When a client says, “I wish I would have,” I don’t try to reframe it right away. I ask them to tell me more. There’s often real wisdom in regret, and it gives insight into what truly matters to them. It’s one of the most human reflections, and it’s rarely about money.
More often, it’s:
“I wish I would have taken more trips.”
“I wish I would have worked less.”
“I wish I would have been there for more of the little moments.”
Ironically, it’s often those very sacrifices that built their current financial security. As financial advisors, we have the privilege of helping clients navigate these reflections — turning hindsight into a compass for how they want to live moving forward.
The Numbers Are Simple. Confidence Is Not.
The numbers are usually straightforward. Most people can understand how long their portfolio might last if they draw from it at a reasonable rate and adjust spending based on performance. Combined with flexibility, that’s often enough to create financial comfort.
But numbers alone don’t create confidence — mindset does.
Rather than dwell on what they can’t change, I help them use that reflection as a guide. I’ll say:
“Thank your younger self for putting you in this position. Now that you know what you know, what do you want your remaining living legacy to look like?”
This question shifts their focus. It’s no longer about regrets — it’s about choice.
Guiding the Next Generation to Avoid Regrets
For those earlier in their journey, I share stories of retirees who wished they had lived more along the way. I encourage younger clients to build financial plans focused not just on retirement — but on whole-life planning.
Simpler, low-cost, low-maintenance portfolios that align with their values give them a better chance of sticking with the plan and living intentionally. I want them to have fewer “I wish I would have’s” and more “I’m glad I did’s.”
Challenging an Industry That Sells Complexity
Unfortunately, the financial services industry hasn’t always encouraged this mindset. Too much of it is built around gathering assets and selling complexity to foster dependency. Advisors often get paid based on what they manage, not what clients understand.
That creates a disincentive to empower people. Clients are made to feel uncertain, leading them to save more, spend less, and stay invested. Products are sold, and systems are built to retain fees and increase the friction of moving assets.
But financial planning shouldn’t be about control. It should be about empowerment.
Just like I go to a dentist but still floss and brush my own teeth, I believe clients deserve both expert guidance and the tools to take care of themselves. An advisor’s role is to offer perspective, support, and reassurance — not to keep clients reliant on them.
Creating a Living Legacy
For those in or near retirement, I remind them that legacy doesn’t start when the will is read — it’s happening now.
Funding a grandchild’s education.
Taking a trip with family.
Supporting causes they care about.
These are ways to live their legacy with purpose. The joy of seeing how their wealth creates experiences and impacts others is far greater than the satisfaction of a growing account balance.
Because in the end, retirement confidence isn’t about hitting a number — it’s about knowing how to use what you’ve built to live fully.
Fewer “I wish I would have’s.” More “I’m so glad I did’s.”
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