Broaden or Deepen Your Expertise Pt. 1: How to Know Which Path to Choose

Are there really only two paths for full-time employees?

Years ago, I was desperate for a promotion. My then-boss advised me: You need to either deepen your current skill set or broaden it.

It was the best, most succinct career advice I’d ever received until that point because it changed the way I looked at my job, my team, and upward mobility in general.

For me, as a content marketer with occasional forays into social media management, email marketing, event marketing and PR, this meant I either needed to become a badass SEO, writer, editor, showrunner, and video producer. Or… I needed to get more paid marketing experience under my belt.

I was at a crossroads in my career. Did I want to eventually become a VP of Editorial/Content Marketing? Or did I want to become a Chief Marketing Officer?

Well, a CMO is more powerful and makes more money, right? Obviously, that’s the superior role. I ought to #LeanIn and do that! Be a #GirlBoss!

So broadening my skill set was the next obvious play. Cue: My first-generation immigrant parents urging, “Anak. You should get your MBA.” (At least to make up for the fact that I didn’t become a doctor.)

I wasn’t exactly keen on going into massive debt, but I had to improve my business acumen. I bought myself a paid subscription to Stratechery and made sure to never miss a new article from First Round Review, my proxies for business school. I took my role as a people manager seriously and made sure to read The Muse, and whatever HR/people-manager resources were available at work. I made my intentions clear to my boss, who helped set me up for ownership of new programs, and I saw myself as the CEO of each one. I’d scope out each project, run request for proposals (RFPs) with new vendors, launch kickoff meetings with stakeholders, delegate what I reasonably could to my direct reports, work proactively with cross-functional peers on what was coming down the pike, and I’d write weekly memos to my boss, distilling key wins and potential roadblocks. I was only a Manager, but I was operating on par with my colleagues who were seasoned Senior Managers and Directors. I was crushing it. For a while.

I had my first failure when my boss was on parental leave. My business unit had big news to announce and since I was the only person on my team who had at least some prior PR experience (and I was hungry for the opportunity), I was the lead on this press announcement.

I was stepping into shoes entirely too big for me. I was working at least two pay grades above my level and leading meetings with the GM of my business unit, our PR agency, the entire Legal department, the CMO, the COO, the two co-founders, and the CEO. I still remember sweating through my silk blouse in that first kickoff meeting. After months of sleepless nights, often starting my work day at 7am and then closing my laptop past midnight, we finally issued our press release and enjoyed our media wins.

Ultimately, it all went fine. But just fine. I had tons of back and forth with just about every team at the company. A couple almost rug-pulls, where the announcement was nearly scrapped.

I was just relieved that it was over. I knew it wasn’t perfect, that I wasn’t perfect. But surely, it was good enough? I was going to get a promotion any day now, right?

Wrong.

My boss came back from parental leave. Eventually she hit me with the feedback, “There were whispers about how you handled that project.”

Whispers?

“They said leadership could have been stronger.”

Well… yeah. Remember? I was working two pay grades above my level. I wasn’t misrepresenting myself, my experience or my title. All those executives… they knew I was just a Manager.

This is a less-mature me. I feel hot tears clouding my vision. I blink them back and clear my throat. I switch gears and find my best corporate words a la The Muse. “I’d love to turn this into a learning opportunity. Are you comfortable sharing what, specifically, I could have done better?”

I go back to my desk and slump over in my chair. I don’t remember what happens next. Most likely, I hopped on chat and bitched to one of my co-workers. Most likely, I went home that night and whined to my fiance. Almost certainly, I cried and complained about the cruel, unfair world. (Remember, less-mature me.)

What I didn’t do was stop. I hop back onto the hamster wheel and vow to get that promotion next time. It’s so close I can taste it. I just need one more win.

I’m on the CMO track. I’ve just got to give it like 7 more years of slugging it out like this. It’s the beginning of a years-long journey, and I tell myself there’s no other option but to forge ahead. Get over it and get back to work.

For another year, I don’t stop. I pick up new projects. Some, I knock out of the park, some, I don’t. Increasingly, I’m getting more resentful. Where the fuck is my promotion? And I finally get it. But at this point I’m numb.

Because I never stopped to ask myself, really ask myself: Do you even want this?

The truth was, I didn’t. I just didn’t really know it.

I didn’t like all those meetings. Even though I felt important.

I didn’t like all the people managey stuff. Even though I felt powerful.

I didn’t like all the office politics. Feeling like I had to strategically mete out favors. The hyper-vigilance at each “casual” coffee meeting with a peer. Having to pretend I liked our VP of Sales. Even though I came to watch “Game of Thrones” as a sport and found it to be the most helpful education in understanding corporate politics. (Yikes.)

I steamrolled over my own desires and pressured myself to climb the corporate ladder — never once stopping to consider the alternatives. I mean, if I was to make it in Silicon Valley, the only way up was, well, up. The C-level track.

~*~

A year or two later, my boss was on her way out. I was tired. Jaded. And pregnant. Incentives no longer aligned and futures no longer intertwined, the corporate niceties were gone and our walls were down.

We finally have our first honest conversation in years.

“Amanda, do you even want this?”

She sees me. Better than I see myself. No, I don’t. But where do I go from here?

“For now? Just have your baby. Go on maternity leave. Come back, phone it in for a few months while you get used to working again, and find a new job.”

The tears cloud my vision again, but this time I let them roll down my face. But where do I go? What do I do? More of *waves around vaguely* this?

“Have you ever thought about being a high-level IC [individual contributor]?”

I ask her to tell me more. She paints a vision of what it would look like to not have any direct reports. To focus only on the work itself — at a better, more sophisticated level. Such a role would offer more autonomy. Maybe even more fulfilling work. And definitely fewer meetings. (With this, I think back to an engineer I once met who said he declines every meeting put on his calendar. I gasped, “But what if you miss something important?” He shrugged, “Then someone will tell me, and I still get to have skipped the meeting.” It was brilliant and simple, and I envied his IC life.)

I feel a pang of regret for the past couple years. Oh, I was crushing it, alright. The “it” being my soul. I didn’t want to be managing shit and the influx of more shit. I wanted to be doing cool work and having fun. I probably should’ve found another job at some point too. I just didn’t want to admit that to myself because it sounded so… mediocre. And I was not a mediocre person. I work two pay grades above my level, remember?

I think I know what I want. Well. Sort of.

I’d still need to flounder around for several more months before finally going on maternity leave. I’d end up spending the next two, maybe even three years seriously soul-searching what I really wanted to do. Or actually, maybe I never stop soul-searching. I’m not sure anymore.

~*~

There are lots of career possibilities. But if you’re an employee at a company, I think you only have two general paths: broaden or deepen your expertise.

But then, there are also two more specific roads that fit into the above: people manager or individual contributor.

✍️ Next week, we’ll get into the tactics. We’ll explore the tradeoffs to all of these and how to forge down these paths.

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📽️ Virtual Event: 15-Minute Frameworks

It’s the perfect time of year to do a lookback, a look-ahead, and see what you might want to do differently or better. That’s one reason I’m really excited about 15-Minute Frameworks, a four-hour virtual event on December 18 hosted by my friends Jay Acunzo and Michael Barber.

For only $15, we get to watch succinct 15-minute talks where marketing leaders like Brendan Hufford, Sarah Stockdale, John Bonini, and the GOAT, Ann Handley, share their favorite marketing frameworks. It’s all recorded, too, so if you can’t join live, you’ll still get the education.

The other reason I’m excited about this is that all of the money will go to Devin Bramhall, a beloved force in the marketing community. Devin is a friend I’ve met this past year. In just one Zoom call, I felt her warmth radiating through my computer screen. She’s undergoing cancer treatment, and since she’s a freelance consultant and our U.S. healthcare system is trash… well, she needs our help.

So if you’re interested in helping, interested in attending the event itself, or both, you can donate or register here.

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🧉 Mulled Wine

As promised, a recipe without backstory.

You have a slow cooker, right? Get it. Anyway, this picture is ugly but it’s all I have.

Ingredients:

• 1 bottle dry red wine

• 1/4 cup brandy

• 2-3 tablespoons maple syrup

• 1/2 sliced orange

• 4 whole cloves

• 2 cinnamon sticks

Put all the ingredients in your slow cooker. Set on Low for 1 hour. (Don’t put it on high because you’ll boil away most of the alcohol.) When ready, change the setting to Warm.

This recipe is nice because it makes your whole house fragrant. Plus, it’s super easy for parties.