Learning From Missed Opportunities: How Financial Advisors Can Be Proactive, Not Reactive

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Common wisdom suggests that you regret more of the things you didn’t do, rather than what you did do. While this usually applies to adventures like skydiving or saying “yes” to a spontaneous road trip across the country, I often see this aphorism in action among financial advisors. These are advisors who recognized an opportunity too late or missed something in a client’s retirement plan that could’ve helped them retire sooner.

To help others avoid the same fate, I’m sharing a real-life case for financial advisors to learn from. This story will show advisors how they can be more proactive, rather than reactive, when it comes to an important component of early retirement planning.

A $25k “Miss”

An advisor I met with showed me a $25,344 "miss." He shared it specifically because the missed opportunity was related to the client’s healthcare costs.

This advisor’s client, who was spending $40,000 per year on COBRA (about $3,400 per month), was under 59.5 years old. To avoid penalties on early IRA withdrawals, they were pulling from non-taxable assets first. That kept their MAGI low enough to qualify for Marketplace ACA subsidies — $2,112 per month to be exact.

After subsidies, their Marketplace options started at $3 per month. Not $300. Not $30. $3.

Unfortunately, by the time the advisor brought the client to Move Health, they were already locked into COBRA for the year.

How Did This Happen?

The advisor didn't miss this on purpose. High premiums came up in their bi-annual planning conversation just the week before the discovery. It was only missed because the advisor started the conversation three months too late.

A $25,344 opportunity was missed because the healthcare planning conversation happened after a decision point.

What Should Have Been Done

I hinted at the solution already — this was a case of bad timing. The advisor didn’t identify the missed opportunity until three months after the client was already enrolled in a COBRA plan.

The advisor knew his client was retiring early and would lose employer-sponsored health insurance. However, at the time, the advisor didn’t have the resources to guide his client through healthcare planning decisions. Hindsight is 20/20; after partnering with Move Health, the advisor wished he’d partnered with us sooner to help this client in time.

Regardless of teaming up with a healthcare planning partner, there are key timelines every financial advisor should know when it comes to health insurance and early retirement. Not knowing them means missing out on big opportunities for yourself and your clients.

Key Early Retirement & Health Insurance Timelines Every Advisor Should Know

If your client is going to retire before the age of 65 (the age of Medicare eligibility), you’ll need to have a conversation with them about their healthcare coverage at least two months before their retirement date. Ideally, you’ll have the initial conversation six months before, so you can then have deeper conversations over the next few months.

Why the two-month minimum? Because after losing employer-sponsored healthcare coverage, clients have a 60-day Special Enrollment Period to enroll in COBRA or the Marketplace. The 60-day countdown begins the day they lose employer-sponsored coverage.

However, clients can enroll as early as 60 days before their loss of coverage date. If clients miss their Special Enrollment Period, they won’t be able to enroll in COBRA coverage at all, and won’t be able to enroll in ACA Marketplace coverage until the Open Enrollment period in the fall.

Here’s how financial advisors can implement these tips with any pre-65 retiree client, at any time of the year:

90–120 days before the client’s retirement date: Discuss their healthcare coverage enrollment timeline.
- They can enroll in COBRA or ACA Marketplace coverage as early as 60 days before their retirement date and as late as 60 days after. If they miss this window, they are ineligible to enroll in COBRA and can’t enroll in ACA coverage until the next Open Enrollment period.
60 days before the client’s retirement date: Identify the specific health plan or coverage option the client needs to enroll in.
60 days before to 60 days after the client’s retirement date: Get the client enrolled in their ideal plan, either through a healthcare planning partner or on their own with your guidance.
Annually: Review the client’s coverage, health plan needs, budget, and preferences each year during the Open Enrollment period. Plan costs, networks, and other details change each year. The plan that was best for them in 2026 may not be the plan that’s best for them in 2027.

Another way to be proactive about healthcare planning is to work certain activities into your service calendar. Judson Meinhart with Modera Wealth Management, Jenifer Fensley with CapSouth Wealth Management, and Clifford P. Haugen with BLBB Advisors all have great tips on how to do that in this video.

Final Thoughts

No one likes that heart-drop feeling of missing an important detail. And yet, this happens all too often when it comes to healthcare planning. Healthcare and health insurance are complex topics. Without an expert or the right resources, it can be very difficult for financial advisors to do on their own.

My challenge to the financial advisors reading this: Go into your CRM and find all your clients who are younger than 65 and retiring this year. Use the timeline I shared above to set up meetings to discuss their health insurance options. Include dates in your CRM for when you need to discuss options and when they need to enroll in coverage. You’ll set yourself and your clients up for success if you do.

Cole is the Head of Growth at Move Health. He has a passion for empowering and informing healthcare consumers through effective healthcare planning. Cole co-founded Move Health after recognizing that financial advisors and their clients were under-resourced and uninformed when it came to healthcare planning, despite healthcare being a top financial concern for Americans nearing retirement. Cole works every day with the Move Health team to further their mission of making health coverage simple and clear.

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