Should I or Shouldn’t I? When to Retire.

May 03, 2023

In almost 40 years of being a Financial Advisor, I have had the privilege of personally journeying with hundreds, maybe thousands, of people toward retirement and then helping them through retirement.

If you ever visit us in our office, you would be surprised to hear how little we talk about money and how deeply we talk about life. That’s because, for us, planning for retirement isn’t first about investments. It’s about personal relationships and passions, loves and fears, and desires and dreams. That means we make the space to ask questions about what matters most.

Today, I want to share three bits of wisdom I give to every retiree we work with when they are considering retiring, or if they have retired. It’s very common that people will come back a few years later and tell me, “I understand what you said now. It makes sense.”



This can sound trivial, but it’s pivotal. When I see people giving up and no longer physically moving or doing the things they enjoy, they tend to go downhill from that point.

So, stay active, stay engaged, and never quit moving.



Growing up in a medical family where my father and brothers were all doctors, I have come to find that I am more intimate to sickness and death with my clients than even they are to their patients. My clients are my friends and family and I have attended many funerals in my career. The fact for all of us is that we have a 100% chance of dying.

Someday you’ll receive a phone call that will change your life. It may be a sickness, a death, a disability, or another life-changing event. Before that happens, live your life intentionally. Cross off your bucket list. Spend some of the money that we saved for retirement on things that are meaningful to you and your family. Treasure today like there may not be a tomorrow. Personally, my phone call came when my beautiful wife Sharon went to Heaven.

We don’t know how long we have, but we get to live today and how we live today determines the love and legacy we leave.



This is big. For most people, their working years are a significant part of their passion and purpose. When that has ended, what is left? If you don’t have passion and purpose in retirement, and in life, it can create a void.

A study conducted by AgeWave found that retirees miss, “people and purpose, not paychecks, when they retire.” 31% of people were honest about struggling to find purpose in the new stage of life, recognizing that they want to feel useful, not just youthful in retirement. They want to keep learning and growing at every age.

It has been an honor to help people reach and enjoy retirement. If we can help you, please call us at 970.622.2366, email [email protected], or visit