Can You Have a Productive Midlife Crisis?

Castlepoint Blog: Financial Planning Basics, Financial Planning Process/Choosing Financial Advisors, Kendall's Counsel, Legacy Planning, Personal Development, The Point
February 14, 2024

One of my favorite things to do is to give books to my clients and friends. Ideally, I try to pick a book that is relevant or timely. One book in particular, Halftime by Bob Buford, I have given away countless times to people in their 40s or early 50s.

This timeless book focuses on helping successful people in their middle age move from a “success” mindset to a “significance” mindset. What’s interesting is that I started giving this book to others around 15 years ago, when I was much younger.

The book did not resonate with me at that time. I was focused on how to be successful and was not ready to think about significance. Now that I’m in my mid-forties, Halftime is very relevant.

One of my favorite concepts in this book is how to have a constructive midlife crisis. Similar to halftime of a sports game where a coach may need to make adjustments to win the game – you need to create a winning strategy to win your second half of life.

The first question to ask yourself in your constructive midlife crisis is, “What do I want to be remembered for?”

One way to answer this legacy question is to write your personal epitaph – a powerful exercise to prepare for your second half.

Some of my epitaph reads like this:

  • Be remembered as a dad who spent so much time with my kids that they accuse me of being around too much!
  • Be remembered as someone who focused on others’ success more than my own.
  • Be a good steward of all that God gave me – including resources, talents, and opportunities.

You also may want to take a stab at some other powerful reflective questions inspired by the book:

  • What’s next for me and how can I be more purposeful in my next season of life?
  • What do I want for my children?
  • How much money is enough?

When thinking of what’s next, consider that there are only a few things that each of us does well – and permit yourself to focus on only the things that will lead to great significance.

For me personally, it’s more focus on going deeper with key relationships and mentoring the next generation. It’s also a greater emphasis on helping others become successful.

When it comes to family, I don’t know anyone who doesn’t want to build a thriving family in the second half. But how many people are thoughtful and intentional with this?

Here’s an idea – meet with each family member and listen to what they want for their lives. Stay curious during these conversations and be encouraging on how they can achieve their long-term goals.

The money question may be the toughest one of all. If you’ve never heard the story of Joseph Heller attending a billionaire party, you might find it helpful for perspective.

Joseph Heller, the author of the novel Catch-22, once attended a party hosted by a billionaire hedge fund manager. Another guest observed that their host made more money each day than Heller would make in his whole lifetime from sales of Catch-22. Unfazed, Heller responded, “Yes—but I have something he’ll never have – enough.”

I like what author Morgan Housel said about this topic, particularly what it means to be wealthy. He explained it as having the optionality to buy or do something at a future time. Being wealthy provides you the flexibility of having the items you want – freedom, time, and possessions – in the future.

Be thoughtful with thinking through your own “wealthy” number. Just as importantly, share it with the people will help you get there, especially your spouse if you’re married.

So maybe you are also around that midway point in your life and career. Take time to answer the reflective questions and then take the necessary actions.

Talking about this book is full circle for me – I have spent the last 15 years trying to help clients answer some of these important questions – now I’m going through the same reflective questions.

This exercise has increased my confidence in my adjustments as I go through my midlife crisis – making sure it’s productive crisis. After all, remember – the game of life is won or lost in the second half – not the first.

The content of this article is developed from sources believed to provide accurate information. The information is not intended as tax or legal advice. Please consult legal or tax professionals for specific information regarding your individual situation. All expressions of opinion are subject to change. This content is distributed for informational purposes only, and is not to be construed as an offer, solicitation, recommendation, or endorsement of any particular security, products or services. Past performance is not a guarantee of future results. Index performance does not reflect the expenses associated with the management of an actual portfolio.

Castlepoint Wealth Advisors | Oklahoma Wealth Advisors | Kendall King - Founder & CEO

Kendall King, CFP®, AEP®

Founder & CEO of Castlepoint Wealth Advisors

Kendall is the Founder and CEO of Castlepoint Wealth Advisors, an Independent Wealth Management firm in Oklahoma City. He is responsible for the strategic direction and vision of the firm, and serves as lead advisor to a diverse group of clients, with special focus on entrepreneurs. With more than 18 years experience in advising clients on a wide range of wealth management topics, Kendall possesses extensive expertise and specialized knowledge regarding IRA and retirement planning topics.

Read more Kendall’s Counsel blog posts and articles.