An end to a career
Saying goodbye to a 25+ year career and giving myself permission to follow my curiosity.
It’s been one year since my job ended. And what I thought would feel like jumping into unknown waters ended up being more like a slow submersion.
What I realize now, after wanting to leave my design career for so long, is that I needed the entirety of this year to take incremental baby steps towards leaving behind this identity. I wasn’t ready to completely drop off a cliff; the way the year unfolded was serendipitously more gentle.
I ended up working more than I thought this year, taking on consulting projects and even pulling in some 10 hour days again, but I also had time to think, to write, to stare out a window, to walk, and to collect things. While the intention at the beginning of this break was to wait out a challenging tech job market and see where the industry settles, I came to a decision awhile ago that I wasn’t going to look for a job.
This feels radical because it is. But I’m a breadwinner! What is this going to look like, what does that even mean? Friends, I don’t really know yet, but now that I’ve made this decision, I’ve come to realize that I needed to create space for closure as I walk away from this 25+ year career.
And what am I leaving behind? A career that supported my family and gave me purpose beyond being a mother and a wife; a career that challenged me with hard and interesting problems to solve and gave me the opportunity to create beautiful products and experiences with some pretty great people and interesting clients. I was designing since the nascent days of websites, in the wild west of interaction design when we put navigation anywhere and had to code every page by hand. I feel fortunate to have witnessed the evolution of this industry and the tools we use to design along the way.
But.
I never truly loved it, and I never kept that a secret.
I loved certain projects and parts of being a designer, but after finally ticking off the one thing left that I wanted to design—a native app—there wasn’t really anything more that I wanted to do. I never wanted to concede that I was aging out of an industry, but I’m relieved that I don’t have to pretend that I’m younger than my age anymore just to give off an illusion of hireability. So, after designing more than 80 websites, games, apps, and digital products over the last 27 years, I’m ready to walk away.
I understand that for many people, a job is a means to an end. This is why we have hobbies and interests. But I’ve also come to acknowledge that this idea of a life-long career and working multiple jobs till burnout might very well be a Gen X stronghold and a badge of honor that I held close. The thing is, nobody else cares how much you work. I needed to change my perspective on all of it because younger generations don’t have any problems saying no to hustle culture.
It isn’t a coincidence that all the recent events of my life have converged towards this decision at this moment: the proverbial empty nest; feeling my own mortality through the death of a parent; changes in an industry that I’ve eagerly adapted to but can now admit I no longer want to keep up with.
It began with turning off my “open to work” status on Linkedin a few months back. Last week, I deleted the app on my phone altogether.
I’m not impervious to insecurity and comparisons. I don’t need reminders of my shortcomings or what I’m leaving behind, or the job titles I never held or companies I never worked for. I’ve had a rich and interesting career, but in my worst moments I felt like I didn’t achieve or climb high enough. I’ve had three startups and businesses that “failed.” My past three attempts to pivot away from design was unsuccessful and I never made the kind of mad tech money that I sometimes regret not chasing. I still feel vulnerable in this aspect, but I had to remember that this is something I can control to a degree. We should feel empowered to filter out the noise that doesn’t serve us, but instead seeds self doubt and fear.
You can have it all, but not at the same time
In my futile, but genuinely earnest attempts to have it all, I raised my children with some creative work-around ways that gave a middle finger to a system that doesn’t support working moms, but I never had it all. Let’s be real. You can have it all, but you can rarely have it all at the same time. Now that I have the perspective and space to reflect back without any blinders on, it’s clear that my career suffered from the “mommy track” path that I put myself on. I protected my flexibility fiercely, but at at the expense of career advancement. During this year of transition, I have let go of these regrets too.
I am a planner, the one in my family who orchestrates the broad strokes of our collective future. This has required me to always choose a paycheck over following my own curiosity and interests. At times, I’ve been envious of other artists, people who could spend all of their working hours pursuing their dreams. I read with great interest the women who become artists and writers later in life after the children have been raised and obligations done. I’ve held on to this idea as a playbook for my future, but I wonder why I need to wait so long.
I am not waiting.
Even though I am weirdly calm and curiously un-panicked about the loss of income, I am also scared. This is the burden of being a breadwinner. I have always been a good saver, but there is no one to financially float this diversion. I do have support of my family. Still, some days it feels selfish and irresponsible, especially since we’re facing two college tuitions very soon, but what I don’t carry anymore is the guilt.
I never liked the trope of “follow your passion and the money will follow” because it’s incredibly privileged. I also have no interest in being a starving artist, so I will continue to orchestrate and plan as I’ve always done.
I guess this is year two of this newsletter. Thank you for coming along this journey with me. I feel incredibly grateful that you are here.
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!
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 :-)