Must we always progress?

Musings on career progression, titles, and redefining progress

I was a serial climber in my career, at least I was until a year ago.

Perhaps it’s because I feel I have nowhere else to climb to in my design career. Of course there are many paths I could climb to: head of design of an entire company instead of a division, c-level of some kind, or founding designer of a startup. However, none of those would feel like progress to me.

Even typing this out feels like I’ve permanently closed the door on any future opportunities, my career is done and over, send me out to sea like a viking funeral. But, in truth, that’s just my past self kicking and screaming at the prospect of change.

My priorities for my career have fundamentally changed.

—

I started getting this feeling a while go. My position had changed, my team had grown, and I was coaching senior enough designers to start diving into the existential crisis questions like “How do I really grow my career?” In truth, this was my dream role, but I was going through the same existential crisis of wondering what’s next in my career. I wrote a piece called What’s after this? to essentially coach myself through it and came to the conclusion that there’s no one right path. There are multiple paths we can take, different obstacles to come up against, and the comfort of knowing we can change our paths at any time. I wrote this all and still didn’t follow my own advice.

I still felt there was only one path: climbing higher and higher. It was all I had known. For a decade+, I looked for whatever I could do to get to the next title jump. And when titles became murky (because tech is tech), I looked at the company itself: how big was it and where was it in its funding rounds?

But the more I climbed, the more I realised I didn’t belong. Not in a glass / lavender ceiling kind of way, which don’t get me wrong, I’ve had to deal with a fair share in my career. No, it was more in a “I don’t think I have any interest in this world” kind of way.

I would sit at dinners, bounce around networking events with no real knowledge of who is funding who, what’s just been released, and who’s talking on what podcast. I used to try to read TechCrunch and other industry news sites religiously in Seattle, but my eyes always glazed over. I never retained anything. I kept up a bit more in Singapore, but that’s only because it’s all my colleagues talked about. Then in Australia I would only keep up with what was shared with me.

It was maddening, I just could not retain the information nor muster the care to do so. I sometimes wondered if I was self-sabotaging by not diving head first into what I thought I should be doing. Given my position, shouldn’t I try to be on top of everything in tech, to care about what’s happening in the industry? And if I’m not, am I really a good leader?

The truth is I do care about things, just not tech. I care about how the world is changing, learning from the past to now. I care about how society is shifting through technology and connection. I care about how politics is happening between different countries and regions. I care about art and how it’s making sense of our selves and our world. I care about how we see humanity, whether that’s through profiles or fiction.

I want to understand both my inner and outer world, and how it all comes together in my work.

When I was climbing, I never lost sight of my interests, but it always had to be a means-to-an-end for the next role. Would I normally dive into the geopolitics of Southeast Asia in the 90s? Yes, but doubly so because it would help me understand something for my work. There was always a hidden motivator, I couldn’t just enjoy.

In truth, my obsession with titles and climbing was to showcase my self-worth to myself and the world. Look at me, I was the weird kid in my hometown, I found someway to be creative, whoops hated that but no worries, I taught myself and switched careers and look where I am now. I was performing for an audience of none.

The performance led me to rotating bouts of burnout. I needed to do something intellectually stimulated, I needed to stretch myself, and I needed to do it 5 years ago because look at how successful these other people are. So much of this was hidden from others, only my best friend and later my husband saw the spirals.

I think what pulled me out of this, what shifted my perspective was seeing my husband go through the same thing. After 15 years in his career in the Singapore Police Force, he left it all behind to join my adventure in Australia. I saw him go through what I was feeling, questioning everything about himself as he puzzled out who he was outside of his career. And there is nothing more heartbreaking than seeing your partner going through it with nothing you can do to alleviate it. Which then in turn made him feel worse.

Through that time, I really began wondering what am I doing all this for? For the next title? What did I even want?

It took two Ramadans to gain my clarity. During this time, the demons are locked away and what you have is just yourself, your own strengths and weaknesses. I’d sit with myself as I’d watch the sun rise and wait for everyone to wake up, wondering what I’d want to change about myself this time around.

I wanted to shift my self-worth. For it to be defined by how much I understand of the world, how I progress in my own skills, where I have my curiosity and how I pursue it, and ultimately, how that shapes who I am as a person.

I ultimately decided that any sort of output is optional. Knowledge outweighs titles.

—

Of course, this shift isn’t without consequences. We can have it all, but we can’t have it ALL, you know what I mean?

If I wanted to get to my next climb, if I wanted to be a startup founder or join the C-suite, I'd probably need to immerse myself fully in that tech world. That would mean keeping up with funding rounds, knowing who's launching what, playing the networking game. And there's nothing wrong with that. I truly admire the founders I meet at herhive and hearing their journey. The passion, the excitement, the rollercoasters they go through demand that kind of engagement.

But it couldn’t be me.

I want to be intellectually challenged, yes, but I also want time for my own pursuits. And that will mean saying no to things that my past self would have been clawing for. It is honestly a strange feeling. If tomorrow I was told I had to step down from my role and do something else, I think I would be okay with it. How weird! A year ago, I would have been spiralling. But at this point, I wouldn’t consider it to be stepping back, but rather, having space to step into something new.

It took quite some time to get here. And yes, this will cost me many opportunities.

The progress isn’t title or responsibilities.

The pursuit is progress.

✌️CJ

—

If this resonated with you, consider subscribing or sharing with others. It means the world to me, thank you!