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Who Will Cry When You Die

21. 
Spend a Day Without 
Your Watch
Last fall, I did something I have not done for many years: I left my watch at home and spent an entire day 
without looking at the time. Rather than living by the clock and planning everything I was going to do that day, 
I simply lived for the moment and did whatever I felt like doing. I became a true human being rather than 
merely a human doing. 
Early in the morning, I went for a walk deep in the woods, one of my favorite things to do. With me, I 
carried an old paperback copy of Walden by the social philosopher Henry David Thoreau, a book I have come 
to love. After finding a beautiful place to sit and read, I experienced one of those moments of synchronicity 
where something perfect happens at just the right time. For me it was randomly opening the book and finding 
the following paragraph in front of me: 
I went to the woods because I wished to live deliberately, 
to front only the essential facts of life, and see if I could 
not learn what it had to teach, and not, when I came to die, 
discover that I had not lived. I did not wish to live 
what was not life, living is so dear; nor did I wish to practice
resignation, Unless it was quite necessary. I wanted to live deep
and suck out all the marrow of life, to live so sturdily and 
Spartan – like as to put to rout all that was not life… 
I reflected on this great man’s words and soaked up the miraculous beauty of the scene around me. The rest of 
the day was spent in a bookshop, watching Toy Story with my kids, relaxing with the family on our patio and 
listening to my favorite pieces of music. Nothing expensive. Nothing complicated. But completely fun. 
 
 


22. 
Take More Risks
I’ll make you this promise: on your deathbed, in the twilight of your life, it will not be all the risks you took that 
you will regret the most. Rather, what will fill your heart with the greatest amount of regret and sadness will be 
all those risks that you did not take, all those opportunities you did not seize and all those fears you did not face. 
Remember that on the other side of fear lies freedom. And stay focused on the timeless success principle that 
says: “life is nothing more that a game of numbers – the more risks you take, the more rewards you will 
receive.” Or in the words of Sophocles, “Fortune is not on the side of the faint – hearted.” 
To live your life to the fullest, start taking more risks and doing the things you fear. Get good at being 
uncomfortable and stop walking the path of least resistance. Sure, there is a greater chance you will stub your 
toes when you walk the road less traveled, but that is the only way you can get anywhere. As my wise mother 
always says, “you cannot get to third base with one foot on second.” Or as Andre Gide observed, “One does not 
discover new lands without consenting to lose sight of the shore for a very long time.” 
The real secret to a life of abundance is to stop spending your days searching for security and start 
spending your time pursuing opportunity. Sure, you will meet with your share of failures if you start living more 
deliberately and passionately. But failure is nothing more than learning how to win. Or as my dad observed one 
day, “Robin, it’s risky out on a limb. But that’s where all the fruit is.” 
As I wrote in an earlier lesson, life is all about choices. Deeply fulfilled and highly actualized people 
simply make wiser choices than others. You can choose to spend the rest of your days sitting on the shore of life 
in complete safety or you can take some chances, dive deep into the water and discover the pearls that lie 
waiting for the person of true courage. To keep me inspired and centered on the fact that I must keep stretching 
my own personal boundaries as the days go by, I have posted the following words of Theodore Roosevelt in the 
study where I write: 
It is not the critic who counts, not the man who points out how the strong man stumbled, or where the doer 
of deeds could have done better. The credit belongs to the man who is actually in the arena, whose face is 
marred by dust and sweat and blood, who strives valiantly, who errs and comes short again and again, who 
knows the great enthusiasms, the great devotions, and spends himself in a worthy cause, who at best knows in 
the end the triumphs of high achievement and who at the worst, if he fails, at least fails while daring greatly so 
that his place shall never be with those cold and timid souls who know neither victory nor defeat. 

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