Some of the Worst Mistakes I’ve Ever Made With Money

Elaine Ryan


I traveled to Eugene, Ore., to address a Women’s Financial Security Forum on the topic of “Saving for Retirement.” I noticed the audience was a diverse mix of boomers, Gen Xers and millennials, and I decided to get a little more personal with my speech. “No one likes to talk about their finances,” I said, “but I thought I’d share some of the worst mistakes I’ve ever made with my money.” I told them about the time I cosigned a new car loan for my college roommate the week after graduation. I didn’t realize I was putting my credit at risk by helping her buy her dream car. Or the time a financial adviser convinced me to roll over my 401(k) savings into a technology mutual fund — right before the tech bubble burst. Ouch. I have family and friends that made mistakes, too — like cosigning private student loans for their children or leaving all their financial assets in the name of their spouse.

Financial missteps are not unique to any one generation. Now that you know some of my boomer blunders, here are a few insights from two of my colleagues — Gen X Gerri and Millennial Mysiewicz!

“Gen X” Gerri Madrid-Davis


The old adage “pay yourself first” became crystal clear to me nearly 20 years ago when I heard someone say, “There are no scholarships for retirement!” It was a critical lesson, as I was pregnant with my first child and worried about the cost of diapers, child care and college savings. Thankfully I’ve always worked for employers who provided a way to save for retirement at work. Of course, I wish I had never taken money out of those retirement accounts! It’s a common mistake many of us make during times of job transition or job loss. I’m now in mid-career and starting to catch up on missed retirement contributions. This won’t make up for the lost “time value of money,” but it will certainly help secure my future.

Sarah “Millennial” Mysiewicz


As a millennial, I don’t have a long financial history, yet I’ve already managed a few doozies. I’d say that my biggest was choosing a college without truly understanding the cost. The five-figure price tag didn’t mean much to me at age 18. I happily signed loan documents without a real appreciation for the magnitude of the decision I was making.

A few years later, I had an employer that offered a 401(k) match, which I turned down. At the time, I had an IRA that was already automatically deducting from my account, and it seemed like too much work to switch. I could kick myself now for not taking advantage of this opportunity!

Helping You Avoid Our Mistakes
Though we represent different generations, we are of one mind when it comes to saving for the future. You need to find a way to save. And we know that people are 15 times more likely to save if they can do so through work. That’s why AARP is fighting in states around the country to create Work and Save plans to help 55 million American workers who currently have no way to save on the job.

While they go by different names, both Illinois and Washington have signed Work and Save plans into law, and other states aren’t far behind. Just last week, the Joint Ways and Means Committee in Oregon passed a Work and Save bill that will soon be voted on by the full legislature. Connecticut, New Jersey and other states are also considering ways to help you retire with confidence.

Follow me on Twitter  @RoamTheDomes for more news on retirement security. And to stay up to date on AARP’s advocacy work in the states, sign up for the  AARP Advocates e-newsletter or visit your  state web page.

Elaine Ryan is the vice president of state advocacy and strategy integration (SASI) for AARP. She leads a team of dedicated legislative staff members who work with AARP state offices to advance advocacy with governors and state legislators, helping people 50-plus attain and maintain their health and financial security.

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