7 Retirement Mistakes to Avoid for a Secure Future

Okay y’all… retirement mistakes. Man. If there’s one topic that makes my stomach do that weird flippy thing even now in 2026, it’s this.

I’m currently sitting here in my cramped home office in the US (think flickering LED bulb, half-dead ficus plant, empty Monster can from yesterday), staring at yet another Vanguard email reminding me my catch-up contributions window is wide open… and I’m still playing catch-up from mistakes I made when I was dumber and thought “eh, I’ve got time.”

So here are the 7 retirement mistakes I either personally committed or watched way too many friends commit — and the stuff I’m desperately trying to fix so I don’t end up eating cat food in 2045.

1. Thinking “I’ll Start Saving Seriously Next Year” (aka The Classic Retirement Mistake)

Look. In 2018 I was making decent money for the first time. I bought a stupidly expensive espresso machine instead of maxing my 401(k). I told myself “next year I’ll get serious.”

Next year became 2019 → 2020 (pandemic) → 2021 (supply chain everything) → 2022 (inflation ate my soul) → and here we are.

Compound interest is brutal when you keep kicking the can.

If I could slap past-me, I would. Start small. Even $50/paycheck into a Roth IRA is better than zero. Vanguard has a nice simple page explaining why starting early literally saves you hundreds of thousands.

foodandwine.com

2. Not Understanding How Insanely Expensive Healthcare Gets After 65

I didn’t. I really didn’t.

I assumed Medicare = free healthcare forever. LOL no.

Between Part B premiums, Medigap, Part D drug plans, deductibles, Retirement Mistakes and the fact that the average 65-year-old couple needs something like $315,000 just for healthcare in retirement (Fidelity’s 2025 estimate — yeah it went up again), I was living in fantasy land.

I now have a separate HSA that I’m actually funding aggressively because future medical bills scare me more than the dark.

Read Fidelity’s latest retiree health care cost estimate here if you want to feel nauseous too: https://www.fidelity.com/viewpoints/personal-finance/plan-for-health-care-costs

3. Keeping Too Much Money in Cash Because “The Market Is Scary”

2022 flashbacks. Everything red. I pulled a chunky portion out of stocks and parked it in a high-yield savings… at like 0.6% at the time.

Then inflation went brrrrr and that cash lost purchasing power while the market eventually recovered.

Biggest retirement mistake I personally made: market timing.

I’m never doing that again. Dollar-cost averaging into broad index funds until I’m at least 70% stocks / 30% bonds feels way saner now.

4. Ignoring the Roth vs Traditional Debate Entirely

I just picked traditional 401(k) because “tax break now, yay!”

Meanwhile my current tax bracket is actually lower than I expect it to be in retirement (weird flex but okay).

I wish I’d split contributions between Roth and traditional. The tax diversification is huge.

The IRS has a decent Roth vs Traditional explainer: https://www.irs.gov/retirement-plans/roth-comparison-chart

seekingalpha.com

5. Not Having a Realistic Withdrawal Strategy (4% Rule Blind Faith)

Everyone quotes the 4% rule like it’s gospel.

I read too many horror stories on Bogleheads forum about sequence-of-returns risk wiping people out in early retirement.

Now I’m leaning more toward 3.3–3.5% initial withdrawal + flexible spending in bad years.

Super boring but I sleep better.

6. Forgetting About Long-Term Care (The Silent Retirement Killer)

My grandma needed in-home care for four years. Cost? North of $280,000 after insurance.

Nobody talks about this until it’s too late.

I’m looking at long-term care insurance quotes now even though it feels like throwing money away… because the alternative is way worse.

7. Waiting Until “I Have It All Figured Out” to Talk to a Fee-Only Fiduciary

I avoided financial planners because I thought they were all salesy commission vampires.

Then I met a legit CFP who charges flat hourly or AUM but is actually a fiduciary.

Huge difference. One session saved me probably $40k in future tax hits just by rearranging some old accounts.

If you’re scared, start with XY Planning Network or Garrett Planning Network — hourly fiduciaries who don’t require you to be a millionaire.

Okay… deep breath.

I’m still not perfect. My emergency fund is okay but not great. My asset allocation is still too conservative for my age according to some models. I definitely ate too much avocado toast in my 30s.