As a personal finance hobbyist forged in the flames of fairly extreme FI/RE rhetoric, my perspective on wealth as a source of confidence was always unemotional, mathematical: By the time I’m worth $X, I can withdraw between 3% and 4% per year and comfortably live on $Y. 

It was a straightforward way to derive financial confidence from stability: a portfolio of assets to draw on if (when) things go sideways. As such, I maintained a utilitarian, linear view of the process: You ratchet up your income as much as humanly possible (and by whatever means necessary!) such that saving the vast majority of it doesn’t hurt, and then you press the eject button from paid labor whenever it stops being fun. The clearly defined finish line and path paved with hard ’n fast rules always satisfied my rubric-loving, syllabus-reading self. 

This wasn’t just my way—it was, in my view, the only way. It wasn’t until I started to unpack that strategy with my friend (and collaborator on an upcoming project!) Tara Reed that I realized there were other valuable lenses through which I could view my finances…and career capital. 

As we talked through my approach (earn, invest, ball out), she shared her own: Rather than deriving confidence from an ever-increasing nest egg that can produce predictable income in the future, she explained that she prefers to devote her energy to developing relationships, businesses, and habits that reinforce her confidence in her own ability to create income. I’m paraphrasing: “I’m not optimizing for stability, I’m increasing my confidence—the confidence that I can turn on that money spigot at any time.”

While these might sound like two sides of the same coin, the implications about the types of choices we’d make according to these worldviews are very different: Where I might walk down a dead-end path today simply because it has a dollar sign attached to it that I can funnel directly into VTSAX, Tara might choose the longer, meandering road with no certain paycheck…that eventually leads to six more. It’s the difference between short-term and long-term thinking.

As I reflected on her ideas about the various ways to reliably produce future income, I was reminded of classic stories about early employees at startups that eventually made it big—they turned down the lucrative six-figure consulting salary to take a risk on a new venture because they believed in the mission, and ended up cashing out to the tune of millions of dollars in equity just a few years later (I know a couple of people for whom this was true, and while their decision looked foolish at the time…they definitely got the last laugh). 

Rather than memorizing the rules of the gameboard and carefully maneuvering one square at a time, these people flipped the whole damn table—risking utter destruction in the hope that their tiny metal Top Hat might land on Boardwalk.

That’s not to say either approach is better than the other, just that they reveal a lot about what, exactly, you’re comfortable placing your faith in: Do you want to rely on the storied success of the public markets, or are you interested in placing a leveraged bet on yourself? 

Take my own example: By selling Money with Katie to a larger media company at the end of Year 1, I took the first stable exit on offer. A bird in the hand, right? It’s obviously worked out well for me, but we don’t know what would’ve happened in a parallel universe in which I had said, “Thanks, but no thanks.”

Still, it’s easy to venture into romantic territory here; in the United States, we love the rags to riches story of The Little Hustler Who Could who french braided their bootstraps, bought some lemons from a black market wholesale dealer, and turned them into gourmet lemonade at a 400% markup. But “betting on yourself” is a lot more charming in theory than in practice, when your mortgage is on the line and the little mouths in your home need to be fed. 

This belies a contradiction within the fantasy of the American dream: The type of stability we’re taught to chase (the W-2 job, the starter home, the 2.5 children and golden retriever named Max) is directly at odds with the risk-taking required to place the type of entrepreneurial bet on yourself that our culture so devotedly celebrates. 

When a single 24-year-old sharing a fifth-floor walk-up uses their nights and weekends to build a company and strikes it rich, it’s inspiring; brave. When a 35-year-old sole breadwinning parent quits their stable accounting job to hang out their own shingle, it’s risky; foolish. 

Counterintuitively, the less you have, the bigger swings you can take. Stability might cap your downside (or, at the very least, create the illusion of a capped downside), but it often places a limit on your upside, too. 

(A brief aside: You can always build a business on the nights and weekends as a parent so that you don’t have to quit the job that supports your family, but as many parents of young children have told me, that often requires an unreasonable sacrifice of time you’d probably like to spend with *checks notes* the aforementioned children…all for an uncertain payoff. And while there’s a bewildering strain of hustle porn that effectively claims, “having children made me grind harder and made me more successful,” I’ll give you one guess as to which gender that type of rhetoric comes from. Hint: It’s not the one who’s statistically more likely to bear the burden of caring for those children.)

Bigger swings become riskier as your lifestyle, business, and family grow, because you simply have more on the line. In my own rush to secure a stable situation (secure income, a nice home, a relatively “safe” investment portfolio), I didn’t notice the opportunities I was forgoing. Being too preoccupied with “responsible” choices often led me down predictable paths with equally predictable outcomes—and while predictability can be great, it’s also inherently limiting. It’s indisputable that the Katie who shared an apartment with a friend for $800 per month could afford to take more chances than the Katie who pays $5,000 per month for shelter.

Funnily enough, I remember thinking at the time that I could never quit my job to pursue my side hustle full-time. It felt “too risky,” despite being a single renter with no dependents and very low overhead in a robust job market where it would’ve been a piece of cake to get another paycheck job if things went bust. Even in my relative “freest” state of adult existence, I didn’t feel comfortable betting on myself—and while I told myself at the time it was because I was just too responsible to take chances, I know in hindsight that sometimes fear often masquerades as maturity.

Of course, I’m thankful for how the last few years have gone: Despite my preference for the safe and stable path, I’ve had (what I consider) fairly outsized returns, both in business and in life. But Tara’s words have rung true in a way I hadn’t expected: She’s inspired me to have a little more faith in my ability without the safety net of a big name institution or someone else’s stamp of approval. Because at the end of the day, short-term thinking communicates something very specific: I don’t believe that I can generate another, better opportunity, so I’m gonna take this less risky one that’s right in front of me—whether it’s a job offer that’s not quite right, or an investment that feels “good enough” but not “great,” or a life path for which the most compelling benefit is stability. 

And hey, sometimes that is the best opportunity you’re going to get—in which case, you should probably take it. After all, if you grew up in a home that was often chaotic and unpredictable, or you’ve experienced dire financial insecurity, sometimes stability is what you crave most (or what you crave most right now). 

But for me, I’m not sure I ever thought twice about what I was optimizing for—or if stability was the most inspiring thing I could aspire to. It was just the most obvious thing. Fortunately, on that path, I still meet people like Tara, who help me think about money and opportunities just a little bit differently…and in those moments of coming together, new opportunities can arise. And the next time they do, I know who I’m betting on.