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#195 - The Unexamined Career

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Recently, someone who knows I help people navigate their career put me in touch with a long-time friend of his. It was a well-meaning but brief intro: "Jim, talk to Aki, he's good at this stuff! Aki, Jim needs to talk to you!".

But that was all we had to go on. I didn't know why I was meant to connect with Jim, and neither did he.
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So Jim and I dial into a hastily-arranged Zoom, and it is awkward, folks: we spend the first half of it just trying to puzzle out why we're there.

I learn that Jim has known our mutual friend since their university days. That he was an early, long-time software engineer at one of the biggest tech companies on the planet. That, like me, he's now based in Singapore.

Jim walks me through his background; I listen and reverse scroll his LinkedIn as he goes from university, to his first job, to the next.

It's all hunky dory, but 10 minutes in, I'm still asking myself, "Why am I here?"

Then Jim gets to the startup he joined five years ago -- and all became illuminated. 💡

To say the vibe shifted would be a massive understatement. It was more like a heavy pall descending on Jim's end, then positively oozing through the ether onto mine.

Fidgeting in his chair and running his hands through his hair, he broke it down: he'd found a startup, interviewed for a leadership role, got the job, and joined the company. But four months in, he was moved into a smaller role, and three weeks later, he left the company all together.

After the summary, Jim marched ahead, narrating the end of his CV to me. But he really didn't have to. It was clear as day now: Jim was stuck. Paralyzed by an experience he'd never come to terms with. A stint that had bruised his ego, and left him deathly afraid of making a bad bet on another company.

Worse, the angst I'd just seen during our casual conversation was showing up in formal interviews, preventing this talented, experienced, in-demand engineer from even landing an offer. 😔

The inner game of resilience

​Last week I wrote about career resilience: the need -- and the opportunity -- to build things like relationships, reputation, community, proof of work, and stories before we need them.

These are the external muscles we hone to better absorb and react to change. To ensure we're in motion before it hits. To build career security in the absence, today, of job security.

But there's also an internal component to resilience. Muscles like awareness, pattern recognition, and judgment. But the rub is that building these muscles is a fundamentally backward-looking exercise.

Knowing you've stumbled but will will thrive again demands looking at the past. And that's where work fails us.

The problem with "work"

By default, we're relentlessly forward-facing at work: we solve problems, we hit goals, then we go out and do it again next quarter.

Resumes are historical documents, but they're focused on achievement and numbers. We're taught to structure them, and our interviews, as "problems, actions, and results". It's performative, not reflective.

The cost of moving on

It isn’t just the forward-facing culture of work that stops us; there’s also a deeper, more personal hurdle: reflection is uncomfortable. Thinking about stumbles means confronting a bad call or a signal we ignored. It’s easier to just keep going.

But we’re just as guilty with our wins. When a promotion happens or a project ships, we don't pause to ask: was it timing? The team? My manager? Moving on without knowing what was at play means we don't fully understand our success.
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The upshot is we don't internalize our career past; the lows or the highs.

This is a problem though in a moment of accelerating change. Because the judgment, awareness, coherence, and pattern matching we lose out on by not reflecting are exactly what we need to steer our course through a wobbly, uncertain career.

Author Shane Parrish puts it well here:

We can’t "redirect" with momentum or figure out where to head next though if we haven't understood the walls we've hit, or the tailwinds we've caught.

Not knowing why we stumbled means we're more likely to trip again. Not knowing why we won makes it harder to repeat the triumph. Navigating with intent demands we see cause and effect.

The $75 billion mistake data point

I've shared before that years ago, while working for a venture capital firm, I had offers from two of our portfolio companies: Dropbox and Airbnb. Both were tiny. I sat in Reid Hoffman's office and walked through my options. He told me point blank that Airbnb would be the bigger company.

Then I called Airbnb's CEO, thanked him, and turned him down to join Dropbox.

Dropbox is now an $5 billion company. Airbnb is worth $80 billion. Reid was 16X right.

Worse, the culture, the role, and the timing were all off at Dropbox. And for a long time, that was the story I told myself: mistake. Bad bet. Move on, Aki.

But when I started writing TalentStories -- doing the kind of reflection I'm talking about here -- I didn't revisit Dropbox to postmortem what went wrong. I revisited to understand my career as a whole.

I stopped seeing Dropbox as just a mistake I'd made, and started seeing it as one chapter in a much larger story. A decision that led, directly and unambiguously, to Singapore and to Uber, which were incredible experiences.

I can trace the line now. And I didn't rewrite the story to make myself feel better. I just looked at it long enough to see what was actually there.

That's the upside of reflection: it doesn't change what happened, it let's us see what happened with more clarity. And when you can see a thread connecting a stumble to a strength, you fear the next stumble less.

Psychologist Adam Grant explains:

Jim revisited

Jim didn't need a better resume. He didn't need a pep talk. He needed to do what he hadn't: sit with the startup experience, approach it with curiosity, and ask what it actually taught him and where it actually led.

Because as long as that experience sits unprocessed, it owns him. It shows up in interviews as anxiety; in coffee meetings as doubt.

I've used this newsletter to look backward, and pick apart my career, warts and all. But I've come to appreciate it not as "journaling", but as a tool for understanding myself, my stories, and my judgment. For finding grace in my misses, and calibrating my hits.

But you don't need a newsletter. You just need to start with an experience you've had. Pick a career moment you've tagged as "a mistake", or "a win". Start there, look back, and ask what it actually gave you.

Thanks for reading and exploring with me -- and have a great end of the week! 🙏

Aki

P.S. If you're in Singapore: we're doing a live TalentStories community event on Thursday, April 23!

​Swarnima Korde is a long-time friend, community member, and guest author of TalentStories issue #96. She now leads talent acquisition in Asia for Mistral, a leading AI research lab.

We're calling it "What the $?#!&! Is Going On Out There?" and it's just what it sounds like: a candid conversation about what's happening in the job market, what top AI companies look for, and how to play a smarter career game right now.

After the chat, we'll break into small groups to connect, and share what we're seeing and learning. (Based on the RSVP's, there will be some serious knowledge dropped in these groups!)

The event is designed for job hunters and job huggers; whether you're actively looking, or are just looking to build that resilience. 💪

Doors will open at 6 for the TalentStories community, and the main event starts at 7. We have seats right now and TalentStories readers get first dibs. Reply here or ping me if you want to join!