Everything I know about personal finance I learned from starting a business.

When I say it out loud, this line of reasoning is perhaps unsavory. But maybe I’ll convince you to stick around anyway. Mastering personal finances through entrepreneurship comes down to one simple idea:

Entrepreneurship complicates your finances.

There, I said it. Despite what the internet tells you, entrepreneurship isn’t all fun and excitement. It’s often confusing and scary. And financially speaking, it forces you to look under the hood of your personal economic machine and truly learn how it all works.

Or at least, that’s how it happened…

Nearly all freelancers are time trapped. The moment you stop performing client-facing work — to take a vacation, have the occasional lazy workday like all your 9-to-5 friends, or catch up on accounting — you procrastinate receiving your next paycheck.

As a result, client-facing work takes priority over business development and professional growth. You’re building everyone else’s businesses instead of your own. This goes against the old entrepreneurial adage that you should work on your business instead of simply working in it. Easier said than done, I guess.

In this article, we’ll investigate why the freelance time trap is deeply…

There’s a lot of buzz around building an online business. Everyone tells you to start a blog. Launch a newsletter. Sell a course. Learn to code so you can launch the next unicorn SaaS company. Starting a business from scratch seems to be the topic of every other article or course I see online.

But is it overrated? What if, instead of enduring the grind of the first two years of business, you just purchased an already-cash-flowing business from another entrepreneur?

I recently sat down with several entrepreneurs and asked them about what it takes to buy and sell online…

The internet is polarized about how young people should spend the first several years of their careers. There’s one side that insists you should spend your twenties traveling the world, living your dreams, and postponing any big responsibilities and career moves until you’re closer to 30. You’re only young once, after all. Don’t settle down before you have to.

The other side says to put your head down. Find a career. Start investing. Make big professional moves while you’re young so that time and compounding can work their magic. …

In March 2021, I crossed the five-year mark as a full-time freelance copywriter. In many ways, the career has been about what you’d expect. I’ve endured the scary volatility of living project to project. I know what it’s like to own my calendar and have choice about who I work with. I make a good living — but I have had multiple clients ghost me without payment. I lived as a digital nomad, earning money through my laptop as I explored the world.

And recently, I had to learn the hard way that no one hands you a congratulatory plaque…

Both women took a turn with the knife.

One at a time they stabbed the side of their Monster can.

Sleeves rolled up on their arms, the women gave one another a nod, popped open their tabs in unison, and the race was on. They put their mouths against the puncture holes, threw their heads back, and chugged.

The winner raised her hands in triumph a moment later.

This was Vans Warped Tour 2015. And no, these staffers weren’t shotgunning energy drinks — they were drinking water.

Appearances Go a Long Way

It’s risky business giving up a 9–5 job to work for yourself as a freelancer. Instead of relying on a biweekly paycheck, you accept a career that ebbs and flows without a predictable pattern. One moment you’re juggling more work than you can handle and the next you’re staring at an empty calendar — and a draining savings account.

I almost gave up freelancing several times in my first year. One month I had to tell my landlord that rent would be late. Another, I had to borrow money from my brother. Multiple times I had to expense essential bills…

I swore I’d never be an active trader.

I’ve invested regularly and aggressively in the stock market since 2018, always under the same strategy: buy index funds that I plan to hold for decades. If someone told me they actively traded and tried to time the market, I’d silently judge them, thinking about all the stats I’ve read about how rare it is to consistently beat the market.

The truth is, I still swear by index fund investing — and it still makes up almost all of my investing portfolio. But lately, I’ve also decided to try something new. …