Lessons from my blue sabbatical

What I learned at the intersection of grief and career transition

Your Five-Year Plan is a newsletter about embracing life’s profound uncertainty.

Maybe your own plans went up in flames; maybe you’re considering a big, scary leap. This is your trusty companion while you’re writing the next life chapter.

Welcome to the conversation—and to the adventure that unfolds when your plans go sideways. This is letter #49. ✨

Lessons from my blue sabbatical

Pilsen mural, captured on Kodak Portra 400 film

In a perfect world, my sabbatical might’ve started with the Torres del Paine trek in Chilean Patagonia, or perhaps the Tour du Mont Blanc in the Alps, after months of plotting my itinerary, penciling in a budget, and crafting multiple backup plans.

Instead, as longtime readers already know, it began with a surprise layoff the day before my mom’s burial.

We don’t get to choose every ending, and the unique texture of an ending informs any new beginning that follows. Because I was grieving, and grappling with everything my mom left behind, I couldn’t fathom putting on a blazer or pasting on a smile for job interviews.

And thus began, almost by default, my blue sabbatical.

I wrote about the financial details that made my sabbatical possible in this post for paid subscribers, and later, the definitive decision I made to leave my financial planning credentials behind. Late last year, I mentioned I was experimenting with a career shift into the world of web design.

Turns out, my experiment was so rewarding that it became a joyful commitment.

So, as I leave my year-long sabbatical behind for the learning curve of self-employment, I want to share a few reflections with anyone else who’s reevaluating their relationship with work while also grappling with grief, loss, or transition.

✳️ Impending loss provided clues about what wasn’t working in my career.

As we accompanied my mom through home hospice, my brother and I juggled our full-time, blessedly remote jobs between 9 and 5. But before and after those hours—and during spare and stolen moments—we were the only place that mattered: with her.

This stretch included wildly stressful tasks: navigating hospice bureaucracy, triaging medical emergencies that we were unqualified to manage. But it also included warm, intimate gatherings with the loved ones who came to help and share heartfelt goodbyes.

My day job was rewarding in many ways, and I adored my clients. But it was these moments of profound, next-level connection that left me noticing the nagging ways in which my work left me hollow—and once I noticed that feeling, I couldn’t ignore it.

✳️ When I lost my job, I realized that creating a flexible financial life was pointless if I didn’t take advantage of that flexibility.

I’ll be chained to my mortgage for the next few decades, but almost every other financial and life decision I’ve made has been in service of flexibility, low stress, and simplicity.

My mortgage is affordable; I have a) lucky timing and b) moving to a smaller city to thank for that one. I had padded my savings account whenever I had money to spare. If you don’t count the cats, I’m child-free.

But what was the point of living below my means if I wouldn’t give myself grace when I really, truly needed it?

✳️ Deciding to take time off work allowed me to grieve fully.

To state the obvious: not everyone has this kind of privilege. But I sure wish everyone did.

It was wonderful that I never had to ignore the physical symptoms of grief in order to meet a deadline, or hope that my emotions didn’t crater at the exact moment I needed to facilitate a meeting. A year later, I’m so much healthier for it.

✳️ I finally had the time and perspective to consider what I won’t tolerate at work anymore.

That includes sacrifices I used to make, and behavior I used to make excuses for.

✳️ Being cut loose from old routines gave me permission to create new, better ones.

Before my sabbatical, work determined my alarm clock settings, my exercise and meal timing, and—yes, even in the most casual of business environments—many of my wardrobe choices.

After a year of experimenting with the details that make up my day, I have the kind of self-knowledge about my preferences that only comes when you remove outside influences.

✳️ One poignant realization: my life transitions would’ve made me better at the career I left.

Suddenly, I had real-world experience with the intricacies of estate planning, something I’d only understood in theory before. I knew the administrative details of transferring beneficiary accounts. I knew how to sell someone’s else’s house and car on their behalf. Most importantly, I could anticipate the complex emotional landscape that might accompany each one of these experiences—all of which would have made me a more skilled, empathetic financial planner, had I decided to return.

Still: even though my next career will have nothing to do with my loss, I’m closer to my humanity now, and that’s a boon in any line of work.

✳️ Turns out, facing the scary stuff led to new knowledge and life skills.

Stepping away from full-time employment was terrifying. So was facing the depths of my sadness head-on. I had to reckon with my grief, and the anxiety I felt as I spent down my savings. For the first time in my life, I had to learn how to face uncertainty.

Doing so required new skills—ones that I built in the process of facing my fears, not by avoiding them.

✳️ Grief sapped my energy. I got it back, but I couldn’t have rushed the process.

My mom’s cousin Susan taught me about the various Jewish traditions around mourning, including one meaningful detail about the twelve-month grieving period following the loss of a parent, after which the bereaved child is supposed to move forward.

Maybe it was just coincidence, but it turns out that the one-year mark is when I started to feel like myself again.

✳️ Loss reconnected me with my community. My sabbatical reconnected me to the joy of work.

As I gravitated toward work that’s better aligned with who I am today, I found passion and verve bubbling up where numbness and resentment used to reside.

I’d grown to be chronically on edge at work, always stressed out, always convinced I wasn’t doing enough. My sabbatical reintroduced me to my innate love of learning, and my love for the kind of tangible creative work that stacks up (like this newsletter!).

✳️ I learned that stress isn’t “just a feeling,” but rather a physiological process with physiological impacts. 

Rachel Katz

offered this brilliant reflection on the subject. Below, she writes about the financial carrots that motivated her to build (and ultimately sell) her company:

What I didn't realize, though, was how much of the money would go toward undoing damage I had done while working like I did, hurting myself like I did, underpaying myself, straining my relationships, pushing my body and mind past their reasonable limits and into a state of constant crisis. I bought time to recover and process the experience, time to not feel constantly under stress, time and resources to deal with health issues like infertility and autoimmunity. I bought myself a chance to repair the damage that my stress wrought in my relationship with my husband, and to rekindle friendships that I had neglected.

After a few demanding years of my own, my body started responding in ways I found concerning, like the hair-trigger fight or flight response that left my heart racing at objectively minor stressors. For me, the cure was time off.

✳️ Both grief and my sabbatical changed my relationship to money and productivity.

My embrace of slow productivity stems directly from the writing I did last year.

And while I used to value my Future Self far above my Present Self, I value them equally now. Life, after all, is tragically short.

That means I’m making more investments in myself now; my financial decisions reflect that shift, but so do my decisions around my time and energy. That feels especially good now that I’m on the cusp of what’s next.

💬 What about you?

What did you learn the last time you took time away from work? “Time away” can mean anything from just a little—a vacation, time off between jobs—to a lot.

Had your own plan-in-flames experience? Taking a leap into the unknown? I’d love to hear more. Just hit “reply” to get in touch, or introduce yourself here.

Warmly,
Maddie