Investing - Theory, News & General • Re: Gen-X Boglehead Thoughts

August 2026 update:

Our youngest (Gen Z since we're naming generations) asked me over dinner if I had ever heard of "Topstep" which I would characterize charitably as a gameified, futures daytrading subscription investment outfit. I said no, but that if it involved daytrading, the likelihood of anyone's success was less than 5% in my view.

It struck me that there's always going to be a gap in culture and experience for each financial generation. Kids who grow up with Robinhood, prediction market apps, and cryptocurrency in the conversation mix (if not also the investing mix) will come to Boglehead concepts from a completely different point of view than me, a Gen-X'er who grew up with a passbook savings account and made $4 a pop mowing lawns; heck, the folks just older or younger than us were also shaped by both the financial education they had access to as well as the markets that they've lived through.

It's never the same river, even if the foundations of saving and investing are similar. To be real, as much as I was a bit dismayed to hear about "Topstep", I have to admit that the name "Boglehead" will probably not connote quite the same thing to a Gen Z person, either.

But there is a distinction. Today's market does seem to be a bit more awash in schemes, scams, and alternate investment approaches. Personally, I think that's the byproduct of a huge run up in equities and changes in technology and media. Jack Bogle's whole goal was to educate a generation of investors about some general best practices, and in the process he helped lower costs and increase access for everyone.

That being said, as the 50something (well, my wife won't get to 50 for a few years) beneficiaries of that run up as well as low cost index funds, my wife and I also can't help but look at today's market and think back to the .com crash and the GFC. We both struggled back then and both suffered long term consequences to both recessions. We are in a much better position now.

Dinner chit chat about futures daytrading doesn't seem like the best omen, however. I guess there's always been options trading and hedge funds making crazy bets while long term investors simply did nothing.

My best take, if I have one, is that the paper value of our portfolio is exactly that, a paper value. We have a plan and a map for what our portfolio will do if there's a 20% or a 40% downturn in equities; we also have a plan for what we'll do if runaway inflation cuts into the value of our fixed income.

By our math, we've got 8-12 more working years, though probably less for me. With all that accumulation and taxation ahead of us, it's too soon for us to convert over to TIPS as many of those closer to, or currently in retirement, are discussing here.

As "later to retire" Gen X'ers (the byproduct of our late start), we're simply rebalancing to our AA with, if anything, maybe an extra lean towards our short term bonds and pre-paying our mortgage. Yes, something tells me that financial gravity will have to assert itself at some point, but the answer for us isn't going to be some "new direction" that we'd never have considered two years ago, as much as it is simply to recommit to our core principles, batten the hatches, and stay the course.

I'm sure we're not alone!

Statistics: Posted by SantaClaraSurfer — Tue Aug 25, 2026 7:34 pm