Episode 22: Pay it Forward
April 14, 2025
Gratitude
Some acts of generosity are too big to repay—and maybe that’s the point. When someone does something meaningful for you, the instinct is often to return the favor. But sometimes, the best way to honor that gesture is to pass the opportunity along to someone else. A moment of clarity from a casual conversation, connected with a memory from years before, reframes the idea of gratitude not as a debt, but as a catalyst. The chain doesn’t have to end where it started.
When I was younger, I went on a trip to San Diego.
And on the plane ride there, this was around 1999, 2000, something like that, maybe 2001.
On the plane ride there, the movie on the flight was Pay It Forward.
So there wasn't a whole lot to do on the plane.
So, you know, got some headphones and watched the movie.
I hadn't heard of it.
I didn't know anything about it.
So I just watched it.
For those of you who haven't seen this movie, the general premise, I think it had Kevin Spacey in it and maybe the kid from Signs.
Anyway, the general premise of the movie is that there is a kid who I think he got a project at school.
You can tell I really looked the plot up here for this episode.
But I sort of just generally remember it.
He got like a project at school and he ends up starting this movement of paying it forward.
And the idea is that if someone does something nice for you, then instead of trying to pay that person back, you do a good deed for someone else.
And the idea is that if everybody did this, you would have a much wider net of good deeds being done because it wouldn't just be person A helping person B and then person B helping person A back.
You'd have, you know, A, B, C.
And I forget if they said, you know, if you have a nice deed, you have to do three others or whatever.
But in some way, this would grow exponentially.
The overall message or idea within the movie, for whatever reason, stuck with me over the years.
This idea of kindness in the world and helping to propagate that and not just – I thought it was a nice message, right?
I didn't necessarily think a whole lot about it over the years, but I just kind of tucked that away and I always had that in the back of my head.
Fast forward many years, 15 years or so, and I had a mentor at that time in my life who was grooming me to take over an elevated role in my career.
I was going to get a big leap forward in my career, far beyond, you know, what I would have gotten had I just sort of stepped my way through the ranks normally.
Huge opportunity for me.
I did get that role or I was given that role, appointed to that role.
And I remember feeling like I – how could I pay this person back?
Like it was such a monumental thing to have helped set me up for that I didn't know – I really felt like I owed him.
So I would say things – I would ask him about this and I'd say like I don't know how to ever pay you back.
And a lot of times, you know, his – he wouldn't really pay it a whole lot of mind.
It was kind of just a – almost treated as like a passing thought kind of thing.
He clearly wasn't really thinking about that.
The only concrete answer he ever really gave me was, well, you know, if you're ever in a position to give me a job, you can pay me back at that point.
But then as I progressed in that role, I ended up speaking quite a bit with one of the people who was his mentor over the course of his career.
So now I was kind of in touch with this person.
And I remember this conversation very distinctly.
We were talking about something else and my mentor came up in this conversation as often he did.
And I said, you know, I don't know how I'll ever pay him back.
And this other person, his mentor, said to me, you can't.
You can't pay him back.
It doesn't make any sense.
He had done something extraordinary for me.
The likelihood that that would ever come full circle was extremely low.
And even if it did, you can't pay back the exact same thing.
It doesn't make any sense.
She said, instead, you should look to paying it forward.
And that's when it all just kind of clicked for me.
I had, again, I had seen this movie and I'm not saying she was referencing the movie necessarily.
It's a common phrase, right?
But it brought that memory of that movie back to me in a very concrete way that directly related to exactly what I was going, dealing with at that particular moment.
It all just sort of crystallized.
And sort of the point of it all is that if you spend your life trying to pay back the people that do things for you, then it's sort of a zero-sum game.
The idea of a zero-sum game being in order for one person to gain, another person has to lose.
So the sum of those two things is essentially zero.
It's not an exact parallel, but that's a lot like what paying someone back is like.
They help you.
You help them back.
It's the end of the chain.
Did anyone really benefit from this?
Or did enough benefit occur?
Depending on how you want to think about it.
It occurred to me at this point that he, my mentor, had been her pay-it-forward.
That somewhere in her life or career, someone had done something for her.
And instead of being wrapped up in paying that person back, she had paid it forward onto my mentor.
And now my mentor had paid this forward to me.
Had everyone been sitting around trying to pay everyone back the whole time, I may never have had the good fortune of benefiting from this chain of good deeds.
By being put into this role, that gave me an opportunity to then help get other people into roles or help people make connections or elevate them in their careers or whatever.
And that is a way to push the world forward, not just pay back a good deed that someone did for you.
But it took that moment.
It took, it took for me at least, having seen this movie on a plane 15 years earlier and then being presented with that same wording.
You can't pay it back, instead pay it forward.
It took all of that for it to mean something to me, for it to be concrete, for it to make sense in a way that I felt like, oh, I get it now.
The point is not that you're trying to pay back necessarily the people that do great things for you all the time.
The point is what can you, who else can you help or do good things for, given the position that you've now been put in.
So I say all of this hoping to free some number of people who maybe for years or decades have wished that they could pay back a favor that was once done for them.
And instead, I offer you freedom from that.
Let that go.
It doesn't mean that you can't be kind to that person or that at maybe at some point you can do something great for them.
But to be always concerned that you were unable to pay back a great deed, all you're doing is shooting for a zero-sum game.
Instead, take whatever it was, whatever that favor was that was given to you and help spread similar things or better things to other people that are important to you.