I Asked 100 Strangers What They Regret Most. The Answer Will Surprise You.

Last month, standing in line at Starbucks, I overheard this old guy telling a friend: “My biggest regret is not marrying the wrong person. That’s obviously embarrassing Who it’s not asking out is the right one.”

That got me thinking. So what do people regret the most?

So, for 30 days, I approached strangers and hit them with a simple question: “What’s your biggest regret in life?”

The answers shocked me.

The setup

I asked 100 people of various ages, backgrounds and walks of life. Cafes, parks, waiting rooms, train stations. The only rule: complete honesty.

Here's what I discovered.

The surprising pattern

Friendly answers: Awful decisions with past relationships, major career mistakes, significant financial mistakes

"No."1 answer (67% of people): Things they never tried

Not things they failed at. Stuff they never even tried to do.

The regrets we have, well, you know the rest

"I’ve never learned to play the piano. SARAH, 45, MARKETING MANAGER

"I wasn’t a young backpacker with no obligations." Mike, 38, three kids

“I never said ‘I love you’ to my dad before he passed.” - Jennifer, 52, teacher

“I first of all didn’t start a business when I had my idea. Carlos, 41, software engineer ** “The First Temptation of Christ” (2019) “At no point was anyone carrying a cross, so cue Jesus’ entrance, which honestly seemed like something straight out of a telenovela.

“The thing I regret most in my life is I never learned a second language. - Emma, 29, nurse

Notice the pattern? "I never..." not "I shouldn't have..."

The psychology behind regret

Social scientists have a term for this: “regret of inaction” versus “regret of action.”

We believe that the risks we take we’ll regret. And yet science tells us we regret what we’ve never tried at all.

Why? Because:

— Failed experiments are stories and lessons????

What could have been turns into this sort of haunting “what-ifs”

We can explain bad results away

We can rationalize never trying

The 20-year rule

The most revealing responses came from those over 50. We asked them what they wished they had known at 25:

“No one will remember you for NOT trying. No one will remember the things you did NOT do.”

“The disgrace of losing lasts weeks. The regret of not giving it a go lasts a lifetime.”

“I focused so hard on getting everything just right that the right moment never arrived. "

The conversation that changed it all

The most forceful response arrived from Robert, 73, who was on a bench in Central Park by himself:

"Son, I’ve made plenty of mistakes in my 73 years. Lost money, said moronic things, made dumb decisions. But you know what I really worry about at night? The woman I didn’t invite to dance, in 1967. The job I was too terrified to accept in 1975. The book never written because I was waiting to get ‘better’ at writing.”

"Bad choices make good stories. But what about the odds you miss? Those are the ones that leave you wondering the rest of your life.”

The most-frequent "never tried" regrets

Creative pursuits (writing, music, art)

Starting a business

Traveling...

Learning new skills

Expressing feelings honestly

Taking career risks

Speaking up in important moments

What the young people said?

Even more shockingly, people under 30 were already experiencing this trend:

"I regret not studying abroad."

“Should’ve asked her out in college.”

“I should have formed another major the moment I realized i hated this.

The regret cycle starts early.

The cure for future regret

If we these 100 conversations — here’s the formula (in fewer regrets):

Ask yourself: “Will I regret not having tried this in 10 years?”

If yes → Try it.

If no → Skip it.

The worst that can happen: You don’t succeed and learn instead.

The best thing that happens: You succeed and expand.

Why not just try: Otherwise, you’ll always be wondering.

Start today:

That thing you’ve been contemplating doing even though you haven’t even begun?

The creative project. The conversation. The trip. The career change. The skill you want to learn.

Your future self is relying on your present self to be courageous.

The final word

After 100 conversations, this is what I do know for sure:

People don't regret taking a chance. They are remorseful of the opportunities they passed up.

Your move.

What have you been procrastinating on that you know you should try? Tell us in the comments — sometimes putting it in writing is the first step toward making it happen.

What WILL you regret NOT doing if you don't begin right now?