Start Reading (or Listening to) Shouldology

PREFACE

Before We Start Walking

We need to talk.

This probably isn’t the conversation you were expecting, but it might be the more important one. You know the Rolling Stones principle about getting what you need instead of what you want? I’m willing to bet this is one of those.

I’ve been having different versions of this chat for years now, with forty-year-olds feeling stuck in their careers, twenty-somethings already questioning their life choices, and even sixty-somethings who’ve spent four decades becoming very good at the wrong thing. The details change. The same questions surfaced every time.

Hearing enough of these conversations, I noticed a pattern. Almost everyone was copying whoever was in front of them, assuming that person knew where they were going. Which raises the obvious question: who’s leading this parade?

It reminds me of this old story. A scientist explains to an elderly woman that the Earth orbits the sun, which sits in a vast galaxy among billions of others. She waves this off. “Young man,” she says, “the world is actually a flat plate resting on the back of a giant turtle.” He asks what the turtle is standing on. She smiles. “Another turtle.” And below that?

“Obviously, Sonny, it’s turtles all the way down.”

While dubious as a cosmological creation myth, it’s an exceptionally accurate description of how most of us navigate our careers. It’s easier to follow someone who looks like they know what they’re doing. We’re capable enough, so we join the procession without ever considering whether or not we should. Plus, there’s a bonus that nobody questions our logic. Point at someone who appears successful; no further explanation required.

We’re all turtles, standing on the backs of turtles who seem sturdy enough.

But if we step off the stack for a moment, we can finally see what’s actually going on. Look at the faces of those we’ve been following, and often we find they’re just as anxious as we are. The dissatisfaction we assumed was ours alone turns out to be nearly universal.

The real problem is that we’ve been building something way more substantial on top of those turtles than our careers. We’ve been defining our identity. Questioning that is uncomfortable, so we reach for quick fixes instead: a new title or a new company. We treat the symptom, only for the problem to return once the novelty wears off. So, if you’re looking for ten simple steps to identify your next turtle cavalcade while leaving your concept of identity intact, this is not your book. But if you’re willing to look inside and find something more enduring, that’s where we start.

What Shouldology Is and Isn’t

I’m serious when I call this a “why-to” guide. Plenty of books offer “how-to” ideas on what to do next. I’d rather investigate why perfectly intelligent people keep doing logical things that yield illogical results. How do so many of us end up building careers we never consciously chose? Or maybe we chose once and then, decades later, are amazed to realize how far our professional identity has strayed from who we really are.

To get there, we’ll wander through psychology, behavioral economics, decision science, philosophy, organizational theory, money, and luck. My goal is to make this less graduate seminar and more the nerdiest conversation you’d ever have with a guy at a bar or on a road trip.

There are no worksheets or exercises. Frankly, I can’t stand books that tell a perfectly good story, then break the spell to recap or tell me to bust out a notebook and take time for personal reflection. That’s not to say those techniques aren’t useful. What I want to dig into is the mechanism underneath. Why do those exercises work? And more critically, what goes wrong when they don’t?

I guess I should introduce myself. I’m Jared. Married, forty-something. Three cats. If you read my LinkedIn profile, you’ll see that I have a PhD in chemistry from Duke. At this point in my life, that mostly justifies why I’m an annoying basketball fan and lets me select “Dr.” in title drop-down boxes. I spent years in R&D and innovation leadership in the consumer packaged goods industry. That makes it very annoying to walk around Walmart with me as I nerd out on packaging claims and new products. I left that, co-founded a startup that failed, earned an MBA, and started writing, speaking, and coaching. Along the way, I accumulated experiences that, from the outside, looked like a fairly successful professional trajectory.

But inside, I spent years deeply confused about why I was doing what I was doing, always following some turtle in front of me, occasionally abandoning one line only to immediately find another turtle to shadow.

This is the conversation I wish someone had with me ten years ago.
And five years after that.
And candidly, probably a year from now.

I’m using my own career as the longest-running case study because it’s the only one where I have access to all the embarrassing internal footage. I’m trying to understand the machinery while I’m still close enough to remember what it feels like to be trapped inside.

Where We’re Going

The book is divided into four parts.

Part One is about recognizing the problem, or more realistically, the struggle to do so. Fair warning: it’s mostly personal memoir with ideas emerging through the messiness of my professional misalignment. If you want the framework first and my stories never, Part One may test your patience. Through my experience, we’ll try to understand how I got stuck and meet the perfectly logical voices in our heads that keep us there.

Part Two is the self-understanding stuff you’d expect, just from a different starting point that I find far more useful a couple of decades into a career. By the end, you’ll have a clearer picture of who you are today and how to point yourself in a meaningful direction.

Most career books end there.

Not mine.

The reality is that the world doesn’t particularly care about our self-discovery. Part Three is about identifying the role that best fits who we are today and translating ourselves into language everyone outside our heads can understand. But even that’s not enough.

Part Four confronts the fact that none of this is a “set it and forget it” situation. Disruption is the rule, and stability is only ever temporary. So we need to build resilience, control what we can, and then get our Elsa on and let the rest go.

Spoiler: This book doesn’t end in a tidy place. There’s no ultimate resolution where we finally get what we want and stay satisfied forever. The world keeps going. The characters, including you and me, keep evolving. That makes this less a hero’s journey, more a Coen Brothers film.

The stories in this book come from real people and real events. These aren’t all tales of success. This isn’t “follow your passion” fantasy, and there’s no universal answer across the grit-or-quit divide. The steps some people took, including me, would be terrible advice for someone else. That’s why we’re trying to understand the game instead of just repeating the motions.

A Few Notes Before We Start

Out of respect for the “survivors” of this career-transformation mayhem, I’ve changed some names and identifying details to protect the innocent. A handful of people gave me explicit permission to use their real names and stories. The events are told as close to the truth as my memory allows. Where I’ve reconstructed conversations, I’ve tried to capture the spirit rather than a transcript. And where I’m the flawed protagonist, I do my best to preserve the idiot that I was.

As you might have guessed from a book with a pineapple on the cover that’s already referenced the Rolling Stones, Frozen, Fargo, and used the word turtle ten times, I tend to get a little caught up in metaphors and pop culture connections. Some of these will become shorthand, giving us easier ways to talk about complicated ideas. If you ever find yourself wondering what I mean by potatoes, elephants, armor, or macaroni, the Should-ictionary at the back will remind you what the heck I’m talking about.

If you do want homework, I haven’t completely abandoned you. At the back of the book, there’s a TL;DR section (Too Long; Don’t Remember) with a quick summary of each chapter, a handful of questions to contemplate, and a Further Overthinking list. If you’re thinking, “Wow, this stuff is great. I just wish it went into more depth and was about 6,000 pages longer,” I have excellent news! Those are the books I’d personally recommend. Consider it the Shouldology expansion pack, prepared by writers who are way better than me.

You’ll also find footnotes throughout. Think of them as me leaning over and saying something under my breath. Mostly, they’re the rest of the joke or a completely unrelated fun fact. If you wish this book were about 1% shorter and less funny, skip them. You can ignore every last one and not miss anything relevant.

That’s not to say there’s nothing intelligent under my ranting. I’ve included a considerable amount of research across various fields. It’s just that nobody on a road trip wants APA citations read aloud from the passenger seat. If you want to check my work, it’s all properly attributed in the Sources and Notes section.

Think of this book as an inverse mullet: party in the front, business in the back.

So, if this is really a road trip, we need one more thing.

The Playlist

Most books open each chapter with an epigraph, some little quote from Shakespeare, an obscure poem, or a dead philosopher. That’s not my style. Instead, I made a playlist. Consider it the mixtape for our journey together.

I’m a music guy. More specifically, I’m a lyrics guy. For each chapter, I selected a song that reflects its theme and emotional territory. Some were background music while I wrote. A few were playing while I lived the story. You’ll recognize some of them. Others, probably not. There is, admittedly, a disproportionate amount of reggae rock.

I regret nothing.

We’re starting with one of those: “Hallucinations” by Bumpin Uglies. Pull it up and sit with it for a few minutes. So much of that song speaks to mid-career confusion, but listen to how it opens. The singer, Brandon Hardesty, starts by admitting that he’s nothing special.

That’s the reality underneath my story, too. Typical career books come from the opposite direction. The author is usually someone who cracked the code, scaled the mountain, and returned with a framework on stone tablets. Or they’re an academic who spent years studying people experiencing the problem without living it themselves. Both can be useful. But after consuming a stack of those books, I struggled to find answers that worked for me.

This is the tale of a guy with real advantages, who consistently makes understandable mistakes, and has a repeated history of following some turtle butt in front of him. I share it not from the summit, but from somewhere on the trail, still walking, with a reasonable view of where I’ve been and a much murkier perspective of what’s ahead.

So, let’s get started.