Wednesday, October 15, 2025

Trying to Take a Break

It was a beautiful Monday morning last summer as I sat down on a lounge chair to relax. I had lost my job five days earlier, but was in no rush to find the next job – or even to look. So I was taking some time off: My plan was to do whatever I wanted to do. I had spent the previous four days backpacking with friends on an already-planned (and wonderful) trip. This was the first day I would have been going to work if I still had my job. I did my morning meditation, solved the Wordle, and started flipping through the newspaper. Soon, I noticed a sinking feeling spreading through the pit of my stomach and a growing sense of dread.

This dread wasn’t about money or health care — I had planned for those things. It wasn’t about any specific need. Instead, it was about my complete freedom, and the lack of structure suddenly staring me in the face. I am a person of habit and routine whose routines were gone, and whose habits no longer felt relevant.

This post is the second in a series of posts reflecting on losing my job.


Reclining patio chair on a gravel patio. Next to the chair is a small table. Sitting on the table is a tablet and the newspaper.

My lounge chair, newspaper, and games waiting for me.

Many months earlier I had started to plan for the paid eight-week sabbatical that my previous employer granted to employees on their 10-year anniversary. Initially, the idea of eight weeks off overwhelmed me. I had never taken more than two consecutive weeks off since college, including for the births of my children and previous job changes. I spent a long time conceiving of how to productively use that much time, and I had come up with a plan. Now I had an indeterminate amount of free time, and a plan, including travel, skiing, and a class, for eight weeks at the end of the year — not now.

Because I am a creature of habit, I create structure around me. That structure benefits me. My job had provided me, like so many people, with a lot of that structure, giving a rhythm to my weeks and years. That was gone, and I didn’t know when I would have it back. I also had intentionally tossed most of the other structure away in service to giving myself time and space to do whatever I wanted.

A Plan

When that sense of dread overcame me, I realized I needed some structure in my day. I needed to know there were some predictable parts to my days, every day. I also really did want to give myself the time and space to relax, regroup, and recover — I was tired and worn out from the shock and disruption of my job loss.

I set up a simple schedule for myself: two structured hours in the morning and the same in the afternoon. The morning hours were for doing useful things. I've always had a to-do list, and this is when I would work on it. That included keeping up with colleagues and updating my resume. The afternoon time was for reading and learning. I love learning and had a backlog of things I wanted to learn. The time might be reading non-fiction. It might be taking an online course. But it would be something.

And that was it. Four hours total in the day. Plenty of time to exercise as much as I wanted, to go for long walks, to take an afternoon nap, or to do the crossword. Plenty of time for just relaxing and enjoying myself, now (hopefully) free of the overwhelming existential terror of complete freedom with my time.

Executing The Plan

I started my plan on Tuesday — day two of my new normal week days. I started to feel better as soon as I put the plan in place: not perfect, but better. My journal for Tuesday includes:

I started building some structure for myself today. I needed it to not feel like I was drowning. I went through my well wishes and captured and organized them. That was really nice.  And I started to push forward on doing things. The progress is good for me. 


After losing my job I got a lot of notes from colleagues expressing sympathy and wishing me well. These came through email, LinkedIn, Slack, and a very nice virtual card. These messages really heartened me. I wanted to acknowledge them and make sure I didn’t forget them (I haven’t). So I collected and organized all these notes and responded to them expressing my gratitude.

Over the next couple of months, my two hours of useful time covered writing, dealing with health care, planning trips, and preparing for a job search. The writing was a combination of correspondences and early drafts of potential blog posts. The writing helped me make sense of my world. It helped me figure out how I wanted to think about everything going on in my life. That writing was just for me, although some formed the kernel of this blog post and series.

In my two hours of learning time, I finished a Coursera class on machine learning. I invested in my knowledge organization processes (i.e., note taking) greatly improving my Obsidian skills. And I learned about the latest on technical resumes and interviews, particularly design interviews. It felt good to do all of these things.

Outside those four hours, I did a lot of hiking, including planning and going on a wonderful backpacking trip with my children. I did a lot of cooking, including taking a week-long cooking class at the Culinary Institute of America. And I ran a lot, getting into great shape.

Three people on a mountaintop, with a mountain range in the background. In the foreground is a man who is smiling. Slightly behind him are a young woman and a teenage boy..
With my kids on the summit of Nippletop mountain in the Adirondacks during our backpacking trip. 

I did a lot of great things in this period. I still regularly faced worry: worry about the present and worry about the future. But that worry didn’t keep me from making the most of my time. And over time, that worry continued to get smaller. In short, I was living my life to its fullest, making the most of all the time I suddenly had.

After Accepting a Job

Last October, I accepted a job offer and the rest of my worry went away. I negotiated a start date of January 2nd so I could still enjoy all the things I had originally planned for my sabbatical. It also let me fully relax for a period of time, knowing that I had the next thing already lined up.

I took a number of trips in that remaining time, including two ski trips, and an amazing two-week-long 25th wedding anniversary trip to Bhutan, Singapore, and Bangkok. It was one of the best periods of my life.

When I wasn’t traveling, I stuck to my schedule of two hours in the morning and two hours in the afternoon. My afternoon focus shifted from interviewing towards starting a new job. I reviewed The First 90 Days. I brushed up and/or learned about the tech stack of my new employer. I still enjoyed and appreciated that structure to my day. It felt good.

Back Into Work

Towards the end of my time off, I started to feel excitement for that next adventure. I also started to feel a tinge of nervousness not unlike what I’d felt as I sat down in my lounge chair on that summer Monday. I was now used to four productive hours a day. What would it be like to go back to a full eight hour day? Would it be too much? Would I have time for the things I had come to appreciate more? Time would tell. It would definitely be an adjustment, but I would take it in stride, just as I had when presented with unlimited free time last year.


Thank you to Heather Beasley Doyle for her feedback on this post and her support through this entire period of my life. Heather is a gifted writer. You should check out her homepage and her writing. 

No comments:

Post a Comment