Don't Be the Best; Be Their Favorite

I swear it was just a normal pen, but in that moment, I prayed it was magic, with a sorcery capable of calming my boss. I'd marched into his office to say something kind of insane if your goal is to keep your job. Naturally, I needed a place to direct all my nerves.

Click-click-click-click!

My boss, our VP of marketing, wasn't angry per se. He was just fired up. Because he wanted to fire ME up. Because I was super close to getting myself fired.

I was 27, and I'd spent about a year as the company's head of content, a coveted and highly visible role. I was in charge of our content strategy, leading a team of 9 marketers who would write articles and ebooks based on my strategy. Together, we ran a blog with over 2 million monthly visitors and a subscription list well into six figures—unheard of among B2B software brands, especially at the time. On paper, the job was glamorous. In reality, I was miserable.

There were many reasons for that, like company culture and politics, team burnout, and the cutthroat nature of promotions. But I thrashed for a different reason. I'd held manager roles like this before, but it was always at smaller startups, where I could both lead the team and write at least some articles. Now, at this growing behemoth of a brand, I spent all my time in meetings.

All. My. Tie. Muh.

Imagine capturing a great white shark in the ocean and keeping it in your pool. Not even a good pool. Like an above ground pop-up pool with the little ladder you throw over the side? Yeah. That pool.

That was me, except unlike sharks, my teeth can't grow back—which is a problem when you spend every minute of every weekday clenching your jaw, suffering through meetings.

Click-click-click-click!

Back in my boss's office, I'd finally told him how I felt. Politely, I swear.

My boss was a company man the likes of which you rarely find anymore, especially in tech. He'd fully bought into the company culture, and we all knew he was headed for the role of CMO soon.

"I just don't think I'm using my superpowers here," I told him. "I'm not sure I'm being fully utilized. I'm not doing my best work."

That got his attention.

(In a good way?)

"Come on," he grunted.

(Oh. Nope.)

Click-click-click-click.

"I mean, I agree," he said to me. "It's a problem."

CLICKCLICKCLICKCLICK.

"I feel like I'm caught between two roles," I continued. "I'm in this manager position where I'm supposed to be a content strategist, but my love is to create. And I'm really good at creating things. That's what got me this job in the first place."

"Hmmm, okay." He was calmer now. The pen was magic after all.

"I think you have to choose," he said. "Given where the marketing industry is at right now, and given where you work right now, you could probably become the best content strategist in the world. But you probably won't be the best creator. So I think solving for enterprise value is also solving for your career here: You should focus on being the best strategist."

So it was settled. With a few tumbles of a tongue fluent in Corporate Bullshit, I had my marching orders. Do the job assigned to you, or I'll find someone who will.

Now, if you've followed me for any amount of time, you realize (a) I'm long gone from that or any other company, (b) I'm known for my creativity, stories, and content, and (c) I clearly rejected the guy's advice. I get it. As Mike Birbiglia likes to joke, "I'm in the future also." You and I both know where this story goes eventually.

But can I be honest? It took awhile. All because of that tiny little word my boss dangled in front of me:

"Best."

I had the chance to be the best.

I loved being the best at things! I always worked hard to be the best at everything. In school, that meant getting straight-As, becoming president of this club and that club, and captaining every team I played for. After graduation, I worked for the best brands in marketing and the best places to work in the nation (if every ranking at the time was to be believed).

The moment my boss said to me, "You can be the best at this," I was cooked. My decision-making dissolved. My perspective? POOF.

Yes! Of course! THE BEST! LFG!

"Be the best."

Just three words.

A short command.

A simple idea.

And terrible advice.

* * *

In my public speaking, I tend to open my keynotes by asking people the same question: "What's the best Disney film of all-time?" People who have seen me speak know this as my signature Goofy Movie bit, because regardless of how you answer that question, you're wrong. There is ONE objectively correct answer: A Goofy Movie.

(Listen, if you know, you know: Powerline? The pop star in the movie? Legit good music, and I'm still waiting on the album to drop.)

Of course, that's a ridiculous question to ask. It's ridiculous not only because I ask it in speeches at Very Serious Business Events, but for another reason we need to understand:

We can't actually answer that question correctly, but that won't stop us from trying.

This is precisely how we think about our work too. We want so badly to be the best at what we do. In our marketing, we work so hard to tell to others that we indeed are the best, and that's why they should care, share, subscribe, and buy. Because look at us go! We're the number-one in the category, the top-ranked, most-beloved, most-decorated. We're the academically sound solution. We're the objectively correct pick. We're the best!

But that's not a real thing. What the heck do you actually mean? What did my boss mean, all those years ago? What would being "the best" content strategist actually entail? How do you rank them? Would anyone know? How would I know?

How is "the best" a worthy goal? WTF does it even mean?

"The best" is not a real thing. Not unless we all agree how we're measuring it (which never happens anyway). If I asked you which player in the NBA has scored the most points during regular season games, we'd know the answer: LeBron James (42,184). But if I switched my ask and said instead, "Who is the best scorer in NBA history?" ... now we'd have a passionate debate about how Michael Jordan and Wilt Chamberlain played far fewer games and averaged way more points, but also maybe Kobe Bryant was the best "pure scorer," but maybe also Kevin Durant has a claim to that too... and on and on we'd debate.

Who scored the most points? Easy. LeBron. Correct answer.

Who's the best scorer? Fuhgeddaboudit. You can't answer it correctly. But again, that won't stop us from trying.

It's so silly.

Being the "best" is something we're so sure matters, so proud to pursue. But it doesn't exist, and it may not matter if it did.

Something revealing happens whenever I ask audiences to shout out Disney films to answer my question. I say to them, "What's the BEST Disney movie?" But how do they hear it? How do they reply to it?

"This is MY FAVORITE."

That, my friend, is what really matters. That's how people make choices, and that's actually attainable.

What are your favorite things inside a field or job function? That's the kind of stuff you will relentlessly pursue and improve upon, which will pay dividends over time, perhaps even immediately. You don't need to find something that you and you alone are "the best" at doing. That doesn't exist. We can't decide it, and it wouldn't matter if we could. There is no objective best, so busy yourself with something else. Pursue what energizes you. Figure out what parts are your favorite, and lean into that. Hard.

Speaking externally, not internally, the notion of favoritism matters even more. When people make choices and pick things, they aren't being rational. They're emotional. They make subjective decisions, then rationalize what they did later. You might compete against the biggest competitors or creators in your space, and certainly, to claim your audience's finite attention, you're up against EVERYONE creating content today. But to compete in that world, you don't need to be the biggest or "the best." You need to be their favorite.

Be their personal, preferred pick for a specific purpose. There's nothing objectively correct about that.

Think of your favorite things in categories away from your work. Your favorite food or restaurant, your favorite animal or color, your favorite movie or holiday. These become parts of your identity. If I told you, "That's my favorite show," or, "That's my favorite city," I'm self-expressing. There's also nothing objectively "best" about those things. My favorite shirt is not objectively the best-made shirt that exists or even that I own, but it feels irreplaceable to me.

What if you felt that way to your audience? Irreplaceable.

By the way, my favorite team is the New York Knicks. If you know anything about sports, you know that for decades of my life, they were among the objectively worst picks. They've been a terrible organization which never wins anything (no championships since 1973), and famously, they've made all the wrong moves as an organization. But they've been my pick. They got my time, my attention, my money. Does that sound like rational decision-making to you? It's not. But it is human decision-making, and guess what your audience is made of.

* * *

Looking back, I can't help but laugh at my boss's advice. In fact, I laugh twice. Not only was it meaningless (that's my first laugh), it actually worked on me (that's my second laugh but the kind of laugh you laugh too loudly to distract from your own embarrassment, like you're saying "HAHA WE ARE LAUGHING HAHA I AM FINE"). In that moment all those years ago, I felt so certain that "the best" was not just a real thing but a worthy thing. Hell, there were times in my career where I felt it was the only thing.

But here's the thing: only by leaning into my favorite elements of the work did I do work others declared to be their favorite. I am not the best creator in the world or even in my space. I am not the best speaker or writer or storyteller or coach, not because I'm not great or successful at all those things, but because ... that doesn't exist. "The best" isn't a real thing.

I can't be the best. Neither can you. But you can be something better, something deeper, something that matters even more.

When people make choices, they play favorites. Are you one of them?

Don't be the best. Be their favorite.

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Jay Acunzo