Mastering the Career Obstacle Course

The other day, I was catching up with Charles, a family friend who I’ve known since I was 10. He had recently been made a partner at his company and I sent him a message to congratulate him. His response literally changed my whole view on individual career progression:

I really followed my passion and I was micro ambitious. I focused intently on what was in front of me every day. What was served up so I could lobby it back and wait to see what came next.

I think when one begins searching too hard for something, they can get easily lost. Further, I think when one puts too much emphasis on any one thing, it eludes them.

Before, I always saw one’s career path being similar to a heat seeking missile – see the objective, focus on it, and shoot towards it at the speed of light. It turns out that career progression is actually like an obstacle course. Here are the stages:

The Glass Wall

The glass wall is interesting because it represents that moment on the job where you know exactly what you have to do, you can see what’s on the other side, but you have to run through a literal wall to get to the other side. This manifests itself in a project or task that you know will get you to the next phase of your career, but it requires a lot of time, a lot of work, or both. This is purely a test of your endurance and bravery because you can’t outsmart the glass wall. You simply have to “power through” and run straight through it – pedal to the metal.

The Puzzle

The puzzle is a tactical person’s worst nightmare. This is where my heat seeking missile approach to progression would die. Imagine, if you will, that there is a quadruple reinforced steel door. No matter how many protein shakes you drink, you will not break through it. The only way to get through the door is to solve a puzzle that will unlock it.

A career puzzle presents itself as a problem that has an unclear or ambiguous solution. You can’t just start trying to work your way out of it; you have to step back, think about what you’re facing, and define your problem. Once that happens, you can take the steps to figure out a solution with a plan. Only after that, can you execute. While it’s the most frustrating career obstacle, it’s also the most rewarding because when you face a similar puzzle later on, you’ll easily be able to solve it this time, akin to a Rubik’s cube. It’s hard to solve the first time, but each time you solve it, it gets a little bit easier.

The Leap of…

Everyone has had to take a leap at some point, both in life and in their careers. In your career, this leap manifests itself in two ways – a leap of faith and a calculated leap. The leap of faith is scary because A. you don’t know what’s going to happen and B. “oh my gosh, am I insane?” The leap of faith has no metrics around it and no precedence. It literally involves you seeing your final objective in the distance, taking whatever sliver of prior knowledge you have, and just going for it. It could fail, it could not, but you still have to take that leap sometimes because it’s better than being frustrated or unfulfilled in life.

The calculated leap still has uncertainty, but is similar to how Indiana Jones uses his whip to swing over the unknown pit. The pit is still unknown, but you have help. In your career, this manifests itself as someone with more power, influence, or social capital reaching out to you with a better opportunity. Is it risky to leave your current situation? Perhaps. But when you have someone you trust and respect on the other side giving you the green light, that’s the proverbial “whip” that will swing you across the unknown chasm.

To paraphrase the wisdom Charles imparted to me some time back, in your career, especially when it comes to a goal that you have, you first have to visualize your “finish line”. That’s your long term goal. But along the way you will have these “career obstacles” that you have to get through. To still achieve your goal, you can’t focus solely on the goal and forget the obstacles, but you also can’t sit and focus on any one obstacle for too long. Run your race, think things through, and be decisive. If you do that, I guarantee that you’ll be dominating your career obstacle course in no time.

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