The biggest regrets financial planners see

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By Andrew Rosen, CFP®, CEP
Posted on May 02, 2024

The old adage is to live with no regrets. It is a great mantra, to be honest, and we regret the things we don’t do much more than the things we do.

Thinking back on my life, I have two large regrets. 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.

A front-row seat to regret

Financial planners get a front-row seat to learn about people’s regrets and accomplishments. Here are some of the biggest regrets I’ve seen, read and heard about from clients, friends and even journalists I truly respect. I hope one of these items strikes a chord with you and can encourage you not to make the same mistakes others have.

Regret No. 1: Spent too much time working. In almost every list I’ve read and people I’ve spoken to, they all say the same thing: They wish they had worked less. The blood, sweat and tears they spilled for their jobs simply were not worth it.

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. When asked, they almost exclusively wish they’d stopped to smell the roses more often.

Regret No. 4: Not following their dreams. So many elders 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 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 aligns 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 with whom you need to share how you truly feel about them.

If you want to make someone’s day or have a paradigm shift in a relationship, be vulnerable and simply share your true feelings. It will be reciprocated in most cases and appreciated in almost all cases.

Regret No. 8: Holding grudges and/or not trying to reconcile. Being angry 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 tricky balance, leaving 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.