wasn't escaping corporate per se. Corporate is what it is. It's designed to do what it is. You guys follow me on TikTok. You know, I rant about the profit, but the fact is I didn't have to stay there. I had options.

And at one point I actually raised my hand and said, bring me back in, even though I know all the downside of this process. So that was a hundred percent mental on my part. And now again, that's, that's where I work with folks all the time and I see it when they leave corporate, they're super excited and the range of emotions. And sometimes it takes them a little longer to find that first client or some have success right out of the box. It's really just following that, that process.

to get through those two milestones. Cause I guarantee you, if you can get the success and hit that milestone too, you will lose that reliance on corporate. And if you're like me, you're going to wish you did it years before. But I also realized I'm not going to go back in time and change anything. And it probably happened, you know, at this pace for a reason, but I do look at folks and I just had a exchange on LinkedIn with, you know, somebody who went to business school in the late nineties.

Brett Trainor (:

And we were in the same class. I just never forget that he was one of those guys that figured this out early, right? I think he was at BP or one of those companies, big company, good job, good career. And he's like, this isn't for me. I need to go start my own thing. And he's had a super successful career, you know, mostly small and some big size, not big companies, but entrepreneurial career where he's really built, you know, that, that solo life. that hit him in his.

maybe late 20s, early 30s, sorry Mark, it's, I get the timing wrong. But for me, was, you 50, I hit that mark. So I, again, we see all ages that are looking to escape. And my goal is really to hit and to help that the folks that are the ones that are stuck that burned out that 80%, that 79%, I guess is actually what the poll showed of people disengaged or actively disengaged from their job, which tells me they're just collecting paychecks.

and it's know what you can do that for the short term but you don't want to do that for extended period of time you'll be miserable and at some point corporate's gonna end that for you anyway so how do we get those folks and I'm talking to you into that process so again my advice is to find somebody to talk to that's been through the process even if it's one-on-one and again I'll you know self promotion of the the collective

We've got folks that are in corporate that talk to each other about what is their plan of how to get out. And again, you can take your time. If you've got a good job, it's paying you well. Maybe you're building a two year roadmap, but I'm telling you, it's better to have that community. And again, I'll talk about lessons learned as I've gone through the process and I shared this, I don't know if it was in a LinkedIn post or a newsletter that when I started the community, my vision was getting people together and then providing the training, right? How do we get the...

the frameworks and the tactics and the strategies, don't get me wrong, those are important, but there's no real one way to do this. And it's really just a matter of getting out. it is the, the take action is a critical aspect of this, but it's the support and learning from each other and providing that value that accelerates the curve on this. So even if it's not our escapee collective,

Brett Trainor (:

Go find that group of folks that's going to help you get through this because again, every person I've talked to and again, I've interviewed, it's probably 1500 people in total conversation. Everyone's absolutely smart enough to do this. There is no doubt about it, but what you can do with the power of people is accelerate that learning curve. You don't have to learn everything on your own. There are certain things you're going to have to do. You're going to have to go with the reps. You're going to have to have the conversations.

but there's a bunch of things that you can avoid making mistakes. Pricing, offer, ideal customer, how do I narrow my focus? All those things are, I'd say learnable, without having to go through it yourself. So anyway, I hope you found this episode helpful. Like I said, I really liked the idea of these solo episodes, especially when things were top of mind or things I'm hearing in the collective or in the community.

And I just want to share again, if we can get one other person out of corporate, that's absolutely miserable and their wife's asking them what the hell was the matter with you? Then we're doing our job. anyway, I appreciate you listening. If you do like this, please do subscribe. It still does help on podcasts. I don't know if you're listening on Spotify, Apple, or any of your favorite podcast platforms, please do subscribe. I'm trying to get out a couple of episodes per week that includes guests and solos.

And that's it for this week. Appreciate you listening. Have a great week.

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