Opposite Thinking - Insights on Solopreneurship from B.J. Novak

At CEX in 2024, Ann Handley interviewed B.J. Novak, and he talked about one of his principles for creativity which he framed as a question: “What’s the obvious, hidden-in-plain-view opportunity?”

He was talking about inversion, a turning inside out of conventions and ideas, and I’ll share three of his examples before I connect this with solopreneurship.

In case you’re not familiar, B. J. Novak is an American actor, comedian, and writer. He played Ryan on The Office (the American version), and was one of the show’s writers.

Novak and his fellow writers and producers received five consecutive Emmy nominations for Outstanding Comedy Series from 2007 to 2011.

In other words, he’s no slouch in the laughs department, and if you think about it, some of the mechanics of humor are bolted on to the idea of inversion: What’s the trope, or what’s the expectation? Now, what’s the opposite, or how can I come at that expectation sideways?

You have to understand both the tropes and expectations (think: rules) before you can break them in a way that some people find delightful and satisfying.

Novak has made a career of inversion, both as a comedic actor and as a writer.

For example, take The Book With No Pictures. It’s a children’s picture book with no… pictures.

If I were to ask you what is the single most important feature of a children’s picture book, what would you say? The pictures! Duh.

Novak looked at genre and asked himself, “What’s the obvious, hidden-in-plain-view opportunity?”

It seems obvious now, right? Turn the one rule or expectation on its head. Give kids a picture book with no pictures.

This Opposite Thinking may sound familiar to those of you who have read my work in the past. Tim Ferriss once used Opposite Thinking to singlehandedly outsell the entire L.A. office of his company’s biggest.

Novak’s Opposite Thinking was equally effective: The Book With No Pictures spent 185 weeks on the New York Times Best Seller Picture Books List, including 34 weeks at #1.

Another example pops up in Novak’s collection of short stories, One More Thing: Stories and Other Stories.

In one of the stories, “Sophia,” a man purchases a sex robot. After she falls in love with him, he returns her.

Regardless of how you feel about sex robots, the story has a brilliant twist. Robots aren’t supposed to have feelings, sex robots most of all. Meanwhile, all of us want to be loved. So Novak touches on one of the contradictions that make us human: When we get what we want from a source where we didn’t expect it, we often respond with disdain or even disgust and reject (or return) it.

What would have made the story boring? Making it exactly what you’d expect.

Novak’s purposeful reversal, as well as poignancy from unexpected sources, is what makes it work.

(See also, the film Lars and the Real Girl)

Sidenote: Novak attributes much of The Office’s success to the “5% Rule,” a rule he learned from writer, producer, and director Greg Daniels who created the show. 95% of a character can and should stay the same. That consistency makes characters work. We feel like we know them and can predict how they’ll respond. However, if characters always do what we expect, we lose interest in them. They need to surprise us 5% of the time. This rule struck me as a handy tool for characterization and as another form of Opposite Thinking, only compressed. 5% of the character needs to be a reversal of what the audience expects.

Novak also used a reversal in his 2022 film Vengeance. Someone bereaved seeking vengeance for a murdered lover, that we can fully believe. We’ve seen that movie before.

But a journalist and podcaster who investigates the murder of an ex, more casual than committed, who lied to her family about still being in a relationship with him, and who ends up taking vengeance on the man (spoiler alert) who caused the woman to overdose and left her to die? That’s new and strange, and yet, in deft hands, the reversal (vengeance for someone he didn’t care much about and hadn’t seen in years) can make the audience lean forward.

Here I am telling you about the film, and I haven’t even seen it. Proof positive that reversals are memorable, if nothing else.

So where does that leave freelancers, consultants, and other solopreneurs who suspect we need more Opposite Thinking in our growth strategies, brands, and dietary preferences?

(You didn’t see that last one coming, did you?!)

Here are some Opposite Thinking ideas to prime the pump

• Branding – Advertising expert Siimon Reynolds wrote a book called When They Zig, You Zag. Seth Godin observed that purple cows stick out, and legend has it that he shipped early copies of his book, Purple Cow, in milk cartons. Apply that idea to your brand. What does everyone expect from someone with your skill set? What kind of brand do [fill in the blank; e.g., copywriters] normally create? What if you did the opposite? How can you stick out?
• Sales – Mariah Coz hates sales calls, yet she needs to sell her high-ticket group coaching program. So what did she decide to do? She figured it out. Everyone may be saying, “Yeah, you have to do this. There’s no way around it. It comes with the territory.” But the innovators are the ones who ask, “Do I really have to?” Think of some part of the sales process you dislike. Apply Opposite Thinking. Perform experiments.
• Focus – Rosemarie Groner didn’t know you couldn’t build a blog if you only had two hours a day. How naive, right?! She started The Busy Budgeter and after about a year old, her blog was earning $5k a month. A year after that, she was earning $20,000 to $25,000 per month. And pretty soon after that, she was averaging over $100K per month. Some of Rosemarie’s growth came down to staying focused: “I eliminated anything that wasn’t important for my growth.” While the “experts” tell you that you need to be doing all the things, you can always find the outlier who ignored most of them and achieved better results. What is your 10x opportunity? What do you need to eliminate so you can focus on that? You can’t get extraordinary results with ordinary focus. You need Opposite Thinking to help you find the better path to growth—and the areas of focus that can get you there.
• Content – Entrepreneur and investor Peter Thiel is fond of this interview question: “What important truth do very few people agree with you on?” Wes Kao would say that your answer to that question is part of your “spiky point of view.” Some of your best content will come from identifying where your beliefs about your work and your clients’ success diverge from most of your peers’ beliefs. What common industry practices do you believe are ineffective? What do competitors do that frustrates you? What limiting beliefs keep your dream clients stuck? Find out where you disagree and write about that.

Let me close with an important qualifier for Opposite Thinking.

It is different from being controversial, contradictory, and contrarian. You can write a LinkedIn post that is a hand grenade, pull the pin by hitting publish, and get some attention for being incendiary. Some people seem to enjoy eliciting strong reactions by being polarizing: “You’re an idiot if… .”

That’s not what we’re talking about here. B.J. Novak’s book didn’t stay at the top of the NYT bestseller list simply because it is opposite and defies conventions. It stayed there because it is a good book, one that children love and keep asking for because its premise delights them: “Everything the words say, the person reading the book has to say.”

Opposite Thinking is a tool, an advantage, that can turn up opportunities to break rules and come sideways at expectations in a way that benefits other people.

Related: Thoughts on Becoming an Opportunity Hound & Going After Dream Clients

Lots of people online use polarization as a strategy to grab attention, elicit emotion, and get something else they want (status, money, power, votes, free Chicago-style hot dugs). Okay. It works. You can do it if you want to. This essay isn’t the one where I want to trace polarization back to its parentage, manipulation.

My point is that you can be opposite without using Opposite Thinking. Opposite Thinking assumes that you have more than a transactional interest in your audience. Before I sat at Hotel Cleveland and listened to B.J. Novak talk, I wasn’t a fan. I knew almost nothing about him. Now, I am a fan because I understood why he uses inversions, reversals, Opposite Thinking: He wants to put work and art out into the world that delights his audiences, from children to those who read short stories to those who watch dark comedy mysteries.

With whom are you trying to connect? What are the tropes and conventions that stand between you and them? How would you like to delight them? What benefits will you provide? What’s the obvious, hidden-in-plain-view opportunity for doing it faster? Give Opposite Thinking a try.

When you’re ready, here are ways I can help you:

1. Free Money. A pricing and money mindset guide for freelance creatives. If you’re unsure about your freelance pricing, this is the book for you.
2. Morning Marketing Habit. This course will help you build an “always be marketing” practice, become less dependent on referrals, and proactively build the business you want with the clients you want. My own morning marketing habit has enabled me to consistently make  6 figures as a freelancer.
3. Custom Business Roadmap. Gain clarity, confidence, and momentum in your freelance or consulting business.
4. Business Redesign. Raise your effective hourly rate, delegate with confidence, and free up 40 hours a month.
5. Clarity Session. It’s hard to read the label when you’re inside the bottle. I've done well over 100 of these 1:1 sessions with founders, solopreneurs, and freelancers who wanted guidance, a second opinion, or help creating a plan.