Nine of the Biggest Regrets I See as a Financial Planner

Check out this list of common regrets among older people and see if there’s something you can address in your own life while there’s still time.

A woman puts her hands on her head and leans back on her sofa in a gesture of regret, her laptop sitting nearby.
(Image credit: Getty Images)

The old adage is to live with no regrets. It is a great mantra, to be honest, and I firmly believe that we regret the things we don’t do much more than the things we do. Thinking back on my life thus far, this holds true. I have two large regrets, if I think about it quickly. 

First, I regret not doing study abroad in college over winter break, as I sat home and missed out on the experience of a lifetime. Second, I definitely regret not having those heart-to-heart father-son conversations with my old man before he passed prematurely. Thinking about these regrets often is the impetus of today’s article.

A front-row seat to regret

In this line of business, you get a front-row seat to learn about people’s regrets and accomplishments. Additionally, I am a sucker for reading all those articles about what retirees say they regret most when they look back on their lives. 

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To me, these are powerful things to share, as I’ve personally seen my two younger brothers study abroad (and love it), and I’ve encouraged many of my closest friends to have those meaningful conversations with their parents. 

Sadly, one person’s regrets can be another person’s opportunity.

With that said, here are some of the biggest regrets I’ve seen, read and heard about from clients, friends or even journalists I truly respect. My hope is that one of these items strikes a chord with you and can encourage you to not make the same mistakes others have.

Regret No. 1: Spent too much time working.

In almost every list I’ve read or person I’ve spoken to, they all say the same thing. They wish they worked less. The blood, sweat and tears they spilled for their job simply were not worth it, especially when they think about all the opportunity costs that time took from them.

Regret No. 2: Not taking better care of themselves.

Most older people look back and wish they’d taken better care of themselves. If they had, in most cases, they would have a better quality of life in their later years. Of course, it is a hard thing to do in your younger years, when you consider yourself invincible, to think what that extra smoke, drink, food and lack of exercise can lead to in your later years.

Regret No. 3: Not enjoying the moment more.

This one comes up all the time in my client meetings. I’ve also heard this from big-time executive friends of mine who tell me they’ve traveled the world through work and haven’t seen a damn thing. Almost exclusively, when asked, they all espouse the same idea of wishing they’d stopped to smell the roses more often.

Regret No. 4: Not following their dreams.

So many elder statesmen (and women) express regret for not following their dreams. Maybe it was because they were scared or didn’t have the right cheerleader urging them on. Perhaps it was life’s circumstances of needing to get a “safe job” to support their young family. 

In any event, not following passions and dreams is something many people end up regretting when they look back on their lives.

Regret No. 5: Not being a better parent/child/sibling, etc.

It is always those closest to us whom we tend to treat the worst. Maybe it is because we are so comfortable around them that we lose any filter or consideration for their feelings. Whatever it is, there probably isn’t one of us who doesn’t feel they could be better in this department.

Regret No. 6: Not spending enough time with the kids.

This goes in line with No. 5, but I think it is worth its own regret. They say you spend most of your time with your children when they are a newborn until they’re 18 years old. As a matter of fact — mind-blowing statistic here — if you take from age 18 through the rest of your life, you will spend the equivalent of a 19th year with your kids. That is it. So, if you want a motivator to spend more time with your kids, look no further.

Regret No. 7: Not sharing their feelings with those closest to them.

This goes in line with my life’s biggest regret. It’s one of those “tomorrow is never promised” concepts. Tell me there isn’t someone right now who you need to share how you truly feel about them. I can think of only a dozen or so people with whom I could be more honest with and share how I feel about them (all positively, by the way). 

I have even started doing this in select situations, and let me tell you, if you want to make someone’s day or have a paradigm shift in a relationship, be vulnerable and simply share your true feelings. In most cases, it will be reciprocated, and in almost all cases, it will be appreciated.

Regret No. 8: Holding grudges and/or not trying to reconcile.

It is hard being angry and takes so much more effort than being happy. Now, I’m not telling you there are people who haven’t wronged you, or vice versa. But as we know, life is short, and most people are too proud to take the first step in making amends. This tends to be a big regret for most, even if we tell ourselves that we are better off without those people in our lives.

Regret No. 9: Not saving more.

No surprise that I hear this one often. Funny, though, as usually people fall into two camps — wishing they’d saved more or wishing they’d saved less and lived more. In any event, it is a hard balance and leaves many of us questioning whether we could have done a better job. I get it, and financial planners are here to help!

There are plenty more regrets out there, but these tend to be some of the ones I come across most often. My only hope in writing this is that you are motivated to avoid at least one of these.

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This article was written by and presents the views of our contributing adviser, not the Kiplinger editorial staff. You can check adviser records with the SEC or with FINRA.

Andrew Rosen, CFP®, CEP
President, Partner and Financial Adviser, Diversified, LLC

In March 2010, Andrew Rosen joined Diversified, bringing with him nine years of financial industry experience.  As a financial planner, Andrew forges lifelong relationships with clients, coaching them through all stages of life. He has obtained his Series 6, 7 and 63, along with property/casualty and health/life insurance licenses.