I Wish I Knew This About Honesty and Regret | Hindsight with Doug Cavaliere

Doug Cavaliere answers the timeless question: What do you wish you knew then that you know now? His response blends humor and honesty—from wishing for a cheat code to avoid regrets, to one powerful piece of advice: be honest in your relationships. It’s a short but resonant reminder that wisdom isn’t just about business—it’s about how you show up for the people closest to you.

Key Topics

• The hindsight prompt: What do you wish you knew?

• “Everything” — the value of experience

• A life with no regrets is the ultimate cheat code

• Relationship advice: lead with honesty

Quotes

• “To come at this again with a life’s worth of knowledge would be the ultimate cheat code.”

• “Be honest in your relationship. Tell the truth from the beginning—you’ll be surprised how they react.”

• “To live a life without regret? That would be wild.”

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