Different Rules

Watching the ground shift

What once felt straightforward now involves more careful navigation. Image generated by Microsoft Designer, prompted by the author.

When Marsha and I get together with friends who are younger than us, the same topics tend to come up, including work, housing, and kids. Or whether now is the right time to make a move or wait a bit longer. Often the conversation drifts toward what they are trying to decide next, and why it doesn’t feel simple.

What strikes me is how carefully everything gets weighed. Decisions that once felt to us like natural next steps now come with timing questions, risk calculations, and a lot of second‑guessing. The sentiment is not one of frustration. People are just trying to be thoughtful. They seem more reluctant to lock anything in.

It isn’t only about whether to have children. It’s also about when, or whether waiting is the safer move. It’s about whether to move, where to move, or whether staying put makes more sense for now. It’s about buying a place, remodeling, or holding off until some future milestone clicks into place. Even when people know what they want, pulling the trigger can feel risky. Many choices feel expensive, hard to unwind, and tightly tied to timing.

What I notice most isn’t exhaustion, at least not in the usual sense. It’s the pressure to optimize, to get things right, or to keep options open just a bit longer. That often leads to delayed decisions or temporary steps meant to buy time. People stay busy, but forward motion is often slow.

That’s what led me to start looking at our own past, to simply understand what might have changed. The intent was not to compare generations or to hold tightly to nostalgia. I don’t think we’re going back to the world the way it was. I’ve just been noticing how the environment has shifted, even though many of the goals have stayed the same.

I should be clear about where I’m coming from. I’m retired now. Marsha was a stay‑at‑home mom for all of our parenting years. Our kids went to great public primary and secondary schools and ended up at great universities. I arrived in Silicon Valley early, bought property early, worked long hours, got lucky, and eventually benefited from a couple of successful IPOs. That wasn’t everyone’s experience, even among our peers, but it’s my own point of reference.

When I think back on my early adult years, what stands out isn’t that life was easy. It’s that fewer decisions felt permanent. Many choices felt reversible. Moving forward, even imperfectly, usually seemed better than waiting.

Work felt more forgiving

I started at Oracle in 1990, straight out of MIT. What worried me then wasn’t whether I’d get a job. It was whether I’d get a good offer.

Recruiting was straightforward. I signed up for interviews at the MIT career center. Companies came to campus, interviewed students, and made offers. I didn’t feel like I had to fight an AI application tracking system just to be seen.

I had studied signal processing, but I decided to try product management. I took an entry‑level job as an associate product manager. Changing direction early felt manageable.

Working at a big company also gave me a clear sense of progression. I moved from associate product manager to product manager quickly. The career path was visible. If I learned the business and did solid work, things tended to move.

Later, a headhunter call led to my first startup, Visioneer. When I eventually got laid off, it was stressful, but it didn’t feel defining. Once people knew I was available, other opportunities appeared, and I ended up working for a friend’s company, Latitude Communications.

Even the harder moments came with an underlying sense that things would work out. That assumption shaped my attitude toward work/career.

Housing provided early footing

Housing played a big role in our sense of stability.

We bought our first condo in 1993 in San Mateo, about five minutes from my office. It cost under $200,000. I was earning just over $60,000 at the time and qualified for the mortgage on my own.

I put about ten percent down and paid PMI. It felt like a stretch, but not a gamble. Buying felt like an early milestone, not something to postpone indefinitely.

When we bought our first house in 1998, the condo had appreciated. We sold it, negotiated a rent‑back, and used the equity for the down payment on our house. We weren’t doing anything especially smart. The market made that step possible at the time.

Once we owned, housing costs stabilized and equity built quietly in the background. That took pressure off other decisions.

For many people now, housing never really plays that role. Renting stretches on. Buying comes later, if at all. Without that early footing, everything else feels more tentative.

Division of labor mattered

Marsha was a stay‑at‑home mom throughout our parenting years. At the time, that is how we chose to divide our responsibilities for our family. In hindsight, I see how much stability it created for us.

I worked extremely long hours. Meetings all day. Getting to my own work at night. Traveling when the business needed it. I missed family meals more often than I care to admit. I could focus on work because Marsha was fully focused on running our household.

That arrangement wasn’t something we ever even debated. We just went that way, and it worked.

Many families today don’t have that option. Both parents work, and both also manage everything else. Couples make it work, but it means constant trade‑offs and very little slack. Work and family demands collide all the time. That alone changes how life feels.

College was still expensive, but it felt less binary

College was expensive back then too. Very expensive.

We paid over $70,000 a year for our older daughter to attend Yale, and close to $80,000 a year for our younger daughter at Carnegie Mellon. Those were serious numbers. Paying for college was not casual even then.

What feels different now isn’t just the price, but what people expect that price to deliver.

When we were thinking about college for our kids, a strong degree felt like it opened doors, but not in a narrowly defined way. A good school signaled capability. What came next still depended on interests, timing, and opportunities that unfolded along the way.

Now, college often feels like it needs to land much more precisely. Not just a good school, but the right one. Not just a degree, but one that carries enough weight to lead to a specific job or to unlock admission to the right graduate program. There’s more focus on whether the degree will clear a series of gates that may be difficult to pass later.

Because of that, the pressure shows up earlier. Families talk about college less as a formative experience and more as a critical link in a longer chain of life steps required to survive in the modern world. When the outcome feels that specific, there’s less tolerance for missteps or detours.

The cost didn’t just go up faster than inflation. The expectations around what the high college cost needed to produce became tighter.

Better tools, higher expectations

I probably worked longer hours than many people do today. There was a culture of staying late together and working through problems face to face.

There were also fewer shortcuts. If I didn’t know something, I had to learn it, find someone who did, or make a call with imperfect information. The tools were limited.

Today’s tools (including the latest round of AI tools I’ve been writing about) are powerful, but they also raise expectations. When work gets faster, more is expected. Time that’s saved doesn’t always feel saved. Work rarely feels finished.

Combined with everything else competing for attention, that makes life feel more constrained.

What shifted

When I step back and look at all of this together, I don’t see the biggest changes in levels of effort or the character of the people. The changes I see are all structural.

Work feels less forgiving. Housing is harder to use as an early stabilizer. Two incomes are assumed. Parenting carries more pressure. Better tools raise expectations instead of easing them.

My own path included plenty of hard work, but it was supported by conditions that made forward motion feel safer. Those conditions are challenging to assemble now.

For me, this isn’t about advice or conclusions. It’s about noticing that the ground moved, and that many of the hesitations and delays I see around me make sense once that shift is acknowledged.

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AI disclosure: I used AI tools during the drafting and editing process to help clarify structure and language. All ideas, judgments, and final wording are my own.