The Worst Career Advice I've Ever Received: "Be the Best"

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What's the worst advice you've ever received? Can you recall? Go ahead, I'll wait. (I literally can't move forward until you scan your eyes further down, so...)

Seriously, what's the absolute worst advice you've ever received? 


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When I was 27, I was put in charge of a content team of about 9 people at a high-growth, well-known tech company, and for the first time ever, I found myself in a purely managerial role. Unlike past leadership positions at past tech companies, where I was able to make stuff AND manage, leading a team of 9 at a rapidly scaling startup required that I ditch my beloved maker schedule (big blocks of uninterrupted time for deep work) and assume a manager schedule (30- or 60-minute blocks, mainly taken up by meetings back to back to back to back to blahhhhhhhhh).

Can I be honest? Sometimes I feel guilty about hating that experience. Everything about the job was supposed to be wonderful. The team was swell. The brand was sterling. The influence of our content around the industry was all that and a bag of clicks. The perks, the power, the pay -- I was supposed to love it. 

But I. Was. Miserable.

One day, I decided to share that fact with my boss, a director who'd been at the company for years and who, we all knew, was being groomed to eventually lead the entire department. 

"I don't feel like I'm being fully utilized," I told him. "I'm not doing my best work."

"Yep. I agree," he told me. Oh. Um. Thanks? (Turns out, he was NOT the best of bosses. That tends to happen when you're continually gazing upward in the org chart as a manager. You forget that the way to climb above is to better serve those below.)

I started clicking my pen nervously. See, the noise can distract a boss from his erstwhile attempt to fire you. Or so I'm told.

"I feel like I'm caught between two roles," I told him. "I'm in this manager position where I'm supposed to be a content strategist, but my love is to create."

"Well," said my boss, now placated by my magic pen, "you have to choose. Given where this industry is at, you could probably be the best strategist. You probably won't be the best creator. So, solving for enterprise value is 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: Shut up and go do your job as assigned. 

Here's the worst part: I thought he was right at the time. I believed he was. I was one of very few people in my position in the entire industry, and at a young age too. Whereas most content teams were one, two, maybe three people, I worked with NINE -- and we were hiring more. It felt like the world was my oyster, and my boss had instructed me to crack it open, toss out the pearl, and cram in some tips-and-tricks blog posts that ranked higher on search.

Blah. Did I say blah already? I don't care: Blah.

Looking back, I can't help but laugh at his advice, because what the hell does "the best" even mean in this line of work? That's so subjective. That's a fool's goal, I think. We don't keep stats to measure ourselves against others in our industry (and don't get me started on social followers).

LeBron James can aim to be the best. Maybe he measures that on most all-star appearances, or championships, or playoff scoring, or hell, merely the public narrative around a very public career declaring him "the best." But last I checked, global media outlets aren't publishing weekly rankings, opinion columns, and talking head TV shows to decide whether or not we're the best.

Be the best? Nuh uh. No thanks. Not a chance. Not a real thing!

How about, be the most fulfilled by the work? What about, find something that drives you ceaselessly forward, towards constant improvement, and learning, and joy, and the chance to bring your full self to your work? 

Or what about this:

Go on a quest.

That's how I frame this work we do: like a quest. It's an ongoing, never-ending exploration of just how deep this well goes, or just how dense this jungle is, or just how high this mountain climbs, or just ... uh ... how tasty ... the pasta ... is?

MY POINT ... is that I am hungry. For pasta, yes, of course, I'm Italian, BUT ALSO for the journey to understand and improve and create. Turns out there is no finish line in all that. There's no finally reaching the status of "the best." There's no "winning." There's only constant improvement, constant motion forward. That's all any career is. As my friend, the author and speaker Andrew Davis, likes to say: We go on quests.

So today, I'm excited to invite you to join me on my next quest, unfolding throughout 2019 and maybe beyond, via my organization, Marketing Showrunners.

Together, we're fighting one enemy in the workplace (Shortcut Culture -- ugh), and we're striving to master one thing (creating consistently great work: original, resonant, and beloved by both us and them).

My hypothesis right now? The key is to understand how to master the art of reinvention, rather than obsess over Random Acts of Creativity -- all those shortcuts and short-term approaches the working world lauds to make the numbers go higher, faster, today. Consistently great work consistently changes in little ways, all the time. Thus, if we want to be innovative or creative over time, we need to master the art of reinvention. Marketing Showrunners exists to advance the craft of marketers making shows to build passionate audiences, and I can think of no better place than the MSR newsletter to explore this big, complex topic. Shows are, after all, a practice in consistency and little reinventions over time.

So why is this a "quest" anyway? Well, I know I have one of those careers where I'm supposed to have answers. The truth is, I have a ton of questions, and I can't wait to pursue them to see where they take me -- where they take us. My role in this working world isn't to dole out answers. I've written way too much already about the problem with experts and gurus and false "secrets to success." Instead, my work packages and presents what I've found, not what I "know." To quote Anthony Bourdain for the umpteenth time to you, this time via one of his tattoos: "I am certain of nothing." 

Creativity isn't a final destination. It's a never-ending quest. In reality, the choice presented by my old boss was an impossible one to make at all, because the outcome (being the best) doesn't exist.

What's the worst advice you've ever received? Can you recall? I was told to pick a job where I could strive towards something that doesn't exist. But this quest? It's very much real, and very much launching right now.

Starting today, you and I can let others obsess over the hacks, cheats, "secrets," and shortcuts. Starting today, we can focus all of our time on resonance, not empty reach. We can choose to think longer term, to build projects and companies that are unassailable and beloved. Let others profess to have "the answers." We have questions. And that's why this work is worth doing.

Screw being the best. I love the quest.

Posted on January 9, 2019 .