The third inning of ReWirement led me on travels back to the familiar grounds of NYC and Silicon Valley – highlighted by connecting with old friends and meeting many new fascinating innovators, entrepreneurs and “Rewirers.”

Although the topics of conversation were vast, two common threads emerged which can be distilled to the words:






While many have defined enough as an ever-changing, never-ending goal of “more,” enough is actually defined as a quantifiable amount of something that would cover your needs and wants.

What is enough?
Do I have enough?
When will I have enough?
Enough of what?
Who decides what is enough?
Can I appreciate the enough I have?
Am I good enough?


Most of my connections felt they didn’t have enough of something.

“Enough of what?” I would ask. And the answers included:





















Who are these people?



I met Roger for the first time as he was dining at an adjacent table on a late snowy evening in a crowded NY Italian restaurant. ….he was clearly perturbed, wound tightly and snapped at the waiter more than once…his son and niece at their table just rolled their eyes.

After a few glasses of wine, My friend and I found an easy opening to say hello as we all finished dinner and found ourselves as the only two tables left in the restaurant.

Roger turned to us and clearly wanted to talk…his niece and son seemed relieved we had engaged him…I said…”what’s your story?” He said…”my name is Roger…I am 84 and my wife of 55 years died last week!” He immediately went on to tell us how much he missed her, how fast time had gone, how they had fought about the dumbest things, too often had late-night arguments to solve everything before they went to sleep and how he wasted so much time trying to change her (unsuccessfully).

All he wanted now was Enough love, understanding and a connection. He shook my hand hard as the evening ended….and admitted that he had “enough” earlier in life but didn’t appreciate it…and then whispered in my ear…”Just remember…you can’t change anyone but yourself.”


The Executive

After recently presenting the opening conference keynote about the Golden Era of Fintech, I introduced a follow-up speaker who is a very wealthy, powerful person who had just flown in on a private jet with handlers…a passionate presenter, a leading expert in the industry, the message resonated with the crowd and a very warm, appreciative applause from the attendees followed. The presenter came over and sat with me as the next person went on stage…I smiled and gave the thumbs up. They then leaned over and asked me if his presentation was “good enough.”


The Relative

I spoke with a close family member who externally appears to excel in all aspects of life, wife, balance, health and wealth; he is highly self-aware yet his past demons and upbringing make enough unachievable. He exclaimed – “It’s enough, it’s just not f#@*ing enough.” I hear this often from many achievers and over-achievers; the sense of “f#@*ing enough” is not tied to measured success. There is a fine line between enough and complacency, and it’s up to you to figure out where that line is for yourself – no one can make that distinction for you.


Oprah summed up this phenomenon of even the most powerful people on the planet (Presidents, Queens, CEO’s) all still wondering if they were “good enough.”


Enough Coffee.

Everyone has their own journey. What’s clear is that if you think someone did a good job, tell them; they need to hear it and sharing gratitude, positivity and happiness is contagious.

Every morning I drink coffee from a mug my son gave me a few years ago. The lines on the cup, printed below, remind me what is “enough.”

Enough:: a man is rich in proportion to the number of things he can afford to let alone.

Enough:: not everything that counts can be measured, not everything that can be measured counts.

Enough:: efficiency asks how to do things right, but sufficiency asks how to do the right things.

Enough:: if you realize that you have enough, you are truly rich.



Often defined as contending with an adversary or coping with the inability to perform well.

So many people have shared their struggles with health, relationships, happiness, weight, confidence, children, elderly parents and more.

My reading over the past few months has led me to the author below who has provided clarifications regarding struggles.


“What we get out of life is not determined by the good feelings we desire but by what bad feelings we’re willing and able to sustain to get us to those good feelings…You can’t win if you don’t play.

Who we are is defined by the values one is willing to struggle for!”

– Mark Manson


"It's important to be aware of and appreciate the good times (or even just calm times).

Truly enjoy those moments because things can change in an instant and it's off to the next struggle. One never knows when that might occur."


Even Mother Nature Struggles.

The struggle for existence, space, growth, and light* is permanent and a necessary part of life.

*See “Enough of What” above


What I know for sure

One of the most important questions we will ever ask ourselves is:

What are you willing to struggle for?

Mark answered it beautifully below:


The key is not to turn off the jets, but turn them down into a new orbit and equilibrium. That’s what ReWirement is all about.

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