Why I Unretired (And Why Re-Retiring Was Even Better)

February 10, 2026

This fall, I had a short relapse into the world of full-time work. I called it “unretiring”, which, it turns out is a real thing, particularly among baby boomers (there’s even a book called Unretirement). But I didn’t unretire for money or because I was entirely bored. I got excited about an opportunity and forgot about preserving my most precious resource: time. I ended up re-retiring four months into the role and I’ve been far happier in re-retirement than I was in retirement. Here’s why.

Does Retirement Make You Happy?

I’ve never had any real career goals except to quit my job. True story. That doesn’t mean that I’m not ambitious. I am so ambitious and without real goals of my own, I let society dictate what I wanted to do with my career. So, I got on that ladder and I climbed it: Engineer, Manager, Senior Manager, Director, VP. That seemed high enough to me and with the help of the FIRE community, I threw in the towel when I had enough money and had had it with the corporate world. I effectively retired at 41. (I say effectively because I still teach a university course on the side, for fun and a tiny bit of money, which I absolutely love doing.)

All through my career, I had the not uncommon thought that retirement would makes me incredibly happy. Having all the time in the world to do anything I liked? Travel, reading, hiking, board games all day long? Priceless. I even did some playing around with what I would do in retirement before I retired. For example, I wrote a book and decided I’d like to keep writing. I teach my course and was planning to keep doing that. Every week, I was going to volunteer more often and go out to coffee, both of which I absolutely did. I figured this retirement thing would be easy. But a little over a year of retirement, I felt like I was missing something.

Why I “Unretired”

There were a couple of things I missed on a daily basis. I missed the amount of socialization you get at work. I am a retired Vice President, so I was going from a day filled with back-to-back meetings to one of pure freedom and maybe one or two coffees. It turns out, I liked that much talking and leading. It also turned out that I really liked solving all the tough problems that came along and collaborating with a team of amazing people to do it. Yes, those same problems that I thought were stressing me out so much when I was working seemed to actually be filling my soul with something that I didn’t get when I retired. Who would’ve thought?

I missed these things so much that when an opportunity came about to be the Chief Operating Officer for an AI start-up with three other people who I really admired and liked working with, I took the opportunity. I went with my first instinct and took that job. I’d never been led astray in the past when I had that good gut feeling about something, so why would it be any different now?

Why I “Re-retired”

The answer to that question is that things are different because everything changes in retirement. And your decision-making processes need to change too. Let’s look at this closer, shall we?

When you’re working and you’re presented with an opportunity (do you want to be the executive sponsor for the new hire group that mostly goes out and drinks? do you want to go to coffee?), you’re weighing it against work time. You will either go do that thing or you’ll work. Of course you should go get coffee, when the alternative is sitting in your office or enduring another leadership meeting. The choice is quite easy.

But when you’re retired, you have full control over your time. You’re weighing every opportunity against your free time, not your work time. So, when someone invites me to a webinar, that means I’m choosing to sit online over my lunch hour instead of having a nice lunch and a walk with my husband. That’s a hard pass. Or when an ex-colleague who kind of drains my energy asks me to coffee, I’m giving up my afternoon tea time on the couch reading. Sorry, energy-drainer, I choose my book.

When you’re retired, the time you’re giving up becomes more precious because it’s yours. When you’re working, that time was always going to be spent working, go get that coffee? It’s kind of working and that sounds like a lot more fun.

In retrospect, I should have thought harder about what I was giving up when I unretired. I thought about all of the things I would be gaining like great colleagues, a nice title, and interesting work. I barely thought about what I was giving up: my time, my ability to show up for my family, my students, and my community.

Truth be told, I knew I’d made a mistake after the first week. But I wanted to give the new job a good shot. So, I worked my ass off, trying to, again, juggle all the things. My husband took on more errands and drove the kids more often. I saw him less. I saw my kids less. Most nights, I woke up stressed out and couldn’t get back to sleep. Occasional headaches that had completely disappeared in retirement came back. It was the same, exact hamster wheel I’d just left a year and a quarter before. And it was just as awful.

Of course, I had good days and bad days. I loved doing discovery calls and leading our founding hypothesis workshop. I loved getting the roadmap cleaned up and on the right track. But I hated how our CEO would always move meetings at the last minute and plop them down over lunch because her schedule was FUBAR. I’d found the antidote to a busy schedule and I knew what I had to do about it.

And so, I re-retired.

You Don’t Know What You’ve Got…

…until it’s gone. It’s so true. Before I unretired, I used to fixate on the things I was missing in my life and obsessively tried to find them again. And I did, big time! I found that working filled a tiny hole in my life, but then it took over everything else too. Now that I’m re-retired, I don’t focus on what’s missing anymore, I focus on what I have.

Freedom.

Time.

Personal projects.

Mid-week game days.

Tons of coffees.

Flexibility.

And that mindset change has made all the difference.

Getting Over Retirement Fears

I think there’s something scary about retiring. There’s a little voice in the back of your head saying that it will be hard to find a job again if you need or want it. What if you run out of money or suddenly want to live a more extravagant lifestyle? Perhaps now I know that I have a real choice. No, it won’t be hard to find a job if I want one. No, it won’t be hard to find work, even in the midst of a terrible economy.

Before unretirement, I used to waffle back and forth between thinking of myself as “on sabbatical” or “semi-retired” and now I think of myself as more fully (probably permanently) semi-retired.

I’d love to never, ever go back to full-time work because who has time for that? Who has time to give up most of their day to a company that cares very little about them? Who has time to almost never have time to see their friends? No one has time to run from back-to-back meetings to the school to pick-up a kid and only spend 15 minutes with them because you’re busy and they’re busy. I don’t. You don’t. I have the time to do the things that matter to me now. I’m calling the shots again.

Thank you, re-retirement!

Search the Blog

Subscribe to Blog via Email

Enter your email address to subscribe to this blog. We will never share your email.

About Amber Field

Amber has over 20 years of experience working in the software industry with agile software teams and specializes in creating efficient, happy teams & clients while helping them scale, execute, and work / live intentionally.
Get to know Amber →

Check Amber Out On:

Browse Posts by Category

Recent Posts

Overwhelmed by AI? It’s OK to Watch for a While

Overwhelmed by AI? It’s OK to Watch for a While

There’s a particular flavor of anxiety that’s causing us all to believe that if we’re not using AI all day every day we’re falling hopeless behind. If you’re overwhelmed, resistant, skeptical, or just genuinely uninterested in the AI hype cycle right now, I want to say something that you might not be hearing very often: That’s okay. You’re going to be fine. And here’s why I think that.

read more
We’re Looking for Partners for UW-Madison’s CS Capstone — Could That Be You?

We’re Looking for Partners for UW-Madison’s CS Capstone — Could That Be You?

One of the things I’m most proud of during my career is creating and running UW-Madison’s Computer Sciences Capstone course (CS 620). Every semester, hundreds of computer science Seniors work in teams of four to six on real software projects for real organizations, using agile development practices. And every semester, I need great partner organizations to make it happen. Last year, we had 27 amazing partners and we’re looking to grow quite a bit to accommodate 40% more students for the 2026-2027 school year.

read more
What I Learned at the Global Agility + Innovation Summit: AI, Judgement, and the Future of Leadership

What I Learned at the Global Agility + Innovation Summit: AI, Judgement, and the Future of Leadership

I just returned from the Global Agility + Innovation Summit, a one-day leadership conference in DC hosted by Sanjiv Augustine and his team at LitheSpeed. It was a day packed with sharp thinking, genuine conversation, and the kind of energy that only happens when a room full of practitioners who actually care about the work they’re doing get together. Here are some conference highlights.

read more