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“I Wish I Had” vs. “I’m Glad I Did”

08/04/25

A few weeks ago, I was traveling for work, and I called my daughter before she went to bed.

I can sense something was off, so I asked her, “Everything okay, sweetheart?”

She said, “Yea, it’s just…we used to go on vacations together, just you and me, and we haven’t done that in so long. I miss that, and wanted to know if we could go somewhere this summer?”

My heart sank into my chest.

She was right.

While we have had a few trips here and there, it wasn’t just the two of us like we used to do when she was younger.

I said, “Let’s figure something out, kiddo. I promise, we’ll make it happen before the summer is over.”

The next morning, I looked up Jersey Shore vacation options and booked a weekend trip.

Right now, I’m writing this newsletter from Point Pleasant Beach on the porch of our hotel room.
While I did feel the guilt and sadness from when my daughter said that to me, the real motivation to book this trip was quite different.

It might sound morbid, but hear me out.

It’s the fact that I know that one day, she’ll be here, and I won’t.

She’ll remember experiences.

She’ll think about the quality time we spent together.

She’ll reflect on the time that I dropped everything for her and took her down for a weekend trip, just the two of us.

And when I’m reaching the final chapter of my life, I’ll look back and remember the same.

I would either look back and feel grateful that I spent weekends like this with my daughter…

Or look back and feel regret that I didn’t.

I encourage you to zoom out and think about what matters most when it comes to how you spend your time.

At the end of your life, you’re not going to wish you worked more.

You’re not going to be grateful for the weekends you spent in the office.

It takes me back to that powerful quote I once heard by the great Zig Ziglar.

“You will either look back in life and say, ‘I wish I had’ or ‘I’m glad I did’.” ~ Zig Ziglar

Rooting for you,
Jay (encouraging you to live without regrets)

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