Why Trying the Same Thing Over Again is Not “Crazy”

For a long time, we’ve accepted this piece of cultural wisdom, “Insanity is doing the same thing over and over and expecting different results.”

But what if it’s wrong—or at least not wholly right?

What if trying the same things, or at least attempting the same goal, over and over, was not crazy?

What if it were a master stroke of genius?

You see, sometimes, timing and opportunity meet.

Those of us who are stubborn may look at a dream life goal with the tenacity of a determined bull and an open mind to the possibilities.

I remember a guy in New York, who thought he was very clever, asking me after years of my saying that I would live in Europe, “When are you going to give up? It’s not possible.”

Only it was.

It turns out, I married a European later in life who wanted to return to the continent.

Somehow, someway, the universe conspired to have him and me meet.

In other words, timing and opportunity met.

How many times do people hear after a try and a fail that “they will never” succeed?

I wonder about parents, grandparents, and older people who say it to young people who are early in the journey of chasing their dreams.

Youth may not yet have learned, through years of experience, that failure is always part of a rich life journey.

Is the message young people hear, don’t try and stay in the safe lane?

Do they hear that risk of any sort and failure is not a good thing?

Sure, when failure happens, it hurts and frustrates, but it’s a massive learning opportunity.

And sometimes, when someone has taken another approach to achieve the same goal, it’s a matter of timing and opportunity colliding.

In the quote about trying the same thing over and over again, the critical words are “same thing.”

I am incredibly fortunate to have talented, kind, and creative young women in my life. They’re in France, Spain, Canada, and the United States. Each one is a testament to one of the most pivotal people in my life who always encouraged me to pay it forward.

Each of them has a goal in her life.

To have a fantastic career, to marry (or not), to have children, and to become a CEO.

What do I see in the sliver of the worlds they share with me?

I see each going for their goals.

And even when they might not quite reach it because it was a hit and a miss, they change things up after learning and iterating, and move forward.

That’s the thing about those who do and fail along the way.

They may look like they’re not succeeding.

And when they fail and fail, they may even look like they’re failing spectacularly.

Oh, poor, poor, trying soul.

But, if you know these people I know, and millions of others who do not quit, and you know they’re intelligent, persistent, and courageous, they might just be failing up toward their goals, waiting for timing to meet opportunity.

I don’t know many answers in life.

All I know is my own experience and my lessons.

But one thing I know and have learned along the way is that persistence, and sometimes timing, is everything.

I have a close friend and colleague who has lived for years with cancer. The doctors have given him tough news, but he’s one who has reminded me to put things in perspective during one of our discussions.

He asked me to think of 57^th Street in Manhattan, and he said to imagine going from east to west.

For him, cancer or illness in general means that we have to pump the brake or stop at the light when it turns yellow or red.

But then the light turns green, and you keep going.

You don’t stop.

You keep going—until there’s no more road.

I never forget his words, because I know his experience.

He will not quit.

I’ve achieved a great deal in my life goals, but I’ve also failed a lot along the way.

Still, I’ve tried, as have the people I most admire in my life, including the talented young women who take the time to say hello to me and share a window into their lives.

© 2025 Linda N. Spencer, My Red Sneakers. All Rights Reserved.