Timing Luck

Parents of high schoolers today have an incredibly tough choice to make: do you pay the insanely high tuition prices for college? Five to ten years ago, there’d be no question; generally, the sacrifices parents made to send their kids off to college were celebrated and the preferred path of economic upward mobility was sending a newly minted high school grad off to a 4-year undergrad program.

It’s now a different story. A combination of uncertainty around how AI will impact what types of jobs will be available (and if there will be any jobs at all!) and the inflation of tuition prices to absurd levels for the average American has made that calculation not so clear. It’s hard to grapple with how fundamental that change represents. The role of college was a rite of passage to professional adulthood. Is it still worth it?

I am not envious of anyone who has to make this decision today. The stories pile on, and there’s an morbid fascination of watching how to navigate this new world with the relief of not having to go through it myself - almost like watching a horror movie from the safety of the couch, uneasy but unable to turn away from whatever the monster does next.

I’ve so far benefitted tremendously from growing up at the right time. I’ve considered this mostly through my lenses of today - primarily career-oriented - but I think it broadly applies to social, emotional, and spiritual experiences as well. People in my age cohort (I’d define as being born between ā€˜91 - ā€˜95) walked a narrow strait - too young to be impacted by the GFC but old enough to minimize COVID’s impact. It’s yet to be seen what will result from the coming fundamental shift in AI, but so far my career vintage has likely felt AI as a tailwind more than anything.

Career

We came of age into the workforce at a ripe time of zero interest rates and major opportunity expansion thanks to the growth of software. It was no longer necessary to wait your turn for career success at a large corporate; rather, it was encouraged to reject the traditional approach and go start your own thing. Facebook, Snapchat, Uber, AirBnB, Instagram, and many, many others paved the way for irreverent twenty-somethings to take venture capital dollars and turn it into open workspaces, free lunch, mobile apps, and hopefully hockey stick growth.

While ā€œLearn to Codeā€ quickly became a meme, it did represent a real force of gravity around the tech industry. These were fantastic jobs by any metric: high-paying, great benefits, upward mobility, limited barrier-to-entry (no college degree needed!), lots of demand. Tech was arcane to seemingly anyone over 30 but was eating the world; new grads were now bring fire down from the gods to the common folk.

For those slightly older, they entered a workforce during the GFC and its immediate aftermath. I’ve heard so many anecdotal stories of bright, well-intentioned students graduating into the workforce and utterly unable to find a job. Saddled with student loan debt, they started their careers in completely unrelated fields without much prospect of growth. There’s been a material impact on career earnings and experience, and has set back those unfortunate enough to graduate then.

On the other end, the period since COVID has been rough for new grads. Sure, I managed some new grads in ā€˜21 and ā€˜22 where work-from-home was essentially a license to game, watch TV, and scroll (I found it extremely difficult to determine whether performance and behavior issues were due to genuine first-real-job reasons - which is expected and important to experience and work through - or lack of focus and effort due to WFH), but the short-term sugar high of an easy paycheck faded to a pretty critical loss of early-career development that comes from in person interaction and competition with peers, modeling behavior of more experienced coworkers, and learning how to operate and exist within a professional organization. Losing those formative years was akin to students taking instruction from home, and we’re seeing there are some pretty stark negative impacts from that.

Immediately following, AI and/or broader operational efficiency gains has made lots of opportunity for new grads dry up. The grunt level work of learning a craft, at least in software, has largely just been handled by AI - the resources needed to build something have shrunk to a laughable amount compared to previous. The skills now needed are unfortunately only available with experience, and we’ve pulled the ladder up from the new grads. As a whole, the circle of life of new grads as apprentices, developing up the skill ladder to them selves becoming senior leaders, is endangered. This is a last-chopper-out-of-Vietnam situation for the lucky few that were able to snag growth-trajectory new grads roles two or three years ago. I really don’t know what comes next or how to fix this, but it’s a structural change that new grads now and in the immediate future will have to navigate through, no matter how unequipped they or anyone else is to help them through it.

Financial

There’s been a bull market since 2009. Index funds. ETFs, zero-cost trading, and modern UI interfaces have made stock market participation much more accessible. Paired with a cottage industry of Millennial-focused personal finance education, those of us who entered the workforce in the 2010s have been able to ride the consistent up and to the right of the market. It’s been a steady enough path that the fun of individual stock picking has nearly gone out of fashion, replaced by ā€œVOO & chillā€.

Maybe this new market behavior is here to stay and is a ā€œeverything gets better with timeā€ story, but it’s hard to imagine this relative market tranquility continuing to last. It’s been a perfect situation for younger workers, putting away money into their 401ks & brokerage accounts and seeing those values grow exponentially over time at the start of their careers. Who knows what the market will be have like over the next five or ten years, but if volatility seeps back into the system it’ll be unfortunate timing for the next wave of early adult investors. There’s certainly been a sense of impending doom the last few years around an upcoming bear market waiting to pounce and reverse course, as the party can’t last forever.

The way things appear at present, we may be the class cohort to have had the opportunity of affordable house. Housing is a financial lever and an inflation hedge, and just getting in the door (literally and figuratively) means going along for the ride as housing broadly gets more expensive. That lever was accessible, ingrained as the default route for the average person, since the middle of last century. Starting around 2020 due to the whacky housing market behavior from COVID, accessibility has gotten vanishingly smaller, if it still exists at all.

I imagine housing feels out of reach for the majority of people not already homeowners under, say, 30. Prices have gone way up in a hurry, past any reasonable level when compared to a few years ago. Mortgage rates are higher than they’ve been in the last 20 years, and they’ve done nothing to slow the increase in housing prices. It’s an adversarial system for anyone who wants to buy a house but hasn’t done so yet. The housing train seems to have left the station, and my cohort just reached typical home-buying age with just enough time to jump on.

Socially Online

There was a brief moment following the emergence of social media where it really was a fun and constructive experience, without all of the screen addiction, Anxious Generation impact that’s become the norm. MySpace, Facebook, Snapchat - these all actually eroded some of the typical social and clique barriers, and made it easier to build new relationships with people that otherwise never would have happened.

These services were still immature and exclusively product-focused, before ads and monetization and algorithms. For my cohort, MySpace was middle school, Facebook high school, and Snapchat early college. Digital interaction had a lower barrier to entry, and which unlocked new relationships and social graphs. They complemented in-person, physical communication as they were representations of close-proximity social networks. This was before usage optimization techniques, so at the time they replaced IRL interaction at a much smaller rate than they do today.

The iPhone wasn’t prevalent yet and WiFi (the main way to connect to the internet) was comparatively slow and limited, so devices weren’t always on and always connected. Services like AIM allowed for low-stakes interaction and online console gaming enabled ā€œhanging outā€ with friends after school or on weekends when otherwise that wasn’t possible.

Sure, there was some cyber bullying, and some weird interactions, and a lot less content moderation then there is today. But everything was immature and growing, and mostly around exploring what you could do with this new technology, even though it was clunky and slow. The sophisticated machines of scamming, bullying, and insecurity would mostly rev up after my cohort had already aged out of that susceptible age group.

For Gen Z, the interaction pattern seems much darker - always-on social surveillance so mistakes / awkwardness is amplified and lives forever, the ability to access endless content around lives that are ā€œbetterā€ than yours, a prioritization of digital personalities - all leading to legislation and lawsuits that represent the ills of the current state of social media. Beyond that, we’ve gotten the delightful concept of the iPad kid and controversial social media influencers using turning their kid’s childhoods into content.

Somehow, it seems like my cohort was able to enjoy all the fun and connection that online social avenues can bring while dodging the big downsides that have later bubbled up and dominated the online social experience.

The Current Moment

The first inkling of this post came to me, as does all discourse of this era, grappling with the impact of AI. I have a newborn, my second, and have spent lots of time in recent weeks with them lying asleep on my chest - nap trapped, if you will.

The difference between being nap trapped with my first (born a couple years ago) and second was that with my first, I was (happily) resigned to being a consumer: scrolling on my phone, watching movies, the like. Now, I was actively building a project from my phone via a remote-control Claude Code session running on a Mac Mini. I had full access to my computer, my creativity wasn’t limited to being physically there. While I got to enjoy bonding time with my newborn, AI built in an hour something that would’ve either taken months or never would’ve been completed at all if I had hand-built it. It’s pretty unbelievable that’s possible, although it now seems so standard after getting used to it. I have to remind myself that it’s genuine magic.

Early on in my software career (really, in undergrad), I realized I didn’t have any special talent that I could fall back on to carry me. My special advantage was my joy of working and putting hours in: being first in the office, staying late, sacrificing nights and weekends to always be available and working. I genuinely enjoyed it & felt the fruits of my labor, but it was trading time for progress. Time is abundant as a single person with limited dependents; it’s quite scarce with multiple children at home. My intent as a parent is to be fully engaged and involved to the best of my ability, and that means doing school drop-off and pickup, available when my kids are home until we put them to bed. If time was my special advantage at work, it was going to be severely lacking going forward.

How perfect, then - how lucky I’ve felt - that the fundamental change of how my work gets done aligned with the structural change of my personal life. After a decade of putting in as much time as I could to try to excel, I see a future where my impact is not constrained by the wall-clock time I have available. Impact will be determined by the product and operational skills I’ve been developing since the start of my career. AI has unburdened our ability to dream, get creative, and execute. The relationship of raw hours to impact has significantly weakened, at least in my case, and a new formula for good work has emerged that doesn’t rely on how much time you have available.

It’s another case of a change in the world arriving at just the right moment in my life. The timing couldn’t have been better, and I feel very lucky for that.

Zooming Out

There’s a degree to which every generation feels that the path that they walked was the best one. It’s a mix of solipsism and familiarity paired with the convenient habit of remembering the good parts and forgetting the bad.

If you zoom out, there’s no straight lines on the graph - each age cohort works through some level of change, is forced to adapt, encounters struggles never faced before, and so on. They feel fraught and dangerous in the moment, but what’s old becomes normal after some time, layered on the sediment of the changes prior, and we look back on the result as if they’ve always been this way. In fifteen years, a current new grad will be writing their own version of my thoughts here.

Even if that’s the case, I feel lucky to have my path travel through the era that it did. As a former manager of mine used to say often: ā€œit’s better to be lucky than good.ā€ I agree, and chalk up a good chunk of whatever good fortune I’ve had to simply just being dropped in the right place at the right time.