The money trap nobody warns you about.

"I finally hit my income goal," she wrote, "but I feel more anxious about money than I did when I was broke."

I stared at that email from a reader for a long time because I knew exactly what she meant.

When I first started making real money as a solopreneur, I thought my financial stress would disappear. That once I could cover my expenses and then some, I'd sleep better at night.

I was very, very wrong.

When success feels uncomfortable

Making money as a solopreneur comes with a completely different set of financial challenges that nobody ever warns you about. And if you're not prepared for them, even a little bit of financial success can feel surprisingly uncomfortable.

If I could go back in time six or seven years, I would tell myself that earning money as a solopreneur doesn't solve all of your money problems. It creates new ones.

When you’re working a corporate job, your financial life feels pretty predictable. You get the same paycheck every two weeks, your taxes are withheld automatically, and you’ve got a clear benefits package. Sure, you might not love the amount, but at least you know what to expect!

As a solopreneur, everything changes.

Your income swings wildly from month to month. You're now responsible for tracking every penny that you owe for taxes. You get to decide how much to reinvest versus how much to pay yourself. And all of a sudden, you're managing money in ways you probably never had to before.

The first year I made decent money as a solopreneur, I operated exactly like I had when I was an employee. I didn't track our income closely, and basically guesstimated our taxes. My income would swing wildly from month to month, but I just lived the way I always had.

That approach bit us pretty hard when tax season arrived.

We got hit with an unexpected tax bill that was more than I had set aside, and I realized I had no idea where our money was actually going or what I was doing financially. But these practical finance challenges were just the beginning.

The weird psychology of solopreneur money

Making money as a solopreneur also comes with emotional baggage I never expected. There's the constant fear that it could all disappear tomorrow. There's this weird guilt about having more than you used to. And then there's imposter syndrome in a whole new form:

"Is this really going to keep happening?"

When you're employed, you often feel like the paycheck you earn is directly attached to the work you do at the office.  You showed up, you do the work, you get paid. It all feels like simple math. But when you're a solopreneur, success can feel accidental. Even when you know you've worked hard for it, there's this nagging little voice in the back of your mind asking whether you deserve it.

I know solopreneurs making great money who still worry about going broke on a regular basis. They’re definitely not in danger of that, but the unpredictability of solopreneur income does something to your brain that's hard to shake. Even when the numbers say you're doing well.

What I wish I'd known

After two years of making the same mistakes, I finally learned what actually works back in 2021. And honestly, none of it is all that complicated.

Pay yourself a salary: The first thing I learned was to pay myself a salary, even when income was unpredictable. During the good months, that extra money went into saving or investing. During leaner months, I had a cushion that I could draw from. This helped smooth out the mental roller coaster of feast-or-famine income.

Track your income, taxes, spending, and overflow: The second thing was that I started tracking everything, but kept it simple. I started with a basic spreadsheet to monitor what we made, what we'd owe in taxes (got this percent from our bookkeeper and tacked on a few extra points to be conservative), what was left over, and how we’d divvy it up between saving and investing. That simple system has evolved over time, but the key was having this starting point, which we’ve done weekly now for almost five years.

Create a spending bucket system: We also learned a simple spending framework from a friend, which was to think in buckets. Focus deeply on the three things that matter most to you and your family, and stay cheap on everything else. We overinvest in travel, restaurants, and taking care of our three dogs. Your buckets will be different, but having them makes decisions a lot easier.

Build an emergency cash cushion: Lastly, building a cash cushion became a non-negotiable for us. I recognize that not everyone reading this will be in a position to do the same, but even starting with one month of expenses in a savings account will make a huge difference in your mindset. It's psychological insurance against the "what if it all goes away" fear that haunts most solopreneurs.

The real shift

But the biggest change isn't tactical. It's actually mental.

As an employee, you're optimizing for a steady paycheck. As a solopreneur, you're optimizing for a sustainable lifestyle that your business can support indefinitely.

This means thinking differently about growth. You don't have quarterly targets or annual performance reviews pushing you to grow faster, like you do in corporate. You just need to afford your lifestyle, save some money, and invest for the future.

Sometimes that means turning down opportunities that would make you more money but cost you peace of mind or reduce your optionality. Sometimes it means taking risks that don’t tie you down and could pay off big. The key is making those decisions based on what works for your specific situation and what is most likely to keep your business alive. Not what looks impressive to other people.

Your business should support your life

Making money as a solopreneur is just the beginning. Learning how to manage it (mentally and practically) is what determines whether success makes your life better or more complicated.

The good news is that these challenges are solvable. You don't need an MBA or a financial advisor to figure this stuff out. You just need systems that work for your specific situation and the willingness to treat financial management as part of your job, instead of a distraction from it.

Your business should support your life, and that includes your financial and mental well-being. If you're making money but still stressed about money? Something needs to change.

And that reader who messaged me about feeling anxious despite hitting her income goal? She's not broken at all. She just needs better systems and a clearer definition of her enough.

The money you've made isn't supposed to make you miserable. It's supposed to make you free.

What's your biggest money stress as a solopreneur right now?

Shoot me a note back. I read every response, and sometimes these replies turn into future newsletters.

P.S. If you're still trying to grow your business, come learn how to earn more revenue with ​The Creator MBA​. It's helped over 6,000 online entrepreneurs scale to 6 and 7-figures through systemization, automation, and offer stacking.