Skilled At Work

How should I plan for retirement when the future is so uncertain?

Plus, how to think about building your legacy.


Curious about what a financial expert would suggest about planning for the future. Seems like there is a lot of uncertainty — and as a millennial, lots of income differences within my generation. What happens if they raise the retirement age to 70? What if something else changes before millennials can retire?

I don’t know if you know much about Dale Carnegie, but in addition to writing the famous self-help book How to Win Friends and Influence People, he also wrote a slightly less popular book called How to Stop Worrying and Start Living.

There’s a reason why How to Win Friends and Influence People is the kind of book that everyone’s heard of and How to Stop Worrying and Start Living isn’t. Everyone wants to become an influencer, after all — and not everyone is ready to do the work required to stop worrying and start living.

One of the first tasks, as Carnegie explains, is to imagine the worst-case scenario in all its worst-case-ness.

Then, Carnegie advises, ask yourself what you can do to either prevent or accept that worst-case scenario.

And then — and here’s why nobody reads this book anymore — you have to do it.

In your case, you’re worried about the federal government raising the retirement age to 70. This is not an unreasonable concern. I’m an “elder millennial,” so I was alive when the government raised the retirement age from 65 to 67, and it’s not much of a stretch to imagine a future in which we can only begin collecting full Social Security benefits after our 70th birthdays.

Can either of us prevent this scenario? Maybe, depending on how we choose to vote in the next few elections, but it’s unlikely we’ll have any direct impact.

This means that you have to accept the scenario as a possibility — and to stop worrying and start living, you have to plan for a future in which you do not receive full Social Security benefits until age 70. You may even want to plan for a future in which you are no longer allowed to collect partial benefits if you retire early.

Does that mean you need to put more money into savings and/or investments every month? Not necessarily. Depending on your current retirement plan, the compound interest associated with your accumulated assets could help you cover the three-year gap between 67 and 70. On the other hand, a bear market (that’s the bad one) could decimate the value of your portfolio no matter how much you save in the next three decades.

This is why I always advise people to focus on savings vehicles that provide guaranteed returns, such as CD ladders, as well as methods of building wealth that aren’t directly associated with investments. Getting promoted — or, in some cases, changing careers — could earn you much more money than you might get from a mutual fund. Moving to a lower cost-of-living area could also allow you to save more, as well as take advantage of opportunities like homeownership that might otherwise be more difficult. Living near family and/or living within a strong community can also provide the kind of support that can sustain you when times get tough. And if you live in the kind of area that allows you to participate in activities you love with people you care about, you might be less likely to spend money on distractions like impulse purchases, streaming media, and expensive vacations. This, in turn, could give you the financial and social resources to help other people who might need support, which is one way to address the income inequality issues that are prevalent across nearly all generations.

All of these changes take work, and some of them come with up-front costs — which is another reason why How to Stop Worrying and Start Living never really took off as a self-help text. Still, it’s an extremely good template to help you prepare for the uncertainty of the next 30 years.

Why save? I’m retired. You can’t take it with you …

No, you can’t. As long as you have enough set aside to cover your expenses for the rest of your estimated lifespan (factoring in inflation, naturally), as well as any money you may need for end-of-life care (which is more expensive than many people realize), you can spend the rest on personal indulgences if you want!

That said, I’d advise you to stop thinking about taking it with you and start thinking about how you can give back. Do you really want your life’s work to end up in the pockets of Amazon and Margaritaville? Isn’t there someone a little closer to home who might benefit from your legacy?

If you have family or a community of friends who have provided comfort, support, and connection throughout your life, for example, ask yourself whether you have the extra resources to provide support in return. Some people leave an inheritance; other people make financial gifts while they’re still alive. If you’d rather not use financial resources, consider giving your time. Driving a friend to a medical appointment, sitting with them as they meet their medical team, and taking notes on the recommended treatment plans are some of the best things you can do for someone you love.

If you don’t have a lot of close family or friends at the moment, consider supporting an organization or a local cause, and consider volunteering to start making a few more in-person connections. They’ll be worth more than you realize, especially as the decades continue to progress.

There’s one more factor to consider, and that’s whether you might be eligible for Medicaid in your later years. If you’re thinking about Medicaid as an option, perhaps after spending down the last of your savings, you may want to set up a meeting with a financial adviser to discuss how to ethically take advantage of this government aid program. Medicaid is designed to help lower-income households access medical care, and many older Americans use both Medicaid and Medicare (a federal health insurance program) to help them manage the expenses associated with advanced aging.

That said, accessing Medicaid could place a burden on your surviving family members. Many people don’t realize that Medicaid may be able to claim any remaining financial assets to cover the costs of providing end-of-life care, including real estate. The recent New York Times article “When Medicaid Comes After the Family Home” offers a good summary of what to expect, so read that carefully and include it in your long-term financial planning. It’s also worth remembering that the infamous Medicaid five-year “Look-Back Period” prevents people from gifting or donating their assets immediately before applying for benefits. Some people set up trusts to preserve their assets while remaining eligible for Medicaid, but this is the sort of issue that you’ll need to discuss with a professional.

All I can tell you, as an advice columnist, is to think carefully about where you want your money to go since you already know that you can’t take it with you — and to have conversations with family members and financial professionals to ensure that any remaining assets are distributed in a way that feels meaningful to you and the people you love.