What Now?


How did I get to Portugal and why am I here?

It was not a long planned-out transition or life goal by any means. I am not at the traditional retirement age, nor am I a digital nomad. I am here because life brought me here. I am here because this move was the answer for me when I asked myself, “What now?”.

Never in my wildest dreams did I think that my 50s would be filled with so much uncertainty, I went through my 30s and 40s building, earning, achieving, piling on, and mapping out; thinking that I was setting myself up for middle age and the rest of my life. All of this only to find me in my mid-50s, with much of what I thought I would have, crumbling away. And crumbling was how I felt my life was going.

        Levada walking on a hot day!

It was not the pandemic for me. That period was not particularly bad for me and mine at all. Other than being locked in with grumpy teens and young adults, seeing the suffering of others, and all the deterioration in America and the world, I was doing well. My family and friends all survived this and very few of us got the virus during the pandemic (although I do know a woman who lost nine family members).  I communicated more with family and friends during this period and picked up hobbies.  The company I worked for did incredibly well financially which trickled down (a little drip for me while some of the others were in a waterfall, but I digress) and my finances blossomed.

For me, the crumbling came after and was unrelated. First, my youngest child of four went off to college. She left me home alone with the dog.  She must go and live her life, I know.

“I would never hold my children back, but when she left, it made me realize how wrapped up I was in raising my family versus living my own life. I never saw myself separate from being a mother; I had been a mother for 30 years at this point and I can’t even remember who I was back before. Of course, whoever I was way back then, is not who I am today at 55 anyway. So, then who am I?”

Navigating the Shadows

Then, I had a heart attack. Heart attacks are for old people I thought. I’m not old.  When I was sent to cardiac rehab because I luckily survived, I looked around the orientation class and wondered why I was sitting there with 80-year-old white men. Why do I have the same heart that they do?  I thought I had been taking care of myself.  I saw my doctors regularly and had all the testing they recommended. I felt like I didn’t deserve to be there. I didn’t earn this.

Then the career began to crumble. I followed the pattern and did the things that were supposed to bring success and take me to the pinnacle. I sacrificed time with my family and myself to get two master’s degrees. I attended and spoke at professional conferences, asked for opportunities, and created change. I made it to the pinnacle of my profession, updated my LinkedIn, and took all the accolades from my peers. But then I was pushed off the glass cliff.  Twice.

Nature started to take its course as death arrived. First, my father died. He was sick, and we were not close, but we were starting to rebuild our relationship after having been estranged for most of my life. I was just starting to get to know him, and he was just starting to get to know me and my children. What resonated most with me about his death was that he was not ready. He was outraged and he felt blindsided when his cancer returned, and he realized he had little time left. I could feel how angry he was.

After that, the husband of a close friend died. I had socialized a bit with my friend’s husband but only got to catch his vibe about six months before he died. It was the husband that I had so much in common with, and I never knew. He husband was only in his early 50s and essentially died because he enjoyed life too much. That was my outside perspective. I felt like my friend was too young to be a widower, and I was too young to be supporting a friend through this.

Then my best friend died. My bestie for life we would say. We had been close friends since we were young girls in college trying to sneak in bars and drink when we didn’t even like liquor. We were yin and yang, but also the same in many ways. From the outside view, I was the wild, free, adventurous one and she was the subdued religious one.”

Each of us had characteristics of the other, though. We were in harmony together.  As I soared through life doing “all of the things”, she always vocalized support, encouraged me, and even suggested more for me to do. She fed my soul and balanced me. She would say,” Go bestie!” to whatever feat I tried to accomplish. As part of my career and for passion, I traveled a lot.  Her health and finances held her back and my travel gave her insight into things she couldn’t do. I traveled for us. Her death was sudden too. Or perhaps I wasn’t paying attention to know that it was coming.

I know that I’m not alone in arriving in my 50s and feeling blindsided by life. I know there are many people in my age group who are suddenly caring for parents, burying family members, and trying to figure out if they have enough money to continue to exist. I know that I am not alone in getting to this point in my life and saying, in a whisper to myself and to the Lord, “Well, what do I do now”?

The answer led me to Portugal.”

No, Portugal is not the answer, but living my life is. After that second push off the glass cliff, I clearly heard the Lord telling me that I needed to take a break from working full-time. That career was no longer my path and purpose; it never really was. It was never meant to define and fulfill me. I needed to fulfill myself in other areas that I had neglected. Did I mention I’m a single parent of four? Yes, there was certainly some neglect of my core self so that I could nurture my children and my career.


                                                                   Relaxing in the sun

Also, losing people who were either young or demonstratively, not ready to die, made me decide to be more purposeful about living my life. Each of the people that I had lost recently had verbalized to me something they wanted to do in the future. My father was trying to get to Japan. He really wanted to go to the Olympics that year, but Covid delayed it, and then death prevented him from going. My Bestie and I talked about going to Italy together next year. She vividly shared her vision with me of how she wanted the trip to go. She always had a heart for travel and never got the opportunity to do as much as she wanted. Her best and last trip was an epic adventure across the United States with her oldest daughter and grandchildren months before she passed.  Thank God for that escapade.

My friend’s husband had hopes and dreams unfulfilled, as well. I laugh when I think about the one that he and I discussed. We were going to go see Big Freedia together, Queen of the Bounce. This man was an opera singer and it never occurred to me he had musical interests beyond that and musical theater! At our last get-together, we practiced our “bounces” and committed to getting to see Big Freedia at her next San Francisco show. We were going to be a spectacle and couldn’t wait! After that party, I looked out for opportunities nearby for us to see Big Freedia together, but it never came. His death did.

So back to Portugal. I am here because it is part of me ensuring that I take the time to heal and live.  I outlined my recent traumas here, but truly this isn’t all.  You don’t get to be Black in America without trauma.  You don’t get to be a single parent of four without trauma.   Life in the US for me had become about building, achieving, and getting and there was no place or space for healing. To get off that crazy ride I needed to remove myself from the “scene of the crime”.  Portugal isn’t perfect but it is a new and fresh place for me to live. I had come here in the past to vacation briefly and for work, so I had a more than basic awareness of Portugal.

My first view of Madeira

“Of all the places I have been (I am a six-continent traveler) this is the country I have returned to the most. There has been a draw to this place that I cannot deny.” 

But being who I am, Portugal is not the end. It’s just a stop and it’s a good place to stop. I didn’t know that I would be here two years from now, that I would retire here, or what retirement would look like, but I do know that resting here and rebuilding here allows me time to figure some of that out.

I hope that my story inspires someone to stop and look at where you are now and if you’re on the path that you want to be on, particularly if you are 55-ish. This “middle age” is a good midpoint to pivot towards you; the you that you want to be. I hope to continue to inspire you and will document some of my thoughts and travels on my YouTube page @Jeanniewhatnow.





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