Vol. 4, Issue 7: What Becomes of the Brokenhearted

Failure, Adversity and The Way Forward

It’s been a minute since we’ve done a personal one here - instead of a screed about the advertising industry’s myriad missteps or its surprising commonalities with seemingly unrelated things. Honestly, one of my favorite things about this newsletter is that I can move so fluidly between the two. Because I’m the writer, editor, and publisher, no one can tell me what to do and no one can tell me to stay away from any topic. It’s pretty refreshing. I won’t stop writing about the industry stuff, but I really love the stream of consciousness.*

*I have several text chains going at any given time where I just take something ridiculous out of my head and send it off to people who I know will appreciate it - so like this newsletter, except shorter and more profane

I’ve talked a lot in the past about learning and growth. As I’ve started to forge this path with JPEG on my own, I’ve probably learned more in the last 10 weeks than I have in the last 10 years, not just about the industry or where I add value, but also about myself—how I work best, what I believe in, and how I respond to adversity.

That last one is what I want to spend a bit of time thinking through. How do I respond to adversity? How do I process adversity and turn it into strength and learning experience?

Because, not for nothing, I’m not great at it and I really never have been. I’m better than I was, because I’m older and I’ve picked up a few things along the way*, but it’s really difficult to take a bunch of body blows and get up, dust yourself off and try again. And the people who are good at that feel like superheroes to me. It’s possible they’re just really good at projecting confidence and ability and that’s the only thing they need to get to where they need to go, but to be honest, getting thrown off your game isn’t really that difficult most of the time.

*Years ago, I was talking to my old therapist about how I’d missed the subway that morning and I was having a shitty time at work, and he looked at me and just said “you know those things aren’t related right?” And I’m not sure I’ve ever been more stunned into silence in my entire life

This is especially true with my kids. Every day, every week, every month, I send my kids out into the world - to school, to their activities and endeavors - and they’re exposed to all kinds of things that are completely out of my control. I’ve tried to teach them and to give them the tools to succeed and empower them to try to push beyond whatever limits they see and go out and get what they want. I ask them to be kind and understanding, to try to see the world through other people’s eyes to give them the empathy they deserve. In general, they’re doing better than I could have expected in my wildest dreams.

But inevitably, something will fall the wrong way. They’ll fail a test that they studied for (or didn’t study for*). They’ll get into a fight with a friend. They’ll lose the game or the point. And, eventually their hearts will be broken by someone or something that they desperately wanted. They will feel physical, mental, emotional pain.

*I continue to be shocked at how studious my children are

That’s the thing about having kids though: their heartbreak is 1000x* more painful than anything I experience myself. You want to run out and protect them, shield them, make everything better for them. But of course, the secret that you know - that we all know because we’ve gone through it too - is that their heartbreak, their failure, their adversity is what will ultimately make everything better. We learn through adversity. We develop strength through heartbreak. We ultimately succeed through failure. I don’t want my kids, my family, my friends to experience pain any more than I want to experience pain myself. But it’s part of the human experience.

*Rough estimate

I’ve seen a few people speaking about this lately - Roger Federer spoke at a commencement ceremony about how the present is what matters and dwelling on the failures of the past does no good - absorb them and learn from them, but don’t dwell on them*. Derek Jeter, also at a commencement, spoke about how failure will happen - it’s part of life - and it’s what you do with it and how you push through that defines you. Last week, I mentioned Tiger Woods and the 10 steps. Feel your feels, but then let them go and focus on the next.

*I found this to be a fascinating statistic - he said he won over 80% of his matches, but only 54% of the total points he played. The line between all-time greatness and being average can be razor thin sometimes

It’s pretty simple to sit here and say “failure is part of life” or “take the time to deal with it and shake it off” - but having the mettle of a professional athlete or a successful entertainer isn’t exactly easy. There’s a reason Roger Federer and Tiger Woods and Derek Jeter are all-time greats in their sport: they have an ability to focus that borders on the pathological. That which doesn’t kill us makes us stronger is easy to say, but hard to manifest.

I caught a clip of Stephen Colbert in conversation with Anderson Cooper and I think this hit me hardest. Colbert said - I’m paraphrasing here a bit - that if we think of life as a gift, and it is a gift, then we have to consider all of it, even the suffering and pain we experience, as part of that gift. The clip is here, if you’re interested in watching.

What struck me wasn’t just the sentiment, but the grace in accepting it. It reframes suffering not as a detour from the point of life, but as an essential part of it. If we reject the pain, we reject part of what makes us human. And if we can learn to hold both the joy and the heartbreak in the same hands - to see them both as evidence that we’re really here, really alive - then maybe that’s where the real resilience lives. Not in never breaking, but in letting the break open something deeper.

What becomes of the brokenhearted? How do we turn failure and adversity into something that we use to fuel our fire? What’s the way forward?

I can tell you what’s working for me. What I’ve finally come to terms with is that the only variable that I can control is me. I can’t control the action, but I can control my reaction. Failure, adversity, heartbreak - these aren’t character flaws; they’re something that happens to everyone. I can’t control that. I will fail. I’ll fail more than I want and almost certainly more than I think I will. And I’ll be angry and annoyed and upset.

But ultimately what I’ve come to peace with is that I can do everything in my power to be successful and I’ll still fail due to things out of my control. There’s this constant push and pull between being process-based and being outcomes-based. In sales especially, the outcomes tend to be what matters. The right processes typically create the right outcomes, but sometimes they don’t. And that’s got to be OK. It can’t be the only thing that defines success.

That’s the work. Letting go of what I can’t control. Owning what I can. Being OK with failure when it shows up. And remembering that heartbreak, while painful, is still part of the gift.

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OK, So … is getting back into the podcast business as well. Right now, tentative timing for launch is over the summer, so stay tuned for updates in this newsletter and on the LinkedIn page. Thanks as always for your support.

That’s all for this week. Until next time, friends.