Stumbling into Retirement

Navigating the Uncharted Waters of Post-Career Life

I retired from my 30+ years wealth management career two years ago. Work had become repetitive, often boring. I had enough money to last my wife, Heidi, and me until we passed, and leave my kids a nice inheritance. 

Just because I was ready to embark on my life’s next chapter didn’t make the transition easy. It was hard to leave behind a successful and lucrative career. Hard to move into the great unknown without clarity about what I wanted to do next.

So how do you decide what you will do after leaving full-time work? In my experience, you can’t save yourself from angst and uncertainty. There’s no use expecting quick solutions when you’re asking worthy questions about how to spend the rest of your days.

Figuring it out was a journey I stumbled my way through. I’d like to share some of the small steps and big questions that helped me, but I want to emphasize that there is no one-size-fits-all approach. You, too, will have to stumble into what works for you.

I missed my paycheck immediately. Even though I have plenty of money to support my wife and me, the transition from living off of earned income to living off of investment portfolio income was surprisingly hard. Especially when you consider that I’d been coaching my clients through the same experience for more than a decade!

Switching my orientation took time. I felt a little panicky. I had to reason with myself. I learned over time to ensure there was enough money in my checking account to cover my bills for the next 30 days, and to designate money in cash and bonds to cover my expenses for several years. As I put that plan into action, my financial worries diminished.

Another surprise was the sense of dread that came over me because my calendar was no longer booked from morning til dusk. Many days, I had nothing scheduled at all. At first, I felt exhilarated. I could wake up and do whatever I wanted! Soon, however, I began to worry about how I was going to fill all this time. 

To prevent myself from panicking and going back to the structure of my job, I decided not to make any big commitments for the first 12 months of retirement. That turned out to be a great decision. I needed time to separate from my career and the familiar routine. Time to wean myself from the ego strokes I had grown accustomed to receiving from clients and colleagues.    

I was tired — physically, intellectually, and emotionally. I needed time to rest and rejuvenate. I added aerobic activity and Pilates to my exercise routine. I regularly slept eight uninterrupted hours a night. 

Although I enjoyed my time alone, I began to miss interactions with other people. I started scheduling lunch with various friends, once a week at first and then several times a week. The lunch dates offer opportunities to connect that are deeply significant to me.

A few months into retirement, I was feeling good — not as stressed, less anxious, more rested, more content, more peaceful. 

I felt liberated. For the first time in my adult life, I was able to do what I wanted, when I wanted, without feeling guilt or pressure to do something else. It felt like playing hooky from school, with no risk of getting caught. 

And then it hit me. Something was missing. This just wasn’t enough to keep me occupied for the rest of my life. I had made considerable progress in structuring my days, but I still had not identified what would give me a sense of meaning and purpose. 

I started diving deeper into my spiritual heritage as a Jew. I began weekly Torah study, attending Shabbat services regularly, and reading nonfiction about the search for meaning. I don’t think you have to be religious to find wisdom and guidance. There are many sources of enduring truth, whether in meditation or therapy or the ancient philosophy of Stoicism, which teaches acceptance of what you cannot control.

My spiritual journey is transforming my life. It teaches me that all humans are connected, and we are more alike than different. It encourages me to be loving, compassionate, and generous. When I grow discouraged by the dysfunction of our society, it reminds me that I cannot fix all these wrongs but it is within my control to leave the world a little better than I found it.

Part of my own purpose is to help rectify how America thinks about money. This blog is part of my contribution. I want to influence a conversation that shifts our focus from the obsessive accumulation of money to striving for fulfillment. A fulfilled life is built on a foundation of love, compassion, and kindness. It centers on vulnerable relationships, engaged activities, and making a difference in the lives of others. That’s a lofty goal, I admit. I’m amazed at how it has infused my retirement with passion and purpose.

Transitioning to my post career life was challenging, often uncomfortable, and absolutely worth the effort.

Until our next conversation,

David

In learning to accept my uncomfortable feelings as I stumbled into retirement, I found solace in reading The Guest House, written by the 13^th-century Persian poet known as Rumi. Read the poem here.

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Small Steps & Worthy Questions

1. It takes time to adjust to life in retirement. Don’t panic and rush back! Be compassionate and patient with yourself. Adjust as you go along.

2. Experiment with mindfulness practices. Use an app to learn to meditate. Go for walks without listening to books or podcasts, just paying attention to your surroundings. I like to sit in stillness on the porch with a cup of coffee for 5 to 10 minutes and just observe the sights and sounds around me. 

3. If you don’t have a financial planner, hire one. Ask these questions. If I retired today, how much could I spend monthly to maintain my lifestyle? If I wait and retire 5 years from now (or sooner), how much could I spend monthly to live comfortably? Get a reality check on where you stand financially.

Would love to hear what has guided and reassured you on your retirement journey. Please share any small steps or big leaps that might help the rest of us.

If you love this, share it with your friends, foes, and even perfect strangers. Let’s change the way America thinks about money.

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