“Insurance is the only product the seller and the buyer hope is never used.”
Which is probably why most people set it up once and never look at it again. The policy renews automatically. The premium comes out of the account. Nothing goes wrong, so there’s no reason to think about it.
But in the background, your circumstances don’t stay “set-it-and-forget-it.” Income moves. Business complexity moves. Net worth moves. (Ideally, all of these move up and to the right.)
For business owners, it’s also the number of employees depending on you. The operating costs that would still come due if you were sidelined for six months.
Your assets have accumulated since you chose a coverage number who knows how long ago.
Insurance isn’t a one-time decision — it’s an ongoing, breathing part of your financial plan. Coverage that fit at 35 isn’t necessarily wrong at 45. But you should take time to verify.
For a high earner with a growing business, a key partnership, or multiple income streams, the gap between what you have and what you need doesn’t stay small. And the faster the growth or complexity come in, the faster your gap widens.
Here are four areas worth looking at before Q4 planning season starts.
1 – Life Insurance: Does the Amount Still Fit?
Life insurance is the coverage most people feel settled about because it’s the easiest one to get into place. With a policy in force and the beneficiary named, it feels handled.
But you the policy value at a particular moment in time — likely one with a lower income, a larger mortgage relative to your assets, and younger children. As income has grown and assets have compounded, the picture may have shifted. Whether the original coverage still reflects your household’s actual needs is worth asking honestly.
For the business owner
For business owners and partners, there are additional layers: key-man coverage, buy-sell agreement funding, partnership continuity.
Those are business continuity questions as much as personal ones, and they deserve their own analysis.
For now, the simpler starting point is the personal question: “does the amount your family would receive reflect the life you’re actually living?”
2 – Disability Insurance: The Math Is Worse Than You Think
Disability insurance is the understudy for your income — it steps in when illness or injury takes you off the stage. The question most high earners haven’t asked is how much of the show it actually covers.
If you’re a W2 employee or a partner drawing salary, your group LTD policy likely covers around 60% of your base salary, up to a monthly cap that often sits between $10,000 and $15,000.
That sounds reasonable until you run the actual numbers.
For someone with total compensation of $400,000 (including bonus, profit sharing, or K-1 distributions) real income replacement from a standard group LTD policy may land at 25 to 35 cents on the dollar. Bonus and variable income almost never count. Group LTD is calculated on base salary, and the cap is absolute.
Most people are surprised it’s this low, and honestly a bit unsettled that they didn’t even know to check.
An individual supplemental disability policy fills this gap.
Most high earners don’t have one.
For the business owner
If you own the business, the problem has two layers. First, there’s often no meaningful group coverage for the owner at all. Second, even if your personal income is covered, the business isn’t.
There’s a product built specifically for this: business overhead expense (BOE) insurance. It covers the firm’s operating costs (think: payroll, rent, utilities, lease obligations) while you’re unable to work.
Without it, the business you spent years building runs down at the same rate you’re recovering. When we raise BOE in insurance reviews, the response is usually some version of: “I’ve never heard of this.”
3 – Umbrella Insurance: Net Worth Has a Way of Outrunning Coverage
A $1 million umbrella policy felt substantial when your net worth was $400,000. It’s a different conversation at $3 million.
Umbrella policies sit above your auto and homeowner’s liability coverage, designed to step in when a lawsuit or claim moves past your primary limits. They’re also among the most cost-effective coverage options available, and one of the most frequently underweighted as net worth grows.
The math is relatively simple: your umbrella limit should bear some relationship to your exposed net worth. If it hasn’t been revisited since you first bought it, it probably hasn’t kept pace. Bonus: it’s also the easiest of the four to address.
4 – Long-Term Care: The Window You Don’t See Closing
Unlike most insurance decisions, long-term care has a closing window most people miss. LTC premiums are meaningfully lower for people who lock in before 60 — in some cases, dramatically lower. Many carriers have tightened their underwriting standards significantly over the past decade. The health requirements to qualify get stricter with age, not more forgiving.
The moment most people first think seriously about LTC is when they watch a parent navigate it. It’s clarifying in a visceral way. It also sometimes comes too late for favorable terms.
If you’ve recently had the conversation about aging parents (e.g., what documents are in place, who’s responsible for what decisions) the natural next question is whether your own coverage is arranged so your kids aren’t having the same conversation about you in twenty years. It’s not usually comfortable to sit with, but still the right question.
The Pattern We Keep Seeing
Most people don’t neglect their insurance out of procrastination. They simply don’t think about it. There’s no annual reminder, no dashboard, no notification that your coverage has drifted out of step with your life.
The thing that actually puts it back on the radar is rarely positive. It’s watching a friend’s business get sidelined for six months. It’s a parent’s long-term care situation forcing a hard conversation about documents and decisions. It’s someone close to you finding out, the expensive way, that group LTD doesn’t cover what they thought.
Insurance doesn’t fail because people forget to think about it.
It fails because nothing ever asks them to.
Before Q4 planning season takes over (or before circumstances force the question) this is worth 30 minutes on your own terms instead of someone else’s.
Stop running on assumptions. Get LTD number that reflect what you actually earn. Make the LTC decision before it’s urgent, not after. Ensure your umbrella reflects what you’ve built, not what you had.If your income has grown meaningfully since the last time anyone looked at this, that’s reason enough. We’d be glad to work through it with you.
