As I consider the future it's sensible to start from the end and work backwards. Here are fictitious letters from my 65 year old self to myself today in consideration of my decisioning along several scenarios:
effort/outcome
failure (-)
succeed (+)
don’t try (-)
-/- (regret)
-/+ (circumstance, luck)
try (+)
-/+ (learning)
+/+ (excellence)
If you have an idea you should try! Here I am 27 years later!, and I must tell you that I look back and I have sharp regrets. I see you, you're playing it safe. And I understand - and there is a place for this. But you should know that your strengths, aptitudes and disposition put you in a very favorable position in this rare time and place in which you've had the great fortune to find yourself. Your grandparents would be proud at seeing what that their efforts have produced.
Saba Shlomo endured unspeakable suffering in Poland just before the Nazis came and destroyed his entire family. He helped found modern Israel as a migrant dairy farmer and early settler.
Saba Nat was on the other side, flying a bomber in the South Pacific to help the allies rid this planet of such evil. He then created and served as President for his company, a metallizing and electroplating factory responsible for creating over 600 jobs in Pawtucket, RI.
Abba helped defend Israel, fighting in two wars as a paratrooper in the special forces, just before you were born.
Remember their legacies. These are big shoes to fill and you have inherited their virtues. Fear was of course present and they got past it to build a future for their families and communities. You are your best self under adverse circumstances. Know this and stand on it. This is your rock. JFK's words ring true: the only thing you have to fear is fear itself. That fear is about 2 items: not having money, not having contributed to your fullest potential. Let me address each:
The fear of not having money:
The fear of not having money is real. But money is transient. Money buys you time to do important work - you've always believed that and acted in accordance with this belief. With kids you're now thinking that the noble thing is safety. But with the benefit of hindsight let me tell you that is not true. Your boys will learn the wrong thing watching such an example, even if they do have money and means growing up. It's not the main thing that matters. What matters is that you instill in them the values to help them thrive in the world they are inheriting: risk tolerance, mental agility, a desire to follow the north star of Tikkun Olam (whatever form that takes on their journey) - making the world a better place, and to love. If you achieve this as a father you will have done well.
Fear of not living to your fullest
The Chassidic Jews have a great parable that I'll paraphrase as follows. When you get to heaven G-d will not ask you why you weren't <some super human, e.g., George Washington>. Rather, G-d will shake that wise head and review the obvious: that you were given miracles: gifts, people, time, clean air, a blue planet, a good brain! I gave you life and the universe - so tell me where was the Ari I created?! We do not know our own potential until we challenge ourselves. Have the courage to be your best self.
So what is failure? Failure is to bias towards safe outcomes, to not trust in your ability to continuously grow and learn - to not trust your potential. Failure is to teach your boys, by your example, that they cannot be their truest selves because of some fear. In short, demonstrating wrong daily practice will lead to poor outcomes for you (even if you're successful) and setup your children for the same. Following such a path is a recipe for living with regret.
Success by contrast is to lead by example, showing your boys how to go live and move towards the light of their own authentic selves. The way you conduct yourself in the world is more important than the worldly outcome.
I'm writing you this letter today so that you understand that the primary failure is to teach your children wrong lessons and to live with regret.
Learning is the ability to review the past and extract lessons. Understanding is the ability to predict outcomes to circumstances. Wisdom is the ability to apply sound judgment and action to circumstances - to know right from wrong. I write you this letter today in hopes of nudging the future to a better place for you, and for me.
Best Regards,
Ari Akerstein - June, 2043