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Insight, Financial Planning

Five Financial Planning Must-Dos in Your Fifties

21 December 2022
55 sports car illustration

By: Jack Rabuck

Your fifties are a big decade for financial planning. You are likely at the height of your earning power. If you have kids, they might be leaving the nest. You are probably seriously contemplating a retirement timeline for the first time. If you want to prepare yourself financially for the decades to come, here are five things you should do in your fifties.

Number One

Take stock of all of your assets and liabilities. You might be surprised how many people don’t know how much they have. It is easy to lose track of a 401k here or a checking account there. 

You might realize you’re hanging onto some debt from helping your kids with tuition – perhaps with a high interest rate — and at the same time you’ve got a big slug of cash sitting in a checking account earning next to nothing. Just the exercise of putting everything in one place may help you make good decisions.

Number Two

Figure out your cash flow situation. It is likely it has changed substantially between your 30s, 40s, and 50s. Maybe you are earning more than ever, and spending more. Maybe a bunch of expenses tied to children are about to end. Will you spend those newfound “savings” or save them? Maybe you’ve just started a new chapter working for a non-profit and earning less than you used to. In any case, knowing how much extra cash flow (or negative cash flow!) your income and expenses are generating is extremely important. 

This can be extra valuable as retirement account “catch-up” contributions kick in and allow you to contribute more than the regular cap. If you aren’t confident about your cash flow situation, you will probably not take advantage of the new savings options at your disposal.

Number Three

Think about your living situation and hopes for the future. Will you remain in your house for as long as possible? Will you move to be closer to family? Will you move into (the increasingly popular and college-campus-like) retirement community nearby?

There are a myriad of options and every circumstance will be different, but having realistic plans for the future is important to avoid an unpleasant surprise. How much does in-home care cost in your county? What about buy-in and monthly cost for retirement communities? Are you on track to be able to afford what you’d like?

Number Four

Assess your risks. Perhaps you’ve paid off your mortgage and the kids are off on their own and you’ve already saved enough to live comfortably. Maybe you can stop paying for that life insurance policy that was very important 20 years ago.

On the other hand, perhaps the earnings to come over the next 10-15 years are critical to your family’s financial security. Do you need life insurance to take care of your spouse in case you pass away sooner than you expect, and your income is lost? Do you need disability insurance in case you lose the ability to work and earn?

Number Five

Define your goals. You don’t even need to necessarily set targets such as an age you’d like to stop working or an amount of money to have in the bank or your retirement account. 

Something as simple as thinking about where you lie on the spectrum between aiming to retire as soon as possible or working until you can’t possibly work any longer (or likely, somewhere in between!) can bring great clarity to decisions that will be in front of you in the coming years. 

Will you take the big promotion with added pay but tremendous stress? Will you move into a smaller house or neighborhood to be able to retire a few years sooner? The good news is there are no wrong answers. The bad news is there are no right answers.


Put all of the above and more into a comprehensive financial plan. Find out if you are on track to get where you want to go. If you haven’t defined where you want to go, start there! Worst case, figure out where you are going if you keep rowing in the current direction.