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Howard Stevenson’s Unfiltered Guide to Success, Failure, and the Art of Living
“I failed once at retirement, three times at dying, and 71 times at making the Forbes list. I’m used to failure. Let’s talk about building a life.”
Howard Stevenson, legendary Harvard Business School professor, serial entrepreneur, and survivor of cardiac arrest (and life’s many curveballs), doesn’t sugarcoat success. In a recent talk, he dismantled clichés about achievement, legacy, and happiness, offering hard-won wisdom from a life spent juggling boardrooms, parenting, and near-death experiences. Here’s his no-BS playbook for redefining success—and why you’ll want to steal his “quiz” at the end.
Success Isn’t a Trophy—It’s a Moving Target
Stevenson opens with a brutal truth: “No one is successful until they die.” Society’s metrics—money, power, accolades—are fleeting. True success, he argues, is a four-dimensional puzzle:
Achievement: Crushing goals (but not at the cost of your soul).
Significance: Impacting people who matter (without becoming a martyr).
Happiness: Finding joy now, not in some distant “someday.”
Legacy: Building something that outlives you (without micromanaging your great-grandkids).
The catch? These dimensions often clash. “You can’t maximize all four. Life’s a juggling act—drop one ball to keep others in the air.”
The Four Myths That Derail Us
Stevenson eviscerates common success advice:
“Follow your passion”: *“Tell that to the 50-year-old ‘actor’ still couch-surfing in LA.”*
“Have it all”: “You’re not Dr. Ruth in the bedroom and Elon Musk in the boardroom. Pick your battles.”
“Balance”: “Forget balance. Juggling isn’t about symmetry—it’s about not letting the glass balls shatter.”
“Legacy planning”: *“Legacy isn’t a 1,000-year trust fund. It’s the ripples you create, not the splashes.”*
The “Enough” Mindset: Stevenson’s Secret Weapon
The antidote to burnout? Define enough.
Money: “My richest friend would pay $250K to get off the Forbes list. I track what I’ve given away—it keeps me sane.”
Achievement: “If you’re still chasing ‘more’ at 72, you’ve missed the point.”
Time: “Live forward. You can’t change the past, but you can stop obsessing over it.”
Howard’s Gift: The Quiz You Can’t Cheat On
Stevenson ends with a gut-check—a quiz he’s used to mentor CEOs, parents, and himself. Keep this honest, or don’t bother:
Who are you?
“Not your job title. What values would your obituary highlight?”What satisfactions are you missing?
“Achievement addicts: When’s the last time you prioritized joy over a promotion?”Who’s on your “board of directors”?
“Mentors are overrated. Build a personal board—one for finance, one for parenting, one for sanity.”Are you cheating at solitaire?
“If you’re lying to yourself about your choices, the game’s already over.”What’s your “ripple” metric?
“Forget the splash. What small act today will outlive you?”
Final Lesson: Live Forward
Stevenson’s parting shot: “Life’s risky. Control what you can—like taking your damn meds—and let go of the rest. And if you’re still comparing yourself to Bill Gates, get therapy.”
Your move: Take the quiz. Then ask: “Is the juice worth the squeeze?”
Howard Stevenson’s book, Howard’s Gift (written after surviving cardiac arrest), is a masterclass in unflinching self-assessment. Available wherever brutally honest advice is sold.
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