WTF am I doing with my life?

Revelations from a sterile conference room

I was sitting in a sterile, windowless conference room 45 minutes into a two-hour meeting. And the only thing running through my mind was “WTF am I doing with my life?”

I was a cog in the machine. While it would be incredibly easy for me to blame my employer for that, it wasn’t their fault - it was mine. I wasn’t taking any initiative. I wasn’t challenging anything. I wasn’t coming with recommendations or ideas.

I was simply going through the motions. And that was the moment I knew I needed something more from my career.

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Sponsor: HockeyStack

Your CEO just slacked you: "We have our board meeting in 2 days. Send me a slide with what's working + anything they need to know."

Did your palms get sweaty reading that?
Or is this an easy ask because you can easily get to this info already?

I'm neurotic about forecasting + tracking performance. I have reports upon reports and dashboards upon dashboards.

So when Emir over at HockeyStack asked me what my perfect dashboard would look like, I immediately started geeking out. And when they sent this dashboard mock-up back to me, I was in nerd heaven 🙌

Q1 just wrapped up. And it's also never too late to add some solid reports or views to your dashboard, so hopefully this provides some inspiration to any of you who are looking to level up your dashboarding game.

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Coasting

Early in my career, I coasted.

I was a BDR and I did enough to hit quota every month, but not much beyond that. I didn’t have much interest in the market we served. I understood our products well enough to be able to speak about them at a high level. But I wasn’t deeply invested in my career.

I grew up in Ohio, went to school in Ohio, and knew that as soon as I graduated from college, I wanted to be anywhere BUT Ohio. I wanted to be somewhere warm. Somewhere by a beach. Somewhere fun and different. Somewhere that I could figure out what “life” meant with all the new freedom that comes after finishing school.

I indexed heavily on the “fun” part for the first year after college and I don’t regret it in the slightest bit. Making new friends in a city 750+ miles from home. Playing soccer again for the love of the sport, not for the goals sought during my club + college days. Going straight to the beach after the work day wrapped up. Finding a new appreciation for reading now that I could choose what to read and learn about vs. it being prescribed as part of a curriculum.

In short, I was trying to figure myself out. My life went from a regimented schedule dictated by coursework + soccer to whatever I wanted it to be. Work was something to be done to pay the bills and allow me to do all of the above. It wasn’t a means to joy or fulfillment.

At least it wasn’t until that moment in the conference room.

Forward progress

For better or worse, one thing that’s been drilled into me from growing up playing competitive sports is that the only thing worse than losing is stagnation.

Not learning new skills. Not improving techniques. Not getting faster or stronger. Doing the same thing over and over and over, not getting better, but not getting worse. A kind of athletic purgatory I’d sit in while I watched teammates getting better, getting more playing time, accomplishing things I wish I could do.

And as I reflect back on that moment in the conference room, this mindset was the source of that voice asking me what I was doing with my life. It sat quietly in the background while I was adjusting to my new life. Like me, the novelty of everything kept it entertained. But after a few years, it was getting restless. It was craving the fulfillment that comes from making progress toward something. And not the easy kind of progress that comes from simply “showing up,” but the kind of progress that comes from intentionality + disciplined focus.

That was my wake-up call.

The apprenticeship

I had no idea what I wanted to do. I liked Charleston and knew I wanted to stay here, so my job options were limited. Our family had an advertising agency going 3 generations back, so from a young age I’d been surrounded by the marketing world. This led me to major in business management & marketing in college where the coursework came much easier to me than other subjects like accounting, economics, and statistics. From my early days as a BDR, I knew that while I could hit a quota regularly, the sales world looked like a hamster wheel to me, so I ruled out the sales route. Marketing seemed to come more naturally to me, so I decided to pursue that route.

My first official marketing job was as a “lead specialist,” AKA marketing grunt work. Lead entry. Manual lead routing. Data hygiene. Far from sexy, but it gave me a crash course in the operational side of the marketing <> sales world. From there, I gradually took on more responsibility in that realm of marketing ops, but knew it wasn’t quite *it* for me. And this is where I stumbled into what I think was far and away the single best thing I did for my career - becoming an apprentice.

One of the perks of working at an enterprise company is that we had every type of marketer. Product marketers. Event marketers. Demand marketers. Channel marketers. You can see where I’m going with this. So I reached out to a few of them to see if they’d be open to me shadowing them, letting me be a fly on the wall during their workday to understand what exactly it was that they did and if that was something I’d enjoy doing.

Serendipity also played a huge part in this. At the time, we were a global company serving 10+ industries and with over 40+ products, driving about $750M in annual revenue. And there was only ONE person running digital marketing for the entire company. When I say “digital marketing,” this literally meant every aspect of the online experience. The paid search strategy + execution for every industry and product served. The webpages. The display advertising. The SEO strategy + execution. ONE PERSON.

And this is where “right place, right time” came in for me. I was experiencing the shift towards the digital world, yet here I saw our company under-resourcing this area. *CLICK* as this insight dropped into my head. Here’s an area that I know will grow inside the company and with tons of uncharted territory as the field of digital marketing was still being defined. The athlete’s mindset I possessed was drooling over the opportunity to charge into this open space.

So I reached out to the Digital Marketing Manager. “Hey Matthew, would you be open to teaching me a little bit about what you do? It seems interesting and I’d love to learn more about it.”

A day later, I got a response: “Hey Sam, happy to chat. Grab 30 minutes on my calendar.”

Lesson 1: don’t be afraid to ask - most people are happy to help when prompted

Fast forward a couple of conversations and few weeks later and I was devouring everything I could about digital marketing. People + resources that Matthew recommended I check out. Printing out 50+ page content and playbooks from Hubspot that I’d highlight and mark up. I was a sponge.

I found a new gear at work where what used to take me 8 hours to complete (hello, Parkinson’s Law) now took me 4-5 hours, meaning that I was spending the remaining hours learning more about digital marketing. Around this time I had my annual review with my manager. We discussed how I was performing, where I could improve, how they could help, etc. During this time I brought up my career + what kind of opportunities existed in front of me. So she shared the common paths available - product marketing, event marketing, demand marketing, channel marketing, etc. - and what progression into them looked like.

Then I asked her about digital marketing. Told her about my more recent conversations with Matthew, what I’d been learning, and that it was an area of interest to me. So I asked, “As long as I continue to accomplish all of my work in this role, and if he agrees to it, would you be ok with me spending a few hours each day helping him out?”

The stars aligned - as long as my work didn’t slip she had no issue with it, and (to the surprise of no one reading this) Matthew had plenty of work he was willing to get help with. And so began my unpaid apprenticeship in digital marketing.

Lesson 2: take initiative in your career. Do the work + prove you can do it before asking to get paid for the work.

Over the following 6 months, I shadowed Matthew, helping him where he needed help, having him explain to me what he was doing and why he was doing it, going from the 30,000 foot view and diving down into the weeds with him as a strategist + practitioner.

Then he threw a curveball my way. He was offered a position at another company (a promotion), and was putting in his two-week notice. “Shit,” I thought to myself. There goes this path…

…or so I thought.

His manager, Amy, (and one of my all-time favorite humans) said that she needed to backfill him. That it would take time, and while she was doing that that she and I were the only people who knew what he did and how to do it. “Would you be willing to help me keep the ship afloat until we have his replacement?”

YESSSSSSSS. Over the following ~8 weeks, I was thrown into the deep end. I didn’t have Matthew to fall back on when I wasn’t sure how to do something. I had to figure it out on my own.

Lesson 3: figure-it-out-ability (S/O to Tory for the phrase) is one of the best traits someone can possess

As expected, Amy found a candidate, Cassie, for the digital marketing manager role. When Cassie came in and saw the sheer volume of work owned by a single person, one of the first things she asked after I brought her up to speed on everything that was in motion was if I could continue to help out.

After the transition of Matthew, me helping Amy keep things afloat, and this new request, a golden opportunity presented itself. Amy worked with my manager to help create a hybrid role as “Marketing Operations Specialist / Digital Marketing Associate” (good luck targeting that one with LinkedIn Ads 😜). In this role, I gained the unique opportunity to work with two different teams within our Marketing department, both ultimately leading towards increasing the number of sales opportunities.

Lesson 4: become indispensable by possessing unique skills/knowledge within an organization

Things were great over the following year. I learned a ton from Cassie. I was getting exposed to conversations higher up the ladder. I was getting tons of reps in across all of the digital marketing disciplines.

Then a second curveball was thrown.

Cassie got an offer from another company and took it.

“Here we go again…” I thought.

I can’t speak on Amy’s behalf, but I’m sure her inner dialogue was a bit more frustrated than mine. But what came next from her was entirely unexpected. I got the cryptic meeting invitation, “Quick Chat” that immediately induces anxiety for anyone who’s operated in an enterprise company (IYKYK), and prepared for the worst.

Instead, the opposite happened.

“Sam, would you be interested in taking over the digital marketing manager position?”

Holy sigh of relief. I couldn’t believe my ears when she said it. How could I possibly take this over? I don’t have the experience, the credentials, the skills + knowledge to own this.

“You’ve already been doing this for 18 months. I’ll be here to support you the whole time, but you’ve grown tremendously during this time and we know you’ll do great.”

Remember lesson 2 from earlier - do the work + prove you can do it before asking to get paid for the work? That just came full circle.

And this leads me to the final lesson.

Lesson 5: find a leader who believes in you and do everything you can to prove them right

Not every career path has an actual path laid before it. If you ever find yourself having that “what the hell am I doing with my life?” inner dialogue, that’s likely a signal to step back and assess why that’s popping up. And instead of feeling like you need to complete uproot what you’re doing and put yourself on a different track, don’t be scared to explore where a path doesn’t exist.

Follow what interests you
Go down the curiosity rabbitholes
Seek opportunities to learn, even if it means not getting paid
And ask for help along the way

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Book quote of the week

“The basic elements of this story are repeated in the lives of all of the great Masters in history: a youthful passion or predilection, a chance encounter that allows them to discover how to apply it, an apprenticeship in which they come alive with energy and focus. They excel by their ability to practice harder and move faster through the process, all of this stemming from the intensity of their desire to learn and from the deep connection they feel to their field of study. And at the core of this intensity of effort is in fact a quality that is genetic and inborn - not talent or brilliance, which is somethin that must be developed, but rather a deep and powerful inclination toward a particular subject.”
- Mastery, by Robert Greene

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No newsletter next weekend with it being the 4th of July holiday here in the US. See you all in two weeks!

- Sam