Alessandra Malito

Mon, May 19, 2025, 7:42 AM5 min read

Can I or should I? That is the question.

I’m going to hit 73 later this year, and my wife just turned 57, so we have a 16-year age difference. I stopped working in March and my wife is still working. This is our second marriage and we have two adult children from previous relationships. Everyone gets along very well.

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We have a personal residence worth $700,000 with no mortgage, and a rental property worth the same also with no mortgage. We also have four other rental properties, but those have mortgages.

My IRA has $1.3 million and my Roth has $150,000. My wife’s 401(k) is worth $600,000 right now, and she also has a Roth with $150,000. We have a joint brokerage account with $600,000 in it and an emergency fund with $30,000. Our total assets are $4.5 million.

Our projected annual income this year is $50,200 from my Social Security and $41,000 from my first required minimum distribution. My wife’s income is $120,000 this year and our rental income will be $35,000. Other income, such as dividends and Roth conversions, equals $30,000. In total, $276,000.

We’re maxing out her 401(k), like we did with mine when I worked. We are continuing to invest into our brokerage account — most of my RMD for this year was reinvested into brokerage. I also moved some positions in my IRA into my Roth IRA.

We are both in very good health. We have longevity running well into the 90s in both of our families. Our adult children are doing well and independent. We have no grandchildren though (yet). My wife is planning to work until she is 62 or 63.

We are currently living in Massachusetts but thinking of possibly moving to Florida in a 55-plus community.

My questions are:

Unsure in Massachusetts

Related: My accountant said I’ll have to pay back Social Security I already received if I retire mid-year. Is that true?

It sounds like you’re living the good life in Massachusetts, with all of that rental income, your savings and good health. That’s wonderful.

I’m surprised how many letters Help Me Retire and the Moneyist have gotten lately from people with millions in assets wondering if they can or should retire. Based on countless studies about retirement security in this country, that isn’t often the case. Millions of Americans would love to have even half of these assets to retire — likely even less.