Lessons from a career in technology - Part Three

Chart your own career path

I wanna be like you-hu-hu…

In the Disney animated feature, "The Jungle Book", King Louis aspires to become human.

It's tempting to idolize someone you admire and attempt to become like them but this is a path to disappointment. Everyone's career path is unique. In this article, I'll draw from my experiences in learning how to chart my own career path.

My Idols

The company sent an announcement to the engineering team requesting they convene at a gathering space in the office. This had never happened before, so we knew it must be a big deal.

We quickly found out that the reason for the gathering was to celebrate the promotion of a senior engineer to a newly-created top level. Until then, the company’s technical career ladder had no rung equivalent to a senior vice president in the management ladder. As the company grew, the founding engineers had risen to the top of the technical career ladder and had no remaining rungs to climb. So, the company created a new level, and this engineer was the first to be given the title in the company’s east coast division. The announcement had the feeling of a coronation. They might as well have crowned him. I was in awe.

This engineer was brilliant and accomplished. He brought deep analysis and clear insights to every technical decision, and the company depended on him for his wisdom and valuable perspective. I aspired to be just like him.

I was at an early stage of my career as a software engineer (“Member of Technical Staff II”), so this new level seemed impossibly out of reach.? I read the job description and it was daunting. Among many seemingly impossible criteria, it required you to become a respected industry luminary. I had no idea how you’d get there, but I treated it as a North Star for my career and decided to try to become like my idol.

Yet, as he grew evermore respected and influential, my progress paled in comparison. Every time I made a step closer to him, he leapt ever further away. I wasn’t catching up. An impartial observer might have wondered why I wasn’t satisfied by my progress, but all I saw was my benchmark disappearing into the horizon. It was demoralizing.

A few years later, I’d reached the rung below the top level. My manager at the time encouraged me to apply for promotion to the top level, telling me that she could make the argument that I was worthy. I told her the idea was preposterous. In my eyes, I wasn’t as accomplished or respected as my idol. I had imposter syndrome. I was afraid of being found wanting and being laughed out of court. I didn’t apply and I gave up the idea of ever becoming like my idol.

I eventually ended up working in the company’s advanced research labs where I joined a team developing innovative new technology.? I was surrounded by brilliant engineers like my idol. It seemed I was the only one in the entire organization who didn’t have a PhD (I wasn’t). This time, I cast aside imposter thoughts because I was thoroughly enjoying the intellectual challenge of keeping up with the smart people I was working alongside. I relished being challenged in a way I hadn’t been since studying for my computer science degree.?

Around this time, I found a new idol to worship – the company’s Chief Technology Officer. I looked forward to his all-hands events where he’d share his technology vision. The ideas he talked about sounded like science fiction. His vision resonated strongly with me as an impatient technologist; I desperately wanted to create the sci-fi future he was talking about right now. Over the time I worked in “the labs” I was privileged to see some of his vision come to light.?I was inspired by him.

The CTO was a passionate technologist. Yet he was also soft spoken and humble, qualities that I shared. I could see myself becoming a CTO like him. I made the mistake, however, of assuming that the qualities he had were associated with the title, not the person. I started chasing the role of CTO.?

To my dismay, most of the CTOs I encountered weren’t anything like my new idol. They weren’t visionaries but were much more focused on the operational aspects of technology in an enterprise. That’s a key role, but not one aspired to. I couldn’t see any course to becoming like the CTO I admired. His career journey was nothing like mine and there was simply no paved path to follow. It felt all too familiar; another person I idolized but would never become.

Much ado about idols

I shared these experiences from my career to highlight the risks of trying to become someone else. As the Wilde quote correctly pointed out, you need to "be yourself".?

The mistake I made was to imagine that with the right steps I could become exactly like someone else. Just like the song, “Seen and Not Seen” by The Talking Heads:

He would see faces in movies, on TV, in magazines, and in books

He thought that some of these faces might be right for him

And that through the years, by keeping an ideal facial structure fixed in his mind

Or somewhere in the back of his mind

That he might, by force of will, cause his face to approach those of his ideal

You are unique. You might start your career with the same degree as your fellow graduates, but you bring “you” to your career. You have qualities that set you apart from others. Over your career you’ll gain unique experiences and skills that further differentiate you. If you worship an idol, you’re setting yourself up for failure because you can’t possibly have the exact same career journey. A career journey is made up of a series of serendipitous events that open new doors and close others. It is uniquely yours.

So, is it a bad idea to have a career idol?

An idol can inspire you to strive to reach distant goals. Without something to reach for your career will be on autopilot, subject to external factors that can lead to new opportunities or conversely hinder your progress. By passively riding your career you risk being “typecast” into a box made for you by others, like an actor who always plays the same role.

Use your idol not as someone to clone, but as a source of attributes you’d like to possess in the future. Think about the things that set them apart from others. Here are some to consider:

Seniority: as you gain experience in a company that is committed to career growth, you’ll gain seniority. You might be anxious to run up the career ladder and skip the hard work and dedication it takes to grow your skills and experience, but this process can’t be rushed. It takes what it takes. Look out for being taken for granted, however. If your career growth is blocked in an organization or by a deadbeat manager, then you’ll need to move on to grow. It’s sometimes true that the best way to get ahead is to get out.

Vision: everyone has an opinion about the future and what is likely to transpire. The world is continually changing due to advances in science, technology, culture, society, and more factors. True visionaries can paint a picture of the future that is believable and inspiring. This quality is present in most startup founders. They can imagine a future state and get others, especially investors, to see and believe in it. To be a successful visionary, you need to not only have vision, but you must be able to successfully pitch it. That requires exceptional interpersonal skills. I’ve met many software engineers who had great ideas but were afraid to stand up and talk about them. I felt the same way earlier in my career but like any skill you only get better by practicing. So, take a leap of faith and start doing just that. And you don’t need to be a startup founder to need great pitching skills. You’ll also need them to pitch an idea inside an organization. Guess what? If your internal pitch still falls on deaf ears, perhaps it’s time to move on pitch it elsewhere.

Respect: this is gained through your actions over time. Just as with seniority, there are no shortcuts to gaining respect. You might have already experienced this when you changed jobs. You might have been a highly respected employee in the company you just left only to find that you have no earned respect at your new company. I’ve experienced this every time I’ve changed companies. Over time and with practice you’ll get good at building respect.?

Respect can have many facets. It might be that people respect you for your technical skills or your vision. Personality can also be a factor. The way you treat people matters. If you’re open and honest, you’ll be seen as trustworthy, and people will be more likely to listen to you. Be careful though, respect is fragile: one bad move can rob you of hard-earned respect. Once lost it’s very hard to regain.

Remember that “industry luminary” characteristic I mentioned? Guess how you get that level of visibility and respect? You do it by communicating in industry forums, speaking at conferences, contributing to industry groups, posting on LinkedIn and gaining followers who are interested in what you have to say. If you’ve got something meaningful to say, say it! That seemed impossibly out of reach when I was looking at that top rung job description.

The career rear view mirror

When I was asked to give a talk about my career in technology, I drew a timeline of my career. It was hardly a linear or predictable path!

I noticed two things about my career progression.?

First, it often seemed like some external force was opening doors for me. I’d find myself wondering, and sometimes asking, “why did you hire me?”, as if they’d made some mistake. I believe that serendipity is a factor in career paths. You happened to be in the right place at the right time with the right people when a new door opened and your career advanced. Many famous people talk about “getting a lucky break”. That’s true of any career in my opinion.

Second, my career journey was an unlikely one. I couldn’t in my wildest dreams have imagined becoming a trusted advisor to the CIO of The Walt Disney Company. And if I’d seen someone in that role, I would have dismissed it as an impossible future for me. Yet I got there, not by trying to be “like you-hu-hu”, but navigating the twists and turns of a career that’s been uniquely mine.

Don’t discount an impossible future. Allow yourself to dream; you might be surprised where you end up. You too might become an inspiration to others!