You Can’t Take It With You

If you’ve had a great career what happens to all your knowledge and experience when you retire?

Great Suit
My wife and I had dinner last night with a friend of hers from high school. Tom, her husband whom I had never met before joined us as well. I took one look at his suit and guessed “high-powered lawyer. “ (I was right, the suit probably added another $250 per billable hour.)

Over dinner we got chatting, and I found out that besides the great suit, Tom was actually a pretty remarkable guy. He was a trial litigator, one of the guys that slug it out in court in front of a judge and jury. And Tom wasn’t just any trial lawyer. He was the hired gun that Fortune 100 companies and hedge funds bring in when billions are at stake.  Listening to some of his stories over dinner was entertaining enough, but after awhile I realized I was hearing something else – this guy played strategy while his opponents were using tactics.

Chess and Military History
It turns out that Tom was a student of military history and a chess player. He described preparing for cases like war. “Most trial lawyers play defense. I’m on the offense from day one. In depositions and filing motions I’ll use misdirection to get the opposing counsel thinking I’m heading in one direction, and I’m heading in the other. When I file for a Summary Judgment, it’s usually from a direction my opponents never expected.” He then went on to give me a tour of 30 years of trial lawyer experience.

So I asked, “Did you learn any of this in law school?”  He laughed. “I went to Harvard. They didn’t teach war there.” “Do any of your junior partners in your firm know how to do what you do?”  “Well they watch me, and I guess they learn by osmosis.”

Then I asked my favorite question.

“When you retire, what happens to all the knowledge and experience you’ve acquired?”

You Can’t Take It With You
I think the question caught him a bit by surprise. I explained, “You have a record in winning trials that’s based on a strategy and methodology you developed and you’ve likely have moved the state of the art in your profession – and it’s all going into the trash bin of history – unless you pass it on.

Teach It or Lose It
I asked Tom to think about writing down a longer version of the stories he told me over dinner, almost like an autobiography but focused on his career.  And for each big trial or milestone summarize it with a “Lessons Learned” section.  I observed that at the end of this exercise, he’ll come to one of three conclusions: 1) he has a great collection of war stories to tell while he’s skiing or playing golf or 2) he can make a book out of those stories or 3) buried in the stories and lessons learned was a strategy that was new, unique and worth teaching to future generations of lawyers.

I suggested that he volunteer to guest teach in someone else’ class at a local law school (and where he lived there were plenty) to see if he enjoyed it.  His war stories would certainly keep students on the edge of their seats. (If you were a law school student having him come in to your class and say, “The first time you run into me, I’d make you wet your pants” might get your attention.)

But more importantly this would help him decide if he wanted to teach as an Adjunct Professor after he retired. If as I surmised, he actually did push the state of the art in his field forward and his teaching went beyond war stories to a theoretical framework, most schools would be happy for him to develop and teach a class.

Why Do It?
I suggested that there were four reasons he ought to take teaching seriously. First, his accumulated knowledge will disappear when he does. Second, it’s incumbent on all of us to make those who come after us smarter than we were.  Third, having students question your assumptions makes you smarter (and at our age growing new neurons are helpful,) and finally fourth, for those of us whose career was on a stage, teaching is just another stage with an appreciative audience.

Not Just For Lawyers
Driving home for dinner, I realized that the same advice for Tom and lawyers would work for professionals in any domain; doctors, engineers, venture capitalists, CEO’s or even entrepreneurs. Don’t let your knowledge and experience die with you.

Lessons Learned

  • If you don’t teach it or write it down, the accumulated knowledge of your career is gone.
  • War stories about your career can be entertainment, or even better if you want to teach, make them the basis of a strategy and methodology worth passing on.
  • Retirement doesn’t have to be only about golf and skiing.

35 Responses

  1. I would have to say you are going a great service to all entrepreneur by writing down both in your book and blog your accumulated knowledge. You’ve had a huge influence on me.


  2. your posts are always interesting and wise!
    thanks a lot

  3. Steve, more I read you, more I’m happy to know you in person August 31 in Palo Alto. What you mean is the reason of my professional life- also if not retired yet, 57 year old but a baby of 20 months – cause I feel exacltly what you mean. Really I don’t do any teaching of my experience, but better saying , i mentor the hundreds of young grads and undergrads that follow my conference “la Storia nel Futuro” projects, with major invited speakers, in italian Universities since 1999. This summer in particular I’m happy: after the 5th great Silicon Valley Study Tour of 2009- 24 attendees from 6 Italian UNi- I have the pleasure to find 8 of them in the Bay Area this year for intern or real job. These 7 guys and 1 girl had no knowledge about Silicon Valley up to last year, today they are young professionals that opened their minds “360 degrees” …and are ready for the global market! To trasfer your knowledge is, in my view, the best thing you can realize, mainly after your 50ies…is just like leaving a part of you to grow, again and again, in other minds and hearts. What’s more to leave in this World??

  4. When my father died I longed for a way to download his soft-drive (brain) filled with experience and logic that the oil industry and any corporate manager (BP?) could have used. There is no such solution – yet. Sahirng the knowledge face-to-face as a teacher is the answer. There are many obstacles to overcome before one can teach – lack of a doctorate degree or even a masters is the first. But, this can be handled with an online graduate program like University of the Rockies. The next step is to walk into a school administrator’s office and ask for a job. Most will say no. Most students could care less. But, if you can stand the insolence and indifference, you will change a few lives.

  5. What a wise and life-affirming story and advice. I have heard good things about Encore career to help boomers and seniors translate their talents into a second kind of work btw.

    If this successful trial lawyer did team teaching or other work with a complementary other individual or two he might also gain fresh insights on his work and enjoy the pleasure of a fresh kind of work

    • Thought you might like to know that a nonprofit in San Francisco called Civic Ventures has been working for a dozen years to promote the idea of encore careers, which we define as careers for people at midlife that offer continued pay doing work that is personally fulfilling and helps make the world a better place.

      We help create pathways for encore careers in health care, education, the green economy, government and the nonprofit sector through college programs, employer awards and Encore Fellowships that pay people from the corporate sector a stipend to try out jobs in the nonprofit sector. We annually award five $100,000 prizes and five $50,000 prizes (The Purpose Prize) to individuals over age 60 who are creating extraordinary social change.

      You can check us out at and read some of the stories of amazing individuals in encore careers.

      Terry Nagel
      Managing Editor,
      Civic Ventures

  6. This is like a teaser post. I want to read his actual stories.

  7. “They Don’t Teach War at Harvard” would be a great title for a book – I’d read it.

  8. That’s an interesting post and I think I wouldn’t hesitate to agree with you if Tom was a doctor or an engineer – passing on their knowledge would be useful for society. But with him being a trial lawyer, I wonder whether
    sharing his knowledge is worthwhile.

    Is it useful for society when a lawyer teaches more complicated trial strategies to future lawyers? Who would benefit from that? Probably only those who happen to attend this class as well as their future clients. Everybody else would suffer, because it makes the legal system even more complex and, as a result of the complexity, more expensive. And it would also help people to win cases not because the law is on their side, but because their lawyer is better than the other party’s. I don’t think that these are desirable goals.

    Please don’t misunderstand me: I don’t mind Tom using his knowledge for the benefit of his clients as well as for his personal wealth. It’s everybody’s right to do whatever he can to win in front of the court. And I could completely understand him passing on his knowledge to his children or other people close to him – then his cause would be to help them. But I think that advanced court strategies are not knowledge that would advance society. And thus, at least I wouldn’t be sad if this knowledge would actually be gone.

    • I second what Tim said regarding the value of passing on advanced court strategies. Such knowledge is a powerful weapon, and a lot of discretion is needed in knowing on whom to bestow it. Regarding a future career path that would reflect this, Tom could become a sage, a mentor to a few carefully-chosen disciples. Perhaps he could still teach at a law school so that he could meet many students, among which he may find some worthy successors. He could apply his engaging storytelling abilities to teaching the standard curriculum, but save the advanced court strategies for the carefully-chosen few.

      Making our successors smarter could be a worthwhile endeavor, but not necessarily so. For example, having medically-smarter doctors would be good, but legally-smarter patent trolls not quite. Intelligence is just part of the picture. Aren’t superbly-smart, yet supremely-self-centered financial analysts largely responsible for the world’s current economic crises? Building character among our successors is more incumbent on us than making them smarter. An ideal future would be inhabited by smart, yet virtuous people who know not just how to advance their individual interests, but to collectively cultivate a beautiful society.

    • As a young lawyer, I’m going to disagree. I’ve been wanting a book like this for years. (Through law school to today.) But nothing quite comparable exists.

      I guess it’s blind faith, but my presumption is that sharing knowledge and moving the ball forward is a good thing. If that knowledge gets into the hands of some ill-intentioned litigator we can only hope it’s also picked up by 10 or so decent folk. I’d imagine the same can be said for any knowledge.

      At any rate, in my experience the truly nefarious types don’t bother to expand their mind so they would never find the book in the first place. That’s why they’re nefarious. Because they’re fools.

    • For what it’s worth, there are TONS of books (and a few good ones) on legal ethics and character that were written on this very model: stories and experience passed down. I’d recommend those books too. They would make a great graduation gift pack!

  9. Thanks for this; it has awakened something in me… the book that I am writing about bankruptcy and life… and bankruptcy really means… must be completed. For those, who do not want to ‘go’ that route, I offer a different perspective. I must get on with the book! Again, thanks.


  10. +1 for the 2011 release of “They Don’t Teach War at Harvard”… where’s the waiting list?

  11. Like LIAD says above – if that guy’s book gets written, please let us know!

  12. nice work, SB.

    I might add [and this coming from a man not ever married (yet) or with child (yet)] that there is something to be said for the power of passing on knowledge of all types to our children and their children (if i live that long).

    As Lou said, just change a few lives. I’m barely 40 and feel like i could today after running my firm for only 15 years.

    thanks, nelson

    ps I too would read Tom’s book.

  13. just for the record, real lawyers think Tom is a buffoon and his strategies are ineffective

  14. Come on. There is a zero percent chance of a summary judgment motion coming from a completely unexpected direction in a major case. Especially if you have “misdirected” opposing counsel so much at depositions that you failed to pin down the witnesses on testimony supporting your motion. I am sure the guy is good, but his unique ability is apparently self promotion rather than litigation.

  15. Steve, first, thanks for writing a great book. It has helped us and continues to help us! Second, we just launched a social learning platform that is great for teaching others. It is free and was recently featured in techcrunch and in the Chronicle of Higher Ed on Friday. If any of your readers are looking for an easy place to share their knowledge, then check out

    I’d love to get your course materials on there as well!

  16. One of the most interesting things about blogging is what I learn from the comments. While my writing style might be oblique I’ve attempted to make my posts clearer by putting a summary statement up front and lessons learned at the end.

    Yet there’s always a percentage of readers who I seem to miss. They focus on the minutia and miss the story. A few of them have commented above and below.

    For those who missed it – The blog post was not about lawyers. Nor was about this lawyers detailed techniques and strategy in summary judgements. I surely don’t know enough about litigation to have summarized it correctly.

    If those who made those comments really are lawyers you seem to reinforce Scott Walker points #5 and 7 in his blog:


  17. […] You Can’t Take It With You If you’ve had a great career what happens to all your knowledge and experience when you retire? Great Suit My wife […] […]

  18. Great article, but I question the use of this for a lawyer. Sure, a engineer, CEO, designer, this is useful knowledge to pass on. But a lawyer is just cheating the system using these techniques. How does this make society better to give some lawyers the edge over others, rather than having a case decided on merit by the judge/jury? Surely we don’t want lawyers tricking the system to win their case?

  19. Wow. There’s an incredible amount of bark-inspection going on in these comments. I’m marveling at the incredible command many of you have of the law and its many nuances. I’m impressed. No, seriously, I’m really impressed.

    Now, can you step back, look at the forest, and see what the point of this story was? (Hint: it has ZERO to do with legal process.)

  20. I think an audiobook would be better. I don’t have time or attention span to read anymore. Plus we save some trees.

  21. I suppose what upsets me about this post is that I have no clever methodologies or strategy to pass on. As a programmer there are minimal things interesting about what I’ve done. I’m not that smart? I dunno.

    I guess I have a new goal to go fail at now

  22. […] Blank, startup guru and author of Four Steps to an Epiphany, writes about an anecdotal experience that speaks to the importance of informal learning and mentorin… that very few people seem to take advantage […]

  23. “In today’s world, there are attorneys who think that the right way to pursue a case is to be superaggressive,” he said. “This case is a lesson that a lot of superaggressive tactics can backfire.”

    I understand the takeaways to this post are not about lawyers or lawyering, but the views expressed by your friend are controversial ones among lawyers at least, so I’m not surprised to see others commenting on that aspect of the post. The reason they don’t teach war at Harvard Law School is because war was quite literally replaced by litigation. It was quite a development in the history of civilization when trial by jury replaced trial by ordeal and trial by combat. While the adversarial nature of litigation will never end, and while Sun Tzu is always an inspiration, there are some of us lawyers who aspire to conduct litigation in a way that would transcend the analogy to war.

  24. Your request is an interesting one, but goes against some concepts of warfare. For example, it is common practice in the traditional Martial Arts communities of Asia prior to only disclose your “tricks” to an individual or group of individuals to the extent to which you trust them. Most masters kept a few tricks secret, even to their death, just in case they got into a bad jam.

    Institutional/collective/public knowledge is great, but if it is sufficiently potent, then it can be abused to our detriment. I’d recommend that this man’s knowledge only be passed on to those that he mentors, trusts, etc. If there is no one that fits the bill, his knowledge dies with him. Granted it is a loss, but that’s better than it being marginalized, abused, or misapplied.

    Discipleship (for lack of a better phrase) is a great way to pass along information, and it is a dying art itself.

  25. Reading your article made me think about the ancient system of master craftsman / apprentice, i.e. training by working with an established practitioner. One of the traditions we’ve inherited from this is the way medics are trained in teaching hospitals.

    So, do you think reading / listening to a few “war stories” is really going to make a different, or is it a more in depth process (“mentoring”)?

  26. Great post! Especially in the fast-paced world of startups here in valley it’s hard to remember that the lessons learned at each stage, in each company, can help others trying to do the same. There is also great opportunity to pass that knowledge on given all the universities in this area. I haven’t been in a marketing “class” lately but I would guess that many schools are still teaching marketing the same way they taught it 20 years ago.

  27. […] of the reasons I took up teaching is my strong belief that it’s incumbent on all of us to make those who come after us smarter than we were.” So when I heard Kathryn gave the University of Chicago commencement speech I suggested that she […]

  28. […] of the reasons I took up teaching is my strong belief that it’s incumbent on all of us to make those who come after us smarter than we were. So when I heard Kathryn gave the University of Chicago commencement speech I suggested that she […]

  29. That’s exactly the reason why we try to codify business. To take what smart and innovative business people have done and turn that into transferable knowledge.

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