Aligning Money With What Truly Matters in Retirement

When people talk about retirement, the focus almost always lands on numbers account balances, withdrawal rates, and whether the portfolio can last 30 years. But I’ve learned that financial independence is not just a math problem. It’s about aligning money with values so retirement feels purposeful, not just possible.
One of my favorite ways to illustrate this comes from Shel Silverstein’s poem Smart. In the poem, a boy keeps trading a dollar for smaller denominations, thinking he’s getting “more” when in fact he’s walking away with less value. That story is a perfect metaphor for how many of us treat money chasing “more” without asking whether it’s worth more to our lives.
I’ve seen plenty of people work long after they’ve reached financial independence. They keep saving because they can, but at what cost? Time, health, and relationships get traded away for dollars they don’t really need. The truth is, older adults face diminishing returns another hour at the office won’t mean much if it comes at the expense of family dinners or long-delayed dreams.
That’s why I always encourage building a financial plan with clarity. A good plan covers the technicals investments, tax strategy, estate planning, withdrawal rules but the real goal is to make sure your money supports your life, not the other way around. Ask yourself: What matters more another 2% of return or more time with your kids and grandkids?
I call this values-based planning. It means identifying what truly matters health, relationships, experiences, purpose and putting those priorities at the center. When you do, decisions about retirement age, work hours, and even spending start to feel clearer. You stop chasing “more” and start pursuing “enough.”
If you’re unsure where to start, reflect on your values and consider working with a planner who helps connect money to meaning. At Root Financial, we use tools like our Retirement Planning Academy to guide people through this process not just building wealth, but building a life you want to live.
At the end of the day, retirement isn’t about leaving work. It’s about entering a season where your time, health, and relationships can take center stage. And aligning your financial plan with your values is the best way to make sure those years are truly well-lived.
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.