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As a financial advisor, I’ve had the privilege of walking hundreds of people into retirement. While the technical side of planning matters, it’s often very clear, both to my clients and to me, when they’ve missed the mark on fulfillment or preparation.
I’ve seen so many regrets in people who are about to retire or who have just retired. Here are the four most common regrets I’ve encountered over the years.
1. Waiting too long to retire
This regret comes up over and over. We all know stories of people who worked hard, made responsible choices, saved diligently, and finally reached retirement — only to fall ill or pass away soon after. It’s heartbreaking.
So many of us are taught to delay gratification, keep pushing, and believe retirement is when we’re finally “allowed” to have joy. We often neglect our mental and physical health during our working years and wait to prioritize leisure, travel, and family time. The sad reality is that, sometimes, the wait proves too long.
2. Not spending more earlier in life
Reading “Die With Zero” a few years ago cemented something I already felt in my gut — most people wait too long to enjoy their money. I’ve seen it with clients, and I’ve experienced it in my own life.
One person who forever changed my viewpoint on retirement spending was my aunt. While she didn’t wait too long to retire, she was deeply conservative with her money. She worried about every dollar spent, even when she had more than enough.
When she died at 72, she left behind a list of dreams and plans that never came to life; she dreamt of taking a train trip through New England to see the fall foliage and adding a sunroom to overlook her garden, among many other things. She never got to do a single one.
These may seem like small or “extra” things, but they were her desires that went unfulfilled because she prioritized caution over joy.
Her experience reminded me that being financially responsible isn’t the same as living a full life. Planning ahead is critical, but so is knowing when to actually use the money you’ve worked so hard to save.
3. Not tracking their progress earlier
This regret usually comes up quietly, buried under the question, “Did I save enough?”
When people don’t track their financial progress over time, they either oversave and miss opportunities for joy or undersave and enter retirement with anxiety and limited flexibility. Neither outcome is ideal.
I always encourage clients to define their personal “bucket list” early. What experiences do you want to have? What memories do you want to create? What gifts do you want to give while you’re here?
Don’t just identify these things — schedule them. Budget for them. Make them real while you still have your health and loved ones.
The sooner you plan for joy, the easier it will be to live a life that’s rich, in every sense of the word.
4. Lack of tax diversification
A major tactical regret I see is having too much of your retirement savings in pre-tax accounts such as traditional IRAs and 401(k)s.
Most people prioritize tax deferral during their highest-earning years, which makes sense to reduce their tax burden. However, when they get to retirement, every withdrawal from those accounts becomes a taxable event.
That $5,000 car repair? You’ll need to pull out closer to $7,000 or more to cover it, once federal and state taxes are factored in. The same goes for money for medical expenses, helping adult children, or travel. It all becomes more expensive when taxes come into play.
I once had a client with 100% of their assets in pre-tax accounts. Every time they needed money, they had to take out 30-40% more than expected. It limited their options and made their retirement feel tighter than it needed to be.
That’s why I recommend building a mix of account types, including:
- Pre-tax accounts — traditional IRAs and 401(k)s
- Tax-free accounts — Roth IRAs, HSAs
- Taxable brokerage accounts
This gives you more flexibility and control in retirement. You can make strategic withdrawals, manage your marginal tax bracket, and avoid unnecessary penalties or surprises. Ideally, you would start thinking about this mix in your 30s, 40s, or early 50s, but even if you’re closer to retirement, it’s worth looking into strategies like Roth conversions for your lower-earning years.
A financially secure retirement is nothing if it’s not fulfilling
Ultimately, the biggest regret isn’t just about money; it’s about missed opportunities. It’s about not living fully, not planning with intention, and not giving yourself permission to enjoy what you’ve built.
If there’s one thing I’ve learned in all my years doing this work, it’s this: a financially secure retirement means nothing if it’s not also deeply fulfilling.
Do you have a story to share about retirement regrets? Contact this editor, Jane Zhang, at [email protected].
The post I’m a financial advisor. These are the 4 biggest regrets I see in retirees. appeared first on Business Insider.
