Boomers Share 10 Financial Lessons They Wish They’d Learned Sooner

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Baby boomers may seem like the last living generation to have a pretty easy financial path, but not all members have had smooth experiences on the road to their current financial foundations. In fact, many had to learn financial lessons the hard way.

From troubles with financial literacy to denial of the healthcare costs that aging can bring, several boomers share lessons they wish they’d learned sooner.

Don’t Have a Naive Attitude Toward Money and the Future

For Linda M., a therapist and writer based in California, not only did aging seem “so far away” that she didn’t even think about the financial implications of her later years, but she said her generation as a whole had a naive approach.

“We weren’t going to get old because we were a very optimistic generation. We thought it’ll all work out. Just relax. It’ll be fine someday.” 

Additionally, she said, a lot of the hippies of her generation spread an attitude that “money doesn’t matter,” that money was “unspiritual and greedy” and that “there were all these philosophical beliefs that promoted a casual attitude toward money, plus a bunch of rebellion to the fifties,” that rubbed off on her in the early days of building her income.

Learn Financial Literacy

Linda lamented not having good financial literacy in general for a long time. As a single parent and a therapist for years, she also didn’t have a high income.

“I was robbing Peter to pay Paul for 30 years actually. So in that kind of situation, how do you save when you need to actually pay off the credit card?” she said.

While she tried to stick to credit cards with 0% interest deals and had overdraft protection set up on her checking account, she hadn’t been raised to know much about money, so she often just put these matters out of her mind until she found herself with debt or a lack of savings.

It wasn’t until her children were grown and she was in her 40s that she dealt with her money troubles.

“I began getting help from my therapist about this kind of stuff. It wasn’t just feelings. It was, well, what are you doing to take care of yourself? So I began to create more structure.”

Deal With Money Attitudes Sooner

She acknowledged that a lot of her money struggles were rooted in “deeper layers of my own background,” and added,”my grandmother who raised me and my father fought about money until the day they both died. They didn’t put me in their will. It was kind of deep.”

Getting free of these issues meant both facing things she didn’t want to look at and setting up practical structures to get ahead.

Be Organized

In one form or another, Linda has been self-employed for most of her professional life, and yet described herself as “disorganized” in the past when it came to keeping receipts and other issues around tracking her finances. It took having an accountant tell her he wouldn’t work with her anymore to drive her to get more organized and eventually hire a bookkeeper who keeps her on track.

In setting up more structure and attending to her finances at multiple levels, she found it not only improved her bank account but also her self-esteem and sense of self-care. 

Don’t Fall Behind on Taxes

Another consequence of not having the financial literacy at the time was that Linda would fall behind on taxes she owed as a self-employed person. Then they’d charge her penalties (like interest), which finally pushed her to make some changes.

“If you’re punished, you might actually learn your lesson,” she said.

Plan For Extra Healthcare Costs

Over the years, Linda has spent a significant amount of money, as much as $20,000, on dental-related costs. She regretted not planning for these healthcare costs.

“You need money for all the things that your insurance doesn’t pay for. Even if you have Medicare, it doesn’t cover all the actual costs of getting older, which we can’t control,” she said.

Invest Sooner

Morris Armstrong, the founder of Armstrong Financial Strategies, may have a more solid than usual financial footing now due to his career, but he said, “I really wish that I had been an investor earlier on in my career. When I started working there were no 401(k) plans and the IRA was something new, starting in 1974.”

Don’t Live Above Your Means

Armstrong recalled a time when he had “more income than discipline.” While he never carried much debt, he spent way too much on “stuff” that “is long forgotten” and wishes he’d been more strategic with his money.

Budget

Armstrong wished he had tackled budgeting more directly sooner, as well.

“If I had followed a budget that included paying myself first, I would have been much better off,” he said.

Don’t Procrastinate on Diversifying

Having a reasonable diversified portfolio and investing for goals is timeless advice that Armstrong wished he’d realized sooner.

“In my early days, I was in the trading world and time spans were much shorter, and goals much different. When I left that world and became an [advisor], I shifted my mindset and also became a student of the markets, planning and behavioral finance.”

While he said he can never get back the time he lost as a procrastinator, he can maximize the time he has left.

Linda agreed that it’s never too late to make changes to prioritize your financial well-being, whether you’re in retirement or years away.

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