Jenn Specific, Sailing With Anxiety, The Best Of Skipper Jenn

Reflections on Mid-Life: What Do You Need to Do Differently on the Path Ahead?


Me on my 44th birthday at Orcas Island.

The middle of a journey is always a good place to look back and reflect so you can look ahead and move forward with greater wisdom and ease. It is important to pause and ask: What have I learned? What choices do I want to continue to make and what choices have held me back? What do I need to do differently on the path ahead?

At dinner last night, on my 44th birthday Eric and I played a little conversation game. We discussed where we were and who we were in 10 year increments. I invite you to play along in the reflections as I write out mine. Stories are interesting, they are not as stationary as they may seem. We cannot change the past, but we definitely can change how we perceive it as we unfold the layers of how it has impacted us.

In 1979 I was four. I lived in Nebraska for a short period of time after starting my life in small town Kansas. My parents were young and poor, 21 and 22, I had a 1 year old baby brother. I was in kindergarten already and was reading and writing grades above my peers. I drew and made art incessantly. I played Dukes of Hazard with neighborhood boys and would get mad when I could only be Daisy so I chased them fiercely and tumbled hard. I knew I could be a better driver than them if they let me play. When I was 14 I lived in Kansas again, it was 1989. I was in eighth grade with the same small group of people I started first grade with and would end high school with. I was getting up extremely early for school so I could rat my long blonde hair with a toothbrush and plaster it with aqua net. I added ice blue eyeliner and crystal pink lipstick and wore crop tops with spandex and stone wash. I was obsessed with Guns and Roses and boys. I was anxious, depressed, sexually active, being actively abused and starting to cut myself secretly.

When I was 24, in 1999, I was a vegetarian granola hippie with long straight no product hair who wore brown patched corduroy and clogs with no bra and no hair removal. I worked in alternative radio in the pacific northwest, partying backstage from Eugene to Seattle with bands and radio reps, doing a lot of drugs and drinking all night. I had dreams of sailing the world and being a writer and was totally stuck in my own story, opinions and dysfunction. In 2009, I was 34 and in graduate school in Colorado for Counseling Psychology and Art Therapy. I had reddish short pixie cut hair, wore some light make up and had just gone shopping for professional attire, slacks and blouses. I was starting an internship in community mental health as a school based therapist. I went home daily in tears worrying about children living on the streets in the cold, I brought them food and hopefully gave solid emotional comfort.  Child protection services knew me by voice I made so many report calls that year. I found myself drowning in trauma as I not only had to process through dozens of kids abuse and stressors, but come to terms with my own history from childhood.

Here in 2019 at 44, I have a funky asymmetrical curly short cut, wear no make-up but occasionally eco-glitter and basically look like a funky middle aged art teacher. Looking back I see how I dress for the part on all occasions, thinking I’m so original but really a walking stereotype. I can own that. I just moved onto a little old sailboat in Seattle which I have refit mostly myself. It is the first and only home I have ever owned. I have a thriving private practice as an anxiety and trauma specialist for kids, teens and adults. I write for fun and sanity and travel as much as I can. It’s strange looking back and seeing how different parts of my life have been and how there are threads of continuity woven in holding my sense of identity together. Throughout all of this I have had several long term lovers and always excellent friends. The friends are who get me through, chosen family who step up at every crazy turn to witness, support and mostly laugh at my jokes and appreciate my unconventional wisdom. “Oh Jenn…..” I’ve heard them all say at various times in various tones. Friends, you know who you are and I love you hard.

The 4’s are always weird for me, almost half way. They feel anti-climatic and inevitable, the first messenger of a new decade to come faster than expected. They are a pause point and for me, pauses can be uncomfortable. As I look back now I see the vantage point of a woman who has been through a lot. Most of us by our 40’s have battle scars. Wounds on our bodies, minds or psyche that we have either been actively processing through or are knocking hard at the door to be reclaimed. More of mine have been coming to roost this past year. Depression has hit, rage and anger have hit, anxiety has pummeled me as I’ve been stretching to grow. Perimenopause turns up the volume on everything and that 14 year old girl in puberty sometimes speaks through my mouth in shitty tones and dramatic overtures. Integration can be hard as I own my strengths and work through the challenges and traumas. One of the key issues I have been struggling with this past year is pace. When I read through the paragraphs above from 1979-2019 I feel exhausted. There has always been an intensity about my life, a candle burning at both ends. I work hard, I play hard, I do everything hard and harder. I don’t know how not to. My nervous system is programmed that way. There is a wisdom in going hard for sure. I’ve gone through a lot and come out the other side. I’ve worked hard to pull myself out of hell and then go back in to help others. At 44 I know I’m still young, and I am tired. Damn tired. Soul tired. Something’s got to change.

I am old enough to know that I am not going to change the fact that I am intense. That’s a thread binding my various selves together. I am not going to not be creative, or not be active and love the outdoors or adventure, I am not going to stop being outspoken. Obviously my fashion sense is spot on and I will, thankfully, remain outrageously weird and humor myself always. These things serve me and I will continue to learn from them as time does what it does. The big question is: what do I need to change going forward? For me the answer has been knocking at my door consistently: What if I intensely learn to slow the fuck down? What if I work hard at finding ease and yielding instead of pushing ahead as if my life depended on outrunning shame or a misplaced sense of worth? What if I listen more and produce less? What if productivity isn’t tied into things or experiences but allowing and being? What if there can be ease with action? What if peace and kindness aren’t just aspirations but a lived experience and embodiment?

I’ve been meditating for 15 fucking years now, studying these very questions. I’ve spent loads of time and money on therapy and it has all helped me understand and clear out a bunch of bad coping habits limiting my view and capacity. Now at 44, instead of a spiral of over responsibility and shame, I think like many in my generation, I am seeing how a giant part of the struggle is our culture and a greatly biased and rigged system. How can any of us slow down and pace in America when there is no safety net? When profits are more important than people? When oppression lies at every crossroad? When kindness and community are limited to small circles of personal preference instead of generalized humanity? How do we find ease when others are hurting, especially for those of us who spend our professional lives in the trenches of social change? Lastly, how do I find ease knowing the planet is daily being destroyed and the future is ecologically uncertain? I have no answers, but they seem like very important questions to ponder. For me, it’s hard to ponder those questions when I am sitting in the despair and busy pace of it. I need a quiet beach with a good vista to even begin. I need it not just once a year on vacation, I need it everyday. I have tried and learned I cannot do the work of social action without setting my nervous system up to digest it.

At 44 I know enough that I cannot possibly predict what is ahead. Uncertainty can be scary, and it is also the seed of possibility. At 54 I wonder what the vantage point will be. I know my 54 year old self is depending on my 44 year old self to keep engaging and be mindful of her choices to get me there. As is often the case in life, I hadn’t seen any of this fully playing out until recently a loved mentor of mine from Naropa reflected to me, “Wow Jenn, you are a monk!” I laughed at the absurdity of it. He said, “No, really, you just told me that you got rid of most of your worldly possessions, moved into a floating box so you could spend more time alone to be mindful, listen to nature and reflect on life. You are a monk.” It caught me by surprise because I knew that my life choices these past few years have been in an effort to simplify and create space. Ironically they have created a shit storm of work this past year in bilges and small spaces with 10-12 hour labor days. It’s like I had to crank up the intensity volume on physical productivity to afford the luxury of having little and living with less. I will leave any irony in that with American culture for you to ponder. I was so busy with all the doing that I hadn’t paused enough to fully see this simple and lovely truth…..I’m dropping out so I can drop in. Sometimes we need people we trust and love to reflect to us what we cannot see in ourselves.

One of the reasons I write about myself is that I believe in role models. I believe we don’t get anywhere alone. People who inspire others are critical to imagination, and without imagination how do we create something new? I have found that all the people I admire as they age have fewer answers and more questions. Fewer tightly held opinions and more genuine generosity, flexibility and presence. They tend to not be attached to the status quo and live lives that are uniquely shaped to their own palette. They are humble, fierce, compassionate, kind and they have integrity. They value and live their truth and purpose in each moment. They are humans, flawed, quirky and beautifully themselves. I deeply appreciate that example and wonder how each step will lead me toward greater openness within this strange creature called Jenn. Who knows, it is an adventure, and one I am creating room for. You can’t step into what is ahead without letting go of what you don’t need anymore. On a final note, another dear friend recently surprised me and said that she figures I have legit become a sea witch. I hadn’t seen that as a life goal, but I love it. My 4, 14, 24, 34 year old selves love it and agree it’s a good thing. I thank all these prior Jenn’s for what they’ve done to set me up for this phase. I hope I thank myself later for this one. Mostly, I wonder what outfit I will conjure up as I step further into the sea witch role, I’m excited because it’s bound to have a great hat, and anyone who has heard my laugh knows I’ve already got the cackle. Sail in peace friends.

This is the accidental photo of me trying to set up the camera to take the pretty selfie on my 44th birthday on Orcas Island. I like it even better. ❤️

16 thoughts on “Reflections on Mid-Life: What Do You Need to Do Differently on the Path Ahead?”

  1. Jenn you are such a breath of fresh air,! You are Legit, hilarious, serious, true, inspiring, intense, lovely, superiffic (its a word in the dictionary of heather) and awesome. I love reading your posts, and you always make me sit here & ponder & reflect on my own life, specifically today my 44 year old self. I am trying to find my next ‘way’ & do away with that which does me no good to make my next days, weeks, years that much better. Thank you Jenn for being you, and I too am grateful for all your previous years that have led to the current YOU. xoxoxo Heather


  2. Your best post yet. Thank you for the inspiration to examine, care for and accept ourselves where we are and to do what we can to care for the world.


  3. What an amazing perspective on life and so beautifully written. Thank you for inspiring me. I am going to ponder this and try to be positively reflective so I can look back at 71 and thank myself. I love you.


  4. Hello Skipper,

    Thank you. I just turned 64. One short year from middle age to officially old. I’m struggling right now with where I go from here. My current lover is not a sailor and I was going to sell my boat and try to live the land life with people that I am unable to comprehend. The endless, insatiable “must have” baffles me. I lived aboard for 6 years, most of it by myself. Probably have 90% of the same clothes I started with except I outgrew most of my pants (hitting 60 does strange things to your body). I’ve lived in an RV since Feb and it’s a struggle just to get up most days. I hate it. I just realized I’ve spent the last 5 hours surfing boats for sale. And my partner is completely unable to understand that the things you do on a boat are not the things you do in a house. I mean only a sailor understands that changing a single light in the boat can affect the VHF radio. Everything we do is a chess game… what will happen to this repair when the wind pipes up to 50 knots? He just doesn’t get it. And I’m really struggling with the whole “people” thing. Since I left the boat, I’m stuck in ennui.

    Anyway, I can only hope I’ve attained the ” that all the people I admire as they age have fewer answers and more questions. Fewer tightly held opinions and more genuine generosity, flexibility and presence. They tend to not be attached to the status quo and live lives that are uniquely shaped to their own palette. They are humble, fierce, compassionate, kind and they have integrity. They value and live their truth and purpose in each moment. They are humans, flawed, quirky and beautifully themselves” status that you speak so beautifully about. Seems such a small proportions of people reach that.

    Keep writing, little sister. You never know who’s listening. Much love, cyndy


    1. Thanks Cyndy!! Yes, very few people go for intentionally alternative lifestyles for sure. You also name another huge complication to choices: partners. Because when we choose to live with someone it changes things up because your stories and future are intertwined. As with being solo in living arrangements there are pros and cons and ups and downs. Romance is definitely an area where the older I get the fewer answers I have. What I will say though is that water people are a different stock for sure and it is hard to be landlocked when the body calls for the sea. I hope you are getting enough water doses in your life to balance it out all out!! Fair winds!! ❤️❤️


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