William Tincup, HR Examiner Editorial Advisory Board Contributor

William Tincup, HRExaminer Editorial Advisory Board Contributor

People die.  Truth is, we’ll all die sooner than we think.  Some live outrageously. Others pursue a more cautious path.  No judgment… regrets are like hot M &M’s.  They suck.

As we age, we all make decisions – subconsciously or consciously– about how we desire to be remembered, and how things should carry on.  Two obvious approaches are: 1) the fuck you, I did it my way – learn it yourself (the bootstrapper), and (2) I care about you and how things happen when I’m gone (the stewards).

Whatever the approach, no one really likes to talk about it. Death. There’s a conversation killer.  No one is really prepared for one generation to exit and another of take over.  But we’ve seen all this shit happen before, right?  What legacy persona is right?

Bootstrappers approach legacy from the perspective that they created their own path with little or no help from anyone.  They don’t fancy investing in others.  In fact, they think legacy is a waste of time.  And while they might thank a few people secretly, they generally believe that legacy is for suckers.   They believe that once dead, people will be sad for 10 minutes and then get back to their reality TV lives.

Which begs the question… is thinking about legacy important?

Stewards believe that investing in people that will come behind them is a worthy pursuit.  They believe that the reason they are successful is because others invested in them.  Makes logical sense, right?  Something about “do unto others” and some such.  You can tell when you’re interacting with a Steward because half the time you spend talking about the past and half the time they ask you about you.  Very little time spent with a Steward is about them.  These folks invest a ton of time in others.  Stewards believe that legacy management is critical.

Well, both of these approaches are arrogant.

Bootstrappers miss the point because with their guidance we could avoid some of the same dumb ass mistakes that they made.  Now, some will say that making mistakes can be useful.  I agree, but I’m really thinking about the avoidable stuff- like pretzel M&M’s. They suck.  Without passing on of that knowledge, we’ll just waste time and resources having to learn it all over again.

Stewards miss the point because the real value in talking with the next generation is giving them insight in to how to make their own decisions. It’s not about doing the same thing forever. Things change. Fast.  And history lessons are weak without understanding the context of the situation.  Also, stewards waste time telling stories to folks that aren’t really ready, willing or able to really do anything with the knowledge.  Worse than that, a lot of what passes for legacy is really ego propping.  Stewards aren’t looking for someone to carry on and make strong decisions. They’re really looking for the “chosen one” who will make them look good when they’re gone– the memorial purple M &M.

Here’s the thing… thinking about legacy is important… maybe even critical… whether or not you take action in regards to your legacy… well, that decision has to fit you.  It doesn’t matter what anyone else says or does… your legacy (or anti-legacy) is yours.  I’m a firm believer that I can’t make other people happy… I can try and often do but I can’t “will” someone else to happiness.  Sucks but true, happiness is a personal pursuit.


If you care about your legacy, great… do it the right way… go deep with people that you love AND that love you.  Don’t just share the successes, the wins… open yourself up and be vulnerable with those that will carry forth your legacy.  In some ways, the people that come after you should want to carry on your legacy NOT feel like that have to.  Legacy lifting should never be a burden.

And, if you don’t care about legacy, great… we’ve already forgotten you.  That’s what you wanted, right?

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