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Financial decisions

73 dilemmas

Debt, investing, insurance, credit — the money decisions that keep you up at night. We break down the numbers and the emotions behind each one.

Lead story

Pay off the mortgage early or invest the difference in the S&P 500?

The spreadsheet said invest — 10% historical returns beats 6.5% interest. The stomach said debt-free by 50.

10 min22,340 readersApr 3, 2026

Pay off the mortgage47%

Invest the difference53%

I have $30k in student loans and $30k in savings. Do I wipe the slate?

Paying it off means freedom from the monthly drain. Keeping the cash means an emergency fund that actually works.

8 min14,560 readersMar 28, 2026

Pay off the loans now44%

Keep the safety net56%

YNAB or 'vibes-based budgeting' — does tracking every dollar actually work?

The YNAB evangelists swear it changed their lives. The rest of us tried it for three weeks and felt like we were auditing ourselves.

6 min8,890 readersMar 21, 2026

Track every dollar53%

Automate and stop worrying47%

Term life vs whole life insurance — the $500k question at 35

The agent pushes whole life: 'it builds cash value.' The internet screams term: 'invest the difference.'

9 min11,780 readersMar 17, 2026

Term — keep it simple71%

Whole life — long game29%

High-deductible health plan or traditional PPO?

The HDHP saves $200/month and comes with an HSA. The PPO costs more but covers the unexpected.

8 min9,450 readersMar 14, 2026

HDHP + HSA46%

Traditional PPO54%

Do I need life insurance at 28 with no kids?

He had no dependents, no mortgage, no reason anyone would suffer financially if he died tomorrow. But rates lock in young.

5 min6,780 readersMar 10, 2026

Get it now — lock the rate58%

Wait until you need it42%