The explore/exploit guide to your first tech job

A YouTube viewer reached out to me the other day after watching one of my videos. He’d just started at a big tech company and wanted to know: How do you navigate the fog? How do you figure out what to focus on? What are things to avoid?

I’ve felt that fog three times—at Sun Microsystems, Oracle, and AWS. And after 27 years and countless conversations with mentees, I think there are three phases that help cut through it.

Here’s the video I made on that, followed by some thoughts on why exploration might be more valuable than any career plan.

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The three phases

Starting a new job can be seen as going through three phases:

Phase 1: Learn the terrain. During your first months, you have permission to not know things. Treat it as a gift! Learn the technology, the culture, the unwritten rules. And remember: you have fresh eyes. You can see things that people who’ve been there for years have stopped noticing.

Phase 2: Build your web. Everybody tells you to “network”. As an introvert, I’m not good at running around, making as many connections I can. And I believe this is wrong, even if you’re an extrovert. Instead, build few, but deep relationships with people whose work you genuinely respect. Research them first, then reach out with specific questions. And: share what you learn, and give back to the knowledge pool. You might feel uncomfortable sticking your head out at first, but remember: it’s not bragging, it’s helping.

Phase 3: Find your edge. Don’t let others box you into a niche, even if some specific experience was the reason you were hired. Your edge should emerge from experimentation, and learning, not assignment. You can combine skills that rarely go together, forming a “talent stack”. This can help you create unique value, and is hard to copy.

The video covers each phase in detail. But there’s a deeper principle underneath all three that I want to expand on here.

The multi-armed bandit problem (or: why career plans are overrated)

In Algorithms to Live By, Brian Christian and Tom Griffiths describe a classic problem from probability theory: the multi-armed bandit.

Imagine you’re in a casino facing a row of slot machines. Each machine has a different (unknown) payout rate. You have limited time. Do you keep pulling the lever on a machine that’s been paying out? Or do you try a new one that might pay better—or might pay nothing?

This is the explore/exploit tradeoff. And it’s exactly the dilemma you face in your career.

Should you go deep on the technology you already know? Or try that new thing your colleague mentioned? Should you stay in your comfortable team? Or apply for that internal transfer that sounds exciting but risky?

There’s no way you can calculate an optimal solution in advance. And given how fast new tech trends come and go, it would be a moving target anyway. The information you need to make the ”right” choice only comes from making choices. You learn by doing.

This means the best strategies here aren’t plans—they’re heuristics. Simple rules like “win-stay, lose-shift” (stick with what’s working, move on from what isn’t) often outperform elaborate planning.

I discovered this book years after intuitively living through multiple explore/exploit cycles. I started my career focusing on graphics and workstations (back then, these were powerful desktop computers that got replaced by normal PCs), then went deeper on CPUs and Microprocessors, when a new, multi-threaded microarchitecture emerged, then spent some years focusing on operating systems, and when Oracle bought Sun, I added a stronger business angle to my work to explain the new, integrated Sun/Oracle stack to customers. Finally, I found AWS and Cloud computing, and a new set of cycles like began, cycling through IoT, AI/ML, digital transformation, and generative AI.

Whenever I went through a successful “exploitation” phase, where work is easy, customers are delighted and management is happy, I would spend time trying out new things, out of curiosity and a desire to learn new things, until I found my “next big thing” to focus on.

An ancient pattern you can observe everywhere: ant colonies, finding favourite restaurants, or watching successful companies diversifying or pivoting across products and markets.

Looking back, I never had a plan. Instead, I had a lot of experiments.

Three dangers

The explore/exploit lens on career building reveals three common mistakes:

Exploiting too early. At AWS, I watched new hires rush to work with customers before completing their ramp-up. They wanted to prove their value. But in doing so, they missed the exploration window—the time when you’re supposed to be learning, experimenting, discovering what’s possible.

Exploring too long. Some people never commit. They hop from interest to interest, building breadth but no depth. Exploration without exploitation leads to being a jack of all trades, master of none.

Failing to explore. We all know that colleague living in the past. I remember, when Sun acquired StorageTek in 2005, some colleagues there had trouble adopting new storage technologies, longing for their good old DASDs instead. I’ll let you look up what a DASD is.

The goal is to shift intentionally. Explore until you find something worth committing to. Then exploit—go deep, build expertise, create value. When that well runs dry or the landscape shifts, explore again.

How to know what’s worth committing to

When you’re ready to shift from exploration to exploitation, run your options through four filters:

1. Does this excite me? Passion helps develop grit when things get hard.
2. Can I get good at this quickly? Leverage skills you already have to get a head start.
3. Is this relevant? Look for opportunities opening up, not closing down.
4. Does it create business value? Because somehow, the numbers need to add up, so we can pay rent.

These filters come up in multiple sources and different variations, like in this article by James Gurney called What should you work on? (Assuming you want to make a living at it.), Paul Graham’s much more detailed article on How to do great work, or the Japanese concept of Ikigai. You can also use them to avoid getting into a career dead-end, as I’ve written in The Four Horsemen of a Dying Career, where they serve as shields against boredom, incompetence, irrelevance, and going broke.

Mini-careers, not one career

The liberating truth is: you’re not building one career. You’re going to have many mini-careers—different roles, different technologies, maybe different companies. Like microservices, this gives you better flexibility, agility, and antifragility, which is the ability to emerge stronger in the face of external change. And somehow, they’ll connect into a story that only makes sense looking backward, like Steve Jobs famously said.

This is actually good news. It means you don’t need to have it all figured out. You just need to get good at navigating each chapter. Explore with purpose. Exploit with commitment. Then explore again.

I’m in exploration mode right now with my YouTube channel. I’m posting videos on different topics, seeing what resonates, figuring out my niche for this new chapter. I don’t know yet what it’ll be. But I’m curious to find out.

That curiosity—that willingness to keep exploring—is what keeps a career alive at any stage. For more on this mindset, see also How to Thrive as an Expert Generalist in the Age of AI.

Your homework

Before you go on, write down the following:

1. Three topics you want to explore in the next six months.
2. Three events or meetups you’ll attend this quarter.
3. Three skills you already have that most of your colleagues don’t.

This should give you some great starting points for exploring your new tech career. And that last list can already be the beginning of your edge.