A: We obsess over finding best practices, but in this era of Advice Overload, we’re losing sight of something: Finding best practices isn’t the goal. Finding the best approach for you is. As a result, in order to improve your marketing, it’s crucial to begin by intimately understanding your context, then using that knowledge as a sort of filter to vet any new idea or tried-and-true tactic.
Your “context” is simply three things: you (the person or people doing the work), your audience (the person or people receiving your work) and your resources (the means to make the work happen). By investigating all three of those things more fully, you can understand which best practices or new ideas make sense for you, and to what degree. Without knowing that, however, you wind up grabbing at everything and anything.
Q: What was the inspiration for Break the Wheel?
A: I’ve been hosting a narrative-style podcast, Unthinkable, for a few years now, and each story begins with the same premise: Somebody has done something exceptional that seems crazy from the outside looking in. But then you hear their side of the story, and they rarely describe any risk-taking or giant leaps. Their work feels logical and strategic to them.
In analyzing all those stories in retrospect, I realized late in 2017: The reason exceptional work looks either radical or refreshing is because we simply lack context. Those individuals made decisions based on their unique situations, not based on the best practice. When all we know are those generalities, sure, it looks crazy.
So I believe that exceptional work happens when we find and follow what makes us and our situation an exception. I believe there’s more power in making decisions based on your specific context than on the conventional wisdom. The problem is, we’re taught how to find the “right” answers from others, but not how to find our own answers. So that’s what the book explores.
A: The book explores what happens when you act like an investigator instead of an expert.
Experts care about absolutes, which may be an okay place to begin your thinking, but investigators care about evidence. They care about asking good questions, rather than glomming onto others’ answers. In doing so, they find information from within their environments and draw conclusions from there. The book shares a series of stories of people who did that, from tiny startups to massive companies like Google and Starbucks, to solo creators and marketing practitioners.
In the end, the book explores how to use your intuition – not as some mythical gift, but as a practical, investigative skill – to make better decisions than any expert or best practice could provide.
A: In addition to changing how we behave (from acting like experts who care about “the” answer to acting like investigators who care about great questions), I’d like readers to walk away with an initial set of questions they can ask in their situation.
Throughout the book, I explore two types of questions: trigger questions and confirmation questions. My research also uncovered three psychological barriers that these types of questions help us overcome when making decisions at work. Then, through the stories and research throughout the chapters, I proposed an initial set of six total questions (three trigger questions and three confirmation questions) that we can all ask to inform ourselves using the details of our context rather than the generic best practice.
In the end, however, I want these to be starting blocks, not the finish line. I encourage readers to use the principles of the book to come up with their own questions and to send them to me so we can continue to push each other past conventional thinking to better think for ourselves.
A: I’m a professional speaker, an author, and a host/producer of documentary series with B2B brands.
A: Kitchen Confidential by Anthony Bourdain. His vivid storytelling affects all my work in all mediums, and his willingness to speak the unspoken truths of a professional are something I aspire to do as well.
The Power of Habit by Charles Duhigg. This may sound odd, but I never finished this book. Instead, what inspired me was the framework or structure of his writing. Duhigg is a master at weaving together stories, insights pulled from those stories, and relatable but impassioned pleas to the reader. Rather than the usual nonfiction approach (premise-story-insights), he creates a seamless experience. I tried to mimic that in my writing as well.
A: The decision to leave Google (but not for the reasons you may think). I didn’t struggle to leave Google because I loved it and would miss it. (I didn’t, and I knew I wouldn’t.) I struggled because all my life I followed the path of the “right” answer in some theoretical sense. I thought if you got great grades, joined clubs and became the leader of those clubs, and networked and took the right internships as a student, you’d land THE job.
So I did those things as a student, then landed at Google, one of the best places on the planet to work, especially back then before other tech companies became so focused on culture. When I hated the job working in sales at Google AdWords, and disliked the big company feel, I thrashed. My brain was NOT prepared for that scenario. I was “supposed to” work there and love it.
Over the years, I realized that careers are merely vehicles for developing self-awareness. The point isn’t to do what others tell you “works.” The point is to understand and execute against what works best for you. That’s the theme of the book, and that was a hard-won lesson in my own career.
A: According to the bylaws of the NCAA, I am a professional basketball player.
Okay, so it’s not quite as cool in reality: I participated in a school-run basketball tournament as a student at Trinity College in Hartford. The winning team split a small pool of money. We were told that we had to drop our best player from the roster before joining, however, because he played for the Trinity team. If he won the tournament, he’d be paid for playing his sport, forfeiting his amateur status in the eyes of the NCAA.
So, yeah, I could have gone pro, but something about this marketing thing just seemed sexier 😉
Q: Is there a piece of content, a social media campaign or a marketing campaign that you worked on that you’re particularly proud of?
A: My newsletter, Damn the Best Practices, has been a breath of fresh air for me. I challenged myself to write a story once a week, and I don’t mean “how-to” or “tips and tricks” when I say that word, story. I mean an actual human protagonist is involved, whether it’s me or, preferably, someone else.
Stories contain conflict or friction, as well as emotion. So every week, I share one new story about doing exceptional work and challenging best practices. Then I include a section titled “Email Antipasto” which are tasty little bites, sometimes paired with the main course, sometimes just for flavor.
Nowhere aside from maybe my podcast have I seen such passionate replies. That’s the power of the inbox and getting permission to share work with someone once a week. That’s also the power of telling a story and making people feel, not simply presenting case studies or facts. I’m addicted to the project, and I’m happy to see the reaction so far.