Financial Mistakes I’ve Made + How to Avoid Them

We’ve all made financial choices we’re not proud of. Some of mine cost me tens of thousands of dollars.

These mistakes happened years ago, but the lessons still hold up, and honestly feel just as relevant today. That’s because it was never really about the tactics, which account to use, which investment to consider. It was about adaptability and resourcefulness in a world that keeps changing. If I were making these same decisions today, I’d use very different tools, including some AI ones.

Here are my five most expensive mistakes, what I learned from them, and what I’d do differently if I were in that situation today.

Disclaimer: everything here is based on my own experience and what I’ve learned along the way. I’m not a licensed tax, legal, or financial professional, so please treat this as a starting point for your own research, not professional advice. When in doubt, talk to an actual expert about your specific situation.

Mistake #1: Not Researching Before Buying My First House

I picked a random agent based on meeting him at an open house, and trusted him because he “seemed nice.” That was it. That was my whole vetting process.

He was new to the field, with barely any experience, but I didn’t know that because I never looked him up. No reviews, no client history, no interview with anyone else. When I asked about negotiating, his advice was that we shouldn’t lowball the sellers because “it’s frowned upon.” This was 2012. The market was terrible. I had all the leverage in the world, and I was in no rush at all. I still didn’t push.

The house itself was lovely, and I have genuinely good memories there (if you believe a house can be a blessing, this one was). But it also came with a retaining wall that made it a real headache to sell years later.

The bigger issue wasn’t the agent. It’s that I never researched the market myself. I had no idea what anything was actually supposed to cost.

If you’re buying now, do this instead: Track comparable listings over time in a simple spreadsheet. Log:

• Beds and baths
• Year built
• Amenities
• What they actually sold for

Once you have that data, you can look at a new listing and estimate what it should cost, instead of trusting whatever number is attached to it.

That mistake cost me thousands, maybe tens of thousands, between overpaying and the harder time selling later.

To be clear, the lesson isn’t “trust no one.” There’s a happy medium between too trusting and too cynical. Trust people, assume good intentions, but verify everything anyway.

These days, when I’m hiring any professional (realtor, mortgage broker, whoever), I always look at multiple options and do my own research to compare against their advice. I used to feel rude questioning people or shopping around. Now I see it as a mutually beneficial relationship. Sometimes it’s just not the right fit, and that’s fine for both sides.

If I were making this decision today, I’d also be using AI as part of my background research, on top of the usual Zillow, Redfin, and MLS data. A prompt like this works well:

“Summarize the last five years of housing price changes for zip code [your zip code], and any local news that could affect property values.”

I tried this for my own zip code and it was spot on (always verify anything like this against public records, but it’s a strong starting point). The lesson isn’t this exact prompt. It’s taking your research seriously and using whatever resources are available to you at the time.

Mistake #2: Not Setting Long-Term Goals

If you know me now, you know me as the planner. That wasn’t always true.

Back in my younger years, I just spent what I had. I never went into debt for things I wanted (that was a hard rule), but if I had $1,000 for the month, I’d cover rent and basic expenses and spend the rest. No emergency fund. Barely any savings.

One surprise expense near the end of college showed me exactly how precarious that was. Month to month, I got by. I never went negative. But I was one emergency repair, one unexpected bill, away from suddenly needing to take on debt.

I was lucky to have my parents as a kind of “get out of jail free” card. It didn’t feel good leaning on that. I promised myself: never again.

So I built an emergency fund, and I started actually planning and saving for future wants and needs: a house, retirement, a big wedding (three, actually, and we enjoyed every single one of them). Even on a $40,000 resident salary in a high cost city like LA, I built up an emergency buffer and contributed to my 401(k) at the same time. The amount wasn’t huge. But the time in the market mattered more than the size of the contribution.

Today, with how quickly industries can shift, that safety net isn’t just about peace of mind. It’s the cushion that buys you time to pivot if your job, or your entire field, changes without warning.

Mistake #3: Buying Stuff Without Intention

To be fair, it’s normal and fine for your spending to go up as your income goes up. There’s nothing wrong with enjoying more expensive things if you can actually afford them.

My mistake was different: I was shopping without any intention behind it. Going from resident to full pharmacist was a big income jump, and as a DINK couple (dual income, no kids), suddenly a lot of purchases felt accessible that hadn’t before. Just because you can afford something doesn’t mean you should buy it, and that’s a lesson we learned the hard way.

Social media didn’t help. This was the peak fashion and beauty YouTube era, and it normalized endless shopping for me. Add in concerts, restaurants, travel, and, at one point, a vinyl collection. The sky felt like the limit.

To be completely transparent, I had a great time. I enjoyed all of it. 

But, looking back on the thousands we spent, sometimes on unnecessary stuff, both material and experiences, the first lesson is simple: we could have bought half of what we bought and been just as happy. We’ve decluttered bags and bags of it since, and not every experience was actually worth what we paid for it.

The bigger lesson was about unconscious social pressure. I never thought I was trying to keep up with the Joneses, but I was definitely shaped by what felt “normal” in our circles. When everyone around you is talking about a new restaurant, or a trip they just took, or how they’re dressing for events, it creates a baseline of what feels like reasonable spending, even if you’re not actively trying to match anyone.

Here’s the thing: you don’t actually know what’s funding other people’s lifestyles. Maybe they’re wealthier than you. Maybe they’re making bad financial choices and going into debt for it. Maybe they just prioritize different things than you do.

Today that pressure is even sneakier, thanks to social media. Algorithms feed you tailored ads, influencers make luxuries look normal, and you end up watching the lifestyles of people who wouldn’t normally be anywhere near your day to day circle. Subconsciously, that reshapes what you perceive as a “societal norm.”

The lesson isn’t to become a hermit or stop spending on anything fun. It’s to be intentional:

• Shopping. Instead of buying five sale items that are “good enough,” save up for the one thing you actually want.
• Experiences. Instead of five “fine” meals out of convenience, pick the one amazing restaurant and make it a special occasion.

Pay attention to how your environment, including internet strangers (myself included), is shaping your spending. That influence is real, even when it’s unconscious.

Mistake #4: Missing Out on the Backdoor Roth, 529, and 457(b)

This one really stings, because it’s literally free money I left on the table for years.

I thought I was being responsible. I knew about the 401(k) and the match, I had an HSA, I was doing all the “right” things. But I missed three legitimate accounts:

• Backdoor Roth. I just assumed I wasn’t eligible for a Roth IRA and left it at that. By the time I figured it out, it was years later, and there’s no fun way to think about the thousands, maybe tens of thousands, in tax-free growth I missed out on.
• 529. I didn’t pay close attention to exactly how much would be deductible from our state taxes. I mostly ignored it, thinking, isn’t this basically the same as every other tax-advantaged account? The point is that a Roth alone won’t be enough, and your other retirement accounts aren’t accessible yet when you actually need flexibility earlier in life.
• 457(b). I had no idea this even existed. Turns out, through my employer, I had access to an account that let me save another $23,000 tax free every year, on top of my 401(k) limit. The bigger advantage: you can access it when you leave your job, regardless of age, which lines up far better with an early retirement goal than a traditional 401(k) or 403(b) does.

Had I known this earlier, I probably would have contributed very differently.

I know the specifics of my situation won’t apply to everyone reading this, and the lesson isn’t really about these exact accounts.

It’s that financial illiteracy costs real money.

Take the time to research what benefits and accounts are actually available to you specifically. Don’t assume. Ask HR, talk to an accountant, or just start with Google and Reddit and figure out how things actually work.

This matters even more today, with policy changes, financial products, and entire asset classes shifting constantly. Not knowing can get expensive fast (though maybe not as expensive as handing your whole portfolio to an advisor charging 1% AUM who also sells you whole life insurance, but that’s a rant for a different day).

Mistake #5: Staying Too Narrow-Minded About What Counts as a “Good” Financial Decision

To be clear upfront, I’m not saying abandon the fundamentals. I still treat those as the foundation, and the majority, of my strategy.

But once I had a solid base, my mistake was assuming that was all there was. I had a narrow view of what a “good” financial decision looked like. Credit where it’s due, that view came from solid teachings from my parents. But there’s more than one way to climb a mountain, and I didn’t see past the one path I knew.

A good example: when we were selling the house with that annoying retaining wall, the thought of turning it into a rental briefly crossed my mind. I looked at the cash flow (rent minus mortgage, taxes, and repairs): a small amount of money for a lot of hassle, taxed at a high rate on top of it. Not worth it.

I missed the full picture:

• I wasn’t thinking about diversifying income streams or asset classes.
• I was completely unaware of the tax advantages, and incorrectly assumed the cash flow would be mostly taxable. It probably wouldn’t have been, once depreciation offset that income.
• I overlooked the equity that would have built as the mortgage got paid down every month, at an insanely low interest rate.

The same blind spot showed up with this YouTube channel. I actually thought about starting one almost ten years ago. I had a travel blog back then, other content ideas floating around, but I never pulled the trigger. It wasn’t fear, or equipment, or lack of time. This was pre-kids. I had so much time.

Honestly, it was just a “high income earner” blind spot: why would I spend time on something that might make $100 in a few months if I’m lucky, when I could pick up an extra shift and make way more? That’s hourly-rate thinking, not wealth-building thinking. I didn’t see it as a long-term business play, didn’t consider the passive income potential, and didn’t factor in that I’d learn entirely new skills and get to scratch a creative itch along the way.

I know millennials get criticized for monetizing every hobby, and I’m not telling you to turn everything into a side hustle. There’s a healthy balance between ignoring opportunities entirely and overdoing it to the point where every enjoyable experience becomes a transaction.

The main lesson is just to stay curious. Don’t assume the basic path is the only path. I’m not saying everyone should run an Airbnb or start a YouTube channel (both come with their own risks and learning curve), but once you’ve got a solid financial foundation, keep learning. Real estate, other businesses, different asset classes, and how technological and geopolitical shifts might affect you. Learn enough to actually make an informed decision.

What I Learned Looking Back

Looking back on the past decade plus, these were the biggest, most expensive lessons I’ve learned. Zooming out, they taught me two main things:

1. Financial literacy isn’t just nice to have. It literally pays.
2. I wouldn’t trade the experiences of learning these lessons. This is the bigger one. The goal was never to optimize every dollar or live like a monk in your twenties. It’s to be intentional with your money so it can actually support the life you want to live, both now and later. Sometimes that means spending on things that bring you joy. Sometimes it means being smarter about the boring stuff so you have more freedom down the road. Sometimes, like in this post, it means making the ridiculous mistakes and learning from them anyway.

I did my best at the time. My “best” has just evolved since then, and honestly, that’s exactly how it should go.

What’s one financial decision you learned the expensive way? 

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