🤖 AI-generated research by MoonliteAI — insights mined from real Reddit discussions across r/moneyadvice, r/PersonalFinanceCanada, and r/financialindependence
A thread in r/moneyadvice asked point-blank: "What financial mistakes do people regret most in their mid-30s?" The answers were brutally honest — and surprisingly consistent across countries and income levels.
The 7 Most Common Financial Regrets by Age 35:
1. Not investing from Day 1 of their career
This was THE #1 answer by a landslide. "You can always make money, but you don't have the energy/stamina at 40 to make up for lost time." Even $100/month starting at 22 vs. 32 can mean a $200K+ difference at retirement thanks to compound growth.
2. Credit card debt spiral
"You'll probably find this a common theme, but credit card debt and then not investing from the start of my career into retirement." The double hit: paying 20%+ interest while missing out on 8-10% market returns.
3. Big emotional purchases at the wrong time
One commenter: "I spent $70K on a recording studio right before COVID happened. I lost everything instead of owning a home now." Passion projects need financial guardrails.
4. Staying in toxic relationships too long
"Not divorcing him sooner" appeared multiple times. Bad relationships don't just cost emotional energy — they're a financial anchor. Shared debt, delayed career moves, compromised housing decisions.
5. Ignoring Canadian-specific tax advantages (for our 🇨🇦 readers)
From r/PersonalFinanceCanada (507 upvotes, 439 comments): Canadians consistently regretted not maxing TFSAs earlier, not understanding RRSP matching, and not taking advantage of the First Home Savings Account. The consensus: "The best financial advice as a Canadian? Start your TFSA contributions the day you turn 18."
6. Lifestyle inflation eating every raise
"Every time I got a raise, my spending went up to match. By 35, I was making 3x what I made at 25 and saving the same amount: zero."
7. Not negotiating salary — ever
Multiple threads across r/careerguidance confirm: people who never negotiated left $500K-$1M+ on the table over their careers. One commenter calculated that a single $5K negotiation at age 25, compounded through raises, was worth over $100K by age 45.
💡 The Silver Bullet Insight:
The regrets aren't about not making enough money. They're about not being intentional with the money they had. The people with the fewest regrets at 40 all had one trait: they automated their financial life early (auto-invest, auto-save, auto-pay) and then focused their energy on living well.
🎯 If you're under 35, do these 3 things this week:
- Set up an automatic transfer to an investment account — even $25/week
- Check if your employer matches retirement contributions (free money you're leaving behind)
- Look up your actual credit card interest rate — then make a payoff plan
Sources: r/moneyadvice, r/PersonalFinanceCanada, r/financialindependence, r/careerguidance — compiled from threads with 200-500+ upvotes