Living life on the edge might just make you cherish it even more. I’ve discovered that testing my limits, like plunging back into the job market after years of being my own boss, really sharpens my appreciation for what I have. Every job interview feels like a dare to myself, shifting from a successful entrepreneur to someone scrambling to make ends meet. It’s a thrilling, if somewhat twisted, challenge.

During one memorable holiday season, I endured a grueling six-hour interview session without breaks, facing a barrage of eleven interviewers. It was a brutal test of endurance: I was starving, desperate for a restroom, all while trying to charm my way into a job. And honestly? I found the whole ordeal bizarrely exhilarating.

Why subject myself to this kind of torture?

Firstly, interviewing is a skill, and skills get rusty without practice. After four years out of the game, I needed to dust off some cobwebs. Also, I was curious if I could reconnect with my old industry, even if it meant joining a less prestigious firm. Returning to this arena, I noticed some former peers weren’t thrilled about my potential comeback, which oddly enough, just added fuel to my desire to remain independent.

Moreover, stepping up to this edge showed me the steep drop awaiting below. I figured if I did go back, I’d stick it out for a year, check out the bonus structure, and then bail.

Appreciation grows when you flirt with danger.

We often take the essential things for granted—relationships, health, and careers—until we’re at risk of losing them. Through this process of re-entering the job market, I faced my worst fear: losing my autonomy. Although I was still in the running for the job, I ended up declining the position. Sending that refusal email was liberating, especially knowing I was walking away from a potential $350,000 – $500,000 a year.

The temptation of more money is real.

A couple of years ago, this same employer and I didn’t get far in the hiring process, as I was committed to my independence. They chose someone else, and now, they were looking to fill the same role again. This entire experience reaffirmed my love for financial independence and my life as a writer, where I control my time and choose the company I keep.

If you ever take your life for granted, test your limits.

Visit the edge of your comfort zone, and you might find that stepping back from it gives you a newfound appreciation for what you have. I don’t need to fall to know I’m better off; my vivid imagination does enough to remind me how miserable I’d be if I returned to an industry I fought hard to escape.

Stepping up to the edge has its perks.

Nothing beats the thrill of starting your own venture. Why let platforms like LinkedIn or Twitter define your online presence? Owning your website lets you connect with millions, sell products, earn passive income, and discover new opportunities. Since 2012, my site has been a gateway to countless consulting gigs, each adding a six-figure boost to my income.

Invest in growth.

Consider investing in sectors like artificial intelligence, where the future’s being written today. You don’t want to look back in 20 years and regret not participating in these groundbreaking fields.

Educate yourself on personal finance.

If you’re looking to navigate life’s big decisions—like the choice between public and private schooling—my book provides insights drawn from over 25 years in finance. It’s packed with strategies to help you build your wealth and live freely.

And remember, sometimes stepping out of your comfort zone shows you just how much you didn’t need to step out at all.