How to Live a Purposeful & Regret-Free Life With Jordan Grumet

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[171] – When you die, will you be able to look back at your life and say that you lived a regret-free life?

In this episode, Jeremy Keil speaks with the author of Taking Stock, podcaster, and hospice, Dr. Jordan Grumet, about how to live a regret-free life. Dr. Grumet shares his personal journey from hospice to finance and his perspective on the evolving definition of financial independence. He introduces two concepts to evaluate one’s life priorities from Taking Stock called “work bursting” and the “reverse lottery test.” Dr. Jordan Grumet emphasizes the importance of finding purpose in life, both before and during retirement. His message is to prioritize purpose and fulfillment in life to reduce the risk of regrets and disappointments later in life.

Jordan discusses:

  • The importance of financial independence
  • What it means to be financially independent and how that definition has changed
  • Why he reframes regrets as disappointments
  • Retirement as a continuum of purposeful activities
  • How to evaluate priorities with time hacking techniques such as the reverse lottery test, outsourcing, and work bursting
  • Why money should be viewed as a tool for creating a fulfilling life
  • And more

How to Live a Purposeful & Regret-Free Life

What does it mean to be financially independent?

Financial independence, as Dr. Jordan Grumet highlights, has evolved beyond the traditional concept of accumulating a specific net worth to retire and cease working.

Originally perceived as having enough money to never work again, the understanding of financial independence now embraces various perspectives. Beyond mere retirement, it encompasses living a life aligned with personal aspirations.

For some, financial independence means covering monthly needs through these avenues, while others find fulfillment in jobs they genuinely love.

The overarching goal is for money to enable you to dedicate time to purposeful and significant activities, emphasizing the importance of aligning financial resources with personal values and life goals.

Use potential regrets as a way to find and stick to your purpose

What we perceive as regrets may be better characterized as disappointments, especially when viewed from the perspective of one’s final moments.

We have limited agency to change things at the end of life, so we should reframe regrets as disappointments, in addition to addressing and transforming them into a catalyst for purpose.

By using regrets as motivation to undertake purposeful actions today, we can turn regrets into a driving force for meaningful living.

Focus on what you can control, when you still have the ability to control it!

Controlling what you can before losing that control is a poignant lesson derived from experiences in hospice care. Hospice teams engage in a life review with individuals, discussing unfulfilled wishes, crucial life moments, and significant relationships. Dr. Jordan Grumet introduces the concept of “deus ex machina,” a last-minute plot twist that can reconcile past regrets.

While these instances can bring unexpected peace, the focus is on avoiding reliance on such twists by addressing regrets and unmet desires earlier in life. Waiting until later may diminish the likelihood of these important connections and experiences compounding over time. It’s important to proactively address regrets and foster meaningful connections now to allow for the compounding of joy and love throughout life.

How can I bring meaning to each moment?

To infuse meaning into each moment, Dr. Jordan Grumet advocates for time-hacking techniques that enhance the efficiency of daily tasks, freeing up more time for purposeful and fulfilling activities.

Outsourcing, viewed as a trade of money for time, can allow you to focus on activities aligned with your unique value and purpose.

One of Dr. Grumet’s concepts, “work bursting,” emphasizes the productivity gained through short bursts of deep thinking, providing both accomplishment and ample rest time. The goal is to be efficient with tasks that may not bring personal fulfillment, allowing more time for endeavors that align with one’s purpose and passion, ultimately contributing valuable and purpose-driven moments to life.

By embracing practices such as these, you can capitalize on bringing purpose and meaning to each moment in life.

Why is achieving a sense of purpose important for a healthy retirement?

Achieving a sense of purpose is vital to living a healthy retirement because purpose is intertwined with various aspects of well-being.

Feeling engaged and purposeful in life serves as a motivating force that can lead to other health-promoting behaviors, such as exercise, stress reduction, and the cultivation of better relationships. The idea is that waking up each day with a sense of purpose provides a reason to engage in activities that contribute to overall health and happiness.

In the context of retirement, there are potential challenges retirees may face when they haven’t done sufficient thinking about what feels purposeful and important in their lives. Retirement, without a foundation of purpose, can lead to stress, jeopardizing both health and happiness.

On the contrary, those who engage in purposeful activities throughout life experience retirement as a soft landing, a continuum of purposeful endeavors, rather than an abrupt stop.

By maintaining a sense of purpose, you can navigate retirement with a greater likelihood of overall well-being, reduced anxiety, and enhanced mental health.

How can I get rid of the “I have to” feeling?

The Reverse Lottery Test is a tool that can help overcome the “I have to” feeling and guide people in proactively shaping their lives with purpose.

The test prompts individuals to envision a scenario where they win a significant amount of money, eliminating financial constraints. In this scenario, they are asked to scrutinize their daily activities and identify which commitments and obligations they would choose to eliminate.

If the realization is that most activities would be removed, it serves as a wake-up call to reassess the alignment between one’s current activities and authentic interests.

The goal is to encourage people to fill their calendars with activities that genuinely interest and fulfill them, irrespective of financial considerations. By doing so, we can cultivate a sense of purpose, ensuring that our time is spent on meaningful endeavors rather than solely money-oriented pursuits.

We encourage you to address this issue before reaching retirement, to help prevent future regrets and promote a more fulfilling life.


To learn more about living a regret-free life full of purpose, check out the resources below!

If you have any questions, feel free to contact us or our guest, Dr. Jordan Grumet, using the contact information provided below!


Connect With Jordan Grumet:

Connect With Jeremy Keil:

About Our Guest:

Jordan Grumet was born in Evanston, Illinois, in 1973. After graduating from the University of Michigan, Jordan received his medical degree from Northwestern University and began practicing internal medicine in Northbrook, Illinois. He is currently an associate medical director at Journeycare Hospice. After years of blogging about financial independence and wellness, Jordan launched the Earn & Invest podcast in 2018. In 2019 he received the Plutus Award for Best New Personal Finance Podcast and was nominated in 2020 for Best Personal Finance Podcast of the year.



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