Mindset
The Bag is Empty
“While money can’t buy happiness, it certainly lets you choose your own form of misery.”
– Groucho Marx
One of the things I’ve come to realize as I’ve grown older is this: there is no point of arrival. You don’t “get there.”
There is no there, there.
I don’t remember the exact moment that truth landed, but I do remember a story told by Blake Mycoskie, the creator of TOMS shoes, on The Rich Roll Podcast – “The More You Give, The More You Live” (Nov 23, 2020).
“And maybe because I started early in my entrepreneurial life and I grew up fast, I achieved pretty much everything that I set out to achieve before I was 40. And that to everyone and myself at the time thought that was like a huge blessing.
But what I found was is that I woke up one day—or a series of days—and didn’t really think that my future was going to be better than my past. And that’s a really scary place to be in.
I think that leads to a lot of mental health issues and devastating situations for people. And it wasn’t that I didn’t like my life or my situation, or my business, or I wasn’t proud of what we accomplished with TOMS, but I realized that if we—anyone—and me specifically in this situation, if we are looking to external accomplishments, external praise, anything, anything, even your kids’ love, for your sense of peace and joy, ultimately you will realize that it doesn’t work.”
Blake then went on to recount an interview he’d prepared for at the United Nations with Ted Turner, the founder of CNN. Turner was someone Blake had admired for years—a larger-than-life figure who seemed to embody arrival.
“I spent months preparing for this interview and was really excited to do it. But right before we went on stage, we’re having this conversation.
Ted said to me, ‘In life and in business, especially in business, it’s like this ladder. And it’s not like the corporate ladder you’re thinking about, but it’s a ladder of believing that if you climb up it, at the top there’s something magical—something that’s going to give you everything you’ve ever wanted.
And as you start to climb the ladder, you see this beautiful bag on the top of it. You can only think what’s in that bag when you get to the top.’
He said, ‘I spent so much of my life climbing that ladder to get a peek into that bag.
And I’ve seen inside the bag.
I’ll tell you what’s in it…
The bag is empty.
And even though I’ve told you, you still need to climb the ladder and look for yourself.’”
In their conversation, Turner’s metaphor of the ladder clarified a simple but hard truth: the feeling of being complete once you’ve “made it” never actually arrives.
Yet Turner wasn’t saying the climb is meaningless. He cautioned that arrival isn’t the guarantee we imagine it to be—and that each of us must discern for ourselves what’s in the bag and whether it truly holds anything of value.
That metaphor stuck with me, too, because I’ve climbed many ladders in my own life.
For years, the pinnacle I sought was professional hockey. I told myself: if I can just get there—if I can work in the NHL—then I’ll have made it. That job would be the bag at the top of my ladder.
And then I got there.
Eleven seasons inside the world I thought would complete me. The logos, the arenas, the flights, the access—living, as one staff member once said, “inside the glass.” It was supposed to mean I mattered.
But the bag wasn’t full.
It was emptier than I expected.
Long hours. No feedback. Constant pressure. And an emptiness in my gut that whispered: this isn’t it.
I had mistaken arrival for meaning.
We are convinced early in life that setting goals, acquiring things, achieving milestones, and climbing ladders is the pathway to fulfillment. We’re sold the idea that one day, at the pinnacle of success, we’ll arrive in a place where everything feels complete.
But the truth? There is always a bigger boat, a better car, a shinier title. We’re chasing the horizon—and the horizon never gets closer.
We’ve even been conditioned to consume this illusion as entertainment. In the past, it was Dallas or Dynasty—soap operas of wealth and conflict. Today, it’s Succession and Billions. We binge-watch these shows not just for the drama, but for the fantasy of power, status, and the inevitable implosion.
Would we really want to live those lives?
History tells us what they don’t show: the eccentricities of wealth don’t solve problems—they magnify them.
The cycle of rise and ruin is hypnotic because it reflects the illusion we secretly live ourselves: there is no final arrival. Always another mountain. Always another rung. Always the sense that we haven’t yet made it.
And then came the accelerant—social media.
In 2004, Facebook launched. In 2007, the iPhone hit the market. Together, they rewrote how we see ourselves. Suddenly, everyone had access to carefully curated lives. Instagram made it aesthetic. TikTok made it constant.
An entire generation was co-opted by an algorithm designed not to connect us, but to compare us.
The results have been devastating.
Suicide rates in the United States have risen steadily since the inception of these platforms, especially among young people aged 15 to 24. Depression now affects more than 18 million adults each year. It is the leading cause of disability for people under 45. Every twelve minutes, someone dies by suicide. More lives are lost this way than by homicide.¹ ²
We are more connected than ever—and more isolated than ever.
Does that mean we shouldn’t dream?
Should we abandon goals altogether?
Of course not. Aspiration is human.
We are meant to explore, build, and create. But the key is understanding that the reward lies in the pursuit—not in the arrival.
Fulfillment doesn’t come at the top of the ladder. It comes in the act of climbing, in the experience of discovering, in the growth that happens along the way.
Life is not a game you win. There is no formula that unlocks eternal satisfaction. When we make it about trophies, accolades, or numbers, we trap ourselves on a treadmill of more.
Another trophy. Another follower count. Another rung.
It’s a hamster wheel disguised as progress.
The truth is, the joy is in the doing—not in the done.
Think of J.K. Rowling. After the success of Harry Potter, she had everything—money, fame, legacy. She could have stopped. But she didn’t. She kept writing, kept creating, because the act of expression itself was the point.
Or Richard Branson. He didn’t stop after building one company. He created airlines, explored space, launched health initiatives. Not because he needed more, but because curiosity and contribution fueled him. The pursuit was the purpose.
And here’s the real irony: size doesn’t matter. We’ve been conditioned to believe that only massive dreams are worthy. But fulfillment isn’t tied to scale—it’s tied to depth.
A simple project, done with presence, can be just as profound as a global empire.
Restlessness and curiosity are not flaws—they are part of being human. They’ve driven explorers across oceans, astronauts to the moon, and artists into the unknown. But every explorer eventually discovers the same thing: when you get to where you thought you wanted to go, there’s always somewhere else to reach for.
Satisfaction can’t come from the false prophecy of arrival. It can only come from the effort and the experience of trying.
You’ll save yourself years of chasing shadows if you stop obsessing about getting it and start focusing on being in it.
Because in the end, as Ted Turner realized—and as I discovered in my own career—
There is nothing in the bag.
¹ Kessler RC et al. Prevalence, Severity, and Comorbidity of Twelve-Month DSM-IV Disorders in the National Comorbidity Survey Replication (NCS-R). Archives of General Psychiatry, 2005 Jun; 62:617–627.
² Centers for Disease Control and Prevention (CDC) Web-based Injury Statistics Query and Reporting System (WISQARS). (2013, 2011) National Center for Injury Prevention and Control, CDC (producer).
