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You are here: Home / Life / A Lesson From One of My Biggest Regrets

A Lesson From One of My Biggest Regrets

September 24, 2023 | Renée Fishman

About 10 years ago, I read a book that completely changed my perspective on life.

Many people can point to books that shifted a paradigm for them, but this book is not one that you’d find on most lists of “top life-changing books.” In fact, I’d venture to guess that most entrepreneurs have never read it.

The book was the prayer book for Yom Kippur. Specifically, a version with commentary by the late Lord Rabbi Jonathan Sacks.

Yom Kippur was not a new experience for me, nor was prayer. I was raised in an Orthodox Jewish home, and from kindergarten through high school I attended a Jewish Day School, where twice a day we gathered for prayer.

Despite 12 years of Jewish education and many hundreds of prayer services, I never really learned about the prayers. Prayer was dogmatic, something we did.

But we never explored the meaning of the prayers, the origins of prayer, or why we pray in the first place.

We especially never learned much about the prayers for Rosh Hashana and Yom Kippur, the Jewish high holidays. Because these holidays fall at the start of the school year, we never learned much about them beyond their surface-level significance.

Even for a religion known for long prayer services, high holiday services are long. Rosh Hashana services can last 5 hours. Yom Kippur goes all day.

It’s easy to get lost. It’s common to tune out. Boredom is almost a given.

Growing up, I learned to find creative ways to pass the time. Counting boxes on the ceiling. Light bulbs in the chandelier. Looking at how many pages were left. And, perhaps the most obvious (other than praying): reading the English commentary.

That’s how I found myself one year, reading Rabbi Sacks’ commentary in the Yom Kippur prayer book. I got so absorbed in his writings that I didn’t even leave during the short afternoon break.

I didn’t even feel hungry during the waning hours of the fast.

I couldn’t wait to get to services to pick up where I had left off, and to read his commentary to the Rosh Hashana prayers. I wanted more.

The next year I got my own set of the prayer books.

Each volume is several hundred pages. Tape flags litter the pages. Faint pencil lines mark treasured passages.

Each year when I come back to them, I glean new insights and new pieces stick out for me.

Suddenly, the high holidays were infused with meaning beyond the surface level “sweet new year” and “day of atonement.” I could appreciate the observance and the ritual in the context of my life.

Unexpressed Appreciation

I had thought, periodically, of sending an email to Rabbi Sacks to thank him. I considered sending him a picture of my holiday prayer books, with their tape flags sticking out from the sides and top.

I wanted to tell him that studying his commentary on the prayers gave me an understanding of these holiest days far beyond what I learned in 12 years of Jewish education.

And how his broader body of work has shaped my understanding of life.

I wanted to tell him that he had touched my life in an extraordinary way.

I wanted to thank him for all he had given me through the gift of sharing his words in these prayer books and in his other writings. And, beyond words, how he had touched me by sharing his humanity: his doubts, his moments of struggle.

Somehow I never “found” the time.

I never made the time. I never took the time.

I never thanked him for the impact his work made on me. For the way his work shaped my life.

Rabbi Sacks died shortly after the high holidays in 2020.

When I heard of his passing, I was hit with a pang of remorse and regret.

I never expressed my appreciation, and now it was too late.

Regrets of the Living

People often speak about regrets of the dying. But dead people don’t have regrets. It is those of us who remain behind who are burdened with what we’ve left unsaid.

Not sending a thank you to him is a regret that returns to visit me at this time of year. And in that regret is a powerful lesson I’ve tried to embody ever since.

There’s a common frame offered, meant to spark us into urgency to do the important things:

What would you do if you only had a year to live? How would you contribute? What would you say if this were your last day on earth?

I prefer a different framing:

How would you show up with others if you knew today was their last day on earth? How would you speak to others if you knew this would be their last conversation?

The Trap of Rationalization

I could rationalize it away: I’m sure many people thanked him over the years.

He was a Lord. The Chief Rabbi of the UK. He traveled to teach and speak, and was revered around the world.

I’m sure he died knowing his work mattered and that he made an impact.

One more “thank you” from me would not likely have made a difference to this great man.

These might be truths, but they are irrelevant.

First, it contradicts one of the core teachings of the high holidays:

That each of us is here for a purpose and with something to contribute. No act is too small.

Who is to say that my gesture of appreciation wouldn’t have made a difference to Rabbi Sacks?

The Value of Appreciation to the Recipient

More generally, who’s to say that sharing our appreciation to others isn’t our greatest contribution to the world?

In fact, sometimes thinking of our life purpose in terms of a contribution to the world might be what gets in our way.

The “world,” is vast and amorphous. No individual has the capacity to impact or change the “world.”

But each of us can — and does — impact individual people every single day. And one of the best tools we have available to us in this effort is the tool of appreciation.

The right expression of appreciation or support for someone’s work can give them the motivation they need to keep going in the face of doubts about whether it’s worth the struggle.

We don’t know what someone might produce absent our affirmation or appreciation.

And what they produce might be life-changing for them and for those they impact.

When a sports team wins a championship, all the coaches and trainers also receive rings, reflecting their contribution to the team victory.

We should not underestimate the value of our appreciation to others; it can be transformative for them and their contribution.

The Value of Appreciation to the Giver

Second, when we express appreciation it’s not just the recipient who is transformed.

It is also us.

I deprived myself when I failed to express my appreciation.

Something within us changes when we express our gratitude to others. There’s an alchemical process that happens internally.

Appreciation of others opens our hearts.

It helps us see the world through a wider lens.

We see more possibility, more hope.

We are infused with more faith.

Our appreciation for others changes the world because it changes us and how we see the world.

And when we see the world through this bigger lens, we interact differently with people, and that has ripple effects.

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