Aging & Regrets

When I turned 30, I had a bit of a mid-life crisis. I wasn’t ready to turn 30! Since then, I’ve spent time thinking and learning about the aging process, and what to expect from each phase of life. I’ve also thought a lot about death, and how to avoid regrets. In this post, I share how a couple from my childhood (Toni and Willie S.) shaped my perspective about living without regrets, and I share a summary of Bronnie Ware’s “Top Five Regrets of the Dying.”

*Note: Realized after filming that when I mention the “tiny school” I had just started when I was 30, I should have also mentioned my first 13 Williamsburg students, my relationship with whom was also a super satisfying part of life.

3 thoughts on “Aging & Regrets

  1. Great thoughts, thanks. And good to hear that 35 went better for you than 30.

    Something meaningful for me in this area has come in learning there are different stages of life, and it is normal to value/act differently at each stage. This is clearly taught in Hinduism as the stages of life (see The World’s Religions by Huston Smith, particularly pages 50-55). Hindus see these stages as:
    1. Student, age ~8-20, the time for learning
    2. Householder (working/parenting), beginning with marriage and ebbing over time, this is the time to satisfy pleasure (through marriage and family primarily), success (through vocation), and duty (through civic participation)
    3. Childless/retirement, this is an opportunity to “discover who one is and what life is about” because we don’t have to live ‘for’ someone anymore
    4. Sannyasin, defined as one who neither hates nor loves anything
    Sometimes we insist on holding onto the previous stage and set of pleasures/values, which costs us the opportunity to move on to the next stage. An example is the transition from the householder stage to the childless/retirement stage. Some of us never move on and cling to children/sex/work/public service beyond the natural transition. These people never end up seeing more to life and therefore may end up with a lot of regret. I believe that not making this specific transition is a root cause for some of the ‘5 regrets of the dying’ that you shared.

    Liked by 1 person

  2. Love that thought, Chris. I’m about to start a new book right now by Jim Rohn called “Seasons of Life” and I think it has some overlap with what you’ve described. Loved the Huston Smith reference. Thanks!


  3. Great post, James! I like the video format. You speak in a short-and-snappy, energetic, really engaging way.

    I appreciate the stories you shared and hearing the inspiration you took from them. I’m excited to learn more from that book!

    Liked by 1 person

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