Personal Finance

Is my company’s lifetime healthcare plan worth working for 8 more years than I had originally planned on retiring?

Rich Duprey

Published: November 13, 2024 10:43 am

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Achieving our FIRE goals is something we all aspire to, but the targets are different for everyone. Because crossing the threshold gives us options, allowing us to fine tune our plans to achieve optimal results, we need to be careful not to let perfection be the enemy of good.

That’s the case with this Redditor posting in r/ChubbyFIRE, a group dedicated to early retirement with an upper middle class lifestyle.

The Redditor and her husband have $3.5 million saved in pre-tax accounts, Roth IRAs, and after-tax brokerage accounts. At age 52, she could retire today, but has the option of staying on for to qualify for the company’s better healthcare options once she turns 60.

I find the Redditor’s position intriguing because it is a common dilemma many of us face: we’re good now, but could be even better with a little more patience. 

The setup

Healthcare is always an important consideration in retirement planning. Medical expenses are likely going to be one of the biggest costs incurred during your Golden Years so reducing the amount you have to pay ought to be a key component of your plan.

The Redditor’s company offers the chance to remain on its healthcare benefit retirement plan indefinitely once attaining certain criteria, which will happen for her in eight years.

Healthcare premiums will cost $166 per month if she doesn’t use the healthcare savings account (HSA) or $90 per month with the high-deductible HSA. When she turns 65, she then also becomes eligible for the company’s Medicare B plan, which features low copays and deductibles. She has been assured by others on the plan that when there is a significant medical event, the plan is very good.

The problem

Sounds like an easy choice, but the problem is the Redditor is burnt out from her job, rather bored with her position, and she needs a break. Unfortunately, the company doesn’t allow for unpaid leave without cause, such as caring for a sick family member.

She’s looked at the health insurance plans available under the Affordable Care Act, otherwise known as Obamacare, and the premiums are onerous. They could run as high as $13,000 annually, far more than her employer’s premiums. She also fears getting a terminal illness that could wipe out a large part of their savings.

The question becomes, should she stay at her job for another eight years or, because they have largely reached their FIRE goals, quit and accept the costs of an Obamacare plan?

The recommendation

While not having intimate knowledge of the Redditor’s exact situation, but rather just a broad overview, it makes it difficult to provide specific guidance. I’m not a professional advisor, so this is ultimately my personal opinion on how I would do it.

Time is short and the benefits available, while good, are not great and there are so many unknowns ahead during the eight years needed to get them. Her health could rapidly deteriorate before then, the company might go out of business, the benefits could change between now and then, etc. 

It is also not like the Redditor is happy with and enjoys her job. The next eight years would be a grueling slog, increasing her unhappiness over time. She could also suffer a heart attack and die the day after attaining the benefit.

Contrast that with having that time to actually enjoy life and being happy. While her costs would be somewhat higher, it would not be insurmountably so. Making the choice to quit and do the things she would like to do seems the correct option particularly because she can afford to.

The takeaway

We all want our retirement planning to be perfect, but it rarely is. There are always tradeoffs that have to be made. Accepting good enough is often better than trying for perfection, especially if it would make us miserable to do so.

Taking advantage of the time we are given is always preferable to slaving away at a job. With the luxury of having achieved her FIRE goals, the Redditor should make the most of it.