On Long-term Thinking

There’s a concept in evolutionary biology called the “adjacent possible”, it’s about exploring what’s reachable from where you are now, the space of possibilities that opens up with each step forward. Stuart Kauffman used it to describe how biological systems evolve, but I’ve come to see it as the perfect metaphor for navigating careers in our accelerating world. Hence why I named my company Adjacent Possible Tech.

The irony of writing about long-term thinking in 2025 is that the very concept feels like it’s undergoing time dilation. We used to plan infrastructure projects with 5+ year burn-down periods. Systems were built with 10+ year lifecycles. Now? Even outside the AI frenzy, the tech industry moves so fast that what we used to call “long-term” is barely medium-term. It’s like we’re living in a temporal compression chamber where the future arrives before we’ve finished planning for it.

The View from the Bleeding Edge

Having spent years working at the far right of the adoption curve, past early adopters, past leading edge, all the way out to bleeding edge, I’ve developed an unusual perspective on time and planning. When you’re working with technology that won’t be mainstream for years, you start seeing beyond the curtain of “available now.” You glimpse what’s coming, what’s possible, what’s probable.

But here’s the thing: this view is both a gift and a curse.

The gift is obvious, you can sometimes see around corners. The curse? Sometimes you’re so focused on what’s coming that you miss what’s already here. And sometimes, you’re just wrong about which corners matter.

When Strong Opinions Bite Back

Early in my career, I was an Active Directory/Exchange/UC specialist with unshakeable convictions. I believed, no, I knew, that enterprise systems couldn’t run on virtual machines. I argued black and blue against virtualization - “dammit you can’t timeslice a CPU and not introduce latency/jitter/whatever!!!”. Physical tin was the only way serious enterprises could operate.

I had what I now recognize as “strong opinions, strongly held”, the death knell of adaptability.

While I was defending the castle walls of physical infrastructure, the entire industry was moving to virtualization. I could have ridden that wave, could have been early to a transformation that would reshape everything. Instead, I held myself back several years because I couldn’t see past my own certainty. The adjacent possible was right there, but I’d convinced myself it was impossible.

That experience taught me the first rule of long-term thinking: your long-term plans are only as good as your ability to recognize when you’re wrong.

The Luck-Planning Paradox

Looking back at my career, it’s mostly luck with occasional flashes of long-term thinking disguised as a desire to grow and learn. The 2008 Microsoft layoffs that took out people I knew, my first real experience with how quickly certainty can evaporate. Life events, kids, relocations, health issues, none of it predictable, all of it reshaping whatever grand plans I thought I had.

But here’s where it gets interesting: the most successful “long-term thinking” moment of my career happened in 2016 when AWS friends pulled me in despite my knowing basically nothing about cloud.

I was over my head. I knew it. My Public Sector customers and I were woefully behind, I still thought private cloud was going to overrun public cloud (another strongly held opinion that aged poorly). But after talking with my soon-to-be AWS colleagues, something clicked. I saw an adjacent possible: I could get in “late” but still early enough to ride the wave of learning and development forward.

The alternative? Continue contracting to PS customers around private cloud and infrastructure projects, watching my skills atrophy within five years as the world moved on without me.

That jump to AWS was the closest thing to deliberate long-term thinking I’d done, and it worked precisely because it wasn’t really about predicting the future, it was about positioning myself to learn and adapt regardless of which future arrived.

The Hierarchy of Time Horizons

So how do we think about long-term planning in a world where long-term keeps getting shorter? I’ve started thinking about it in layers:

Beyond 5 Years: The Fog Zone Trying to see beyond five years in tech is like trying to see the top of an exponential curve while standing on its steep section. We’re moving too fast, changing too quickly. Anyone claiming to know what technology will look like in 2030 is selling something.

2-5 Years: The Adjacent Possible This is where strategic thinking lives. Not predicting the future, but positioning yourself to take advantage of multiple possible futures. It’s about building capabilities and relationships that open doors rather than planning which specific door you’ll walk through.

6-18 Months: The Execution Window Concrete plans, specific skills, deliberate moves. This is where most actual career progress happens, close enough to see clearly, far enough to make meaningful changes.

Right Now: The Learning Edge What you’re curious about today shapes what’s possible tomorrow. The best long-term thinking often disguises itself as present-moment curiosity.

When Long-term Thinking Is a Trap

Industry experience teaches you where long-term thinking is fruitful and where it’s waste. Public sector, for instance, is often allergic to long-term thinking. Politics changes things. People changes change things. And public sector lethargy stops change. I’ve watched customers push out project dates rather than commit to hard deadlines, turning two-year projects into five-year sagas that deliver yesterday’s technology tomorrow.

In these environments, long-term thinking becomes an exercise in frustration. Better to focus on immediate value and adaptability.

The trap is thinking that long-term planning means predicting and controlling the future. It doesn’t. It means positioning yourself to thrive regardless of which future arrives.

If I’d Only Known (But I Couldn’t Have)

If I could tell my younger self anything, it wouldn’t be “here’s what’s going to happen” or “focus on cloud early” or any specific technical advice. It would be this:

Your career will be shaped more by your ability to recognize and step through adjacent possibles than by any grand plan. Stay curious. Hold opinions loosely. The future is coming faster than you think, but it’s also weirder than you can imagine.

And sometimes, what looks like long-term thinking is just luck wearing a strategy costume. That’s okay too.

The Meta-Lesson

We need long-term thinking more than ever precisely because we can see less far than ever. It’s not about predicting the future, it’s about building the capacity to adapt when the future arrives ahead of schedule.

The adjacent possible isn’t just about technology. It’s about recognizing that from where you stand right now, certain moves open up entirely new spaces of possibility while others close them down. The trick is learning to see which is which, and having the courage to step through when the moment comes.

Even if you know basically nothing about what’s on the other side.