
Q: Jay, I feel like my life is going nowhere. What am I doing wrong?
“He made all the right choices.”
“She just keeps following her perfect path.”
“They all make it look so easy.”
It can be easy to look at the lives of those around you, or the lives of those you admire, and think you’re living wrong. And then wonder what’s wrong with you for not progressing in that same clean, upward line.
But that straight, uninterrupted line you see is an illusion.
We do this thing where we turn other people’s lives into tidy storylines. In hindsight, every choice looks obvious. “Sure, that promotion/move/relationship was always going to happen.” When we look backward, it can seem only logical that somebody’s life went a certain way.
Of course, Steve Jobs led Apple to make the iPhone; it was only obvious!
Naturally, Taylor Swift re-recorded her first six albums when she couldn’t reclaim the rights to them!
Of course, my sister got that promotion. Life’s always been so easy for her.
We see success and think it was inevitable for others, and not us.
That’s why I think it can be helpful to look at life not as a straight line, but as a winding river.
Have you ever looked at a map of the Amazon River? It’s enormous. It flows through mountains, rainforests, and lowlands. It’s fed by over 1,100 tributaries, some of which are over 900 miles long.
Some parts are windy like a snake
Other parts are thick
In some parts of the river, the water flows fast
In others, it flows slowly and shallowly.
From where you’re standing, you only ever see the success of others from the shoreline—when they’re arriving somewhere. You see the moment they land the job, meet the partner, launch the thing. You don’t see the quiet stretches, the rapids, the days they were stuck in the rocks, questioning everything. You’d have to live in the boat with them, every single day, to see the downturns and detours. And that’s just not realistic.
It also means this: just because you’re in a turning tide right now, or tangled in some heavy reeds, doesn’t mean the water has stopped moving for you. Your river is still flowing, even if it feels slow or shallow.
You are always going somewhere.
And when you reach your next shoreline, other people will see that moment and decide it all “made sense” for you, too.
How would you describe your life’s river right now?
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Your Questions Shape What’s Next
I’m dreaming up some bold new ways for us to connect next year, bringing the Q&A we share here in the newsletter closer to your real life. But first, I want to hear from you.
If I was sitting across from you, and you could ask me one question—about mindset, love, leadership, purpose, creativity, or anything else on your heart right now—what would it be?
Your questions won’t just help me understand what you’re facing—they’ll directly shape how I show up, what I create, and how I serve you next.
Today’s Wiser Choice
I want you to think about your personal river.
Try This: Set some time aside to map out your personal river. Where are the twists and turns? What major obstacles are coming up on your map that you can start thinking about how to navigate better? Are you headed for some rapids? Or some smooth times? Have fun with it!





