I receive a lot of questions about finance and life and I do mean a lot. I would say I answer over 100 questions per month for various friends, family, and others. They tend to be the same types of questions, just altered for a specific season of life.
Separately, someone told me that anyone can write an article because you get to pick the topic, research it, and control the narrative.
Challenge accepted! I will attempt to answer real questions from real people as best I can. Sometimes I won’t have a good answer for you and I’ll admit that. Here are questions from July.
Question 1: "I'm 28 with $40K in student loans and no savings. You say to start early, so is it too late for me to achieve FI?"
Max's Answer: No, it's not too late, but you need to get serious about this right now. I didn’t get serious about it until my later 20s, so I know how powerful the time is between 18 and 28.
Let's do the math. If you can get to a 20% savings rate by age 30 and maintain it, you'll reach FI in about 31 years of working, retiring at 61. That's actually better than most Americans who work until they physically can't.
But here's the thing: you're asking the wrong question. The question isn't "Is it too late?" The question is "How fast can I accelerate this?"
If you can pay off that debt and get to a 30% savings rate by 30, you'll retire at 54. Get to 40% and you'll retire at 47. The math doesn't care that you started with debt. It cares about your savings rate going forward.
Your homework: Calculate your current savings rate, then figure out how to increase it by 5% this year. Every percentage point you increase your savings rate cuts months or years off your working life.
Remember: someone who starts investing at 35 with a 40% savings rate will retire before someone who starts at 22 with a 10% savings rate. It's not when you start. It's how much you save.
Remember this handy calculator?
Question 2: "My coworker more than doubled his money last year with Nvidia and Tesla stock. Why would I just buy index funds?"
Max's Answer: Your coworker is going to lose money. Maybe not this year, maybe not next year, but eventually the market will humble them.
Here's what your coworker isn't telling you: they're probably only talking about their winners. Did they mention the stocks that lost 50%? The "sure thing" that went to zero? The hours spent researching companies that still picked losers?
I've seen this story dozens of times. Someone gets lucky with a few stock picks, thinks they've cracked the code, then gets destroyed when their luck runs out. Meanwhile, the boring index fund investor steadily builds wealth.
The S&P 500 returned about 25% in 2024. Your coworker beat it by taking on an extreme amount of individual stock risk. (Oh, and Tesla is down about 17% in 2025 while the S&P 500 is up about 9%.) Studies show that 90% of active fund managers (people with teams of analysts and Bloomberg terminals) can't beat the market consistently. (source) What makes your coworker special?
Index funds aren't exciting. They don't give you bragging rights at parties. But they work. Over any 20-year period, they've never lost money. Can your coworker say the same about their stock picking?
Stick with index funds. Let your coworker gamble. You're building wealth.
Question 3: "Should I pay off my 4% student loans or invest in the stock market?"
Max's Answer: Mathematically, you should invest. The stock market has averaged 10% annually over the long term, so investing should come out ahead.
But math isn't everything.
Here's what I actually recommend: pay off the loans. Why? Because debt payments reduce your flexibility, create monthly obligations, and add stress to your life. When you're debt-free, you own your income.
Plus, paying off a 4% loan gives you a guaranteed 4% return. The stock market might give you 10% on average, but it could also lose 20% next year. The loan payoff is certain.
There's also a psychological factor. Once you're debt-free, you'll probably save even more aggressively because you'll see how much better life feels without monthly payments.
Exception: If your employer offers a 401k match, get the full match first. That's free money. Then pay off debt. Then invest everything else.
The goal isn't to optimize every dollar perfectly. The goal is to build wealth consistently without taking unnecessary risks or creating stress that derails your plan.
Bonus: what if my debt is at 0% or 2%? Mathematically, you should clearly invest. In fact, I did exactly that about a decade ago when interest rates were near zero. However, for most people, I find it better to pay off all debt except for the mortgage. There’s just less temptation to divert the funds to spending.
Question 4: "How do I get my spouse on board with FIRE when they think I'm being too extreme?"
Max's Answer: Stop talking about FIRE and start talking about freedom.
Don't lead with "We need to save 50% of our income so we can retire at 40." That sounds crazy to most people. Instead, talk about what financial independence actually gives you.
Try this: "What would you do if money wasn't a factor?" Let them dream. Travel? Spend more time with kids? Start a nonprofit? Change careers? Then connect those dreams to FI: "What if we could make money optional so you could actually do that?"
Show, don't tell. Start with easy wins that improve your life immediately:
Cut cable and show how much extra money you have
Cook dinner together instead of ordering takeout
Take a (frugal) weekend trip funded by money you saved
Make it collaborative, not dictatorial. Ask for their input on big decisions. "Our car lease is up. Should we buy used and invest the difference, or keep leasing?" Let them see the math.
Most importantly: don't sacrifice everything for FI. If your spouse loves expensive dinners, budget for some expensive dinners. The goal is to optimize your spending, not eliminate all joy.
FI should make your relationship better, not create constant fights about money. Find the middle ground that moves you toward FI without making life miserable.
Also consider that your spouse may be right. Are you being too extreme? An 80% savings rate isn’t realistic.
Want to know some ways to save money that even I think are too extreme? (these are all real things people have done)
Washing and reusing paper plates and ziploc bags
Wearing the same shirt inside-out to get "two days" of wear
Going to hotel continental breakfasts without staying at the hotel
Showering at the gym exclusively to save on hot water bills (even when you're not working out)
Eating the free samples at Costco for lunch every day
Only charging your phone at work to save on electricity
Yes, you might have an 80% savings rate, but you’ll probably end up divorced.
Question 5: "I lost my life savings in the 2008 crash and I'm scared to invest in the stock market right now. Shouldn't I wait for the next crash to invest?"
Max's Answer: You're asking the wrong question. The question isn't "What if the market crashes?" It's "What if I don't invest?"
Let me give you some perspective. Since 1926, the stock market has had a major crash roughly every 10-15 years. 1929, 1973-74, 1987, 2000-2002, 2008-2009, 2020. And you know what happened after every single one? The market recovered and went on to hit new highs.
Here's what's scarier than a market crash: inflation eating away your purchasing power while your money sits in a savings account "safely" earning 2% while inflation runs 3%. You're losing money slowly and predictably instead of risking losing money temporarily and unpredictably.
You said you lost everything in 2008, but it’s unlikely you invested all of your money right at the peak. Still, let’s say you did. Your portfolio loses 50%. Terrible, right? If you held on and kept investing, you'd have fully recovered by 2013 and been way ahead by 2015. The reason you lost money is because you sold at the bottom in 2009.
The solution isn't market timing. It's time in the market. Start investing now, but do it gradually. Invest the same amount every month regardless of what the market does. When it's high, you buy fewer shares. When it crashes, you buy more shares. This is called dollar-cost averaging, and it takes the emotion out of investing.
Remember: you're not investing for next year. You're investing for 20-30 years. Over any 20-year period, the stock market has never lost money. Ever.
The biggest risk isn't a market crash. The biggest risk is letting fear keep you on the sidelines while inflation and opportunity cost destroy your purchasing power.
Start investing today. Your future self will thank you.