Ever sold yourself short?

If you can think back to a moment you wished you’d backed yourself more—taken that chance, made the ask, leapt—you’re not alone.

The truth is, most of us regret the risks we didn’t take far more than the ones we did. By a long shot. That cautious voice hammering “What if…?” usually wins. And that’s because we’re lousy negotiators when it comes to our own lives. Not so much with others—with ourselves. Especially with the person we’ve yet to become.

Why? Because your brain treats your future self like a total stranger. Let me explain.

Research by Peter H. Diamandis and Steven Kotler (detailed in their book The Future is Faster Than You Think) found that that when we imagine our future selves, the part of your brain that lights up when you think about yourself starts to shut down. It’s the same reaction as when you ponder a complete stranger. And the farther into the future you go, the more cognitive effort is required and the alien you seem to yourself. No wonder we so often make shortsighted decisions and sell our future time so cheap—we just can’t picture ourselves in it!

That’s why people struggle to save for retirement, ditch bad habits, or make tough calls today that pay off tomorrow. Our biased brains trick us into thinking the person who’ll reap the rewards (or suffer the discomfort) isn’t really us at all.

The hidden ‘timidity tax’ compounds over time

This neurological quirk teams up with what Harvard’s Daniel Gilbert calls the “end of history illusion”: We admit we’ve changed heaps in the past, but we massively underestimate how much we’ll transform in the future. We think we’ve already peaked as who we’ll be.

The fallout? We shortchange our future selves. We cling to safe choices that keep us in jobs that no longer fit, relationships we’ve outgrown, or lives that feel too small. I call this the “timidity tax.” It’s sneaky—it doesn’t hit you now, but it racks up compound interest. Sticking with comfy today can leave you less secure, less fulfilled, and way more uncomfortable down the track. The irony?

In shielding ourselves from uncertainty now, we betray the person we’re evolving into.

I once interviewed Richard Branson at a global leaders’ retreat on his private Necker Island (yeah, tough gig, but someone had to do it). I’d spent the afternoon kite surfing with him—and nearly got blown to Cuba (slight exaggeration) but knowing he’d once flown a hot air balloon across the Atlantic (and nearly died), I had to ask: Have your goals ever been too ambitious? He didn’t miss a beat before replying:

“If your goals aren’t scaring you, they’re too small for you.”

Not gut-wrenching terror. Not paralysis. Just that, “I’m-not-sure-I-can-pull-this-off” aliveness. That’s the sweet spot – the gap between where you are now and where you could be if you made more consistent bets on yourself (present and future!) It’s where your deepest potential lives, and where you make your greatest impact on others.

Look at history’s greatest leaders—they pursued bold visions and chased big dreams that were no sure thing. Some thought they were too audacious. When Martin Luther King Jr. proclaimed “I have a dream,” he wasn’t talking current reality. He was claiming a future that didn’t exist yet, but one he believed was worth fighting for. As I shared in a recent keynote speech (above), in doing so he stretched what everyone else thought possible and rallied a nation.

Yes, King’s dream came at a cost. And no, not every dream was fully realized — not everyone is judged by the content of their character. But his life was profoundly worthy because he refused to betray his future self.

Risking ‘worthy failure’ honors your future self

You don’t need to seek to end racism or world hunger for your future self to high-five you. My family took on such a risk when we decided to climb Mt. Kilimanjaro – Africa’s tallest peak- at 19,341 feet/5,895m. We had four teenagers then. Friends thought we’d gone mad. We lived at sea level; our “big” climbs were sand dunes, not summits. Odds of all six summiting? Slim.

But that wasn’t the goal. If we failed, it’d be a worthy failure—one we’d never regret trying. Nine brutal hours from base camp, we all stepped onto the summit. Every one of us. Back at base camp, I learned our guides had placed bets we wouldn’t all make it. Huh! But that’s precisely the point: Only when you dare to do something that can feel, in the present, a little too ambitious, can you discover how much you can actually do.

Better decisions require empathy for your future self

So, how do we over-ride our neurobiology? How do we stop treating our future selves like strangers and start casting a vote for the person we’re on our way to becoming? By building empathy. Don’t just vaguely daydream—slow down, step in. Feel it. What does that life look like? What do you you look like (enlist GenAI to create an image of you 20 years from now)? What makes you proud? What regrets did you dodge by getting brave today? This isn’t fluffy stuff. This is science applied to your life!

The more vividly and often you connect to the future version of yourself, the more real they become. And the harder it is to let them down.

As leaders and change-makers, we should never underestimate our power to pivot, make changes and pursue challenges our future selves will thank us for. Bold goals, rooted in a big “why,” aren’t reckless in shaky times—they’re vital. Like Ranjay Gulati says in his recent article for HBR, “Now is the Time For Courage!”:

When uncertainty is running high and our instinct urges us to grip harder to the familiar, courage is most essential—and most rewarding.

So… what’s your Courage Gap?

It’s the space between what feels familiar today and the future that’s calling your name; between the person (and leader) you are right now and the one you have it within you to become (the one the people you care about most need you to become.)

Let me leave you with three questions:

1. Where are you underestimating yourself right now?

2. What change are you avoiding because you’re not sure you’ve got what it takes?

3. If you risked a worthy failure—one that honors your future self rather than short changes them—what would it look like?

As I wrote in The Courage Gap (a book your future self will be glad you read):

Dare to risk failures worthy of the person you’re on your way to becoming. 

So, what’s your Kilimanjaro? Whatever popped into your head—it’s no coincidence. If nothing did, start small: do one brave thing today.

Your future self will thank you. I guarantee it.