Jealous of Solopreneurs? Here’s Why You Should Be..

Let’s get real: being a solopreneur sounds sexy, doesn’t it? Working in your pajamas, calling the shots, and dodging pointless office birthday cakes (because seriously, how many slices of dry sponge can one person handle?). But let’s not kid ourselves—while solopreneurship is the dream, it also comes with its fair share of baggage. The difference? That baggage is yours. You packed it, you carry it, and ultimately, you get to decide where it goes.

Working for yourself gives you freedom; the number one value the US population valued in recent research.

Tim Denning wrote about the undeniable allure of solopreneurship, and honestly, he nailed it. But I’m here to expand, sass it up, and toss in some wisdom from Justin Welsh—the king of the one-person business game. If the 9-to-5 grind makes you want to scream into the void and fancy going it alone, this one’s for you.

The Solopreneur Label: Love It or Leave It

I get it. The word “solopreneur” might sound cringy, like a made-up term someone threw together during a TED Talk. But let’s call it what it is: freedom in disguise.

Unlike employees, who are often underpaid and overworked (yep, I said it), solopreneurs have one massive advantage: you set your price, your pace, and your priorities. Sure, if you don’t deliver results, the income stops—but that’s not scary; that’s liberating. Why? Because it forces you to get good at what you do. No hiding behind busy work or those dreaded “sync meetings.”

The Truth About “Freedom” at Work

Denning hit the nail on the head when he said, “Less money means more time spent working. Working hard at a job you don’t really love is the definition of prison.”

Can we talk about that for a second? You might think you’re “safe” in a job with a steady paycheck, but guess what: that paycheck is a fraction of what your employer is making off your work. Capitalism 101, baby! Meanwhile, you’re clocking in extra hours and canceling vacations because the team’s “understaffed.”

Newsflash: your boss isn’t losing sleep over your burnout.

Now, contrast that with solopreneurship. You work when you want, where you want, and—here’s the juicy bit—you create something meaningful. Something you actually care about. That’s the kind of freedom that hits different.

Jealous of Solopreneurs? That’s a Sign

Let’s spill some tea: if you’ve ever felt jealous of someone who works for themselves, that’s your soul trying to tell you something.

I’ve been there. Watching people take random Wednesday afternoon hikes while I slogged through meetings that could’ve been emails. I used to roll my eyes and think, must be nice. Turns out it is! That picture on the top of this article is from my boat on a Tuesday!

But like Tim’s mentor told him: “You can either be jealous or start talking to them to figure out how they live this life.” That’s a mic drop moment right there. Instead of side-eyeing successful solopreneurs, get curious. Ask questions. Study their habits. They’ve got the freedom you want, and trust me, they’re not keeping it a secret.

Solopreneurship Is Harder—But It’s Worth It

Let’s not sugarcoat it: solopreneurship is no walk in the park. There’s no paycheck fairy depositing money into your account just because you showed up. But the rewards? Oh, they’re sweet.

Justin Welsh, who built a million-dollar one-person business, is living proof that solopreneurship is about leverage. He turned his LinkedIn expertise into a passive income machine, but it didn’t happen overnight. He focused on:

• Building a killer personal brand.
• Experimenting like a mad scientist.
• Finding what worked and scaling the heck out of it.

Take a page from Justin’s book: work smarter, not harder.

How to Get Started: Small Bets, Big Payoffs

Denning mentioned the importance of experiments, and he’s spot on. Solopreneurship isn’t about waiting until you “feel ready” (you never will). It’s about trying, failing, and learning.

Think about it: one wrong decision won’t ruin your life, but one right decision could change everything.

Here’s a roadmap to start experimenting:

1. Teach What You Are Fantastic At: What skills do you use at your 9-to-5? Package them up and sell them.
2. Solve a Problem You Solved for Yourself: Pain +Credibility + problem-solving = profit.
3. Go Small First: Offer a service or product on the side. Validate the idea before going all-in.

Pro tip from Justin Welsh: Start with a low-risk digital product. It’s scalable, low-cost, and a great way to test the waters.

Why Most People Won’t Do It

Let’s address the elephant in the room: most people won’t even try. Why? Because they’re scared. Scared of failing, scared of judgment, and scared of the unknown.

But here’s the truth: staying in a job you hate is also scary. In fact, it’s terrifying. So, pick your hard.

Your Freedom Plan

Solopreneurship isn’t a one-size-fits-all journey. Maybe you start small by freelancing. Maybe you write an eBook or launch a course. The “how” doesn’t matter as much as the “why.”

Here’s your action plan:

• Step 1: Write down one thing you’re really good at.
• Step 2: Figure out who is suffering because they don't have that skill.
• Step 3: Start showing up and talk about it. Consistently I might add.

Sounds simple? That’s because it is.

Final Thoughts

Look, solopreneurship isn’t perfect. Some days are tough, and the self-doubt is real. But the freedom? The joy of doing work that matters? The satisfaction of being in control of your life? That’s priceless.

So, stop romanticizing the idea of solopreneurship and start doing the damn thing. Your future self will thank you.

As Denning said, “Freedom exists. You just need a vehicle to make enough money to be comfortable so you can increase your personal profitability.” And as Justin Welsh might add: “If a corporate dropout like me can do it, so can you.”

Now, go build the life you actually want. You’ve got this and I've got you!

Jo Knight Dutkewich is a former corporate senior leader and consultant to some of the world's best brands. She helps solopreneurs to break up with procrastination, perfectionism, overthinking & self-doubt to achieve consistent $10k months. She also hosts the Ambitious Introvert with Jo Knight Dutkewich Podcast on Spotify. She lives on Vancouver Island in the Pacific Northwest with her husband, 3 sons, animal menagerie, and judgmental cat..