The beginning of my career was marked by tumult, undiagnosed ambition, and lack of direction.

I am under no illusion that this phenomenon is unique to me; I am simply stating my reality.

For the first 22 years of my life, I assumed life was linear (despite the series of therapists who kept telling me otherwise !!!) and possessed an obsessive need to be the first/best/youngest/most impressive in every arena.*

I emerged from college with a very specific skillset I had little interest in using, a vague sense of cynicism toward the ~corporate ladder~, and zero exposure to any concept of “career development.”

As I stepped into the so-called real world, I spent many days ruefully daydreaming about what life could have been like if I had had the courage to step outside the narrow path of “should” I had drawn for myself arbitrarily.

I regretted not spending my college years experimenting and exploring, for putting up blinders and attempting to convince myself of passion that didn’t necessarily exist.

Because a year after graduating, I had left my job and returned to square one. I was 2,500 miles from home in the midst of an unprecedented pandemic with rent to pay, little direction, and even less (i.e. "no") health insurance.

the original upheaval

Leaving my job as a traffic engineer and attempting to break into the tech industry felt like stepping into a cramped room with no doors or windows, just a tiny screen displaying an image of a life I wanted to live. I knew it existed in concept, but I personally had no access.

Though deep (deep) down I figured I was capable and intelligent, I had very little confidence in my ability to communicate that capability and intelligence to others.*

No one in my community was part of this world I yearned for, so I sought out literally anyone who was willing to talk to me. Surely there was a way in, I simply had to find the path and unlock the door.

With each conversation, Youtube video, podcast, blog post, book, webinar, online course, etc. I consumed, I unlocked a small piece of the puzzle and I slowly began to construct an understanding of this fantasy world I craved.

(I think this is the first - and last - time the phrase “this fantasy world I craved” has ever referred to B2B SaaS. Significantly less kinky, I would presume, than most applications.)

When I eventually began my first tech job, though I was proud of myself for landing on my feet, there was a part of me that, at the ripe age of 24, already felt behind.

And because I was at a Series A start up with a boss who was exactly one month my senior, I was still very much flying by the seat of my pants.

the progression

Until this point, my academic and professional career had been dominated by diagrams and calculations; org charts and managerial tracks were not something I even knew existed. 

When my boss told me we would have weekly one-on-one meetings, my jaw dropped. Time dedicated to my growth and development?! Never had someone invested in me in this way.* I was locked in. My dreams were coming true.

Though I grew tremendously at that startup, the initial sheen of excitement eventually faded and when a new opportunity knocked, I left.

And ended up in a role that wasn’t a great fit. Bummer.

What had seemed like a lateral move with upward potential ended up, in practice, being a much slower growth environment, resulting in what felt like professional backsliding and a bit of a dead end.

Unfortunately, because it wasn’t egregious or unbearable (and it enabled me to progress in my extracurricular pursuits), it took me longer than I would have liked to figure this out.

But as I did, I became frustrated with myself for having become complacent and mediocre. That dream job I had initially worked so hard to achieve should have been a first step in an exciting and propulsive career. 

How had I allowed my momentum to stall?

I knew something had to change, so when a new opportunity arose, it was time to pivot again.

the opportunity. and the caveat.

I had never seriously considered working in product, but the more I learned, the more it made sense as my next move.

However, once I reviewed my official job offer, my ego got involved.

Both the title, Associate Product Manager, and the description felt entry-level, almost offensively below the intelligence and experience I thought I brought to the table.

Unable to help myself, I brought this up with my would-be manager as soon as I saw the offer. I argued that my experience was beyond the scope of the role and it felt like accepting it would be one more step backwards in a career that already felt like it was stalling. I proposed stripping the “Associate” designation from the title.

He was receptive and we had a great conversation, but the answer was no. This was the role that was available; I could take it or leave it. Seeing as the alternative was to remain a “technology evangelist,” if my concern was the prestige of my title, I didn’t exactly have anything better to fall back on.

My pride was in crisis. Since making the leap from traffic to tech, I've worked hard to climb through the ranks and build my career and, had I stayed at my former company, I would now be a director overseeing four teams in multiple countries.

But instead, it seems, I’m starting at the bottom. Again.

And the voices in my head that felt behind at age 24 are screaming about the idea of “associate” at 29.

the upside

As I continue to hopscotch around, I’m finally beginning to accept the nonlinear reality of life that all these therapists keep pitching. Rather than actually feeling like I’m back at square one, I’m able to recognize the value and breadth of my multi-faceted life experience.

Now that I’m several weeks into the role, feeling like I’m “above” my title has actually given me the confidence to take risks and speak up in ways I historically haven’t.

Rather than deferring to those in authority because I’m scared of being wrong, I’ve found myself making decisions and taking charge even when I don’t have all the information and speaking with authority on things where I’m not an expert.

It’s like this weird sense of reverse imposter syndrome: my annoyance and embarrassment at my place on the org chart has fueled me to do whatever it takes to move up it as quickly as I can.

And it does make me wonder: is this how men function in the world?* Confident enough to make decisions without being certain of every specific detail or potential outcome?

I kind of think so, because I've seen it in action. And it's unfortunate that I had to take a step down the ladder to begin to taste this reality.

Though a bit of an immediate bump to my ego, this move has helped me replace pride with agency and entitlement with resolve.

And because I showed my cards before I even took the job, my manager knows I’m hungry for responsibility and eager for promotion, and I’m no longer scared or ashamed of being honest about my ambition.

As I continue to navigate my increasingly nonlinear life, I would venture to guess that there are many detours, lane changes, and culs-de-sac to come. And maybe, had I learned that earlier, I would have been a better traffic engineer.