From Mad Men to operations, my career path pushed me to answer tough questions

This is part of our "Who Is WhoCo?" series, which explores the unconventional career paths of our own team members.

On the one hand, I never had typical childhood aspirations of becoming an astronaut or something like that. I was always a fairly realistic kid. On the other hand, by the time I reached my first year at Penn State – countless hours of Mad Men under my belt, I was ready to throw myself into the world of advertising.

Of course, my motivations weren’t all rooted in the swarthy mythology of Don Draper. I’ve always been fascinated with how people made decisions – purchasing decisions, in particular. 

But all it took was a single internship to realize advertising wasn’t for me. 

To be clear, advertising is an incredibly exciting industry. More importantly, the environment and people in no way resembled the dysfunctional nature of Sterling Cooper. Still, there was something about the work I was doing and the mission didn’t excite me the way I expected. 

With the benefit of hindsight, I can see now I was learning in real-time what problems I did and did not like solving. I was taking my initial steps into learning what my superpowers were, even though I didn’t realize it at that moment. 

Though I struggled to put concrete words to it at the time, I still came to a realization many people experience in varying degrees, across different points in their careers…

“I see now that this job isn’t what I want”

On its surface – with the epically cool sheen of Hollywood – advertising was glorified. Once I got behind closed doors and learned how the sausage got made, however, it wasn’t as exciting for me.

From there, I made the leap into strategy consulting. 

Consulting, like advertising, isn’t for everyone. It’s a really hard profession. The hours are long, you’re tasked with a lot, and you’re given a lot of responsibility. 

And I loved it. When it’s a good fit, consulting is a fantastic way to gain a lot of exposure to big companies and critical problems early in your career. Was it a lot of pressure? Absolutely, but it was great. I was working with some of the most recognizable brands in the world, helping them work out some of their most pressing problems. 

Still, consulting didn’t quite satisfy me. 

You put so much of yourself into a project – sometimes working 100 hours per week – only to walk away after all of your deliverables have been completed. You don’t really get to follow along with the results. 

That’s when I realized I needed to be in a role where I could see something through beyond the completion of a project and know the work I was doing actually mattered. 

I could have spent my whole career in consulting, but this is where my path fundamentally shifted. I decided to take the risk and move on. It wasn’t easy. It was just such a different move. It was for less money and it was for a completely different industry. I was definitely going to be stepping out of my comfort zone.

I landed at an early-stage startup where we were building a research marketplace, connecting freelance researchers with consulting firms, ad agencies … you name it. Because of the dynamic nature of my role, I was able to have a lot of influence and shape the company. And then, the pandemic hit, and like many companies, things started to turn grim. To keep the company afloat, a large majority of the team was laid off.

That’s when I decided to take stock.

“What do I want to do, and where do I want to go next?”

I sat down and outlined the things I really wanted:

  • I wanted to work for a leadership team that was experienced and whom I admired. 
  • I wanted to work on a problem that excited me. (This is a big one, but we’ll come back to it later.)
  • I wanted to be in a collaborative role – because, up to that point, I was always a facilitating middle man, never really a part of a true team. 

I’m sure I’m not the only one who has ever searched – or is currently searching – for those specific things in their next role. 

There’s just one problem, though.

If you’ve ever looked for a job online (which I’m guessing is just about all of you), you know job boards don’t come with those specific filters. And even coming up with those “dream job” traits takes serious reflections. So, how the heck does one find companies that check those boxes?

On the flip side of that, I know hiring managers and recruiters struggle with hiring for specific, very intangible things – shared value systems, that a candidate fits exactly where your company is now and where it’s going, etc. I began exploring ways to solve this problem, investigating the market, and ideating solutions that could potentially evolve into a business of my own. 

Then, as luck would have it, while researching the market, I came across WhoCo. It was led by founders who were very experienced and had done it all. We shared a common thesis on the market, and (most of all) the company that was tackling a problem I desperately wanted to solve. Today, I’m the team’s operations manager.

What satisfies your internal and external career checklists?

In many ways, I’ve been quite lucky. Not everyone stumbles across their own WhoCo. However, these experiences have taught me that putting yourself on the right path for your career requires you to examine two sets of factors – internal and external.

  • Internal factors deal with your own self-discovery. What are your superpowers, what problems do you absolutely love solving, what do you enjoy doing, where do you find the most fulfillment, and where do you see your fulfillment waning?
  • External factors deal with how you determine career and company fit. What kind of company culture do you like, what balance do you need between life and work, how much money do you want to be making, how do you want to dress for work, and what kind of lifestyle do you want to lead?

How to develop your internal and external career checklists

Wouldn’t it be great if this were the moment where I unveiled some super-comprehensive checklist every single one of you could use to put you on the right career path in 30 minutes or less? 

If that’s what you were hoping for, I regret to inform you that nothing like that exists. There is no cookie-cutter checklist out there that will tell you, with little to no self-exploration, where you are supposed to go next and what you should be doing with your life.

You need to do the work. But the work can be a lot of fun if you give yourself over to the process. Fundamentally, your goal with these checklists is to probe deeply into your own work history to understand what intangibles you’re looking for in your next role.

For instance, going back to my own story, consulting didn’t work for me because, although it paid well and I was good at it, I hated that I was no longer involved with something I had poured myself into once the project was over.

Developing these checklists isn’t easy though

Where many struggle, myself included, is to unlock:

  • What superpowers you bring to the table 
  • What problems you are passionate about solving

Depending on where you are in your career, you may not know the answers to those questions because you haven’t been exposed to those situations yet. In short, you don’t know what you don’t know about yourself. 

My advice here is two-fold.

First, challenge yourself to be uncomfortable and do things that scare you. Don’t hold yourself back artificially due to preconceived notions you may have about what your path is supposed to look like. If you always play it safe, you’ll always stop just short of uncovering your true potential.

Second, I urge you to set aside hang-ups you have about job titles. As someone who is extremely goal-oriented, I get how important it is to have a defined path, as well as an idea of what steps you need to take to keep advancing forward in your career. 

Traditional job titles have made that easy. You start in a frontline position, become a manager, advance to director, VP, and so on. 

But these labels can lead you to say “yes” or “no” to roles through the lens of optics – or the story you want to tell the world about who you are and what you do. Meaning you can all too easily say “yes” to the wrong role that sounds good on paper and “no” to a great role just because of the label slapped on it. 

Of course, the discussion around job titles is a bit more nuanced than that. My point rather is to challenge you to think outside the normative boxes job titles unintentionally stuff us into.

If I could tell my young self one thing, it would be, “Buy Bitcoin”

I had an opportunity to do it when it was $200, and I didn’t do it. 

All jokes aside, if I could tell my young self a second thing, it would be this:

We all have insecurities when we’re young. There are moments in business where you need to move fast and forward, and to speak up means you’re the one slowing things down. But differing opinions lead to new ideas. 

Also, who wants to risk rejection early on in their career, right?

But that’s what I wish I knew when I was just starting out on my journey. I wish somebody wise had imparted it on me earlier in my career and told me, "Look, if you believe in something, speak your mind and stand by it."

This is something I still struggle with sometimes, but just like you, I’m still walking the path of my own journey. We’re all still learning and growing together.