The Aspiring Solopreneur Podcast | For Solopreneurs and Freelancers

Why Your Solo Business Isn't Giving You the Life You Wanted (And How to Fix It)

Written by Joe Rando | Apr 30, 2026 12:45:48 PM

 

Watch the Episode on YouTube

The Ownership Trap is a pattern where solopreneurs, people running one-person businesses without employees, build companies that demand just as much (or more) of their time and energy as the corporate jobs they left behind. The trap isn't caused by laziness or bad intentions. It's caused by a flawed starting point: designing the business before designing the life.

In this episode of The Aspiring Solopreneur, hosts Carly Ries and Joe Rando break down the three core causes of the Ownership Trap and introduce their "Life First" framework as the antidote.

What causes the Ownership Trap? The 3 Root Causes

1. No Design Most solopreneurs start by asking, "What am I good at?" and build from there. While logical, this skips the most important first question: "What do I want my life to look like?" When the life comes second, business decisions, the clients you take, the hours you work, the services you offer, get made without any filter for whether they actually support the life you want. The result is a business that generates income but slowly swallows your time, energy, and freedom.

2. No System Without the right infrastructure in place, solopreneurs default to managing their business through email threads, Slack messages, sticky notes, and mental checklists. This leads to dropped tasks, missed commitments, and 2 a.m. anxiety spirals. The good news: this isn't a character flaw. It's a systems problem. The right tools and processes, even simple ones, can dramatically reduce the mental load of running a solo business and give back hours every week.

3. No Plan to Evolve A business that works perfectly for you today won't necessarily work five years from now — because you'll change, and the market will change. Many solopreneurs hit a wall after years of success and realize they've built something they no longer want to operate. Without a conscious process for evaluating and evolving the business over time, that wall becomes a crisis instead of a pivot.

Who is this episode for?

This episode is for anyone who:

  • Left a corporate job to start a freelance or solo business and feels like they're back in the same trap
  • Is working more hours than ever but still feels behind
  • Has been told they have a "motivation problem" when something deeper is wrong
  • Wants to build a solopreneur business that genuinely supports their lifestyle

Key Takeaway

If your solopreneur business feels like a job, it's not because you're failing — it's because the business was built without your life at the center of the design. That's fixable.

Life first. Then business.

The Aspiring Solopreneur is a podcast for one-person business owners who want to build sustainable, life-supporting businesses. Subscribe on Apple Podcasts, Spotify, or YouTube.

EpisodeTranscript

Carly Ries: If you're a solopreneur who's working more hours than ever, missing dinners, losing sleep over forgotten tasks, and wondering where your freedom went, you haven't failed. You've fallen into the ownership trap. And today we're breaking down exactly how it happens, why it's so easy to miss, and what the three root causes are that keep so many solopreneurs stuck building a business that runs their life instead of supporting it. You're listening to The Aspiring Solopreneur, the podcast for those in pursuit of a life first business. I'm Carly Ries, and my co host Joe Rando and I spend every episode with solopreneurs who are proving there is a better way to run a one person business and experts who are helping make it happen.

We like to say life first, then business, so let's get right to it. Joe, this episode actually kind of piggybacks after our statement episode that dropped last week of our life first movement, the whole life first, then business. I just said movement, don't wanna repeat myself, but that's the lens that we're looking at everything moving forward. Because after nearly 300 episodes, that's a common thing we see with solopreneur is that they wanna run a business that supports their life, not one that controls their life. So in today's episode, I kinda want to break down what we've seen and the I don't know, the one constant that we've seen. you're so good at explaining this. Before we get to the villain and all of that, what is kind of the cause, like, what have we seen that's been happening that has made us want to move in this direction?

Joe Rando: Well, I think at some level, we kind of always knew it was about this kind of thing. You know, why are you a solopreneur? why start a solo business and not have employees? Well, there's gotta be a reason for that. And, you know, it seemed that the reason for a lot of people was they just wanted control. They wanted to be able to kind of say how things were gonna be. And, having employees is a great way to scale, but it isn't necessarily a great way to have complete control because you've just got a lot of responsibility. I think we've kind of distilled this doubt of this idea of the life first business. And the problem I think that we're seeing a lot, and I'm not saying everybody, but a good chunk of people that we talk to, that we get to know, are building a business that trades the kind of corporate trap of being stuck doing what you're told to do with another trap that they build themselves, right?

Because they build a business based on what they're good at, their skills. And they start there and they end up building a business, but the whole life aspect is kind of left as the afterthought, if that makes sense.

Carly Ries: Yeah, absolutely. And it's funny because they take what they know, and they're realizing that, or what we've realized for people is that a lot of times when people are stuck in a rut, it's not a motivation problem. It's a design problem, because they're taking those corporate ideas and trying to bring it into their own life. And then they are really down on themselves when things aren't working, but really it's all in the design. It's not that they're unmotivated. And they can blame themselves so easily. so that's why we wanted to name the villain, name what the causes are that's allowing people to feel this way, and then as LifeStarr, come up with a solution. So can you name that villain for us? What have we seen as a problem?

Joe Rando: Well, we've named it the ownership trap. But, the idea here is it shouldn't be the kind of thing where people go, oh, I was stupid. I fell into the ownership trap. The ownership trap is kind of a natural result of starting in a very rational manner, which is I'm starting a business, I'm good at X or Y, and therefore I'm gonna think about how to build a business using my skill X or Y to generate revenue as quickly as possible, because that's what a business is all about is generating revenue and making a profit. So it's not lazy thinking, it's not on rigorous thinking, but it misses a first step, which is, the idea that you're doing this for your life.

So maybe the first design parameter should revolve around the life you want and not the business. so before you start designing the business, you wanna be thinking about how you wanna design the life, if that makes sense.

Carly Ries: Yeah. Oh, absolutely. I mean, I think I've told you this before. When I first went out on my own, I was saying yes to everything because it was a money thing. And I was like, well, oh my gosh, I knew it. I could make more as a solopreneur than I ever could in the agency world.

And then I wasn't seeing my husband, and I wasn't walking my dog. And I was like, no no no. I mean, even when I was still working at Agency Life, I was working insane hours. And that's why I left agency life because these hours were just outrageous.

And then I brought those outrageous hours with me into one person business hood. And it was what am I doing? There was no plan. And I want people to avoid that if they can. From the get go, the paychecks are obviously enticing and sometimes and often necessary.

But still you don't wanna get in the trap of just going after those. You need to really have that full picture of what you want.

Joe Rando: Absolutely. And I mean, I did it too. you know, I built a solopreneur business. I did a great job of designing it around my life way back when. But then I did such a good job. I actually didn't have enough hours to work and being who I am, I had to find a way to work four hours.

So I started another business called Retail Analytics and it was great. And then all of sudden it wasn't. We got a $130,000 a year customer for our software and then never got another one because the internet came along and everybody wasn't sure if there were gonna be stores because this was about stores. I ended up pivoting to a service business and I think through what that was gonna mean for my life. And it was horrible.

We ended up having to do surveys at night. So we're working days. We had surveys going on at night. I was playing weekends to catch up because it was just so crazy and so much work and wasn't really making any money. And it was just this terrible decision that I made de facto because it was the quickest way to get revenue and didn't think about what I wanted my life to look like.

So, I really screwed it up because I had a great life first business built, and then built another one that wasn't.

Carly Ries: I know, grass is always greener, Well, So that's like the number one cause, or the first cause of the ownership trap. We say no design. But you kind of just alluded to the second cause in your last story, which is no system. Can you elaborate from there?

Joe Rando: Sure. I mean, when we work at companies, sometimes there aren't, but sometimes there are systems in place for keeping track of things, communication, processes, and those kinds of things. And a lot of times when solopreneurs get up and running, they don't bring those things with them because they can't because the tools aren't made for solopreneurs. Things like standard operating procedures seem like something they do for a big company. And you wind up managing things through kind of communications, through email or Slack or whatever communications channel and all the commitments being made are done there and the tracking is done there.

And, maybe you have a paper system, maybe you have some online system that you're using, but it doesn't talk to anybody else to keep track of the actual to dos and projects and things. And it winds up becoming, at least for me, the way it worked for me was I would wake up at 02:00 in the morning going, oh, I forgot that. And, you know, now I'm lying in bed going, gotta remember this. And, if I don't get up and write it down and put a post it note on my computer, I'm not gonna sleep again. And it was awful.

And running a business that way can get very stressful. Things get dropped and missed. I just didn't find it to be fun at all. So having a system in place to actually manage all the stuff going on, all the moving parts, is really critical to having a life first business.

Carly Ries: I do just wanna reiterate, it is a system problem. Like you just said, it's not a character flaw. I think people get in this, and they're like, oh, I'm not good at tracking this. I'm not good at this. I'm not good at that.

And it's like, a lot of people aren't great at it, but if they have a good system in place, then it solves everything. So again, I think you can get really in your head and impostor syndrome can creep in in this phase. I just wanna remind people, it's not them. It's just the systems that they have. So that's my pep talk.

Joe Rando: I think that's a very big blanket, good blanket statement that it's almost never character flaw with these kinds of things. It's really about having the processes and the systems in place to manage things. And to make sure that you're working efficiently and not doing things that don't need to be done. A lot of the outsourcing, automating, all these things together can help you to build a business that you can actually manage and still have a life to live. But part of the problem, Carly, is that when we don't start with that kind of set of criteria that come down to viewing it through the lens of how is this gonna impact my life?

Decisions are made without that consideration. So you might look and say, well, gee, I can get this system, but it's gonna be $250 a month. That's a lot of money. I don't really wanna give that money up. But then if you look and say, well, wait first and foremost, I wanna be able to be home for dinner.

And if I have this system in place, I'm gonna be able to shave eight hours a week off my time, which is gonna help me stop missing dinner. Now that two fifty investment is being seen in a different lens than if you're just looking at it saying, Oh, it's $250 I don't really think that's something I wanna spend right now. So when you start having this lens of what your life was supposed to look like, you can really allocate your efforts and resources differently toward that end, Surprisingly, when you define that as the bottom line, then, you know, the decisions enforce that bottom line, not necessarily the bottom line on your income statement.

Carly Ries: Well, what's interesting though, is that can also change whatever that is over time. And like you were saying, you had a great life first business, and then you're like, oh, but I needed something more. And that's another third cause.

Joe Rando: Don't do that.

Carly Ries: I'm doing it, I'm doing that. But alright. I'm gonna throw that back at you and use that as an example over and over again just to remind you. But that leads us back to the third cause of the ownership trap, which is you don't have a plan to evolve. So what can you speak to on that note?

Joe Rando: Well, that things will change. And if the world doesn't change, then you're gonna change. And I've talked to so many solopreneurs that say, I've got this great business, I've been doing it for five years, and I'm just done. I just don't really wanna do this anymore. I want something new and I'm pivoting over to this or to that.

And the idea of doing that is great. And it may be not that you're tired of it, but that the world's changed. I mean, I think a lot of solopreneurs have been impacted by AI and how it's changed either the demand for what they do or how they should do what they do. But this process of conscious evolution is critical to any business and especially a solopreneur business, because you know, it's very easy to keep doing what you're doing when you're the only person kind of in charge.

You know, if you've got a company full of people, somebody's gonna be saying, hey, something's going on, raising the alarm or whatever. But when you're on your own, you're the only one that's gonna raise the alarm and you have to think through how you're going to modify your business, whether it's a tweak or a major pivot in order to address either changes in yourself and your needs and the life you want, or changes in the world around you, or some combination of those.

Carly Ries: Exactly. So you guys, I guess what we're trying to say is if your first business as a solopreneur feels like a job, it's not because you are failing, it's because you are stuck in a system, like we're talking about, that is broken. And you likely have one of these three problems going on, and you've fallen into the ownership trap. So just think about that. Joe, you look like you're gonna say something.

I don't wanna cut you off.

Joe Rando: Oh, just so we're not gonna leave you hanging forever. We'll be providing solutions.

Carly Ries: Exactly. This is your little carrot episode. And you guys well, and thank you so much for tuning into this carrot episode. We're really excited about the way that all of this is going and the direction we're taking from here on out on the show, as well as with our company at LifeStarr. So if you wanna keep following us with this new journey, this new content for all of you, then be sure to subscribe to The Aspiring Solopreneur on your favorite platform.

Share this episode with a friend. And I mean, if you think this is the best episode you've ever heard in your entire life, leave us that five star review. We'd so appreciate it and it helps us spread the word. We'll see you next week or next time on The Aspiring Solopreneur. You may be going solo in business, but that doesn't mean you're alone.

In fact, millions of people are in your shoes, running a one person business and figuring it out as they go. So why not connect with them and learn from each other's successes and failures? At LifeStarr, we're creating a one person business community where you can go to meet and get advice from other solopreneurs. Be sure to join in on the conversations at community.lifestarr.com.