Let’s start this post with a scene from one of my favorite (comedy) movies.
(Source: Now Playing Youtube Channel)
I love this scene for so many reasons: the absolute banger by Survivor (“I Can’t Hold Back”), the stunning beauty of actress Jayma Mays—but most of all, because it shows the unlikeliest man doing something simple (yet romantic) to score way above his league. What guy hasn’t imagined a moment like this? You overcome the fear and anxiety of approaching someone out of your league… and then absolutely kill it with a simple, romantic gesture.
But that’s not what I want to talk about today.
In this post, I want to talk about the notion of being held back. It’s a theme I’ve been pondering for a while now, and I wanted to use this post to flesh it out. It started when I was listening to a podcast by Jay Shetty—specifically the episode he did with James Corden. It’s such a great conversation, and I encourage you to listen to it all the way through.
In the podcast, James uses a simple analogy to explain the process of letting go. Remember when you were a kid and you had a helium-filled balloon? He talks about how we want to hold on to that balloon—how we might tie it around our wrist because, perhaps, we accidentally let one go before and we know better now.
But what happens when you hang on to that balloon? If you keep it long enough, it withers, wilts, and slowly deflates. But if you let it go? Something magical happens. We not only get the experience of watching the balloon soar into the sky, but we also make room for something new in its place.
In both cases (holding on and letting go), we eventually lose the balloon. But when we hold on, it withers and becomes something less than magical—something that just holds us back from experiencing the magic of letting go and the openness that invites new experiences.
As if that wasn’t a great analogy on its own, Jay chimes in with a quote that has stuck with me ever since I heard it. And this is what I want to explore in this post. The quote:
“Perhaps the thing that is holding you back is the thing you won’t let go of.”
—Jay Shetty
When he said that, it was like bells and whistles went off in my mind. It’s such a simple statement, but it flips the internal script that we all carry at times—especially in those moments when we feel like something is holding us back.
I’ve felt this many times in my life.
When I was young, I felt held back by overly strict parents.
When I had kids, I felt held back by having to care for them (at times, anyway).
In my career, I felt held back by bills and obligations, by the idea that I couldn’t do what I wanted because I’d never be able to afford it.
But what did all of those things have in common? Was it really true that I was held back by the people I loved and my responsibilities to them?
Absolutely not.
In fact, I learned that wasn’t the case when I lost my mom and realized just how much the pain and grief of not having her changed me.
No—what held me back wasn’t any of those things. There were a few core things that held me back:
- The notion that I was supposed to be somewhere other than where I was in that moment.
- The limitations I placed on myself for not doing what I really wanted.
- The fear of losing what I had in the pursuit of what I wanted.
I think these are things we all struggle with at one point or another. So let’s look at them.
1. Now Here or Nowhere
This one’s more of a spiritual or religious theme. You see it a lot in Buddhism. In fact, I’d argue that all religion, at its core, is really just an attempt to bring us back to the present—to help us find peace and contentment in the chaos of our reality.
My biggest struggle has been thinking too much about the past or the future.
When I think about the past, I feel sadness for something I had but can no longer experience. The magic of balloons I’ve already let go. Gone. No matter how much I wish or hope, I’ll never recapture those moments. This is especially true when I think about my mom and how often I took her presence for granted.
But I also think too much about the future—worrying, trying to control outcomes. I have full-blown conversations in my head before I even interact with someone. I’m moving the chess pieces in my mind, hoping I can think my way to the outcome I want. But most of the time, those conversations never even happen in real life.
And what do these two habits have in common? They use up massive amounts of energy and emotion… and do absolutely nothing to change reality.
What if I let go of the past—and the need to control the future—and focused on the here and now?
2. Self-Limiting Beliefs and Ideas
Maybe the worst of the three are the limitations we place on ourselves. The ideas that we aren’t “this” or “that” enough to deserve what we want.
How many years did I sit at a desk, obsessing over the fact that I wasn’t in the career I wanted—before I finally found the courage to do something about it?
Or even worse, I held onto these limiting ideas about what I was supposed to be.
And sometimes, those ideas were grounded in truth. For example, while I sometimes felt held back by my responsibilities to my kids, it wouldn’t have been right to let go of that obligation.
But the problem wasn’t the responsibility—it was my narrative about the responsibility. I created a story that limited my ability to imagine how I could meet that responsibility and pursue what I wanted.
For instance, when I quit my job and went back to school full time, I didn’t stop seeing or supporting my kids. I found a way to do both. It was hard—but it was also fulfilling. And it wouldn’t have been possible if I hadn’t let go of the belief that I couldn’t do both.
3. The Fear of Loss
This might be the hardest one. Maybe it’s the part I struggle with most.
When I have a great day, a powerful experience, or an amazing chapter in my life, I often try to recreate it. But each time I do, it loses a little bit of its magic.
I remember one of the best days I’ve had: I hiked around a lake, went to Starbucks and wrote for a while, then saw a great movie. Simple—but awesome.
And I’ve tried to recreate that exact day multiple times. Sometimes it comes close—because I do love hiking, writing, and watching movies—but it’s never quite the same.
One time, I tried to recreate that day after my mom died. I thought I could summon that old happiness. But all I did was remember how much I missed that time when mom was still alive. It was such a crappy day.
Why? Because the present moment wasn’t asking me to recreate the past. It was asking me to face my grief. To turn toward it. To feel all of it. And to learn how to carry that loss forward.
Trying to recreate old joy often keeps us stuck. We think we’re letting go of the balloon—but we’re really gripping it tighter than ever, terrified of what comes next.
But what comes next is experience. Growth. Life. We have to cast off that old balloon and be comfortable in the moment of not having one.
Not every moment in life can be a guy on a Segway scoring with the hot girl.
Sometimes, we have to be the guy in the dark, crying over the loss.
Because the deeper the tears…
The sweeter the laughter will be.