Jenna, thanks for sharing your story and vulnerability. This is a timely piece for me as I am retiring from the Navy this coming summer after 24 years. It is the only career I have known as an adult. My wife and I had a long discussion about what comes next and I am definitely not in a rush to go back to work after taking off the uniform. I want to give myself the freedom to follow my own curiosity and pursue work that aligns with my passions rather than just seeking another paycheck. We will see how it goes!
Matthew, first of all—congratulations (? Is this the right thing to say?) on your upcoming retirement from the Navy. I have a cousin who also retired from the Navy after the same number of years. What a remarkable career. Second—thank you for your service.
Sounds like you have the right idea to take the time to reflect, and even mourn, the end of your career. It takes time. Some of the emotions may even surprise you. I'm still open to some consulting work as I have college to pay for, but I am really ready to make a big change. I do feel like it's taken years and years to make any specific moves that lead to where I am right now, but I don't want to put my curiosity off any longer. I don't want to have more regrets in life.
I think congratulations works just fine. It has been a good career but it definitely took me away from family and other pursuits which may have been more personally rewarding. I concur on the no regrets. My second story is going to be one for the ages!
I can only imagine from what I know from my cousin and having to uproot his family's lives every so years. I am excited for you and looking forward to seeing where the year takes you.
Thank you for sharing this. So many parallels with my own journey, including the regrets I've had to let go of since climbing off the career treadmill.
Thank you for sharing - I found your words inspiring. As a clinical psychologist who’s been in private practice for nearly 29 years I am tired and ready for something new. The financial side of things is what keeps me in the profession but I’m trying to segue into something more sustainable and enjoyable.
The financial aspect is usually the thing that keeps us in our jobs and careers. I found that I had to change my relationship with money, and then things started to gain more clarity. Only then could I imagine getting off the hamster wheel.
The very best of luck to you Jenna, a change well deserved and earned. I too am in a career which has served me well, provided a living for my family and allowed us a comfortable albeit modest lifestyle, however as you said I don't "love" it, and I'm sometimes envious of those who seem to be exactly where they are meant to be in life. I'll keep going for another while! but would like to some day make the change you are making now. Keep us updated :-)
I loved reading this and appreciate your journey. I remember well those old website coding days (yet ANOTHER thing we have in common). I just wrote about going through old tax returns, and I came across papers from that time, and was struck by the arc from there to here. I also identify with needing a year or more for a change of this magnitude to settle. These last couple years I’ve struggled to write in ways I never have before and had to ask myself, am I still a writer? Scary to come face-to-face with that question. Things have settled, and the answer is, yes, I’m still a writer, but my relationship to writing has completely changed. I have also (begrudgingly) come to accept a level of uncertainty I was unwilling to face before.
I read that newsletter! And you are a writer! It's really interesting to go through and see the arc of time and experience. Inspiration, confidence, and prolific creative output ebbs and flows. I do find that my confidence gets a little more shaky the older I get which is sort of interesting?? I thought we were supposed to grow sure of ourselves in old age? 🤔
This resonates so much, Jenna. Thank you for sharing. We need to normalize the idea of repotting our careers, especially as our life expectancy gets longer. I shared my own perspective on repotting here - check it out, if you'd like: https://abbydavisson.substack.com/p/the-long-term-benefits-of-repotting
Jenna I used to read your blog and lost track of you at some point and am so happy to find you here. I’m facing a lot of these same questions; I have about 19 months until my son graduates from college so am in this weird in between area but I’m ready to let go of all of this. It’s amazing though how a part of me is desperate to hold on to what we’re “supposed” to want and do, even though I never wanted any of it in the first place.
Hi Amy! I'm so glad you're here. Yes, this phase in our lives is very much in-between (liminal!) and there is still that constant pull as you described. I would think, however, that as we get older, we have earned the choice to let go of what is expected of us. I wish you clarity on some of these questions soon.
I’m glad that you had the time this year and a longer off ramp to consider all this. This really resonated. I’ve been thinking a lot about my career too—what constitutes a “good career”, the sacrifices, feeling selfish at times, and where to go from here that would leave me feeling more engaged and fulfilled.
I relate to so much of this. The career in tech - programming for me - that while interesting and challenging has never been something I love. Being the breadwinner. Watching others (all men) take promotions while I tried to balance motherhood with work. Feeling like I’m aging out of the industry now that I’m turning the corner towards late 40s. I am often weighed down by own practicality. I'm also a planner. Anyway! I'm not really going anywhere with this. It is nice to know I'm not alone in these feelings. Best of luck in your next adventure!
I was a homeschooling stay-at-home parent for 25 years before my younger kids recently went off to college. My husband was the breadwinner, and I stayed at home in part because my area didn’t have jobs for me and also because my husband spent weeks and sometimes months overseas at a time. So I didn’t have a career outside of the home, but I really related to the feelings you describe in your essay. My days sometimes feel very strange. I had intended to focus on my self-publishing business but I’m finding that I’m kind of tired and unfocused much of the time. I love your newsletters and can’t wait to hear more about how you’re doing on this journey.
Thank you for sharing Maya. I can relate to being tired and unfocused. I don't like to admit this sometimes, but I don't feel as sharp as I used to. I hope you interests and ways to spend your time that gives you joy.
Thank you Jenna, for sharing your incredibly honest and introspective journey over the past year. It takes a deep understanding of oneself and courage to embrace change. I was once at this crossroad and I can understand your decision to follow your curiosity and interests even in the face of uncertainty. As you embark on this new chapter, I wish you continued calm, courage, and the fulfillment that comes from pursuing your passions.
Taking time to read you comment again (without the rush of Thanksgiving travel). Thank you again for such a thoughtful comment of encouragement and positivity. I hope your crossroads took you to a place of fulfillment and joy.
My mom retired this year from a career she worked in her entire life. It's a career she never truly loved but put up with, but it provided for our family, put me through college, and provided the life she wanted for herself now. Since her retirement, she's been traveling around, spending more time with family and friends, and I can see she's starting to live her second life now.
I keep wanting to leave this tech career I found d myself shoved into I never really wanted… well, started off in design and kept veering into tech and now I find myself having to learn how to be a cloud engineer and screaming “F******CCCKKKKKK NOOOOOO!!!!” to nobody in particular last night in a clenched fist rage that scared my normally supportive 14 year old dog who is always the first to lean up against me when she senses I’m not ok… But last night, I scared her and she went outside to sit in the dark.
I can’t do this into my sixth decade, staring into my last chapter, with my soul crying needing music and art and words. I can’t continue to be held hostage by grandkids and everyone else wanting me to stay put so they feel more comfortable. I’m dying in the liminal… this has to be the last year of tech. Has to be, even if I run out of runway before anything else kicks in. Right?
Yeah. It’s never really the money, is it? Always something else entirely. But I’m gonna sit with that for a while and wish I was a little bit more brave.
It's hard to step away from something that has been the core of our identity for decades. The current job market and environment certainly makes that easier because some of us have little choice (e.g., ageism, etc.). If it's not about money, and for many money really is what's stopping people from leaving, then yes, finding something else to fill the time is a challenge that doesn't get discussed enough. I have projects and interests lined up and even I have (am still?) struggling with the transition. But once you step away, it's hard to go back. I might do a project and the thought of it is already making me anxious, even as I put hard limits on my weekly hours.
I love this comment of encouragement. Thank you ❤️
Jenna, thanks for sharing your story and vulnerability. This is a timely piece for me as I am retiring from the Navy this coming summer after 24 years. It is the only career I have known as an adult. My wife and I had a long discussion about what comes next and I am definitely not in a rush to go back to work after taking off the uniform. I want to give myself the freedom to follow my own curiosity and pursue work that aligns with my passions rather than just seeking another paycheck. We will see how it goes!
Matthew, first of all—congratulations (? Is this the right thing to say?) on your upcoming retirement from the Navy. I have a cousin who also retired from the Navy after the same number of years. What a remarkable career. Second—thank you for your service.
Sounds like you have the right idea to take the time to reflect, and even mourn, the end of your career. It takes time. Some of the emotions may even surprise you. I'm still open to some consulting work as I have college to pay for, but I am really ready to make a big change. I do feel like it's taken years and years to make any specific moves that lead to where I am right now, but I don't want to put my curiosity off any longer. I don't want to have more regrets in life.
I think congratulations works just fine. It has been a good career but it definitely took me away from family and other pursuits which may have been more personally rewarding. I concur on the no regrets. My second story is going to be one for the ages!
I can only imagine from what I know from my cousin and having to uproot his family's lives every so years. I am excited for you and looking forward to seeing where the year takes you.
Thank you for sharing this. So many parallels with my own journey, including the regrets I've had to let go of since climbing off the career treadmill.
I wish creative fulfillment for us both.
Thank you so much Sarah. May we both go forward with no regrets and only creative fulfillment.
Wishing you much joy and contentment in the time ahead. I loved reading this.
Thank you so much Aileen. Very much appreciate your comment here.
Thank you for sharing - I found your words inspiring. As a clinical psychologist who’s been in private practice for nearly 29 years I am tired and ready for something new. The financial side of things is what keeps me in the profession but I’m trying to segue into something more sustainable and enjoyable.
The financial aspect is usually the thing that keeps us in our jobs and careers. I found that I had to change my relationship with money, and then things started to gain more clarity. Only then could I imagine getting off the hamster wheel.
The very best of luck to you Jenna, a change well deserved and earned. I too am in a career which has served me well, provided a living for my family and allowed us a comfortable albeit modest lifestyle, however as you said I don't "love" it, and I'm sometimes envious of those who seem to be exactly where they are meant to be in life. I'll keep going for another while! but would like to some day make the change you are making now. Keep us updated :-)
The "envy" serves as inspiration and motivation. And then one day, it is our turn.
I loved reading this and appreciate your journey. I remember well those old website coding days (yet ANOTHER thing we have in common). I just wrote about going through old tax returns, and I came across papers from that time, and was struck by the arc from there to here. I also identify with needing a year or more for a change of this magnitude to settle. These last couple years I’ve struggled to write in ways I never have before and had to ask myself, am I still a writer? Scary to come face-to-face with that question. Things have settled, and the answer is, yes, I’m still a writer, but my relationship to writing has completely changed. I have also (begrudgingly) come to accept a level of uncertainty I was unwilling to face before.
I read that newsletter! And you are a writer! It's really interesting to go through and see the arc of time and experience. Inspiration, confidence, and prolific creative output ebbs and flows. I do find that my confidence gets a little more shaky the older I get which is sort of interesting?? I thought we were supposed to grow sure of ourselves in old age? 🤔
This resonates so much, Jenna. Thank you for sharing. We need to normalize the idea of repotting our careers, especially as our life expectancy gets longer. I shared my own perspective on repotting here - check it out, if you'd like: https://abbydavisson.substack.com/p/the-long-term-benefits-of-repotting
Ooh, I like the metaphor of repotting. I have never heard it being described like that before. Thank you for reading—and I'm off to read your post!
Jenna I used to read your blog and lost track of you at some point and am so happy to find you here. I’m facing a lot of these same questions; I have about 19 months until my son graduates from college so am in this weird in between area but I’m ready to let go of all of this. It’s amazing though how a part of me is desperate to hold on to what we’re “supposed” to want and do, even though I never wanted any of it in the first place.
Hi Amy! I'm so glad you're here. Yes, this phase in our lives is very much in-between (liminal!) and there is still that constant pull as you described. I would think, however, that as we get older, we have earned the choice to let go of what is expected of us. I wish you clarity on some of these questions soon.
I’m glad that you had the time this year and a longer off ramp to consider all this. This really resonated. I’ve been thinking a lot about my career too—what constitutes a “good career”, the sacrifices, feeling selfish at times, and where to go from here that would leave me feeling more engaged and fulfilled.
I know you've been having some similar thoughts. Maybe we need another coffee catchup!
I relate to so much of this. The career in tech - programming for me - that while interesting and challenging has never been something I love. Being the breadwinner. Watching others (all men) take promotions while I tried to balance motherhood with work. Feeling like I’m aging out of the industry now that I’m turning the corner towards late 40s. I am often weighed down by own practicality. I'm also a planner. Anyway! I'm not really going anywhere with this. It is nice to know I'm not alone in these feelings. Best of luck in your next adventure!
Tech is (still!) hard for women. And I'm glad to hear from you. Sometimes we need the space to say, and write, these thoughts out loud.
I was a homeschooling stay-at-home parent for 25 years before my younger kids recently went off to college. My husband was the breadwinner, and I stayed at home in part because my area didn’t have jobs for me and also because my husband spent weeks and sometimes months overseas at a time. So I didn’t have a career outside of the home, but I really related to the feelings you describe in your essay. My days sometimes feel very strange. I had intended to focus on my self-publishing business but I’m finding that I’m kind of tired and unfocused much of the time. I love your newsletters and can’t wait to hear more about how you’re doing on this journey.
Thank you for sharing Maya. I can relate to being tired and unfocused. I don't like to admit this sometimes, but I don't feel as sharp as I used to. I hope you interests and ways to spend your time that gives you joy.
Thank you Jenna, for sharing your incredibly honest and introspective journey over the past year. It takes a deep understanding of oneself and courage to embrace change. I was once at this crossroad and I can understand your decision to follow your curiosity and interests even in the face of uncertainty. As you embark on this new chapter, I wish you continued calm, courage, and the fulfillment that comes from pursuing your passions.
Taking time to read you comment again (without the rush of Thanksgiving travel). Thank you again for such a thoughtful comment of encouragement and positivity. I hope your crossroads took you to a place of fulfillment and joy.
Congratulations ❤️
Missed this comment - thank you so much Paolo!
My mom retired this year from a career she worked in her entire life. It's a career she never truly loved but put up with, but it provided for our family, put me through college, and provided the life she wanted for herself now. Since her retirement, she's been traveling around, spending more time with family and friends, and I can see she's starting to live her second life now.
I'm happy for your mom. I'm happy for my mom too, as she is living her second life only now.
I keep wanting to leave this tech career I found d myself shoved into I never really wanted… well, started off in design and kept veering into tech and now I find myself having to learn how to be a cloud engineer and screaming “F******CCCKKKKKK NOOOOOO!!!!” to nobody in particular last night in a clenched fist rage that scared my normally supportive 14 year old dog who is always the first to lean up against me when she senses I’m not ok… But last night, I scared her and she went outside to sit in the dark.
I can’t do this into my sixth decade, staring into my last chapter, with my soul crying needing music and art and words. I can’t continue to be held hostage by grandkids and everyone else wanting me to stay put so they feel more comfortable. I’m dying in the liminal… this has to be the last year of tech. Has to be, even if I run out of runway before anything else kicks in. Right?
Gerard, ok, so what is stopping you from leaving tech? Is it the salary and money? Or something else entirely?
Yeah. It’s never really the money, is it? Always something else entirely. But I’m gonna sit with that for a while and wish I was a little bit more brave.
It's hard to step away from something that has been the core of our identity for decades. The current job market and environment certainly makes that easier because some of us have little choice (e.g., ageism, etc.). If it's not about money, and for many money really is what's stopping people from leaving, then yes, finding something else to fill the time is a challenge that doesn't get discussed enough. I have projects and interests lined up and even I have (am still?) struggling with the transition. But once you step away, it's hard to go back. I might do a project and the thought of it is already making me anxious, even as I put hard limits on my weekly hours.