Entrepreneurs, by nature, are risk-takers. That’s what sets them apart. They willingly venture into uncharted territory, shoulder uncertainty, and challenge the status quo. In doing so, they unlock the possibility of greater rewards—financially, personally, and socially.
But our broader society is trending in the opposite direction.
More and more, we’re exchanging personal freedom for security. From Social Security to Medicare and the Affordable Care Act, we’ve created a system where individuals are protected from many of life’s financial uncertainties. While these programs offer safety nets, they also chip away at our ability to opt out, to choose a different path, or to build something entirely our own.
It’s a quiet but powerful trade: comfort for control.
The Investment Analogy: Risk vs. Reward
Let’s look at how this same principle plays out in the world of investing.
You have a choice:
Invest in 10-year Treasury Bills, which are considered nearly risk-free, and earn around 2.5% to 4.5% annually.
Or invest in a diversified portfolio of stocks, which carries more risk but can return 10–12% over time.
Most people—when given the freedom to choose—opt for the stock market. Why? Because they understand that a modest increase in risk can yield a significantly higher reward.
Yet this kind of choice disappears in other areas of life.
For example, you can’t opt out of paying into Social Security, even if you’d rather build your own retirement nest egg. You can’t decline Medicare taxes, even if you plan to use a private health plan. Programs meant to ensure equality of outcome—however well-intentioned—remove individual autonomy in exchange for collective protection.
Government and the Erosion of Choice
Government programs are rarely temporary. Once introduced, they tend to grow and entrench themselves. As Milton Friedman famously noted, “Nothing is so permanent as a temporary government program.”
It’s a bit like Frankenstein’s monster—designed with noble intentions, but eventually taking on a life of its own. Every new entitlement or regulation might solve a near-term problem, but it usually does so by reducing the range of choices available to the individual.
Want to homeschool your children? Start a new business without a state-mandated license? Or skip insurance coverage you don’t want? In many cases, you can’t. The safety net has become a web.
So What Can You Do?
You don’t need to quit your job or launch a startup tomorrow to begin reclaiming your freedom. But you do need to take back your appetite for risk—even in small ways:
Start a side hustle that isn’t tied to a corporate structure.
Invest not just in index funds, but in yourself—through education, networking, or mentorship.
Opt out of “safe” defaults and choose what aligns with your goals, even if it’s less conventional.
Challenge assumptions about security. Ask, “What do I lose in exchange for this guarantee?”
Entrepreneurs understand that every gain comes with some uncertainty. But they also know that the ability to choose—the freedom to act on your values—is one of the most precious assets of all.
What trade-offs have you accepted for the sake of security—and where might you start reclaiming your freedom by assuming a bit more risk?
