Why Most People Don’t Aim as High as They Could

Daily writing prompt

What’s something you would attempt if you were guaranteed not to fail.

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Fear of Failing: “Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do.”

I was excited when I saw today’s writing prompt: “What’s something you would attempt if you were guaranteed not to fail?” Not because I had a ready answer—but because this question hits at the heart of why some people achieve extraordinary success while others never even try. The answer is simple, yet powerful: fear of failure.

Having spent years in the corporate world at the vice president level, I had the chance to observe countless high achievers. One trait stood out among the most successful—and often the most confident—people: they acted as if failure simply wasn’t an option. Not that they believed they were invincible, but on the surface, fear didn’t show. They moved with a quiet certainty that others often mistake for arrogance.

I often think about early Indy race car drivers when I try to explain this. In the early days of racing, cars were slower, and lap times longer—not because drivers weren’t talented, but because the risks were enormous. Crashes were often fatal. Speed records weren’t just about skill—they were about safety. As cars became safer, drivers could push harder, take bigger risks, and set new records that would have been unthinkable just a few years earlier. The lesson: when the environment is safer, people dare to go further.

Even in modern life, the principle holds. Take Shark Tank investors, for example. They look so cool and confident when they throw $50,000 to $100,000 at an inventor. But let’s break down the numbers. If an investor has a net worth of $10,000,000 and invests $100,000, that’s just 1% of their total wealth. To put it in perspective, for someone with a net worth of $10,000, 1% would only be $100. That’s why it looks effortless—they’re risking only a tiny fraction of what they have. Confidence isn’t arrogance; it’s proportional risk.

Now, consider most people as they age. You’d think experience would naturally increase confidence—but that’s not always true. If someone has lived a “play it safe” life, accumulated a modest nest egg, and avoided risks, their confidence can actually decrease over time. They fear losing what they’ve built, even if their wealth is more than sufficient to live comfortably. This is why many elderly people hoard money, avoid investing in anything risky, and live overly thrifty lifestyles. Their fear isn’t about real financial danger—it’s about losing the life they’ve carefully constructed. Ironically, the very caution that kept them safe early on becomes a cage, limiting bold action and preventing them from achieving more.

The lesson is simple but profound: the greater your perceived safety net, the further you’ll dare to go. By preparing, planning, and building resilience, you can absorb setbacks without fear. Opportunities begin to feel like challenges you can handle, rather than dangers to avoid.

So ask yourself: what would you attempt if you were guaranteed not to fail? And then ask this: what can you do today to make failure a little less frightening? Your highest goals aren’t beyond your reach—they’re only beyond your courage.

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