1. Not living a life true to oneself. It’s easy to get swept into societal expectations, family pressures, or even career paths that don’t align with who we really are. Retirement planning should give us the freedom to live the life we want, not the one we feel forced into. That means putting our dreams whether it’s traveling, volunteering, or even moving closer to family into our financial plan. Without clarity on what we truly want, no amount of money will bring fulfillment.

2. Working too hard. Many people realize too late that their jobs kept them from family moments, personal health, and time for joy. I’ve seen this mistake often, especially with high achievers who believe more income equals more security. But retirement is a reminder that time is the one thing we can’t buy back. By balancing work and life today and not waiting for retirement we protect ourselves from this regret. Financially, that means knowing how much is “enough” and not chasing endless growth at the expense of living.

3. Not expressing feelings openly. Bottling up emotions can lead to strained relationships, resentment, and even health issues. Financial planning intersects here, too—money is often an emotional topic. If we don’t talk openly with our spouse, children, or advisors about goals, fears, and concerns, misunderstandings build. Expressing ourselves honestly ensures our financial plans support not just our wealth but also our relationships and peace of mind.

4. Losing touch with friends. It’s easy to let friendships slip away in the busyness of life, but as people age, community becomes one of the most important determinants of happiness. A meaningful retirement plan should include resources for social connections whether that’s travel with friends, joining clubs, or even budgeting for regular visits with loved ones. Loneliness is costly, not just emotionally but also physically, and prioritizing friendships can prevent this regret.

5. Not allowing oneself to be happy. Happiness is not automatic it requires intentional choices. Too many people wait for the “right time” to enjoy life, only to realize that time never comes. In retirement planning, this means striking a balance: yes, save diligently, but don’t defer all joy to the future. Allow space in your budget for hobbies, experiences, and things that bring joy now and later. Happiness is often found in the small decisions—choosing gratitude, reframing challenges, and giving yourself permission to enjoy the life you’ve worked for.

For me, these five regrets are powerful reminders that retirement is about more than numbers. It’s about living a life without “what ifs.” A financial plan should help create freedom, not fear. By living true to ourselves, balancing work with life, expressing our feelings, keeping friendships alive, and choosing happiness, we can avoid the regrets Bronnie Ware recorded and instead step into retirement with confidence, clarity, and joy.

You should always consult a financial, tax, or legal professional familiar about your unique circumstances before making any financial decisions. This material is intended for educational purposes only. Nothing in this material constitutes a solicitation for the sale or purchase of any securities. Any mentioned rates of return are historical or hypothetical in nature and are not a guarantee of future returns.

Past performance does not guarantee future performance. Future returns may be lower or higher. Investments involve risk. Investment values will fluctuate with market conditions, and security positions, when sold, may be worth less or more than their original cost.

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