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What I Learned About Myself and Not Working in Retirement

Updated: Apr 23

Working and Not-Working

I've worked 46 years, and spent 11 years not working. They were three mini-retirements. Near the end of my first stint of not working for a paycheck I thought, “I guess this is what retirement must be like.” Sort of, sort of not.

Each retirement followed a significant life event. I took time away from work to relax, rest and recharge. My goal was always the same, to gain some sense of inner peace or calm.

What I experienced was actually much different. I thought retirement was the freedom of not working. I thought that was what I was looking for. I was wrong.

My life felt empty. I went from being very focused and on purpose to feeling like life was a blank canvas on which I could paint. There was no time urgency and I could indulge my whims without guilt. I finally had the freedom to putz around, to do whatever I wanted.

I discovered a lighter, adventurous side of myself. I had the time, desire and the money to explore the world. To travel and indulge in the things that interested me. The first time, I was content with sitting around, shopping and traveling.

The second and third time I approached not working like I was planning a vacation. I asked myself questions like "What do I want to do? What do I want to experience? Where do I want to go? What do I want to see? When do I want to do it? Who do I want to do it with?" The same basic questions you would ask if you were planning a vacation.

What I discovered is the joy of not working only lasted as long as the trip or adventure. I kept indulging my whims and desires. It was a blast; I had loads of fun. I saw a lot of the world. It was awesome until I began to feel antsy. Through each period I felt like a bump on a log. It was a very serene, peaceful but dull existence. I thought waking up with no intentions, drive or anyone expecting me to "work" would be great. It was anything but.

Then I would get anxious about how much money I spent. It was painful to admit that I had to rein in my spending. That was depressing plus, and I felt bored. Why was I bored?

That is when I would begin to get a serious my entrepreneurial itch. An itch I could not help but scratch. The desire and creative urge to build something was overwhelming.

Most disturbing was when I realized I misunderstood retirement.

I thought of retirement as one long vacation. What I didn't expect was that I would become bored with not working or that I would spend every nickel fulfilling my dreams. Plus constant travel was exhausting. It is a lot of work to travel. I loved meeting new people adapting to local customs and restaurants. I wasn't prepared for the constant change, new beds and missing home.

Needless to say, I no longer see retirement as one long vacation.

Today, I don't call it retirement. I like to think these periods as a reprieve of not working for a paycheck. A period of time where I make adjustments in when, where and how I live.

These days I set a clear intention to change my point-of-view. To take the time to get clear about my values. Get clear about how I want to live the last third of my life. To take the time to explore and ponder my legacy. To invest time and energy into the people and causes I care about.

It only took eleven years of not working for a paycheck to figure out what retirement would look like. Eleven years of adventure to find a sense of balance. To figure out how to deal with the two invisible tensions of retirement, desire and time.

I had to learn how to deal with the tension and anxiety of fulfilling old dreams and desires. To decide if they were still relevant to a sixty-year-old.

What I now know is that I have to get clear. Clear about my values, priorities and make a plan.

Three Small Steps, One Giant Leap To Freedom

Most professionals suggest you "begin with the end in mind." In my experience that doesn't feel congruent. I find getting clear about my values is the first step. To identify what is most significant. Once I know what is most important, then I set my priorities and develop a plan.

I like to think of planning as a thought experiment. I use my time to think about and experiment. I talk to friends, read and ponder what is most important to me. I make my mistakes in my mind and on paper with my plan. This way I avoid making mistakes with time and money.

I prefer to be spontaneous. Through experimentation, I have discovered that living the dream is possible. When I get my values, priorities, and planning in alignment, I can feel confident.

Then I am confident that the last years of my life, will be the best years of my life.

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