"I Wish I Had" Verses "I'm Glad I Did"
There are two kinds of people at the end of their lives. The first group says, “I wish I had.”
I wish I had taken the shot.
I wish I hadn’t waited so long.
The second group says, “I’m glad I did.”
I’m glad I went for it.
I’m glad I made the call.
That’s it. That’s the split.
After decades of life…after all the noise and complexity…it comes down to that simple divide.
And here’s what hit me (Mike) hard listening to Mel Robbins interview Dr. Rahul Jandial, a world-renowned cancer surgeon talk about thousands of patients at the end of their lives…
No one says, “I’m glad I played it safe.”
No one says, “I’m glad I stayed practical.”
No one says, “I’m glad I waited until everything was perfectly lined up.”
They wish they had been bolder.
Now let’s bring this into business. Because the same divide exists.
There are two types of business people.
The first group builds careers or businesses full of quiet regret.
They played defense instead of offense.
They listened to the crowd instead of their gut.
They stayed in something too long…or never started the thing they knew mattered.
They look back and say, “I wish we did that.”
The second group… They’re not necessarily more successful on paper. They don’t win every time. They don’t avoid failure.
But they don’t carry that same weight. Because they acted.
They made the call.
They took the swing.
They followed the instinct when it didn’t make sense to anyone else.
They made bold moves when the optics weren’t right.
And when they look back, they can say, “I’m glad i did.”
Even when it was messy.
Even when it hurt.
Even when it didn’t work out.
Because regret doesn’t come from failure.
It comes from inaction.
It comes from ignoring that internal voice.
It comes from what Dr. Jandial, the surgeon, called “moral injury”…doing something that goes against who you are or not doing something you know you should.
So here’s the question I want you to sit with… Which one are you becoming?
And more importantly… What are you not doing right now in your business that your future self is going to wish you had done?
Not in theory. Not someday. Right now.
The call you’re avoiding.
The decision you keep pushing.
The idea you haven’t greenlit.
The move you know is right but feels uncomfortable.
Because there is no moment of arrival where this gets easier. There’s only a series of moments where you choose.
Only you can make the decisions that determine whether one day you’ll look back and say “i wish i had”…or “i’m glad i did.”
Love,
