The Cost of Playing it Safe

I pull into Hero’s Coffee for the first meeting of a new entrepreneurship group my friend Andy and I are starting. At the moment, the group consists of two members: Andy, the founder… and me.

I’ve been part of similar groups before—people show up excited for a few months, but then life gets in the way and things fizzle out. To be honest, I didn’t expect this one to be much different as I sat down across from Andy with my cold brew.

After some small talk, he pulls out his phone and says, “Here are the goals for my business by the end of 2025. If I can increase revenue by X%, I’ll have enough of a marketing budget to elevate my customer base to the next tier. What are your goals?”

I lean back, a little embarrassed. I wasn’t prepared for that level of conversation. For the past few years, I’ve operated my speaking business with a sort of “Jesus take the wheel” mindset. The phone kept ringing, gigs kept coming in, and I never really developed a strategic plan. Things just... worked.

We continue talking—our short-term goals, what’s working, what’s fallen flat. Near the end of our hour, Andy asks:

“What’s been your biggest failure so far?”

I’m stumped again. As I think it over, I realize I haven’t encountered a lot of failure. I begin to speak my thoughts aloud:

“I haven’t failed much… but honestly, I haven’t had massive success either. I’ve mostly stuck with what I know works—and to be blunt, it’s gotten boring. I haven’t taken risks, and without risk, there’s been little reward. I’ve just been floating.”

As I heard the words leave my mouth, it hit me: I’ve been incredibly risk-averse over the last five years as an entrepreneur. I’ve done just enough to stay afloat and look successful, but I haven’t risked in any meaningful way.

And that realization unsettled me.

Because when we stop taking risks, we start walking a thin line—the line between being comfortable and being stuck.

And the longer we stay on that line, the more likely we are to end up stuck.

When we get stuck, our confidence shrinks and our regret grows. We miss opportunities. We silence our values. From the outside, things might look fine—maybe even impressive—but on the inside, we begin to feel hollow.

So if you’re hesitating to take a risk, ask yourself this:

What’s more dangerous—failing, or staying exactly where you are?

Fact

Regret over inaction is stronger than regret over failure.

Action

Write down one thing you're avoiding because of your fear of failure.

Question

What story am I telling myself about what could go wrong? What else might be true?

Quote

“A ship in harbor is safe, but that is not what ships are built for.” - John A. Shedd