Read Time: 4-minutes
Happy Saturday,
Here is this week’s edition of 6-Point Saturday — financial insights to help you make smarter money decisions.
Table of Contents*
*Clickable in the online version.
Point #1 — Your Money & A Michael Bay Movie
“There was a period in his career when Seth Rogen would feel terrible after watching a great movie.
A writer, actor, and director himself, he’d burn with envy, measuring his writing, acting, and directing against the writing, acting, and directing of whatever brilliant thing he’d just watched.
Then he’d go back to his own work and start twisting and turning it into something more like the thing he envied.
Once, after watching some Michael Bay action movie that blew him away, he wrote a Bay-like action scene for a comedy he was working on.
When he showed the pages to his writing partner Evan Goldberg, Goldberg said, ‘‘What Michael Bay would think of this is what we think when Michael Bay tries to be funny.’ He was just like, ‘We do different things.’’
So Rogen scrapped the action scene, and from then on, whenever he watches a great movie and catches himself ‘feeling like, ‘‘these people are better than I am,’ I go, ‘We do different things.’’ That is something that I now tell myself a lot. And it is something that is very helpful for my psyche—not feeling like I’m in competition with this person, or like that person is taking away from what I’m doing. Because we do different things.”
We see something we admire. We feel a tinge of envy. Then we immediately start twisting ourselves to play a game that was never ours to play.
Whether based on our skills, traits, or abilities, some games aren’t worth playing. On the other hand, we’re also uniquely equipped to excel at others.
This shows up everywhere in our finances. Your friend buys a house and suddenly renting feels like losing. A coworker goes heavily into the next investment trend and your index funds feel boring. Someone from your law school starts a company and staying employed feels like settling.
You were happy until you started measuring yourself against someone playing a completely different game.
This isn’t to say that other games aren’t worth considering. It’s that carefully thinking through the tradeoffs can minimize future regrets.
So, let’s look at 6 tests to consider before you start playing games you later regret.
Point #2 — 6 Tests to Ensure You’re Making the Right Financial Moves (Part 1)
Before you start running someone else’s financial playbook, here are 6 questions to ask yourself:
1. Investing Strategy
The financial news media can make it feel like you always have to be chasing the latest market trends: individual stocks, crypto, and whatever sector is hot (AI, defense, etc.). But research shows most full-time professional fund managers don't beat a simple index fund over the long run.
Ask yourself: Am I picking this investment because it fits my actual financial plan, or because I’m being influenced by others?
2. Buying vs. Renting
Homeownership can be an excellent decision, but it often gets sold as the ultimate American dream. The problem: buying a home you're not ready for to signal that you've “arrived” is one of the most expensive games you can play. And temporarily renting (while investing the difference between your monthly rent and a potential mortgage) can be one of the smartest.
Before you buy, run through these due diligence points:
Do I have 20% down?
Can I cover 1% of the home's value annually for maintenance?
Am I planning to stay at least 7–10 years to break even?
Does this mortgage leave enough cash flow for my other goals?
Ask yourself: Am I buying because this fits my life right now, or because renting gets a bad rap?
3. Spending
Lifestyle spending isn't necessarily an issue — I recommend around 20% of your take-home on anything you like. But spending to signal status to people whose opinion shouldn't matter to you can be problematic. A clear sign you're playing the wrong spending game: you're financing a lifestyle you don't actually enjoy for an audience that isn't really even paying attention.
Ask yourself: Does this purchase bring me genuine value, or am I stretching my finances trying to keep up with my peers or signal success?
Point #3 — 6 Tests to Ensure You’re Making the Right Financial Moves (Part 2)
4. Career Path
If you’re a higher earner, you can be especially vulnerable here. The default game is “more”: a higher title, a more prestigious role, and a higher-profile company. But things like prestige and personal fulfillment aren’t always part of the same game. It’s better to consider what combination of income, autonomy, flexibility, and impact is optimal for you.
Ask yourself: Am I pursuing this role because it moves me toward the life I want, or because it's what society says success looks like?
5. Employee vs. Entrepreneur
Entrepreneurship has been the trendy and glamorized choice for years. But this doesn’t necessarily mean it’s the right game for you.
Being a top employee is an underrated game. At least if you embrace AI to enhance your value amid AI-related layoffs. So, before automatically assuming entrepreneurship is the best game to play, be honest about:
Whether you’re willing to trade more hours for more autonomy and equity?
How do you actually handle financial risk and uncertainty?
Can you wear every hat — sales, marketing, finance, operations — at least well enough to get started?
Ask yourself: Am I drawn to entrepreneurship because it fits who I am and my priorities overall, or because it seems like what others are doing?
6. Retirement Timeline
The FIRE movement (Financial Independence, Retire Early) became the aspirational default for many high earners. And for some people, it's genuinely the right game.
But aggressive early retirement optimization can have a cost: years of extreme frugality, delayed spending, and a finish line people regret.
Ask yourself: Am I targeting early retirement because it fits my spending goals today and down the road, or because retiring at 45 sounds like “winning”?
Your Move: Which of these areas is most relevant to you right now? Are you playing the game that makes the most sense for you?
Point #4 — “It’s a Weird Mental Hurdle”
“…I (37M) have been at a Big Tech company for a while, and I've always been a "buy and hold" person with my RSUs. Usually, I only sell maybe 20% just to fund big purchases and let the rest ride. It's worked out well so far, and I have no major debts. My cars are paid off, no student loans, etc. I have a healthy 401k balance, max out Mega Roth, leverage ESPP, and do all the things I've learned from this subreddit over the years (Brokerage account, HYSA, 529 plans). The biggest expenses we have are childcare and the mortgage for our current home.
My wife and I have 18mo twin boys now and we're looking at an upgrade to a "forever home". Having the extra space would be a nice-to-have when the kids are this young, but I suspect it will be a must-have in the next 2-3 years. My current home has a really good interest rate from back in 2020, so it feels painful to give that up. I also just got a promotion too, which is great for the TComp, but honestly even with the bump, the prices here are just insane. I live in Seattle. To actually afford the upgrade and not have a mortgage that makes me sweat every month, I'm going to have to sell way more stock than I'm used to.
I do have a healthy amount of equity in my current home and plan to put it on the market to aid in the down payment. Also, the plan would be to sell like 40% of my upcoming RSUs this year to help fund both the new mortgage and living expenses and then maybe 30-40% every year after that to keep our cash flow healthy.
I’m feeling a lot of FOMO about it. My company stock has been the main way we built wealth, and it feels weird to stop "stacking" it. But at the same time, our base salaries definitely don't cover an upgrade like this in a good neighborhood, and I don't want to be "house poor" even with the promo.
Has anyone else made this shift? Is it normal to "liquidate" like this once you have kids and need to move up or is there something I am missing? I feel like I'm moving from being an investor to just someone paying for a lifestyle and it's a weird mental hurdle.
This individual is doing a lot right between their investing accounts and overall planning. But did you notice the game they’ve been playing?
They’re in accumulation mode: stacking equity compensation, growing net worth, letting it ride. It's a great game, and it’s clearly working for them.
The problem is that accumulation mode can become its own trap. When you've played it long enough, switching feels like losing.
So they frame the upgrade as "just someone paying for a lifestyle.” As if spending the wealth they built, on the life they built it for, is somehow a step backward. When it’s actually the whole point.
At some stage, the game has to shift from building wealth to deploying it toward the things that actually matter to you. A forever home for twin boys in Seattle isn't lifestyle creep. It's the game paying off exactly as it should.
The key to getting over this mental hurdle? Revisiting your values and reminding yourself what you’ve actually been building toward. So that when the moment comes to spend it, it feels like winning instead of losing.
Point #5 — Quotes of the Week
Which of these quotes resonates most with you?
“It is the eyes of others and not our own eyes that ruin us. If all the world were blind except myself I should not care for fine clothes or furniture.”
“Define the game you’re playing, and make sure your actions are not being influenced by people playing a different game.”
“Ignore people playing status games. They gain status by attacking people playing wealth creation games.”
Point #6 — My Question of the Week
If nobody in your life could see your financial decisions, what would you do differently? What would your finances look like if you designed them entirely around your own values (and no one else's)?
Reply to let me know! I read every response.
Thanks for reading — I hope you found a helpful idea or two.
I’ll see you next Saturday with more.
Have a great weekend,
Benjamin Daniel, CFP®
Founder, Money Wisdom
P.S. Want to take control of your money, stop stressing about your expenses, & feel confident about your financial future? There are 2 ways I can help you:
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Disclaimer:
This material is not investment or tax advice. No responsibility for loss occasioned to any person or corporate body acting or refraining to act as a result of reading this material can be accepted by the publisher.
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