Some News: I'm Writing a Book!

After three years, 500,000 words, and 300 blog posts, I can finally graduate from "blogger" to "author." Not bad!

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It’s been a big week! On Monday, I accepted an offer on my book proposal from Penguin Random House’s imprint Portfolio, and I’m ecstatic to get started writing this thing. It’s been a goal of mine, for a while now, to write a book, and I would like to write several books before I’m dead. This week was a meaningful step in the right direction. For today’s blog, I want to share a few thoughts with you all on why I wanted to write this book, as well as what the book will cover.

(At the bottom of this piece, for premium subscribers, I’ve also included more details on what the book process looked like for me behind the scenes over the last few months. Additionally, once I’m a further along in the writing process, I’ll share some book previews with premium subscribers.)

Let’s get into it.

Why Write a Book?

New blogs, podcasts, videos, and social media posts bombard our phones and computers each day, and the shelf life of “content” continues to decrease as a result. Every “content creator” is competing with every other “content creator” for eyeballs in a cycle that will only continue to accelerate. How many blog posts have you read that you still forward to friends, months after the fact? How many specific podcast episodes will you recommend to your friends more than a week after listening to them? How many YouTube videos, tweets, or Instagram Reels published more than 72 hours ago can you recall? Not many.

Books, however, transcend the noise of our daily content diets.

You can put your phone away, pick up a book, and zone out from the rest of the world for hours. Even if you read on a Kindle (and I do love my Kindle), you are still isolated from social media, allowing you to focus on just the book. Between the reader’s heightened focus and the length of time it takes to finish a book, it’s no surprise that books stick with us far longer than other forms of content. A good blog post might stick with you for a week, but a good book stays with you for life.

The length of a book also allows the writer (in this case, me) to explore an idea with far more depth than they otherwise could. Blog posts are fantastic for conveying specific points and timely messages, but to really, truly, flesh out an idea with such detail that it hits a reader’s soul, you need more than 2,000 words.

Consciously, for the last six months, and subconsciously, for the last couple of years, I’ve had an idea that I couldn’t not write about. It’s an idea that I’ve hinted at in each of the blogs pinned on my home page, as well as in dozens of other articles that I’ve written over the last few years, and I’m excited to finally give it the attention it deserves.

That idea goes something like this:

I’ve long believed that, despite having access to more resources, more opportunities, and more money than any generation before, a lot of folks fail to do what they want with their lives. This isn’t the result of a conscious decision; it’s the result of a million small decisions that quietly compound over time, starting around the time we graduate from college.

Every 20-year-old has ambition plans for what they want to do with their lives, but real life gets in the way of those plans when we graduate. With bills to pay, the need to start making money supersedes everything else, so we accept a job offer somewhere doing something to alleviate that need. We probably had a vague idea of what we wanted to do, but come on, no one really knows what they want to do at 22. I certainly didn’t.

So you work for a year or two to land that first promotion, because a promotion means more money, and more money means more security. This cycle continues over and over and we progress through our careers. While we continue making decisions that represent a financial and professional improvement from our current situation, we never stop to think, “Is this (whatever ‘this’ is) what I want to be doing with my life?”

And then you blink, and you’re 50, and you think, “Damn, where’d the time go? And you can’t get that time back. You may have sleepwalked through a career that you never intended to pursue. Perhaps you ignored an entrepreneurial itch when you were young, for the sake of some ill-defined level of financial security. Maybe you delayed your dream to see the world, year-after-year.

When you’re young, it’s easy to tell yourself that you’ll get around to that thing (whatever it is) later, but you don’t realize that the window of opportunity to best take advantage of many of life’s experiences is smaller than we think. And once many of those windows close, they don’t reopen. We get so caught in our day-to-day routines that we don’t have a sense of urgency in taking control of the captain’s seat of our lives, so we remain in the passenger seat instead.

I consider myself fortunate that the pandemic hit when I was in my early 20s, as it gave me some time to take stock of where I was in life, and more importantly, where my trajectory was aimed. I was restless, I didn’t particularly like my job, and I was horrified that “this was it,” and I was just going to be stuck in this cycle until retirement. Thankfully, after some soul searching, I made major changes in my personal and professional life, and I’m quite happy with how stuff has played out this far.

Had I not had the opportunity to take a step back and reevaluate what, exactly, I wanted out of life, I would probably still be on that same track, with slightly more money and slightly more angst, a few years later. And that would have sucked.

My worst fear is that people sleepwalk from their youth to their graves without stopping to map out what exactly they want from life. My goal, with this book, is to warn folks of how life can pass them by if they’re not careful and provide some thoughts on how to avoid falling in that trap.

Put simply, I’m writing the book that I wish I had read at 23.

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Now, a bit more about the book process itself.

Funny enough, I had a half-baked idea for a book detailing the various manias of early 2020s financial markets before I started writing my blog, and I wrote a chapter or two of this “book” in early 2021 before stopping after I realized that I didn’t actually know anything about books or publishing.

Six months later, I started writing this blog after trying and failing to land a job writing for a few media companies (I had quit my job in August 2021 and wanted to travel for a while before starting graduate school, and I thought a remote writing job would be an excellent way to help subsidize those travels), and I thought that writing a blog for a few months would give me a portfolio of work showing that I could, in fact, write.

That blog landed me a job editing a daily financial newsletter (which ended up subsidizing some of said travels), and I just kept blogging away. After a year or so of blogging, I had ~10,000 subscribers, my audience was growing, and I was preparing to move to New York, when an editor from a finance-focused publishing house reached out to chat with me about potentially working on a book.

I was pumped, and we met for drinks in New York to talk about what a book might look like. At this point, I had decided against the “financial mania” book idea, I didn’t have any other strong inclinations, and, because I’d had a few friends recently sign book deals, I knew that I’d probably have more demand for a book later if my audience were bigger.

So I kept typing away, and one year later, Lydia Yadi, my now-editor from Portfolio, reached out to chat. Portfolio was, to me, the best of the best among the business/life advice imprints. They had Morgan Housel, Ryan Holiday, Scott Galloway, and more.

I was ecstatic.

I’d also developed my voice and niche over the last year, and I found myself writing more and more about topics like opportunity costs and investor psychology than pure “finance,” and I realized that the book I really wanted to write had more to do with how our handling of opportunity costs determines the outcomes of our lives.

At this point, I knew I wanted to write a book, and I knew, broadly, what I wanted to write about. But I needed an agent. If you ever write a book, and you’re going to pitch to publishers, get an agent. A good one is invaluable.

Fortunately for me, my friend (and Portfolio author, funny enough) Nat Eliason was working on a book, and he put me in touch with his agent, David Fugate. We hit it off immediately, chatted about the book idea, and I got to work on the proposal. What I didn’t realize, going into this process, is that a proposal for a nonfiction book is, effectively, a summarization of what the book will be about, as well as a marketing plan for how you’ll promote your book to your audience.

For me, it was quite difficult to write chapter summaries of a book that had yet-to-be-written. When I write, my initial idea often looks far different from the final product on paper, but when you pitch a book, you have to outline the product before it’s done. And that’s tough.

After spending three months working on the proposal, I hit a wall, and I took a break in February. I was about to start a full-time job, and graduation was coming up in May, so I decided I would pause my proposal edits until then. Once May came around, the idea clicked.

The narrative went from a broader discussion about “opportunity costs” to a more focused examination of how our early-life trajectories can prevent us from living the lives we want. It felt personal because of my early career angst, and I realized that the book I needed to write was the book I wish I could have read.

David helped me clean up the proposal and he shopped it around to different publishers, and a few weeks later, we had a deal with Portfolio. The irony of this whole thing was that Portfolio was the first major imprint to reach out to me, and Lydia, my now-editor, was the editor who really pushed me to consider writing a book in the first place.

I couldn’t be happier with my setup, and I’m excited to start working on this thing. The book writing/publishing process is slow, so don’t expect to see it in stores in 2024. However, as I make progress, I’ll keep you guys posted, and I’m planning to share a few sections from the book with y’all as the book approaches completion.

Thank you again for the support, and I’ll see you in your inbox next week!

- Jack

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