What If You Won the Lotto? Thoughts on Marketing and Living a Life of Choice

My partner Jared and I sometimes like to play the lottery, and there’s one important rule we always follow: Every time we buy a ticket, each of us has to come up with a new, outlandish thing we’d do with the money if we won. Here are some of my favorite answers so far:

• Build my own Hobbiton and move all my friends into it.

• Buy a gigantic gothic mansion and turn it into a year-round Halloween haunted house.

• Start a bacchanalian cult/commune in the middle of the woods.

Since we’re unlikely to win, the idea is that instead of “paying the poor man’s tax,” we’re intentionally purchasing the entertainment value of the ensuing conversation, which is always a lot of fun. But recently, Jared asked me the same question in a more serious way: “If we won the lotto, what would you literally do right now? Quit your job? Go on a shopping spree? Pack your bags and fly to another country?”

In the context of real life, the question was a little more difficult to answer. As a financially doomed millennial, I’d long given up on the idea of retirement or a future of leisure. And since Eva and I started Copilot Publishing, I’ve discovered that I actually like what I do when I’m not buried under the insurmountable weight of a larger company’s task list. I like the work. I like the clients. I like you, my precious handful of email subscribers and blog readers. Not everyone can say that. Despite my sometimes anxiety-inducing bank account, I realize I enjoy a lot of privilege, and I wish more people could feel this lucky.

So I’ll ask you, now: If you won the lotto today, what would you do? More to the point:

Lately, I’ve been applying this notion of choice to the way I coach my clients. Too many people look at social media, email marketing, and platform building as a necessary evil, a chore that must be done to support their business. In some ways, that’s true. You don’t necessarily have to do “All the Things,” but you do have to do something if you want anyone to find your art, read your writing, buy your product, and/or hire you for your services.

And that “something” should be enjoyable, at least on some level. Have you ever been to a workshop or seminar where you could tell the speaker just absolutely did not want to be there? It’s excruciating for everybody. Marketing’s the same way: If you hated making that social post or writing that email, the person on the other end isn’t going to enjoy it, either.

And that’s the whole point of marketing: To reach the people who are actually going to be interested in and excited by what you’re doing. You’ve gotta give ‘em some genuine enthusiasm if you want them to return it.

This is also why I think it’s necessary for authors to be personally involved in their marketing campaigns. I am 100% willing and happy to manage your entire social media presence, from content writing and design to posting and advertising (especially if you pay me!), but I am certain you’ll get better engagement if you participate at least some of the time, because your ideal audience wants to get to know the real you. For this reason, the campaigns I build are typically about one-third author-generated material and two-thirds Jenn-generated (Jennerated?!) And even then, the material I create is always based on the author’s own work, their own words.

The other thing to take into account is sustainability. Whatever marketing activity you choose, you should be prepared to do it for the long haul. The people who start a social media account and instantly become an overnight viral sensation are few and far between. For most everyone else, it’s a long game that involves consistent content-sharing and promotion until one day, the right post, the right person, or the right opportunity comes along and gives them a boost.

Even if you’re a master at faking it—a clever wordsmith who can inspire and entertain the masses regardless of how you actually feel—it’ll start to drain you in the end. Nothing’s more exhausting than doing something you dislike.

So pick a marketing tool you think you can sink your teeth into. If you love writing, start a blog or email list. If you’re an extrovert who is energized by interacting with others, post on X/Twitter and trade comments with people who have the same interests. If you’re more of a visual art person, post inspiring photos and graphics on Instagram. If you’re one of those magical unicorns who actually likes being on camera, get on TikTok. 

If you don’t think you’ll like any of those activities, I encourage you to challenge that assumption. You can’t really declare how you feel about something until you give it an honest try. (I was so nervous the first few times I posted on TikTok, my finger would shake when I hit the record button. Now, I think it’s a blast!)

Finally, if you’re feeling lost or overwhelmed and unsure of where to start, I’m available. Send me an email. I’d love to hear about your work.

PS: There’s this Vietnamese superstition my mom always talked about while I was growing up, that if you dream about poo, money’s coming your way. Well, I dreamed about A LOT OF POO the other night, so of course, the next day, I ran out and bought the lotto tickets pictured in this post. Cross your fingers for me. Hopefully, I’ll be writing my next blog post from a hobbit hole! 💩💰🧙‍♂️