Here is a question that has been bugging me for months: do financial advisors actually follow their own advice?
I mean, your dentist probably does not floss every single day. Your doctor has definitely eaten gas station sushi at least once. So what about the people who tell us how to manage money?
I reached out to seven financial advisors — ranging from a 28-year-old CFP to a 61-year-old wealth manager with $200M under management — and asked: "What is your biggest personal money regret?"
1. "I Waited Until 31 to Start Investing" — Rachel, CFP, Age 38
Rachel runs a fee-only financial planning practice in Denver. She did not start her own portfolio until 31.
"I had every excuse. Student loans, a car payment, saving for a wedding. When I finally ran the numbers on what I missed — about $147,000 in compounding over nine years — I literally felt sick."
She now tells every client under 25: "Put in $50 a month. Future you will want to send present you flowers."
(For context, $50/month from age 22 to 31 at 8% average return grows to about $7,800. That $7,800 compounding for another 30 years? That is the $147K Rachel is talking about.)
2. "I Bought a House I Could Not Actually Afford" — Derek, CFA, Age 45
Derek manages portfolios in Chicago. In 2018, he bought at the absolute top of his bank approval: $479,000 on a $485,000 max.
"When the furnace died six months in — $8,200 — I put it on a credit card at 22% interest because I had no emergency fund left."
The irony? "I tell clients every day to buy 20-30% below max approval. I did not do it myself because the house had a nice kitchen and I am apparently not immune to granite countertops."
3. "I Ignored My Own Emotional Spending Patterns" — Priya, CFP, Age 34
Priya specializes in behavioral finance. She spent two years studying money psychology before recognizing her own pattern.
"Every stressful week, I would online shop. $30 here, $45 there. A candle. A kitchen gadget. A throw pillow. It added up to $400-500/month during bad months."
She only caught it testing a budgeting app for a client. "$5,200 in miscellaneous purchases over ten months. I thought the app was broken. It was not broken."
Her fix: a $150/month "stress spending" budget. "Having a boundary made the compulsive part stop."
4. "I Did Not Get Disability Insurance Until After I Needed It" — James, ChFC, Age 52
James is a chartered financial consultant in Atlanta. In 2019, he needed surgery and three months of recovery. No disability insurance.
"I sold disability insurance to clients. I showed them the statistics — 1 in 4 workers disabled before retirement. And I did not have a policy because I kept thinking I would get around to it."
Three months without income: $48,000 lost earnings plus $12,000 in uncovered medical costs.
(The Social Security Administration confirms more than 1 in 4 of today’s 20-year-olds will become disabled before 67. The Council for Disability Awareness reports average long-term disability claims last 34.6 months.)
5. "I Tried to Time the Market in March 2020" — Samantha, CFA, Age 41
Sixteen years in wealth management. When COVID crashed the market, she panicked and sold everything in her personal account.
"I know. I literally wrote a newsletter that week telling clients to stay the course. Then I went home and sold at the bottom."
She bought back in June 2020, missing the fastest recovery in history. Cost: about $34,000 in missed gains.
"Knowing the right answer and doing the right answer are two completely different skills. Your brain does not care about your CFA charter when the market is down 30%."
6. "I Let Lifestyle Creep Eat My Entire Raise" — Omar, CFP, Age 36
Omar went from $65,000 to $140,000 in four years. Savings rate stayed at $400/month.
"Nicer apartment. Tesla. Eating out five times a week. A Peloton I used for three months. It is currently a very expensive coat rack."
His rule now: "Every raise, automatically redirect 50% of the increase to savings before you see it in checking."
7. "I Did Not Have the Insurance Talk With My Parents" — Linda, CLU, Age 61
Her father passed in 2012 without long-term care insurance. Three years in memory care: $267,000. "It wiped out almost everything my mother was supposed to live on."
"I specialize in elder care financial planning. And I never had the conversation with my own parents because it felt awkward." She paused here. This still bothers her, twelve years later.
"Talk to your parents about money. I know it is uncomfortable. Do it anyway."
The Pattern
Seven advisors. Seven regrets. Every one boils down to: knowing what to do is not the same as doing it.
If you feel bad about your money decisions? Cut yourself some slack. Even the experts mess this up. But learn from their mistakes — the tuition was expensive and they are giving it to you free.
Disclaimer: This article is for informational purposes only and does not constitute financial advice. Consult a qualified financial advisor for guidance specific to your situation. Sources: Social Security Administration (ssa.gov), Council for Disability Awareness (disabilitycanhappen.org), Bureau of Labor Statistics (bls.gov).
