Q&A with Lindsay MacMillan, Author of The Heart of the Deal

Lindsay MacMillan is the author of The Heart of the Deal, her debut novel about love, friendship and mental health in New York City. Lindsay worked at Goldman Sachs between 2015 and 2022, rising from an intern to vice president. She made the most of internal mobility across the Executive Office, Asset Management and Consumer Wealth Management Divisions in both New York and London.

Your novel tells the story of Rae, an investment banker and closet poet who, on her 25th birthday, sets a goal to be married by the time she turns 30. How much of the book, if any, is based on events that took place in your personal life?
Lindsay: The book is a novel, and the characters and plot are fictional.

With that said, the story was certainly inspired by a season of my own life. My friends and I were working corporate jobs in our twenties in NYC, texting each other from office bathroom stalls, sharing ice cream pints in shabby walk-up apartments, plunging into relationships with emotionally unavailable partners, and feeling the pressure to have our 10-year life plan figured out.

The specific characters and plot points are made up, but it captures a season of my life, and I hope it’s something my friends and I can treasure as a time capsule of growing up in New York together. It’s emblematic of all the emotional volatility, female friendships, and self-growth that came from stepping off “the right track” and carving our own paths.

For me, the power of writing fiction is how it can expand beyond my own life and speak to a collective experience. I certainly see large bits of myself in the characters, and my favorite thing is hearing how other readers do too.

In the book, Rae dreams of leaving her job in investment banking to become a published poet; she develops a plan of action to set herself up for success. At what point in your life did you know you would become an author, and what steps did you take to ensure your own success as a writer?
Lindsay: I’ve wanted to be an author since I was six years old. In first grade, I actually wrote down the dream on a “What I want to be when I grow up” poster. (The poster still hangs in my mom’s house!)

When I was 18, I wrote my first 450-page manuscript. It was born from catharsis as my parents were getting divorced. That’s when I started to experience the power of writing fiction to escape our own life stories, while also getting closer to them. It’s this really cool paradox.

Then I went to Dartmouth and took every creative writing class and started learning about the publishing process. I wrote and pitched three books in college. But I wasn’t breaking in, and I also had a lot of other interests – business, for example.

I wanted to get a solid career foundation, and I’m most fulfilled intellectually when stretching both sides of my brain, so I went to Wall Street and kept writing as a side hustle.

During the six years I was at Goldman, I was still writing and networking as much as I could in NYC. With no connections or celebrity platform, it certainly wasn’t easy to break in, and I got so many rejections (literally hundreds) and cried many, many tears – on subway platforms, my tiny studio apartment, and yes, even Goldman Sachs bathroom stalls.

But I finally got my break and signed with an agent in 2020. Then once I got two book deals, I decided to take the leap to pursue writing full-time and really build a brand that extends beyond the book.

It’s easy for people to look at me and think my publishing success happened overnight, but it’s been a decade of trial and error and rejections. There were so many moments I could’ve given up – and logically thought I should give up – but that inner voice wouldn’t let me.

Like Rae, I’ve learned to trust my intuition and keep going, but it hasn’t been a linear path by any means.

The novel focuses a great deal on mental health in the careers and relationships of mid-twenties professionals. What do you hope readers learn and take away from the book in regards to mental health?
Lindsay: Some readers have been surprised – even upset – that a “cute pink book” tackles deeper topics like mental health.

The book starts off more as a rom com and then veers off track, breaking the traditional “formula” to explore the messiness of relationships marked by mental health challenges.

Mental health is such a prevalent aspect of relationships today, especially among twentysomethings working demanding jobs, and it was so important for me to explore this and make the book feel like real life.

As Rae tries to support her partner Dustin, who battles depression, the book raises the questions: How do you love someone who is struggling to love himself?Does true love mean letting go or holding on?

I hope that the inclusion of mental health in the book can get us talking more about mental wellness and how we can support our partners, friends, colleagues – and ourselves – the best we can.

It has been four months since leaving your role at Goldman Sachs and deciding to pursue writing full-time. In what ways has your life changed? In what ways has it remained the same?
Lindsay: My life has changed in so many ways, from where I live to how I structure my day. The best change has been finally being able to prioritize my writing career.

For years, I was working two full-time jobs (Goldman by day, writing by night) and it’s an immense privilege and relief to be able to focus on just one. Not only do I have more time for my writing pursuits, but also for sleep and nature walks and family dinners – the little things that fill life with beauty.

I also moved from London back to my Michigan hometown to live with my mom to save money (authors make a disgustingly small cut of the book’s sticker price). And the past month, I’ve been on the go from NYC to California for my book tour, speaking at events and crashing on friends’ couches, so it’s definitely different from sitting in the office all day.

As far as what’s stayed the same, I’m still working full days and using many business skills – content marketing, brand partnerships, financial modeling, and now I’m pitching deals alongside my Hollywood agents for a TV/film adaptation of the book (please reach out if you have any connections!).

Though I love many things about being a full-time author, there are certainly things I miss about Goldman – the caliber of the people, steady paycheck, and the scale of the resources and platform.

Also, since I’m working for myself now, I have to be more intentional about setting work/life boundaries. I’m passionate about writing, but I can’t let it consume me, and that’s something I have to watch out for since it’s my full-time job now.

You just finished a three-week book tour to promote The Heart of the Deal. What are the challenges that come along with promoting a book as a first-time author?
Lindsay: It’s incredibly difficult to break in as a first-time author, as the market is so crowded and dominated by established authors and celebrities. Generally, publishers put very little support behind you if it’s your first book, so I hustled to do pretty much all the marketing and PR myself.

I decided not to hire an external publicist, not just because of costs but because I found that I was getting traction when pitching people directly and being the face of my brand. Katie Couric actually interviewed me about the book, which was a huge win, and I also wrote bylines for Business Insider and Thrive Global, all of which I got by reaching out directly.

Beyond the PR, my marketing strategy has been grassroots as I’m partnering with hundreds of book clubs, co-working spaces, and women in business organizations across the country. It’s time intensive and not hugely scalable, but so far it seems to be working. We actually sold out of all 13,000+ copies of the book in the first week and are already on the third print run, which is an exciting proof point as I get started.

With that said, there’s a long way to go and I’m excited to keep building on the momentum for the next book.

Can you share any details about your next novel slated to be released next summer?
Lindsay: Yes! I wrote it while living and working in London for Goldman. It’s called Double-Decker Dreams, and is the story of an American consultant based in London who has sky-high dreams for her love life and career.

She has her sights set on marrying an English prince and becoming a big-shot CEO – but the closer she gets to those dreams, the less she actually wants them.

It’s really about someone who is deconstructing – and then reconstructing – what she thought she wanted to build a life that better serves her. The central thread with my books (so far!) is that they feature strong, relatable women who are redefining success.

Double-Decker Dreams is publishing in June 2023 and will be available for pre-order soon.

The genre for my books is called “women’s fiction,” which is a term I can’t stand. There’s no such thing as “men’s fiction,” it’s just called “fiction.” Society just assumes women will read books with male characters, but not that men will read books with female characters. Not only is this sexist, but it’s just plain wrong. Just because the main characters in my books are women doesn’t mean that all kinds of people can’t relate to them, or at least learn something from them.

I’ve loved hearing how many men are connecting with The Heart of the Deal and hope they’ll do the same with Double-Decker Dreams.

How did your time at Goldman Sachs help you to overcome the many obstacles of breaking into the publishing world?
Lindsay: My years at Goldman helped me as a writer in so many ways I never could have predicted. Not only was it a valuable life experience that would help inspire a novel about a woman in finance, but the skills I learned also helped me get an agent and develop a successful PR/marketing campaign.

For example, in my first role as an investor at Goldman, I learned a lot about how companies pitch to raise capital. There were so many parallels, I realized, between entrepreneurs pitching investors and authors pitching agents.

Not only did you have to hustle to get the meetings and endure mountains of rejections, but you had to succinctly articulate your value prop, competitive differentiator, and comps in the market. Sifting through all the pitch decks and building out investment memos helped me translate those skills to pitching my book.

Many writers don’t have the benefit of a business foundation, and it’s made me more savvy not just in pitching, but in how I’ve organized a grassroots marketing plan and met my target audience where they are (a content strategy I learned in the Executive Office). My time at the firm also helped me get my finances in place to be able to take a risk and pay cut to go all-in as an author.

I call myself an “authorprenuer” because I’m approaching my career as an author with an entrepreneurial-minded lens, incorporating business strategies I learned while at Goldman. I’m committed to helping equip other authors/artists with these skills too, as it’s hugely empowering.

The Goldman brand name also helped me get the high-profile PR for The Heart of the Deal. There’s so much power in the brand, and having been a VP here helped me stand out from the crowd when it came to getting attention for my book.

I feel incredibly grateful for the support of the firm as I follow this dream and can say with confidence that my time at Goldman has made me a stronger author and businesswoman.