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Choosing Between Your Legacy And Your Mortality – A Father’s Lesson

Posted by AGORACOM at 7:33 PM on Friday, May 23rd, 2008

Paul Kedrosky, one of the best known business/technology/VC bloggers and colleague of mine, is probably one of the most “together” guys I know. Uber Smart + Successful + Renowned + Family Guy + Down To Earth … read about him here.

In short, he is just about everything a guy wants himself or his son to become (OK, I’d like to add in Super Bowl MVP but let’s not get crazy). To reach your pinnacle should mean the right to rejoice, celebrate, take a breather, give a speech and sleep in the next day…

…. but it doesn’t.

In a recent blog post he stated “I’ve started to feel scraped somewhat thin.”


The great paradox of leaving a charmed life – the downside – is that the charms keep coming. You are so well respected, so well liked that opportunities abound. Business opportunities, social opportunities, personal opportunities, family opportunities you name it.

Things get better and better – to a point. Then, all of the opportunities start crashing into each other like multi-ball bonus pinball. Fun for a few minutes at the arcade with your buddies – but not fun when it becomes a prolonged way of life. You find yourself:

  • staying up all night reading and writing strategy documents
  • accumulating unthinkable air miles
  • shaking a million hands
  • meeting unbelievable people
  • bouncing around more great “ideas” then you could ever get to
  • dining at some of the finest restaurants in the world
  • forgetting what timezone you are in
  • ….and struggling to find time to do the things that really make you happy and healthy.
The situation is best summed up by Kedrosky’s statement “I’ve started to feel scraped somewhat thin..
Many have experienced it but few have actually written about it, let alone summon the advice of blog readers, which is exactly what Kedrosky did in this post back in March.


When you run into this situation, you are essentially being forced to choose between your legacy and your mortality. If you haven’t been there, it sounds simple enough. Hang out on the beach with your family and friends – but you have to be in the situation to understand that one is not possible without the other.

It is a blessing. It is a curse. It can’t be avoided any further. Your day of reckoning has come.

My response to Paul and excerpts from follow-up responses is re-produced in its entirety below. It came from my father long ago. It received a favorable response, so I’ve posted it here for you, for someone in the future asking the same question, for my children.


Response #1

My father taught me a very valuable lesson a long time ago – everything you do comes with a price, so you have to decide early on what you are willing to pay for and what you are willing to leave on the shelf.

In your case, you appear to be struggling with choosing between the infinite amount of incredible opportunities in this web era and having the freedom to live an amazing life.

Both are incredibly rewarding but every moment spent on one takes time away from the other.

It is difficult to choose between your legacy and your mortality. You want to be a part of so many great ideas with so many great people – but everyday away from your kids/family/friends/self is a day you will never get back.

This is the burden of being successful and surrounding yourself with so many great people. You participate in so many great things but – at some point – you run into diminishing returns.

You are going to have to let some things go. Simple as that.

From the little I know about you, that will mean leaving some opportunity/money/legacy on the table and spending that time enjoying life. The hard part is choosing which initiatives you keep and which you discard.

Easier said then done? Yep … but my father did exactly the same thing and he is pretty much the happiest guy I know on the planet.

That’s the route I am taking.

Don’t know if my musings helped at all but that’s my two cents “in the spirit of the open way in which blogging works best.”


Follow-Up #1

Karthick, you are right that we all go through this “fatigue and rebound” phase…but there also comes a point in everyone’s life where you no longer want to go through this cycle.

Athletes retire. Entrepreneurs (the smart ones) scale back by picking their best 1 or 2 streams and leaving the rest on the table.

The person who leaves nothing on the table is more than likely the one with 1 or 2 ex-wives, detached kids and a big belly.


Follow-Up #2

Beau – well said. Most of all, be ruthless with your own desires and dreams.

Alex, thanks for the question. For the most part I think you go primarily with bread and butter (lowest risk) because they are easier to execute and enable you to live your life.

You can pick one “blue sky” item but that can only be something you do as a pet project and whose heavy lifting does not depend on you. Otherwise, you’re back to square one.

The notion of leaving so many things on the table utterly sucks. You’re surrounded by great people with great ideas that not only make money but also make an impact on the lives of others and further your legacy…but it has to be done or (as Beau said) you get consumed.

What an amazing thread. This needs to be the focus of further discussion. Paul could probably create a one-day conference out of this and it would be sold out. It’s obviously something on the minds of many people.

Is Paul Kedrosky the business version of Jerry Maguire? Can we all learn from the moral of the story? I think we want to. I know our families/bodies/souls want us to.

Utopia comes from leaving some happiness behind.


“Utopia comes from leaving some happiness behind”. I don’t know where I came up with that but I hope it means I learned my father’s lesson well – and that my children will too.