What I Wish I Knew Before Writing My First Book

The hardest part of writing your first book is not knowing what you do not know.

Over the past year, I have connected with around half a dozen people who were considering writing their first books. Some were introduced to me, while others reached out directly. Most were wrestling with versions of the same questions I had faced a few years earlier. How do you know whether an idea is strong enough for a book? How does publishing actually work? What should you expect from a publisher? And once the book exists, how do you get anyone to read it?

Those conversations made me realize how much I had learned through writing, publishing, and spending a year promoting The Uncertainty Advantage. Much of that knowledge came from making mistakes, trying things that did not work, and discovering parts of the publishing industry I had not known existed. I wanted to document those lessons while they were still fresh, both for myself and in the hope that they might save another first time author some time and frustration.

The Uncertainty Advantage came out in Canada on August 19, 2025. It has sold about 2,500 copies in its first year. I feel good about that result. For context, a 2018 Winnipeg Free Press article reported that the average Canadian written trade book published by a Canadian owned publisher sold 343 copies in its first year.

There are other indicators I am proud of. The book debuted at number one on Amazon Canada in multiple categories and remained number one in some categories for an extended period. At the one year mark, it has a 4.55 out of 5 rating on Goodreads (with 44 reviews) and a 4.8 out of 5 rating on Amazon Canada (with 29 reviews). Amazon categories can be quite specific, so I do not view those rankings as equivalent to appearing on a major national bestseller list. They were still encouraging evidence that people were finding the book.

Sales also understate readership. Based on an AI assisted scan I conducted of current library catalogues, my best estimate is that The Uncertainty Advantage is now available through roughly 100 library systems, institutions, or individual locations across Canada and the United States. That figure could be somewhat off because different catalogues count systems, branches, physical copies, and digital holdings differently, and collections constantly change. The book has appeared in major systems including the Chicago Public Library, Toronto Public Library, Ottawa Public Library, Calgary Public Library, Edmonton Public Library, and Brooklyn Public Library.

I barely thought about libraries when the book came out. I now appreciate how important they are for discovery. One library copy can reach many readers over its lifetime, including people who would never have purchased the book themselves. BookNet Canada found that 26 percent of Canadian readers discovered books through public libraries in 2025, almost as many as the 27 percent who discovered books in bookstores. The number of people who have read or encountered The Uncertainty Advantage is almost certainly higher than the number of copies sold.

More meaningful to me than any of those numbers have been the dozens of emails, direct messages, notes, and personal conversations with people who have told me the book helped them navigate a difficult career decision, deal with uncertainty, or think differently about their future. Those messages are difficult to quantify, but they are probably the part of publishing the book that I have appreciated most.

At the same time, 2,500 copies does not make The Uncertainty Advantage a breakout bestseller. It has been a successful Canadian book, particularly for a first time author, but it has not reached tens or hundreds of thousands of readers. I think that distinction matters. There are useful lessons in both what worked and what might have allowed the book to travel much further.

Figure out what book you are writing before you write it

I started writing during COVID. I had an idea for a book about developing entrepreneurial skills and some extra time, so I began. I had no proposal and had done too little work to identify exactly who the reader was or what problem I was solving. I assumed that if I kept writing, eventually I would have a book.

Eventually I had a manuscript, but I had started writing before doing enough thinking about what the book needed to be.

A big shout out here goes to my writing coach, Amanda Lewis. Amanda was enormously helpful in getting me to crystallize what book I was actually trying to write. Much of our work had little to do with polishing individual sentences. She pushed me to get much clearer about what book I was qualified to write, what niche I could credibly occupy, who the reader was, and what I could contribute that another author could not. The entrepreneurship book I had started writing gradually became The Uncertainty Advantage, focused on helping young people navigate uncertainty in their careers and lives.

If I were doing it again, I would write the book proposal very early in the process. I would study competing titles, talk to potential readers, and force myself to articulate exactly who the book was for, what problem it solved, and why I was the person who should write it. I would do all of that before writing tens of thousands of words.

I would also test not only whether the problem was real, but whether the central argument was surprising enough to make someone want to buy an entire book about it.

I still believe The Uncertainty Advantage addresses a real gap. The book is not primarily about proving that the world is uncertain. It gives people practical ways to respond through self compassion, adaptability, antifragility, generalist skills, entrepreneurship, and relationships.

But if I were developing another book, I would spend more time looking for tension in the central idea. When I began writing, the argument that young people needed to become much better at navigating uncertainty felt less obvious than it does today. Since then, artificial intelligence has accelerated dramatically, workplaces have kept changing, and uncertainty has become part of everyday conversation. Saying that we live in uncertain times can now sound almost trite.

Some of the nonfiction books that travel furthest contain an idea that makes you pause. They challenge something you assumed was true, reverse conventional wisdom, or promise an outcome through a path you did not expect. The reaction you want is something close to, "Really? Tell me more."

I would also think harder about whether the title communicates the return for the reader immediately. A book title functions a bit like an email subject line. Someone scanning Amazon or a bookstore shelf has only a few seconds to understand why the book matters to them. The Uncertainty Advantage communicates the central concept, but if I write another book, I might try to make the practical payoff even more explicit.

Feedback was another major part of making the book better. Roughly a dozen beta readers read versions of the manuscript, and I went through multiple rounds of feedback as it evolved. Some comments contradicted one another. Some were difficult to hear. But repeated feedback helped me see where an argument was unclear, where a story dragged, and where something that made perfect sense in my head did not make sense to a reader.

I would engage beta readers through multiple stages again. Early readers can challenge the thesis and structure. Later readers can focus on whether individual chapters, arguments, and examples work. Waiting until you think a manuscript is finished to invite serious criticism is a mistake. It is much easier to rethink a chapter when you still see it as a draft.

I would also rely more heavily on my own experiences from the beginning. Most of the underlying ideas in The Uncertainty Advantage are not uniquely mine. There are already plenty of books about adaptability, relationships, entrepreneurship, self compassion, and risk. What nobody else can replicate are my experiences leaving Goldman Sachs, building Venture for Canada, coming out as gay, or dealing with my own difficult relationship with uncertainty.

I came to believe that lived experience is a more reliable source of originality than trying to invent a completely new idea.

A good publisher does much more than print your book

The formal publishing process made the book significantly better. Dundurn Press was not simply a company that printed and distributed a manuscript I handed over. Its editors challenged the writing, identified weaknesses, and helped me produce a much stronger book. Dundurn also brought expertise in production, design, publicity, bookselling, and distribution that I did not have.

That experience made me much more positive about traditional publishing, particularly for a first time author.

With traditional publishing, a publisher chooses the books it wants to publish and assumes the financial cost of editing, producing, and distributing them. The author generally earns royalties and may receive an advance. With hybrid publishing, the author usually contributes financially to publishing the book while receiving services such as editing, production, and distribution. With self publishing, the author effectively becomes the publisher and hires whatever outside help they need.

Good hybrid publishers can still be selective, and both hybrid and self publishing can make sense. If you already have a large built in audience, understand how you will reach readers, have publishing experience, or place a high value on control, either model might be right for you.

But if you are writing your first book and learning the industry as you go, I think there is a lot to be said for exploring traditional publishing. There was real value in having people willing to tell me when something was not working. Amanda, my beta readers, and Dundurn all made The Uncertainty Advantage better in different ways.

I also underestimated distribution. Dundurn helped get the book significant placement at Indigo in Canada, as well as into independent bookstores and other retail channels. That matters. It is one thing for a book to technically be available when someone searches for it. It is another for someone to walk into a bookstore, see it on a table or shelf, pick it up, and start reading.

BookNet Canada found that 58 percent of Canadian readers preferred print books in 2025. I would not interpret that as meaning 58 percent of book sales happen in physical stores. I do think it reinforces the broader point that physical books remain very important, particularly alongside the finding that 27 percent of readers discover books in bookstores.

Some hybrid publishers have strong distribution, and a skilled self published author with a large audience may not need the same infrastructure. But established traditional publishers often have longstanding relationships with retailers, booksellers, distributors, and sales representatives. Because they publish selectively, their books also arrive in those conversations with some degree of institutional credibility. For me, that infrastructure mattered.

Publishing a book, though, is only one job. Finding readers for it is another.

Book marketing is much broader than launch month

The biggest marketing lesson I learned was that I had initially been asking the wrong question. I spent a lot of time thinking about how to persuade individual readers to buy one copy. In several cases, the much better question was which organization might buy a hundred.

Institutional sales became one of the highest return uses of my marketing time, and I did not pursue them seriously until well into the year. If I published another book aimed at students, professionals, leaders, or another clearly identifiable group, I would think about institutional buyers from the beginning.

A university might use a book for a student program. An employer might connect it to professional development. A conference might distribute copies to participants. Libraries can put the book in front of readers who have never heard of you. These are very different propositions from asking one person to buy one copy.

I also spent considerable time securing endorsements before publication. As a first time author, I think that was worthwhile. The Uncertainty Advantage received endorsements from people including Michele Romanow, Sukhinder Singh Cassidy, Andrew Yang, former Bank of Canada governor Stephen Poloz, and Eric Ries, author of The Lean Startup.

I doubt many people buy a book solely because of a name printed on its cover. But endorsements provide legitimacy when a potential reader has never heard of the author. If respected people are willing to read a book and publicly attach their names to it, that sends a useful signal.

There was another benefit that I had not anticipated. The process helped me build and deepen relationships. After Eric Ries endorsed The Uncertainty Advantage, I later became a beta reader for his next book, Incorruptible. I really enjoyed the experience. Other endorsement conversations also strengthened relationships that continued well beyond publication. A book can create social and professional capital in ways that are difficult to capture in a sales spreadsheet.

Speaking became closely connected to the book as well. I led a workshop at Rhodes House for Rhodes Scholars about navigating uncertainty early in their careers. I spoke at the Banff Forum in Quebec City, with young professionals at Global Affairs Canada, and to around 100 senior executives at RBC in Toronto. I also led a virtual session through Georgetown for a Rockefeller Foundation funded project supporting former USAID employees who had lost their jobs and were navigating career transitions.

Those experiences were useful for reasons that went beyond book sales. They put the ideas in front of very different audiences and forced me to see what actually resonated. A room of senior banking executives responds differently from young public servants or people suddenly navigating a career transition. Speaking became another way to test and refine the ideas.

I cannot claim that every invitation happened solely because I had written a book. I already had relationships and a professional track record. But the book gave me a defined subject on which someone could invite me to speak. It turned a collection of experiences and opinions into something other people could understand quickly.

A few other things worked well. A launch team of about 70 people received advance copies and helped create momentum around publication. My email newsletter grew to around 2,200 subscribers and became the most durable marketing asset I built. If you think you might publish a book several years from now, I would start building an email list today.

I also created the Uncertainty Score, a free online assessment connected to the ideas in the book. Roughly 1,000 people have completed it. It became my preferred call to action on podcasts because asking someone to take a free assessment is easier than immediately asking them to buy something. They receive something useful, some join my email list, and they can discover the book afterward.

Plenty of things produced little obvious value. Goodreads and StoryGraph giveaways did very little that I could identify. Instagram did almost nothing for me. TikTok generated no value I could measure, and I disliked making content for it. Some of the roughly 50 events I participated in took considerable time and produced no visible result.

That does not mean those channels never work. They just did not work particularly well for me. Authors receive endless generic marketing advice, but you cannot do everything well. I would now put much more weight on finding channels that fit both your audience and the kind of work you are willing to keep doing.

LinkedIn was more useful, but not when I treated it like an advertising channel. Personal stories and useful ideas performed much better than posts asking people to buy the book. Most people do not care that you wrote a book nearly as much as you do. They care whether something you wrote helps them, entertains them, or makes them think.

Podcasts sat somewhere in between. I did about 40 during the year. Smaller shows rarely produced direct sales I could identify, but doing them repeatedly made me much better at explaining the ideas in the book.

I also hired a publicist who helped secure larger podcast appearances and written coverage, including placements in Fast Company and Business Insider. I eventually hired her again, so I clearly believed the work had value. But I still could not tell you how many books a particular article or interview sold.

Book marketing is extremely difficult to attribute. Someone might hear you on a podcast, later see the book at Indigo, read something you wrote on LinkedIn, borrow it from a library, and eventually recommend it to a friend. Which activity gets the credit?

There is also a common misconception that book marketing is mostly about launch month. Before publication, it is easy to organize everything around the release date and perhaps the first three or six months afterward. A year after The Uncertainty Advantage came out, I am still spending a meaningful chunk of my time finding new ways to introduce it to readers.

Some of the things I am focused on now were barely on my radar at launch. I am continuing to pursue institutional sales, trying to expand library availability, speaking to new audiences, appearing on podcasts, and experimenting with different ways of connecting the book to conversations happening today. I am still learning what works.

Unless a book is tied to a very specific moment in time, publication should probably be viewed as the beginning of the marketing process rather than its end. A book can keep finding new readers for years. The better question is not simply, "How will I launch this book?" It is, "How will people still be discovering this book one year, two years, or five years from now?"

If I write another book, I will think about marketing much more as an ongoing system than as a launch campaign.

My sense is that a substantial share of my sales came through people I already knew, institutions I could reach, or people who encountered the book through those networks. There was also an organic group of readers who found it through bookstores, Amazon, libraries, media, recommendations, and other channels. I cannot reliably separate one source from another.

That is why I would be careful about comparing my 2,500 copies with another author's sales. I had spent more than a decade building relationships through Venture for Canada. A first time author without that starting point cannot simply copy my marketing tactics and expect the same result.

Decide what you want the book to do

If your main objective is making money from book sales, I would be cautious. Writing a serious book takes an enormous amount of time. Promoting it takes more. There are easier ways to make money.

For me, much of the return has been indirect. The book created speaking opportunities and conversations I would not otherwise have had. It strengthened relationships and helped create new ones. It gave me a framework for engaging audiences ranging from university students and public servants to senior business leaders and people going through major career transitions.

Just as importantly, writing it forced me to spend several years thinking seriously about ideas that mattered to me.

What the book gave me that other formats probably would not have was coherence. Before The Uncertainty Advantage, I had experiences and opinions about careers, entrepreneurship, anxiety, adaptability, relationships, and risk. Writing the book forced me to decide how those ideas fit together.

It also created something that can travel without me. Someone can lend a book to a friend, assign it to students, borrow it from a library, give it to an employee, or discover it years after publication.

For someone considering writing a book, that is the question I would start with. What do you want the book to do?

If the answer is simply to reach as many people as possible, a newsletter, podcast, or another format may be more efficient. If the answer is to make money, there are probably better uses of your time. A book makes more sense when you want to develop a body of ideas, build credibility around a subject, create something people can share and use, or open doors to conversations that would otherwise be difficult to access.

If I ever write another book, I would apply what I learned much earlier. I would spend more time testing the proposition before writing the manuscript. I would look harder for the tension or counterintuitive argument inside the idea. I would make the return for the reader as obvious as possible. I would engage readers throughout the writing process. I would think about endorsements as both credibility and relationship building. And I would think seriously about distribution, institutions, bookstores, libraries, and long term marketing before publication.

Most importantly, I would still expect there to be unknown unknowns.

Some of the things you expect to work will accomplish almost nothing. A marketing channel you were told was essential may be useless for you. A conversation you barely thought about may sell a hundred books or lead to an opportunity you never anticipated.

That may be the most appropriate lesson I took from publishing a book about uncertainty. You can prepare carefully, make good decisions, and still not know what the outcome will be.

So do the preparation. Build the audience before you need it. Invite criticism before you become attached to the manuscript. Make the argument interesting enough that someone wants to know what comes next. Write something only you can write. And make sure the reason you are doing it is strong enough that the project still makes sense even if the results surprise you.