The obvious path

My passions formed early. 

I’d been a math and science geek from a young age, obsessed with transformers (electrical, not Decepticon), storm drains, and the night sky. I have distinct memories of my parents forcing me to stop spending my Saturdays doing math problems for fun and instead go outside to play with my friends. They insisted at the time they were doing me a favor, and they were right. I was 6 years old.

Throughout school I focused my energy almost exclusively on math and science classes, and showed a disinterest if not active disdain for coursework that led me astray. During my senior year I was president of the science club, took extra math classes for enjoyment, and was adamant that I would become an astrophysicist. I was 18.

In college I diverged from physics but still ended up with a mechanical engineering degree. While I didn’t exactly put my degree to use during the year I spent in Las Vegas as a pro gambler/poker player, I eventually found a job in Los Angeles as an aerospace engineer working on control systems for private and military aircraft. What I had been passionate about as a child had blossomed into a career I could be proud of. I was 23.

The thing was, I hated engineering. What on paper was a complex and exciting career, was in practice reduced to countless hours spent in a dingy cube analyzing Excel data and writing thousands of pages of test reports for the FAA (that is, when the sheer volume of data or words wasn’t crashing my crappy computer). By the time my two-year anniversary came into focus I was so miserable that I was on the cusp of moving back to Vegas to resume playing poker full time, at the cost of living near my friends and family, something I was loathe to do.

The detour 

I obviously can’t ask them directly, but I can say with 98% confidence that my 6, 18, and 23 year old selves would’ve all considered a career in sales to be a personal failure, if not career suicide. Even as a young professional, I couldn’t imagine the thought of pursuing something not tied to a passion that, like science, had been in place since childhood. Ironically, it was a feeling of failure, powered largely by the misery I felt in a career choice that was at least passion-adjacent, that opened the door and eventually drove me into the arms of something I had once looked upon with derision. 

It happened by chance. A few months before my work anniversary I had reconnected through social media with an ex-gf from college, and was surprised to hear that she was living on the other side of the country and working as an associate in Cisco’s sales training program. 

I wasn’t surprised at her choice. She was smart and gregarious – the latter being what I assumed was required in sales and a major reason why, as an introvert, I never considered it as a career. And yet, in the midst of up a conversation where I referred to my morning bathroom break as the best part of my work day, she laughed (awkwardly, and understandably) and proceeded to share with me two things that radically changed the direction of my life and career: 1) Cisco was looking for technically-minded people to join next year’s sales training program and 2) she thought I’d be a great fit.

Thing was, the application period had opened months ago and was closing shortly – if I was interested, I had only three days left to apply. Ironically that shortened time horizon was exactly what I needed, as it gave me little room to second guess my decision. 

I spent the next few evenings updating my resume and drafting my application, and submitted the application with one day to spare. Within weeks I was offered an interview, and shortly after the interview – a job. In spite of what my 6, 18, or 23 year-old self might have said, I opted for the uncertain path.

Fast forward 13 years, and what I learned in that training program has led to a successful career spanning five companies across four states. I’ve made some incredible friendships that led countless hilarious stories (that as my favor back to my parents, I won’t repeat here), and have built a knowledge base and skillset that I use nearly every day and that continues to positively influence my personal and professional lives and those of my friends and family.

The sweet spot

We’ve been told for years to adopt a low-fat diet, yet obesity and obesity-related diseases continue a precipitous climb. We’ve been told that love is all that matters in our relationships, yet divorce rates still hover around 50%. We’ve been told to follow our passion to achieve success, yet more of us than ever are unhappy with our careers. And when we fail to achieve our fitness, relationship, or career goals, we’re told that we simply haven’t tried hard enough. 

Perhaps the problem isn’t that we’re not doing enough, it’s that we’re doing the wrong things. 

In a career context, passion is an important but insufficient barometer by which to choose your career moves. Look, I love baseball. I attend at least a dozen games each season, travel to spring training every year, and regularly sit through games on TV (a fact my wife still can’t wrap her head around). But no matter my passion or love for the game, I know that I’ll never become a major league ballplayer. Were I to evaluate my career based on whether or not I became a baseball player, I’d always feel like a failure.

Instead of thinking of and evaluating our career along a single axis, we should be doing so in three dimensions, with the ideal career located where each is maximized (i.e. the center of a three-circle Venn diagram). Friend and entrepreneur Sachin Rehki describes this in nice detail here, and can summarize as:

Passion – what we’re interested in

Skill – what we’re good at

Opportunity – what people need enough to pay for

“What am I passionate about?” is the wrong question to guide your career decisions. Instead, you should ask “What am I interested in that I’m also good at, and that is important enough that people will pay me for it.” 

Bringing this full circle(s)

Most people think of career progression as a series of promotions that ultimately end in retirement and death – this is a very limited worldview. There’s a better way to think about career progression, and one that is much more likely to lead to a long and fulfilling life and career: 

Career progression (n) – A series of moves that successively improves the fit of your career along each of the dimensions of passion, skill, and opportunity. 

In a perfect world, each career step would carry with it an improvement across all three dimensions. In practice, every job will require tradeoffs, and you’ll need to decide which trade offs work for you. To evaluate those trade offs, it’s helpful to consider two factors: 1) the current impact of each dimension on your life satisfaction, and 2) the future potential that each job offers across each dimension.

  1. You shouldn’t discount the impact of the non-passion dimensions on your career satisfaction. A new job you’re good at and that pays well may be more than enough to compensate for a lack of passion, especially if you’re early in career or if your old job was lacking significantly in one or more dimensions. For me, sales fit this bill perfectly. When I started my sales career I didn’t have a passion for it, but it paid well and I was very good at it. Had I equated my satisfaction solely with my passion, I may have never made the move.
  2. When evaluating a career move the future potential of that move is as important, if not moreso, as the present state. This is especially if you’re taking a significant hit on one or more dimensions.  While I wasn’t passionate about engineering, and sales was even less interesting (at least initially), I knew that sales could could future doors at virtually any company. That belief paid dividends when, about a year after leaving Cisco I landed a job leading business development at an education startup; a role I absolutely loved and that led to a number of other incredible opportunities.

Hope you enjoyed this week’s newsletter. As always, I welcome any questions, feedback, or ideas for future topics. 

Until next time,

Greg