How do we know when we've arrived?

I've had a fire under my ass the past couple months.

I think in part it's my fear that I'm getting older and too comfortable. If you're over 30 and in the tech industry, I'm sure you can identify with this fear. It's crippling to think you might be rendered irrelevant, and even worse when faced with the irony that it's because you're too experienced.

And really, all of this stems from our tendency to compare ourselves to others. To think that if we're not running a big company or sitting on millions (or billions) of dollars from an exit, we might not have fully self-actualized.

But something struck me last night as I was getting ready for bed. I tried to imagine my ideal future. Have you ever tried to do that? For me, the canvas was blank. Or at least out of focus. I couldn't really define what it was I was after.

Is it money we're after? Sure, financial independence and certainty would be better than not having it. I don't know about you, but I love to work and often find myself restless on days I'm supposed to be relaxing. How is money going to fix any of that?

Do we want recognition? I love to foster connection and think it would be fun to speak at big events, to autograph books, or to have a cult following on Twitter. But when I close my eyes and imagine myself in those shoes, I'm actually more stressed out and feel under tremendous scrutiny. I think we tend to idealize being culturally significant, but fail to recognize the tradeoffs.

So what is it?! I've been leafing through Tony Robbins' Awaken the Giant Within. For me, the most illuminating point he makes is that material wealth and cultural significance don't create lasting contentment. It's actually our contributions that give us lasting joy.

It bears repeating: The investment with the greatest existential returns is a gift given unconditionally.

Granted, Tony Robbins is the king of pop psychoanalysis and if you want to hold his statements to the fire of more rigorous inquiry, I don't blame you. But when I inquire about my own life, chasing fame or fortune has never made me contented. And my tiny brushes with both have left me feeling hollow and unfulfilled.

Gratitude and charity, on the other hand, have always, 100% of the time, left me feeling energized and capable. What's even more striking is the irony that gratitude and charity inevitably lead to fame and fortune. Who doesn't appreciate and honor someone who gives to others without asking for something in return?

I'm writing this as a reminder to myself, but I hope it's helpful for your journey as well. The path to contentment and wealth is paved with kindness, gratitude, generosity, and contribution. These are difficult to enact each day because we're constantly bombarded with messages that lead us to believe the contrary.