How to Play Financial Chess by Generation

Reaching 40 is an interesting psychological and financial chess game. Your body feels different, and your bank account still isn’t heavy. It’s a near-cosmic awareness of your mortality with a dash of existential dread—the feeling that you forgot to grab something from the grocery store but can’t remember.

Every Saturday, I can expect to spend anywhere from $200-$300 just by stepping out the door. Two drinks, a shareable appetizer, and two entrees will run you an easy $140 plus 10% sales tax and +15% gratuity. At this rate, I’m convinced that gratuity is a bougie way to say more fees.

The grocery store run is becoming a new ‘Price is Right‘ guessing game. I can’t tell you what I got for $198.94 last weekend. In retrospect, I could have done without the avocado, but what good would that have done? With three proteins and a luxury carton of eggs, that’s the stuff of legends.

Jumping back into the 2009 Nissan Versa, I wonder if today’s the day the car stops running ($30k min). The engine check light stays on. I might need to paint it over with a permanent marker. Getting home, I walk by the utility closet with more existential dread. Is today the day that the water heater ($8k) dies on me too? There is always an extra cost. I remember when Microsoft Suite was a one-time fee and now even Adobe PDF wants to charge an annual subscription. The former is $150 for the family plan (up to 6), just in case you want a functional computer.

Genuinely, I don’t know how households with kids that earn less than $100k, survive. Everything is expensive and each generation will fill the brunt of the cost differently.

Generational Language Barrier

Boomers are clocking out (and retiring). Most are doing so with less than $200k in savings. “They ain’t got it.” Living off of less than $2k per month from social security isn’t the “Dream.” GenXers are all but ignored by the media and they are one step in 50. They are both figurately and literally the Sandwich Generation, stuck between a rock and more consumer debt.

Millennials are the old heads now. Guys, my age, are now known as “Uncs.” This expletive is supposed to be endearing but then again, they call everyone Bro. As a generation, we can no longer hold onto scapegoating Boomers. You can yell about $400k home prices until you are blue though. Much good that will do for you. It won’t reduce prices and it won’t miracle a new HGTV home in a prime location. The generational blame game doesn’t pay the bills.

As the next biggest generation, it’s on us to figure out something new or to mentor the next generation to do better. This is a real-life cause-and-effect chess game with very high stakes. All you should hope for is to learn the strategies while the rules are constant. Make no mistake, this socio-capitalistic game will change, as will the players.

Gen Z is a different story altogether. Some of them are rebranding unemployment as a mini-retirement. You have to dissociate to consider being broke, a mini-retirement. They are a creative bunch that has decades of work ahead. I don’t think they got it. Folding and bending at any sign of work, they are a brittle bunch, nearly incapable of survival without a cell phone.

Playing Chess with the Bills: The Cost of Living in Crisis

Since the early 2000s, Americans have gone from crisis to crisis.

We’ve made significant gains and booms in the last two decades. While times have changed, and so has the cost of living standards. Americans have opted to bury themselves in a consumer debt spiral fueled by monthly subscriptions, travel lounges, and credit card reward churning. It blew my mind when I found out that Savage Fenty is subscription-based. Go figure; a subscription for underwear but then again, people are getting meals delivered that way. At this rate, it’s clear that Americans can’t walk and chew credit card interest fees (+24%).

The median household credit card balance in the United States is around $7,226. 

With minimum payments (interest + 1% balance), It will take you 322 months (nearly 27 years) to repay the debt. In that time, you will pay $13,782.10 in interest plus the principal. Every purchase will cost you 3x the initial cost (+9% annualized average interest gains). Consequently, $1,000 spent on credit (today) is worth $5,000 (tomorrow). Every decision you make carries an outsize 5x effect on your wealth.

To make matters worse, the average age of vehicles on the road is over 12 years.

Families will be looking for a new purchase soon enough. In 2025, the average monthly car loan for new vehicles is around $742.

Used vehicle loans are going for approximately $525 per month. Gone are the easy low payments of $250 per month. The cost is the cost. I have friends wrestling with this price tag as student loans and credit card interest fees rage on.

Finally, the less said about the affordable (luxury) home crisis, the better. On a fixed basis, a single person can expect to spend as much as $3,000 on expenses monthly. Married couples (with kids) are throwing as much as $4,250 monthly on a sinking ship. It’s no wonder 1 in 5 Americans reported having anxiety disorder in 2024 (according to NIMH).

Over 40% of adults are considered obese, but at least we have Oxempics.

America’s Reversion to the Working Class

Americans are at an impasse. For many, it feels like we are going backward. This, while holding onto the hope of quick social media fame in the likes of Mr. Beast, Kai Senat, and the Hacktua Girl. While some influencers strike it BIG, more find out they are mere chess pawns. Many influencers struggle to make a living wage. NeoReach reported that roughly half (48%) of creator-earners only make $15,000 or less. Only 15% make $100,000 or more annually. Even that might not be enough since it’s all pre-taxed with no benefits. It’s a financial gamble.

In 2025, the median American household will spend approximately $77,500.

Over 68 percent of these expenses ($52,700) will be allocated to Housing (plus utilities), transportation, and groceries. To stack matters against you, the total cost represents a 20% increase since 2019. At this rate, I expect the big three to cost as much as $70,000 by 2030. American families are in a bind.

The 1950s era of “cheap” global goods is over. We can no longer afford our high-end consumer lifestyle replete with ample square footage to entertain. The waterfall kitchen island might be a must-have, however, it’s far from a NEED. Before the repossession happens, opt out of higher-end appliances and outdoor features.

Although prices have gone up, we need to be honest that our tastebuds have gone up too. Our society shifted from Dunking Donuts to a myriad of roasters, brewers, and experimental specialty lattes ($7 plus taxes and fees). With the growth of the middle class overseas, competition and demand are high. When demand is high, supply is low, costs go up and people struggle more.

So how is every generation coping with these financial changes?

Baby Boomers Generation

Between 1946 and 1964, 72 million baby boomers were born, grew up, and eventually had to deal with their finances. Ranging from 58 to 77 years old, many are either in retirement or will be in the next 10 years.

If you (or your parent) are in this generation, get your documents together as soon as possible. A lot of wealth and tears are lost. Without a will or an estate plan, those who survive you will be struggling to figure out what you were doing. To keep it simple, your family risks losing half the wealth that you worked for.

If you haven’t retired, consider holding off until later to pick up social security. It’s a gamble, but in most cases, waiting a few more years can be the difference between an extra $250 to $750 per month. This isn’t the time to get cute with opportunities or big expenses. You should not pick up any new debts or loans from this point on. Additionally, you should avoid credit cards or specifically carrying a balance. around 40% of homeowners aged 65 and older are retiring with a mortgage, a trend that has increased from 24% in 1989 to 41% in 2022. This is a trend you should avoid.

I recognize that people want to give back in this age group; and, aim to give back in other ways versus financially.

It’s expensive to subsidize someone else while you are relying on social security benefits. There is no shame in saying NO. As of early 2024, approximately 3.8 million Americans owe $112.2 billion in outstanding Parent PLUS loans. More than 1 in 10 borrowers default on their loans four years after their child graduates.  At this rate, their debt is playing a game of chess against their desired wealth. Time is just about up for the next high-pressure move. You likely should consider selling the big home for something more manageable with better views.

Gen X Generation

A 2022 multi-generational financial literacy study found that Gen Xers—adults born from the mid-1960s through 1980s—are financially confident. In truth, they don’t seem to have the finances to back it up. Compared to other generations, Gen X is most likely to have credit card debt.

Gen X households are experiencing financial pressures from caring for their adult children and aging parents. From daycare (+$1k/month) to adult daycare (+$5k/month), there isn’t enough money to plan for the future. While the “Great (white) Wealth Transfer” could be a much-needed boost in the future, the current financial pressures are depressing discretionary spending.

Gen Xers can prioritize their financial goals, establish clear boundaries, and communicate openly with family members about their financial situation and expectations for support. Try not to run the financial play because you feel behind. That’s the quickest way to get and stay behind. Many spent tens of thousands to get rich quickly, only to lose tens of thousands plus tax.

For all that is good and merciful; make a budget and stick to it. I’m not going to lie to you or sugarcoat it. Now is not the time to make bad chess moves. “If you don’t got it, you don’t got it.”

You are better off investing for the future. Most will need at least $1.8M to maintain their lifestyle. Today, the median Gen X household has $93,000 in retirement savings. That’s not enough, not by a long shot.

Millennials Generation

Millennials, ages 28 to 43, are financially distinct. This generation is more racially diverse, better educated, and more tech-savvy than our elders. At this point, we lived through the 2000 tech bust, the 2008-2009 Great Recession, the COVID-19 pandemic, and record-high inflation.

And, we are likely the last generation with a shot to set up generational wealth for future family members. This is the time to double down and pay off debt while investing. Twenty years is a great runway to improve financially. According to a report by the Center for American Progress, millennial wealth grew significantly during and after the pandemic. Some millennials saw their total net worth more than double. How?

Staying employed is one thing. While you should trade opportunities in your early 20s, well into your 30s, you probably shouldn’t chance it. Most people are staying unemployed longer. It’s an excess drain on your wealth. This is like going back for turns in chess while everyone else moves forward. If you are a millennial, don’t lose hope of owning a home. Beyond ownership, those who get married and stay married also increase their long-term prospects. There is a single’s tax and it gets more expensive with age.

Go out and figure out your financial goals and then go home to help build your wealth. Millennials will need over $2.5M to maintain their current lifestyle. As of now, the median retirement savings is closer to $140,000 (5.6% to goal). The future is too expensive to avoid planning for.

Gen Z: The Pawns of Chess

I don’t know about the next batch. Gen Z believes that earning $587,797 annually is adequate for success, along with a net worth of $9,469,847. They are “definitely cooked.”

Although forty-one percent of Gen Z investors (ages 22-27) said they consult their parents and other family members for all things money, most are getting a mixed bag of information from social media. Be careful. For Gen Z, the best thing to do is to learn to be grounded again. They can save a lot of money by learning how to cook, clean, and even pick up their food from restaurants and even grocery stores. The obsession with everything cheap and easy has rendered the latest pawns in this financial chess game, useless.

Beyond that, Gen Z would do better to ease off of credit card debt and invest more. Avoiding the mistakes of millennials and ‘riding shoulder’ on investments will yield a lot of opportunities to retire better than most. I would also recommend not defaulting to the mental health card when things get tough or challenging.

I’m going to be honest here. Most of those kids are going to crash out financially and never retire. They will become the new silent generation by the age of 40. With too many social norms changing, I can’t stress enough why Gen Zers need to relearn and retool in life. May as well start from ground zero before it’s too late.

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