Legacy Planning

A Personal Story

In this episode, Bestselling Author Allan Crockett shares a deeply personal story about nearly boarding a plane that later crashed and killed his friend. A powerful “do not get in that plane” gut check saved his life, but it also left him fearful of flying for years. Later, a former airline pilot challenged him with the words, “It’s not too late,” prompting Allan to finally learn to fly. He uses this story to invite listeners to name the dream that’s been nagging them and to take the first concrete step toward it.

A Word About Risk

In this episode, Bestselling Author Allan Crockett reframes risk for entrepreneurs who have already achieved business success and are stepping into what’s next. He contrasts youthful, “drive all night” risk with later-life reality, explores the gap between spouses’ risk tolerances, and shows how to build security and freedom without blowing up your relationships or your retirement.

What Would You Do If You Knew You Could Not Fail?

In this episode, Bestselling Author Allan Crockett introduces Section 5 of his book—“A Clean Slate”—and uses a client story to show what it looks like to rebuild a business (and a life) when you’re free from financial pressure. He invites listeners to ask a powerful question: if you knew you couldn’t fail, what would you create in your next chapter?

Legacy Planning

In this episode, Bestselling Author Allan Crockett explains the critical difference between estate planning and legacy planning, showing why high-capacity entrepreneurs must think beyond wills and wealth. He unpacks how your post-exit life—how you use your time, talents, and relationships—creates the real “multi-generational inheritance” your family remembers.

Agreements Vs. Expectations

In this episode, Bestselling Author Allan Crockett contrasts the emotional chaos of expectations with the clarity of agreements. Using stories about airline upgrades and Christmas bonuses, he illustrates how unspoken expectations often lead to frustration. Then he explains how simple agreements—at work and at home—can transform how you navigate time, money, shared plans, and everyday life after business.