There's a Lit song that's been stuck in my head for weeks: "My Own Worst Enemy." And it's the perfect metaphor for my entire solo journey.

I've blocked myself at every stage—consulting, fractional leadership, and now with The Escapee Collective. Not intentionally, but by doing what corporate trained me to do: overanalyze, overstructure, and wait for perfection before taking action.

In this episode, I walk you through the three times I made the same mistake—and what I'm doing differently now.

If you're overthinking, over-structuring, or waiting for the "perfect" website, pitch deck, or system before you start—this one's for you.

In This Episode:

1. The consulting mistake: Building the perfect website, pitch deck, and pricing before having a single conversation with a client (and why it led to zero wins)
2. The fractional repeat: Doing the EXACT same thing again—new methodology, new deck, same lack of results
3. The Escapee Collective lesson: How TikTok took off with zero plan, then how I complicated it again with masterminds, classes, and modules—and why I had to simplify
4. Why corporate trains us backwards: Plan first, act second works in corporate—but solo requires the opposite
5. What actually works: Conversations, experimentation, messy wins FIRST—then structure
6. The 79% reality: Why most burned-out corporate workers won't take action (and how to be in the 35% who do)
7. How to catch yourself: Recognizing when you're building systems before you have proof

Key Takeaway:

Action beats planning. Momentum beats perfection. Get early wins first—THEN build the structure around what's working.

There's a lit song that's been stuck in my head for weeks and Gen Xers for sure will know this. Millennials probably will know it as well, called I'm My Own Worst Enemy. And it's kind of been a perfect metaphor for my journey so far, at least my solo journey, which is now over six years. And what I have found and again, a little bit of self reflection is, you know, I've kind of blocked myself at every stage, not intentionally, but just by the way, in some of the actions that I took, I ended up

Again, being my own worst enemy as far as growth and getting started and getting traction, et cetera. From consulting, when I started, I went from corporate to management consulting to solo consulting, fractional leadership, experimented with a bunch of different ways to monetize my experience and ultimately now with the escapee collective. And I followed the same pattern. You think I would have learned maybe the fourth time would be a charm. I've learned quicker on the third time. So I'm applying it to what I'm doing.

corporate or with the escapee collective. But again, it's just nature or maybe it's the way that corporate trained us is to overanalyze, put systems in place and don't take any chances, right? You can't screw up. Don't make a mistake. And it's a complete opposite for what you need to do when you're going solo and I don't care what you're doing outside of corporate, it's really going to be the same thing. So today I'm going to walk you through

Like I said, the three times I've done it and what I'm doing differently. So if you were overthinking, over-structuring, waiting for perfection, then this is a good episode for you. Cause again, one, you're not alone in doing that. And two, learn from my mistakes, solve it quicker. You're always going to be, you're at your own worst critic, your own worst enemy, but there's some things you can do to, move by this much quicker than, than I probably did. So like I said, in the early days, you know, corporate kicked me out.

almost six years ago, or maybe it's more than six years. One of these days I need to look at that date to see when that actually was. But anyway, it's been a while and I decided to do consulting. made sense because when I was in management consulting, my role was part, it was hybrid. So I was doing some delivery work, but I was also doing sales work. And so I figured if I was doing it for this company without a lot of leads and a lot of, not a lot of support, I could absolutely do this on my own.

And what I did, my process was I built, yeah, it wasn't a perfect website, built a website, polished a pitch deck, actually worked with and hired one of the consultants I was with at the Magic Consulting firm to help me build the perfect consulting deck. And, you know, I came up with pricing and offering solutions, scripted my discovery calls and, you know, even outlining methodology. I literally had all of this built before I had my first conversation with

you know, a small business or a customer. And as you can imagine where this is going, the result was nothing, right? Zero clients. Because I wasn't doing the thing, what I needed to do most, which was to take action. And eventually that's what I did. I just started having conversations, right? I thought I knew the answer to what these businesses needed instead of asking them, like listening for what their problems were.

I came fully armed with solutions telling people this is what I do. just a little bit of an example of that is I was focused on helping legacy, so pre-SaaS companies with digital transformation, which in the enterprise world, they get it. They know what they're trying to do. Their processes weren't aligned with the modern buyer. Technologies were not aligned.

And it made perfect sense. But then when I went downstream, small midsize companies, none of that worked, right? They, looked at me like, what is digital transformation? I've got a problem with growth, right? I need more revenue. I need to take some expense out of this business type of an approach. And so I really had to start rethinking it. And what I did, I wish I could say it was completely intentional was just went, started having conversations with business owners and listening to what their problems were.

I was still kind of hung up on pushing my solution. This is the way I work. We do a six week kind of a roadmap, validate what we've heard, get the requirements, and then do the engagement. I got fortunate that I was able to connect with somebody in my network that I used to work with. It was not a company that was struggling. They knew what I did and brought me in to help drive that project.

Again, better lucky than good sometimes, but lessons learned. like I said, what I started to do was trust my gut a little bit more. I still was way too rigid in identifying the opportunities and what the solutions were. I was only going after six figure deals. If it wasn't big enough, then I wasn't the right partner for these folks. In hindsight, I should have listened and said, yeah, I can help you solve this. Maybe it's not a full consulting engagement.

Maybe it's some advisory, maybe it's some strategy work, maybe it's, you know, whatever it is, don't even have to label it. And ultimately it would have led to more opportunities as we just started to work together. So I slowly learned, I wish I could say completely because after about 18 months, I moved more towards fractional leadership. That was something that was a little more exciting to me.

Um, I liked the consulting, but I just realized I didn't like the project plans and virtual stakeholders anymore. So moved in towards diffraction of leadership. And again, it was the same thing. What did I do? I had a new pitch deck, a different met methodology or the way I like to work. Right. And this is what, um, my approach is this is how I train. This is how I work this identified process, et cetera, et cetera. It was all about me, not about the client.

And right here's the pricing, et cetera, et cetera. And what happened? was the exact same thing, right? I struggled to find new customers because I wasn't listening to what their problems were. was, you know, putting me first because this is the way I do it. This is the way it works. This is what's going to work best for the client instead of being flexible. And again, listening to what their challenges are.

and then putting together a solution that matches what they need. And again, I wish I could say that I learned my lesson there because I did have some success, but what really started to help me rethink this entire process was again, taking my own advice and starting to listen. And that's when my whole world kind of opened up because

Um, I realized that there was multiple ways to monetize your corporate experience. Like I I had heard about consulting. knew there was some project work that folks were doing, but I didn't realize fractional was a thing. And last count, I think I, over the course of the six years and monetize my experience nine or 10 different ways I should go back and, and do and take a look at that again. But.

what like I said, what really opened it up instead of searching for those six figure deals, which are important, right? They can be the cornerstone, especially as you're going solo was starting to take advantage of the opportunities that were there with different companies that had different challenges, right? I did some business development work for a company and it wasn't pure sales. It was really just leveraging the folks that I knew in my network and connecting them with this brand that needed access to it. That worked out well. Like I said, I started doing some advisory.

You know, got on Tik TOK, just a bunch of different things and it started monetized. So I'm like, all right, now I've, I've got this, right. I figured out how to, crack the code and that, which takes us to part three of this lesson, which is this, the escapee collective, right. It was all about, kind of a, think I've shared this story before, but when it was, it was so slowly, it started as a passion project for me, right. I had done the consulting, I've done fractional.

bunch of different clients with different smaller projects and started to figure this out. And then I, there's gotta be other folks at that time, Gen Xers like me that wanted to path out of corporate, but thought you had to start a full on company or do like fiber work, like gig work, door dash, those types of things. But there is this whole world that's opening up for, you know, independence, solopreneurs to leverage their, their skills. So I wanted to teach this to other folks and help others like me get out of.

of corporate about for about six months on LinkedIn with it being relative crickets. Essentially I wasn't getting any traction. I goofed around a little bit on Tik TOK thinking, well, I'll just rant and see if anything happens there. And sure enough, right. Better lucky than the good. again, back to thinking about experimenting, Tik TOK kind of took off over a two month period where I went from, you know, a couple hundred followers to

10,000, then 20,000 over the year, we got to 50,000, then 70,000 followers. And it just validated to me, again, listening to the audience this time, that there was a real opportunity to help folks get out of corporate and head down the solopreneur path. And again, where I've started learning from my earlier lessons was I just didn't assume I knew what folks wanted because this world is different to me, right?

25 plus years in the B2B space, go to market. So direct to consumer, D2C, B2C, whatever you want to call it, it was a new world for me. So rather than assume I knew what folks wanted, I offered, again, early on through TikTok, before I had a Slack community, before I had the paid community that we have now and some of the other tools, I basically offered a free 20 minute strategy session to see

If corporate life outside of corporate was for you and I had over 300 people sign up for those sessions So I got validation that yes, there is an opportunity There are people fed up and burned out in corporate and looking to take control and gain control their lives back And so that's where I started to build Eventually what became the escapee collective I started with a slack channel, which was free Just to house people until we could figure out how to work together

Right. started to figure that out. I had listened, right? That's how we built this. But then again, I fell right back into my old trap and started to complicate things again by, by, by going down with the traditional path. Right. So we've got people in the community, the collective now we need classes, we need masterminds, we need networking, right? All the traditional stuff. And it really just got

to be too much, right? I wasn't listening to the audience anymore to figure out what they really needed. It was, I'm gonna say it was chaos because it wasn't, but I wasn't hitting what the core members needed. It was what I thought they needed versus what I was doing before, which was delivering on what I had heard, what I realized. Part of it was easy because I was building for others what I needed for myself. But then again, I just fell down that same path of overanalyzing.

work it and sell, you know, one day, actually just a few months ago, so November, December woke up and basically said, what am I doing? What is this path? Right. It's, it's, it's not, we're not heading down the direction I wanted to go. And I realized I was doing it again, right. was the same path over complicating and, just doing what I thought made sense versus actually listening to what the community. So I stopped, right. I simplified it.

I got rid of all the things other than the collective and doubled down on what this community really needs, which is around connections, peer to peer sharing. That piece of it has been huge. And education, right? So it's what I found by listening is...

That's what people are really missing is when you go solo, you really are solo. It is a lonely journey. You don't have anybody to talk to. You become your own worst enemy because you're only in your head. And, you know, I'll go back just a little bit to, to reinforce this story about, you know, being in your head was when, um, I initially left corporate and again, I'm going be quick about this because I've shared this story before, um, got into management consulting.

by accident, well not by accident, I was looking for contract work, which I found and it turned out to be a really good deal with this management consulting firm. was longer term and nature was a big project. were going through a big implementation. They needed industry expertise, which I could provide. I was on the inside, so I knew how this works. It was a perfect fit. And instead of trusting my gut and instinct and building my solo practice,

I convinced them to bring me back on, bring me on full time as an employee, right? Versus keeping the heading down the solo path where I was in control. Now is giving up full control to join something that was comfortable. Again, I didn't have anybody to talk to. And so in my own head, it made sense. So again, part of reinforcing why you shouldn't be doing this alone, finding two, three, five, 10 people that you can trust that will give you honest feedback is super helpful.

And again, it worked, right? So I doubled down and focused on one area, which was these members, the engagement, and again, providing that education. We're heading back in the right direction. Are we there yet? No, but just like the other two times when I stopped over structuring everything and started experimenting, testing it, seeing what resonates, and then starting to double down on that really paid off.

What's my point with all of this is too often when you're leaving corporate and you tend to want to overanalyze everything, right? Over-structure everything, have the perfect website. mean, all the things I outlined that I've done multiple times in this solo journey. And what I found is when you really want to grow and when I say grow, not scaling grow that, I know how to do this, but I really want to make a lot of money now.

I'm talking about growth, just getting started, starting to stack those few wins. You got to be opportunistic, right? You got to trust your gut. You got to do some brute force. You do whatever you can to start to uncover those opportunities. And then once you start to win a few deals, you see where the patterns are. You see what's resonating with folks then to put some structure and process around it to, to re reinforce that. And you really don't even have to do that then.

Right. If you get consistent with what you're doing, you know who you're looking for. You're really only building it for yourself. I mean, I think with the escapee collective, we're now over a year and a half. we've only been circle for about a year, but I didn't have a website until January of this year. Right. And yet we grew like crazy. So all the things that you think you need in order to be successful isn't really what you need. It really is just get out there, take action.

Just like Nike said, just do it. Action beats planning all day, every day in this process. And for the folks that think they don't have the experience, you've got more than enough experience. I work with folks in the collective that want to think about what are the conversations they're going to have. They want to plan for it. want to have everything I outline. I want to have what the delivery is going to be, what the offerings are. The fact is, if you just start having conversations with folks and listening to what their challenges are,

you're the light bulbs going to go off in your head and go, I absolutely can solve this. And guess what? It does not have to be perfect. It really doesn't. It just needs to be able to solve the problem for the client. I guarantee you, you're going to undercharge for the first couple, which is okay. You're going to get some wins. You're going to learn a lot. Hopefully at least you're going to get some testimonials from it that you can use elsewhere. And part of it, you're going to figure out what you like to do and what you don't like to do. Like I said, one of the biggest,

wins for me through this this six year process is really starting to focus and feel and figure out where I want to spend my time and honestly what gives me the most energy people will talk about purpose I think you chase your energy obviously in the early days when you have to pay the bills and get the traction you do what you have to do to get to get this going but I guarantee you and I see it all the time folks with almost zero experience that are willing to take action

are going to win. They're going to be successful because they're doing it. So there's no excuse for folks that have 15, 20, 30 years of experience not being able to provide this value. like said, there's no manual for this, right? There's frameworks you can follow. But like I said, I really like to keep it simple. I've had my most success when it's more back to trusting my gut. I think I wrote a newsletter article on that, that, you know, when I trust my gut, listen,

Again, because I think part of that is you're starting to talk to folks like you would want to be spoken to and not what some manual tells you or some LinkedIn influencer tells you to do. It's really around the basics, listening, understanding, and applying everything that you've learned in your career. And then just having more conversations. Yes, over time, you can absolutely start to structure and stack and build processes into it. But don't.

Don't fool yourself. think part of that is that safety net that we tell us that the more prepared we are, the less chance of failure. Guess what? You're going to fail a lot, but it's OK. Nobody's judging you. And the fact is, I don't even look at it as failure anymore. just, right, it wasn't the right fit. Either what I do or the problem they have, I can't solve it. Or even if I can and I didn't communicate the value correctly, that's OK. There's a bunch of other opportunity and clients out there.

Again, just circling back to being your own worst enemy. I'm still that way. I'm dealing with now remind myself probably on a weekly basis that I do need to get out of my own way. And then to remind myself that right. There's not a lot of people doing what we do. may feel like it's saturated, but it's not. Um, I had a post not too long ago talking about, right. That 80%. So 70, I think was actually 79 % of folks in corporate.

right now are disengaged or actively disengaged from their work. I take that to mean they're burned out or they just don't care about their job. But what really shocked me is when I did some my own research to follow up that only 35 % of that 80 % is going to do anything about it, right? The other folks are either if they're fortunate enough just to retire that when that job ends, they're just going to stop working. But the vast majority of those folks are going to try to

ride out this current job or find another job in corporate. So like I said, there's not as many people out here doing this. So there's the opportunity for the folks that are willing to take those first steps. And you don't have to exit corporate to start this. If you're still in corporate, you absolutely need to start having these conversations now. Like you were when you were thinking about changing a job, you're networking. It's the same thing. Hey, I'm thinking about starting my own thing. And here's what I'm thinking. Here's the problem I think I can solve. Love to get your feedback.

people want to help you when you tell them that you're starting your own thing. They like to help when you're looking for a job, but they really like to help when you're starting your own thing. So anyway, I thought I would share this again, lot of self reflection more recently, but you know, when I shared this story with a couple of early escapees, they found it very helpful. So I thought I would share that with you guys as well. So

Appreciate your listening. If you do enjoy the podcast, please do subscribe on whatever platform you're on. It helps like we can get in front of other people and do connect with me on LinkedIn. Send me any questions that you may have or other future topics for the podcast. I'm always listening and appreciate your support. Have a good day.