Financial Planning
By Robert Grosman · Published July 21, 2026
The most expensive financial mistakes are rarely dramatic. Nobody loses their future in one bad afternoon. Instead, the damage comes from quiet, common, entirely rationalizable habits that compound in the wrong direction for years. These are the five I see most often — across individual clients and the business owners I work with most closely — and the fix for each.
People carry insurance on the car, the house, even the phone — and leave completely uncovered the income that pays for all of them. For a business owner, that income often funds payroll too, not just the household. Yet a long illness or injury is statistically far more likely during a career than a house fire.
The fix: treat income protection as non-negotiable infrastructure. That means adequate life insurance for your family and own-occupation disability coverage for yourself.
“After the promotion.” “Once the business stabilizes.” “Next year, when things settle down.” The problem: insurance is priced on age and health, and both move in one direction only. Waiting five years means paying more for the same coverage — and a single health event in the meantime can raise the price dramatically or close the door entirely.
The fix: buy insurability while you have it. Coverage secured young and healthy is the cheapest it will ever be.
A 401(k) from this job, a forgotten one from the last job, an old life policy someone sold you at 25, a brokerage account — none of them aware of the others. I see the business version of this constantly too: key person coverage bought once and never revisited, a buy-sell agreement funded to a valuation from five years ago.
The fix: a coordinated review that puts every piece on one page and checks the whole against your actual goals. This is the core of real financial planning.
How your money is taxed on the way out matters as much as how it grows. Households that save exclusively in pre-tax accounts sometimes discover that required withdrawals in retirement land them in a higher bracket than they ever expected.
The fix: think in buckets, not balances. Strategies for building tax-advantaged flexibility are a core part of our retirement planning work.
A plan built when you were single and renting doesn't fit a married homeowner with two kids and a business. Beneficiaries go stale. Coverage sized for one salary quietly becomes inadequate — or a business that's tripled in value since the buy-sell agreement was signed. The plan wasn't wrong; it expired.
The fix: review annually and at every major life event. An hour a year is the cheapest insurance there is.
None of these feel like mistakes while you're making them — that's what makes them expensive. Mine is free and comes with no obligation; the worst outcome is confirmation that you're on track.
Delay, in every form. Delayed insurance costs insurability, delayed saving costs compounding, delayed reviews let small gaps grow.
Annually at minimum, plus after any major life or business event. Most reviews take an hour and most changes are small.
Not strictly, but every mistake on this list is easiest to see from outside your own household or business. My job is pattern recognition — I've watched these five play out hundreds of times.
This article is for general educational purposes and does not constitute specific financial, tax, or legal advice. Individual circumstances vary. Consult with a licensed advisor, accountant, or attorney before making financial decisions.