The Million-Dollar Decision I Got Wrong (And Why I'm Grateful)

The inventor of Ethernet kept showing up at my office in Naperville, Illinois.

Bob Metcalfe would walk potential customers through the network I’d built. Thirty nodes running on 3COM hardware, the largest deployment of their technology in existence. He’d point at my cables, my machines, my workarounds for bugs that were literally soldered into the circuit boards.

Then he offered me a job. Pre-IPO shares at roughly a dollar.

I turned him down.

3COM went public in 1984. The stock split multiple times. The company grew to billions in market cap. I have no idea exactly what those shares would have been worth, but I know it was life-changing money.

I watched it happen from the outside.

This is a story about what happens when you face a defining decision with an empty toolkit. No mental models. No frameworks. Just gut feeling and fear.

Comfort won. And what I learned from walking away has shaped everything I teach about thinking clearly.

How I Ended Up with the Largest 3COM Network in Existence

In 1981, I was a software engineer at Deltak in Naperville. I’d been recruited by Bob Davis, a man who would become one of the most important mentors of my career. Deltak was the leading provider of video and computer-based technical training, and most of our content was created on Wang word processing systems. Clunky, isolated machines that couldn’t talk to each other.

That same year, a small startup called 3COM released its first product: Ethernet cards for PCs called EtherLink. I don’t remember exactly how I heard about them, but I remember the feeling. Here was a technology that could connect computers. Make them share resources. Turn isolated machines into something greater than the sum of their parts.

I jumped at the chance to build out a 3COM network for my small software team.

What started as a modest experiment grew. Five nodes became ten. Ten became twenty. Eventually, we had thirty computers connected on a single 3COM network, running EtherShare for file sharing, EtherPrint for shared printing. A genuine networked computing environment in an era when most offices still thought of computers as expensive typewriters.

The early hardware was rough. Those first EtherLink cards had hand-installed wire jumpers to fix PCB board layout errors. We were working with technology so new that some bugs were literally soldered into place. But it worked. And apparently, it worked better than anyone else had managed.

That’s when Bob Metcalfe started bringing customers to Naperville.

He’d co-founded 3COM with Howard Charney to commercialize the Ethernet technology he’d invented at Xerox PARC. Now he needed proof that it worked at scale. My network, cobbled together in the suburbs of Chicago, was his best evidence.

I was in my early 20’s. Barely old enough to drink a beer. And I was watching the inventor of Ethernet walk executives through the deployment I’d built. Answering their questions. Showing them what was possible.

Looking back, I can see how extraordinary that was. At the time, I was just trying to make things work.

Two Offers, One Empty Toolkit

A few years later, I decided to leave Illinois for Silicon Valley. The Midwest had been good to me, but the future of technology was clearly being built on the West Coast. I wanted to be part of it.

Almost immediately, I found myself with two offers.

The first came from 3COM. They’d watched me build and maintain that network. They knew I understood their technology at a practical level. Bob Metcalfe made me an offer that included pre-IPO shares at roughly a dollar per share.

The second came from Individual Software, a small company where Bob Davis, my mentor from Deltak, had recently become VP of Products. Bob knew my work. He’d recruited me once before. He was offering me the chance to keep working with someone I trusted.

Two paths. Two futures.

Here’s what I had in my toolkit to evaluate them: almost nothing.

I was in my early 20’s. My wife and I had just had our daughter. My only real work experience before Deltak had been a year at Anchor, a job I’d taken to support my wife while she finished her nursing degree. Now I had a newborn at home, a wife counting on me, and two job offers that would uproot our young family and move us across the country.

I had no framework for evaluating startup equity. No mental model for assessing risk versus reward. No understanding of how to weigh the known against the unknown. Just the weight of new fatherhood and the terror of making the wrong choice when people depended on me.

I had gut feeling. I had fear. I had comfort.

Comfort won.

I chose Individual Software. I chose the boss I knew over the opportunity I didn’t fully understand. I chose safety over asymmetric upside.

With a newborn daughter and a family counting on me, safety felt like responsibility. It felt like the adult choice.

It was the wrong choice. But I had no way to see that.

The What-If That Never Fully Leaves

I’d be lying if I said I never think about it.

Every few years, something triggers the memory. A conversation about early networking. An article about startup equity. A moment when I’m coaching someone through a career decision and I recognize the same blank toolkit I once carried.

What if I’d joined 3COM? What if I’d trusted the opportunity over the comfort? What if I’d had even one mental model to help me see the decision more clearly?

I would have been there for the growth. The IPO. The era when networking transformed from curiosity to infrastructure. I would have been part of the story instead of watching it unfold.

That’s the what-if.

But here’s the thing about what-ifs: they only show you one timeline. They don’t show you what you gained from the path you actually walked.

The Value of Getting It Wrong

Living through failure does something that reading about failure can’t.

I’ve had successes across forty years in technology. I co-founded a company through IPO. I was CTO of HP during an era when we won “Most Innovative Company” three years running. But I’ve also made decisions that cost me opportunities, relationships, and time I can’t get back.

Each failure added tools to my toolkit. Not abstract concepts I read about, but lived models I earned through consequences.

There’s a mental model called “the map is not the territory.” It’s the idea that our beliefs and assumptions are simplified representations of reality, not reality itself. A map of Denver isn’t Denver. It leaves out the smell of pine trees, the feel of altitude, the conversation at the corner café. Every mental model, every framework, every belief you hold is a map. Useful, but never complete. I learned this one by having my map be catastrophically wrong, more than once.

There’s another model called inversion. Instead of asking how to succeed, you ask how you’d guarantee failure, then avoid those things. I learned that by watching projects collapse in ways I should have predicted, if only I’d asked the right questions upfront.

And there’s the premortem. Imagining your project has already failed and writing the story of why. I learned that one by running too many postmortems after the damage was done, wishing I’d seen the warning signs earlier.

I go deeper on all three of these models in Episode 8 of my Thinking 101 series below. If you want the frameworks, not just the story of what happens without them, that’s where to find them.

Here’s what I’ve noticed about Silicon Valley, about shark tanks, about the mythology of innovation success: they’re full of people who got lucky on their first swing.

First startup. First investment. First product. Massive success.

And many of those people (not all, but many) are people I wouldn’t trust to make sound innovation decisions today. Because they never built a toolkit. They never had to. Success arrived before they developed the mental models to understand why it happened or how to repeat it.

They have one map, one simplified representation of how success works, and they think it’s the complete picture. They’ve never had to discover what their map was leaving out.

The Paradox of the Better Decision

Would I undo my choice if I could?

The honest answer is: I don’t know. And the reason I don’t know is precisely because of what I’ve learned since.

If I’d joined 3COM and ridden that wave to financial independence, would I have become the kind of thinker who can see around corners? Or would I have become one of those people convinced that their first map was the only map worth having?

I genuinely don’t know.

What I do know is this: the twenty-one-year-old who chose comfort over opportunity was doing the best he could with nothing in his toolkit. He had a newborn daughter. He had a wife who’d supported him through lean years. He had fear dressed up as prudence. I don’t judge him. I just wish I could have handed him a few tools.

What I’d Tell My Twenty-One-Year-Old Self

If I could go back to that moment, two offers on the table, a new baby at home, no framework to evaluate any of it, here’s what I’d say:

Check your map. You think you’re choosing between two jobs. You’re actually choosing between two completely different trajectories. One is linear: work hard, get promoted, build a career. The other is exponential: ride a technology wave that’s about to reshape how every computer on earth communicates. Your map shows two similar options. The territory, actual reality, says otherwise. What is your map leaving out?

Invert it. Don’t just ask which job is better. Ask: how would each choice fail? Individual Software fails if the company struggles or if you’ve capped your learning by staying with what’s familiar. 3COM fails if the technology doesn’t take off or if you can’t perform without a mentor. Now look at the actual landscape. Networking is exploding. You built the largest deployment they have. Which failure is more likely?

Run the premortem. It’s five years from now. You chose wrong. Write the story. If you picked Individual Software, maybe you’re comfortable but watching an industry transform without you. If you picked 3COM, maybe you’re in over your head but learning at a rate you never imagined. Which regret is easier to live with?

I didn’t have those tools. I chose blind. And the cost was a front-row seat to one of technology’s greatest success stories, from the parking lot.

The Gift You Can Give Yourself

That twenty-one-year-old version of me had to spend the next four decades building the toolkit I wish I’d had.

You don’t.

If you’re facing a decision right now, a fork in the road where one path feels safe and the other feels uncertain, don’t trust your gut alone. Your gut is shaped by what you’ve already experienced, and if your experience is limited, your gut is navigating without a map.

Use the tools. Check your map against reality. Invert the problem to see where failure hides. Imagine it’s a year from now and you chose wrong, then write the story of what happened.

And if the unfamiliar path has asymmetric upside, if the downside is survivable but the upside is transformational, take a hard look at why comfort is winning.

Sometimes safety is wisdom. Sometimes it’s just fear wearing wisdom’s clothes.

I couldn’t tell the difference at twenty-one. Maybe you can.

This article is part of the Studio Notes series, where I share the real stories behind innovation: the human costs, the political battles, the strategic blunders, and the personal consequences that never make it into the official narratives. Subscribe to ensure you never miss a post.

If you found value here, consider becoming a paid subscriber. And watch for Episode 8 on the Thinking 101 playlist this Wednesday. It’ll teach you the mental models that could change how you make decisions.