This post expands on notes I shared with a mentee about navigating the job search.
A job search isn’t just about landing an offer. It’s about choosing where you’ll spend 8+ hours a day, every weekday — and what you’ll get in return. When you’re thinking about switching roles, focus on three things: what you’ll be doing, who you’ll become, and what you’ll get in return.
What matters?
Moving on, there are three key things that matter in each role:
- What are you going to be doing day-to-day?
- What are they going to pay you?
- What are your future prospects?
Most things can be batched into one of these categories. I factor WLB, commute/remote work into 1 and 2, personal growth and development into 3. For me, remote work is non-negotiable. I’ve done it for years and plan to keep it that way.
That said, I know how tough the market is right now. If you’re under financial stress, burned out, or just need to land something, then the only priority is meeting your needs. There’s no shame in that.
Everything I say below assumes a certain amount of privilege — that you have options. Once your needs are met, you can start optimizing for trajectory.
Example - the intern trade
For interns, the decision is simpler. Most just want a “real job in tech” doing meaningful work, learning how companies ship software, and gaining enough experience to get hired again.
Compensation is usually fixed. The real value is in what it unlocks: a return offer, a strong resume stamp, and real connections. I still run into people I interned with years ago (granted, I was basically a professional intern after six of them).
If you’re choosing between offers, prioritize great mentors, interesting domains, and companies with names that open doors — either through brand or network.
What I optimize for now
At this point in my career, I still care most about what I’ll be doing and who I’m doing it with. Compensation is a cutline. It has to clear the bar, but it’s not what makes the decision.
I care about my time. I don’t want to spend my days wading through bureaucracy, playing politics, or doing work that doesn’t stretch me. I want high-agency roles — ones that force me to build taste, intuition, and product sense.
That usually means what I find interesting (and will field from inbounds) are small, scrappy teams with more sphere of influence over the internet than they should have at their size; or high-growth orgs with strong technical cultures. Places where I can see how others work. Bonus points if I get to watch people outside of my function. I spend tons of time sharpening my skills in the areas that I work - I want a workplace that will show me how world-class designers and product managers think.
I want to see leaders in action. I want to understand customers. I want to learn about (product) growth. I want to learn to operate. I want to have fun.
Find the right org
I mostly agree with Jeff Atwood’s take:
“The people you choose to work with are the most accurate predictor of job satisfaction I’ve ever found.”
But I’ll add this: even great people can’t thrive in a broken org. A happy team in an unhealthy org doesn’t stay happy for long. The culture sours. Morale drops due to operational load, bureaucracy, unpaid tech debt, or layoffs. People leave.
A good org can uplift teammates that you get along with but may not feel “connected” to. But even the best teammates can’t fix bad management, unclear direction, or perverse incentives.
So ask questions. How are managers evaluated? Have there been recent reorgs? Did teams go from unmanageable size to healthy ones — or the other way around?
The path shapes you
Each time I take a new job, I try to think carefully about how it fits into the broader arc of my career — and my life. Most of my closest friends - who eventually became my neighbors, and will someday be the unofficial aunts and uncles of my kids - have some connection to Atlassian, the first company I worked at out of school.
My mentors span a few former employers.
One of my best friends works at Discord.
Every single job I’ve taken has shaped me either personally or professionally. When I’m going through the interview loop and I interview with engineers on the team or in adjacent teams, I ask myself:
“In the future, do I want to be like the people interviewing me?”
That question is one of my strongest filters. Stay somewhere long enough, and you’ll start to resemble the people around you, for better or worse. What does their career look like? What positions have they held? What have they built? What are they passionate about? Work backwards from there.
Let me give you a concrete example of how this played out for me.
When I was at (pre-Elon) Twitter wondering how the hell to get out of there, I thought hard about who I wanted to be. I told my then-manager I wanted to be a top-tier systems engineer, a container security expert, and someone who worked on large-scale compute. Unfortunately, Twitter wasn’t going to get me there.
I started thinking about where I’d seen other obsessive nerds doing cool work and Discord came to mind.
They’d been my dream company since grad school. I’d read their engineering blog and admired their culture from afar.
I reached out to someone on their security team, unsure if it would lead anywhere.
It turned out he was the hiring manager. And more importantly, the kind of leader I wanted to work for.
He hired me. And after I showed I could deliver, he and the team gave me room to grow.
With support, trust, and room to stretch, I failed spectacularly at a bunch of things, had a few outsized wins, and ultimately became the engineer I set out to be when I left Twitter.
TThat role changed more than just my skills. It shaped how I think about leadership, autonomy, and what “good” feels like at work.
It showed me what it’s like to work in a place that fits — where the team is strong, the culture clicks, and you leave work proud of what you built.
It was a place where work often felt like play.
After I left, I found myself looking back and thinking: Was I actually happier there?
Eventually, I decided to find out. So I went back.
And I am.
No matter what Blind will tell you, the TC chase isn’t everything.
Great jobs shape your future.
And for me, that all starts with one question:
Would the person I want to be work here?