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If you’re like me, growing up the whole goal was not to live the life your parents lived.

Not that my parents were inadequate or that they have lived dishonorable lives in some way. Quite the contrary—they’re hard working, have always been there for their children, really sacrificed themselves entirely to try to give us the best lives possible.

— § —

It’s that last bit that’s the problem. Growing up, I watched my parents fight time and money day in and day out, always trying to stay just a half step ahead of a reality that always threatened to catch up.

We were in that class of people that always had food to eat and a roof over our heads, but who could never afford to buy a future.

What I mean by that is that in general, there is a tradeoff at the heart of modern society: pay more today so that you can pay less tomorrow.

This is evident in:

  • The buying of insurance which reduces future costs vs. paying as you go because you can’t afford insurance

  • The selection of goods (the “affordable” option that will break in a month vs. the “quality” option that will hold its value or even appreciate as a collectible)

  • The maintenance of key household items (repair now to prevent future costs and a shortened lifespan or merely do what you can manage to pay for now knowing that it will lead to problems that will cost more to fix “down the road”)

  • How any of it is paid for (pay for everything with a credit card that you pay off every month and you get free money and goods; pay for everything using cash and you break even; pay for things using credit when you need to “make payments” and you’re in the hole, paying interest)

  • “Paying yourself first” in retirement funding (rather than spending every paycheck) so that you can “have the income you need later”

These are the kinds of tradeoffs that (1) make social mobility harder to accomplish the lower on the ladder you are, simply because you can never seem to make, in practical terms, what you know to be the advantageous choice, and (2) make for a life of stress if you aren’t coming out on the winning end of those exchanges—a life in which you can always see the promised land, but the goalposts are moved a little farther out every day, so that you “can’t ever quite get ahead.”

— § —

So it was that my primary goal in life (and my parents primary goal for me) was to enable me to land farther ahead than this—to lead the kind of life in which one isn’t rich necessarily, but can afford to do the things that are advantageous:

  • Buy insurance when it’s offered, rather than paying spot

  • Buy the quality goods that will last, rather than the cheap goods that you’ll have to replace soon

  • Keep everything in life well-maintained so that repair costs remain low and durability is high

  • Take advantage of the financial economy—investing, credit card perks, and so on

  • Can invest, whether in 401k savings, or in real estate, or in the market, in such a way as to generate a large and compounding return over the years

— § —

I thought I had done all the right things. Studied very hard. Got a college degree, then a masters degree, then a doctorate. Work in tech, where jobs are legendarily “good” and “plentiful.” Got married before having kids. Learned to do many maintenance things to home and car and appliances myself. Instead of being “quietly dedicated” and passive about work life (and life in general), I have been aggressive and conspicuous in trying to pursue goals and outcomes and make the right connections. I generally work such long hours that my ex-wife routinely teases me for being a workaholic. And so on.

But it hasn’t mattered. I am not “ahead.”

If anything, I’m even farther behind than my parents were. Turns out that the big mistake was college, which imposed debts that I will be paying off for the rest of my life. The second mistake (though it’s hard to call it that given my wonderful children) was marriage, which added tens of thousands of dollars in legal debt just as my student debt went into repayment.

And the irony is that I now don’t think that any of those things I mentioned actually mater. One thing matters—your social skills. As far as I can tell based on life experience, that is the only and only real predictor of success.

— § —

But aside from any of that, I ultimately find myself living exactly the life my parents led. It’s obvious which decisions are advantageous vs. where additional costs and long-term boondoggles lie.

But in the day-to-day of things, I am forced to go with what I can afford—even if I know that it will cost more in the end.

I can hear what the Wise Financial People say on the radio and on the websites. “Don’t be a fool, be money-wise; the cheaper option isn’t always cheaper; spend a little more now to avoid spending a lot later,” and so on.

It doesn’t matter that I know these things, or that I hear “expert” after “expert” offering advice that confirms my instincts.

You can only afford today what you can afford today. And contra the theoretical world of financial planning, there are a great many things that you just can’t wait on until you can “better afford it.”

This is America. You need a car. It nees to run. You need to go to the doctor when you need to go to the doctor. Your kids need clothes when they need clothes. It is what it is.

— § —

And so in midlife, here I sit, sometimes musing that I have taken a different and often much more arduous path than my parents took to arrive at exactly the same place, or maybe even a worse one, watching as the goalposts move just a little farther away every day, constantly feeling as though I’m setting money on fire and if I only had 20% more salary, I could flip the field and start coming out ahead.

But that salary history is what it is; you never get a 25% or 30% pay raise in a year or job-to-job; you get 5 percent here and 5 percent there as you move between jobs and put in your long service. You keep up with inflation and see your salary increase at a rate that provides evidence of your value—but not at a rate that really helps.

— § —

I keep hearing my dissertation adviser in my head. I know I’ve written of this before. He was in his mid-60s and saying to me, “I continue to have big plans, yes, but I’ll carry them out—I still have a lot of energy!”

And I compare to myself (and to my parents). Mid-40s and already burned out and exhausted from trying to keep up, not seeing the net worth really increase, never managing to really climb the mountain, despite climbing and climbing and climbing. Always faced with a stream of fires than often in part stem from past “disadvantageous decisions” that couldn’t be helped, and doing financial jiu-jistu to figure out how to pool and organize cash and manipulate calendars in just the right way to enable at least the fires to be put out.

I don’t know how you break out of that generational cycle, but despite having what everyone thought was the right plan, I’ve gradually come to the realization this decade that I failed to do it. I am living the life my parents lived and fondly hoping, as they once did, that I can help my kids to do better.

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