Stop Waiting to Get Around to It Raising the Barr Weekly Memo: Issue 662

This week my wife, Cantor Laurel Barr, delivered a fascinating sermon to her congregation, at Temple B’nai Abraham, in Elyria, Ohio. Everyone was fully engaged, focused on her uplifting and thought-provoking message. She shared the story of a recent lunch my wife and I had at the farm of a remarkable congregant in his nineties, known to many simply as Farmer Dave. He built a full and accomplished life, yet admitted he still wished he had slowed down, traveled more, and made more time with his wife.

Even the most successful among us carry regrets when we keep waiting for the “perfect time.” That’s why her message struck me so deeply: every year, people promise themselves they’ll get around to it. The problem is that “someday” rarely arrives. That’s why at Rosh Hashana services, each congregant was handed a small token: a round disc labeled “tuit.” A literal “round tuit.” The message was simple: you’ve now got one. No more excuses. Do it now.

What resonated with me was that this lesson isn’t just spiritual, it’s strategic. Leaders and professionals who delay decisions, defer action, or avoid risk inevitably accumulate regrets. In business, those regrets often look like missed opportunities, stalled growth, or competitors seizing the moment. 

The themes of reflection, regret, and renewal woven into Rosh Hashana offer a surprisingly practical framework for leadership. Here are the key takeaways for anyone serious about making the coming year one of impact.

1. Reflection Without Action is Useless

The High Holy Days call for a soul-accounting. We examine where we succeeded and where we fell short. Businesses need the same discipline: quarterly reviews, client feedback, financial audits. But self-analysis is wasted if it doesn’t change behavior. The true test is whether you act differently when faced with the same situation again.

Business application: Stop producing reports that gather dust. Tie every review to specific actions: what will we do differently tomorrow?

2. Procrastination is Expensive 

Too often, opportunities slip away because people convince themselves the timing isn’t right. Projects get postponed, partnerships are delayed, and important conversations are avoided. The chance for meaningful progress is lost simply because action was deferred. In business, leaders delay decisions under the illusion that they’re waiting for the “perfect time.” That time never arrives. 

Business application: Create a bias for action. Launch the pilot program, test the new market, call the client. Perfection is a myth; progress is the only currency that counts.

3. Regret Can Be a Teacher

Many accomplished leaders eventually admit they wish they had slowed down, invested more in relationships, or pursued experiences beyond work. Even with impressive achievements, regret often lingers. We should not deny regret. We should face it and then use it as fuel for change. 

Business application: Every leader has choices they wish they had made differently. The mistake isn’t the regret, it’s failing to learn from it. Ask: what does this regret reveal about how I should lead today?

4. Gratitude Fuels Resilience

My wife’s sermon beautifully balanced regret with gratitude. Realizing and acknowledging that the path not taken often leads to profound blessings. Leaders who practice gratitude toward teams, clients, and even past challenges gain perspective. Gratitude doesn’t eliminate ambition, it sharpens it by focusing energy on what matters most.

Business application: Begin meetings by recognizing wins, large and small. Gratitude fosters morale and resilience, especially in uncertain times.

5. Change is Urgent, Not Optional

Rabbi Nachman of Breslov said: “If you will not be better tomorrow than you are today, then what need do you have for tomorrow?” Improvement isn’t a luxury, it’s survival. In competitive markets, the refusal to change is the fastest route to irrelevance.

Business application: Build a culture where iteration is constant. Challenge teams to identify what they will improve this week-not next quarter. 

The Call to Action

The round “tuit” my wife handed out at services is more than a playful token. It’s a challenge: stop waiting, stop excusing, stop stalling. Rosh Hashana reminds us that this is the season of renewal. For business leaders, it’s a reminder that time is the one resource you can’t replenish.

So here’s the question: What have you been putting off? The new service launch? The strategic hire? The tough client conversation? I am officially handing you your round tuit. No more waiting. This is your moment.

I want to thank my wife, Cantor Laurel Barr, for her inspirational sermon and for providing me with the ideas and insights for this week’s newsletter. Let her words entice and challenge all of us to take action now.

And stay tuned. On October 1, 2025, I will be announcing the launch of the AI Insider Lab, a bold new platform designed to help you harness AI to transform your business and life. This is not just another program, it’s your edge for the future. If you’re curious, serious, and ready to be part of something extraordinary, reply with JOIN.

We wish you, Shana Tova. May this year be filled with sweetness, health, and joy. And may we all see a year of peace.

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