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How to Die with No Regrets

Forbes Contributor and self-described “serial entrepreneur and professor turned venture capitalist,” John Greathouse recently posted a summary of entries from H. Jackson Brown Jr.’s, Life’s Little Instruction Book.

According to Greathouse, Mr. Brown sat down at his kitchen table in 1990 (the same year I graduated from Law School) to write out some advice for his son who had just entered college. Those early musings eventually morphed into a series of very popular books.  (Mr. Brown became the first author to simultaneously hold the number one positions on both of the New York Times’ hardback and paperback lists).

Greathouse selected 43 of Brown’s snippets of advice he thought were most relevant to business executives wanting to live a regret-free life.

Surely his selections apply to lawyers trying to win new business.  The Greathouse List is repeated here:


1. Never give up when you truly believe. The person with big dreams is more powerful than the one with all the facts – the smartest person in the room seldom beats the one with the most passion.

2. Believe in love at first sight – be open to instant infatuation with respect to both people and business ideas.

3. Never laugh at anyone’s dreams – no one has the right to opine upon someone else’s desired future because no one can attest to the validity of an unrealized dream.

4. Find a job you like and you add five days to every week – I often tell my children, “I never worked at day at my startups because we were having too much fun.” Admittedly, not every day was a carnival, but I certainly enjoyed the majority of my startup workdays.

5. Every so often, let your spirit of adventure triumph over your good sense – good judgment arises from mistakes, mistakes arise from bad judgment. Thus, a bit of occasional bad judgment is good for you.

6. Great love and great achievements involve great risk – nothing ventured, nothing gained. Go venture.

7. Never let the odds keep you from pursuing what you know in your heart you were meant to do – entrepreneurs never calculate probabilities, even if the chances are one in a million, “one” is all you need to win.

8. Never deprive anyone (including yourself) of hope, it might be all they have.

Be Nice

9. Be the first to say, “Hello” – always set a friendly tone with a warm smile, a hearty handshake and a robust greeting.

10. Buy whatever kids are selling on card tables in their front yard – and let them keep the change. 

11. Be kinder than necessary – there is an infinite supply of kindness, so don’t fear depleting it.

12. Give people a second chance, but not a third – be nice, but not stupid.

13. Be tough minded but tenderhearted – hold people accountable, but consider uncontrollable factors that impact someone’s performance.

14. Every so often, push your luck – push your luck slowly and deliberately, but be ready to quickly pull back, as you often won’t know you have pushed your luck too far, until after the fact.

15. Win without boasting, lose without excuses – internalize your failures and externalize your victories.

16. When lending people money, be sure their character exceeds their collateral – honesty matters, both yours and those with whom you associate.

17. It’s not your job to get people to like you, it’s your job to like people – you can only control your own actions and feelings, don’t try to control those of others.

18. Never resist a generous impulse – if you hesitate, you’ll quickly rationalize a dozen reasons to act charitably… later. Unfortunately, “later” rarely arrives.

19. Fight fairly. Give generously. Laugh loudly. Love deeply.


20. Become someone’s hero – when someone asks you to be their mentor, smile and say, “I would be honored.”

21. Do your homework and know your facts, but remember it’s passion that persuades – history if filled with passionate leaders, I know of none that were unemotional.

37. Take care of your reputation. It’s your most valuable asset – honesty is a serial entrepreneur’s most potent weapon.

38. Watch for big problems. They disguise big opportunities – great entrepreneurs turn challenges into breakthrough innovations. Embrace problems, never flee from them.

39. Earn your success based on service to others, not at the expense of others

Be Happy

40. Happiness is not based on possessions, power or prestige, but on relationships with people you love and respect – if you doubt this wisdom, consider all the rich, powerful and famous people who are miserable.

41. After you’ve work hard to get what you want, take the time to enjoy it – in Startup Life, Brad Feld advises entrepreneurs to spend 10% of the proceeds of a financial windfall on something frivolous. What’s the point of accumulating capital if you never derive pleasure from it?

42. Don’t think you can relax yourself to happiness. Happiness comes as a result of doing – as David Pink has noted, most people are motivated by mastery, autonomy and purpose. These needs are heightened with inactivity, which is why most happily retired people have active lives.

43. Be happy with what you have while working for what you want.


Craig Brown has worked with managing partners, attorneys, CEOs, and executives, as a coach, consultant and business executive for over 20 years.  He is a Principal in the business development practice at LawVision Group and ss far as he knows, he is not related to H. Jackson Brown Jr. but he likes his advice.

He can be reached at cbrown@lawvisiongroup.com


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