The Top Retirement Regrets, and How to Avoid Them
One of the most important parts of retirement planning is learning from the mistakes of others.
In the latest episode of the Conquering Retirement podcast, the Annuity FYI team discussed the three most common regrets people face as they approach retirement, and what you can do now to avoid them.
Start Early
What’s the biggest regret investors share? Waiting too long to start saving. Time is the one resource you can’t get back, and the power of compounding means small contributions in your 20s are worth far more than significant contributions in your 50s.
The people with the most successful financial outcomes save every month in the same way someone pays rent every month. Saving $10 daily ($3,650/year) starting at age 25 could grow to about $730,000 by age 65 at a 7% return, and closer to $1.2 million at a 9–10% return.
Understand Risk Tolerance
Another major regret is being either too aggressive or too conservative with investments. Both can create serious problems:
Too aggressive: Market downturns late in life can trigger panic selling, permanently reducing retirement income.
Too conservative: Low-yield vehicles like CDs may feel safe, but they can’t keep up with inflation or long-term needs.
The solution? Understand your risk tolerance, diversify your investments properly, and adjust your portfolio as retirement approaches.
Control Spending and Savings
It might sound obvious, but living beyond your means and underestimating the impact of small expenses can erode your long-term wealth.
Failing to consistently contribute to a 401(k) or not fully funding it, especially when employer matching is available, can lead to unnecessary shortfalls. The good news? Every dollar redirected toward savings compounds into significant future income.
Diversify with Annuities
Most retirees today should plan for a 30-year retirement, and rising costs can erode even the best-built portfolios. Integrating annuities with stocks, bonds, and real estate can create a more balanced and dependable plan, allowing you to stay retired with less financial stress. While some annuities provide guaranteed income, they may not be as easily converted to cash as other investments and tend to work best when integrated into a diverse retirement strategy.
Final Thoughts
The more strategic you are about saving, risk, and diversification, the more you can minimize regret and maximize your retirement lifestyle.Start early, know your tolerance, diversify wisely, and make retirement planning a top priority.
Want more expert insights? Check out the full podcast playlist here.
Sources
- IRS – Saving for Retirement
- Vanguard – Risk, Reward & Compounding
- Investopedia – What Is an Annuity?
- Investopedia – Annuities: Pros and Cons

