By Marc C. Shaffer
How One Book (and One Life) Changed My View of Work, Family, and Freedom
We often talk in financial planning about preparing for retirement, building wealth, and creating meaningful legacies.
But, we don’t always talk about regret.
Regrets is not a concept that’s top of mind for many when developing a financial plan, so we find ways to utilize the concept to help uncover thoughts, dreams, and REASONS that may not be forefront in many minds. Thinking about regret helps you plan and become more aware because it activates your ability to simulate the future, evaluate your values, and anticipate emotional outcomes.
A few years ago, I read The Top Five Regrets of the Dying by Bronnie Ware, a palliative care nurse who spent years listening to the final reflections of her patients. The insights she gathered were honest, raw, and deeply human. Her book struck a chord with me, especially because I lost my mom just one month after her 70th birthday. And 70, no matter what the numbers say, is still too young.
A Life of Hard Work and Hard-Earned Freedom
My mom spent three decades working at the phone company in Topeka, Kansas. When I was a sophomore in college, she made the decision to retire at age 52. I remember being surprised when I found out she had never finished her degree at the University of Kansas. I encouraged her to go back to school, but she had other plans. She was ready to be done working, and she longed for freedom.
She got 18 years of it before cancer took her life.
She loved her family deeply. She showed up for my school events and sports games even while managing a full-time job. She worked hard, but she never let her work define her. It was simply a tool to support the life she wanted to live. That mindset has stayed with me and continues to challenge me today. As a business owner and father of two young kids, I often catch myself overcommitting. My mom’s legacy is a powerful reminder to keep striving for balance between the professional and personal sides of life.
The Five Regrets That Changed My Perspective
In The Top Five Regrets of the Dying, Ware shares the most common reflections she heard from those nearing the end of life. Here are those five regrets, in their words:
- “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”
So many people looked back and realized they had followed a path shaped more by external expectations than internal desires. They delayed dreams and settled into routines that didn’t bring them joy.
Reflection: My mom’s decision to retire early and live life on her terms is a shining example of someone who chose her own path. It inspires me to regularly reflect on whether I’m living the life my wife and I truly want, or one that’s simply expected of us.
2. “I wish I hadn’t worked so hard.”
This regret appeared over and over, especially from those who had missed important time with family. When you imagine future regret, you’re essentially running mental simulations of possible scenarios. This helps you forecast consequences, which is key for smart decision-making.
Reflection: My mom understood this well. She made time for the things that mattered. I am still learning from her example, striving to ensure my work supports life, not overtakes it.
3. “I wish I’d had the courage to express my feelings.”
Many people regretted holding back their emotions in order to keep the peace or avoid difficult conversations.
Reflection: While my mom wasn’t overly emotional, she spoke her truth when it mattered. This regret reminds many to say what needs to be said and to show love and gratitude while we can.
4. “I wish I had stayed in touch with my friends.”
Over time, relationships can fade if we aren’t intentional. Later in life, many wished they had nurtured those friendships.
Reflection: My mom had close friendships and hobbies, but I do think she missed out on building community in a broader way. That’s something I’ve prioritized, through professional groups, Rotary, and work itself. I’m grateful that financial planning creates ongoing opportunities to connect with people and deepen relationships.
5. “I wish I had let myself be happier.”
Some people only realized late in life that happiness is a choice, not something to be earned or delayed.
Reflection: My mom found happiness in her own way, especially in retirement, travel, and family. But this regret reminds all of us to seek joy now. Life isn’t just about what comes next. It’s about appreciating what’s here.
What This Means for Financial Planning
When individuals and families come to us for financial planning, we focus on more than just the numbers. We’re helping people create a life they’re proud of, one with fewer regrets and more freedom. By imagining regret, you filter out short-term temptations and focus on long-term satisfaction.
Thinking about retiring early? We’ll help explore how to make that a reality.
Want to be more present with family? We can build that flexibility into your financial plan.
Have dreams of travel, impact, or legacy? Those deserve a place in your planning too.
We believe your financial life should reflect your values, not delay them.
Final Thought
If you’ve never read The Top Five Regrets of the Dying, we highly recommend it. It’s not a sad book, it’s an empowering reminder to live with purpose, presence, and courage. My mom lived that way. She loved fiercely, chose freedom, and never let work overshadow what mattered most. We carry her lessons with us, in our homes, in our hearts, and in the way we serve others through the financial planning profession.