This as-told-to essay is based on a conversation with Lisa Fail, 61, who lives in Durham, North Carolina. In late 2024, after about three decades in tech, she decided to take a career break. The following has been edited for brevity and clarity.
I’m super lucky. I’ve really loved every job — maybe not when I was a teenager working at McDonald’s — but the rest of them have been amazing. Good people, fun work. Not everyone has had that experience.
The choice to step back came about two years before I left. Work was always my thing. I have a husband and two kids. They’re amazing, yet work was where I put a lot of energy.
Before I decided to leave, I said to my boss, “I’m looking for something else. What’s next for me?” He said, “Well, I realized at a certain age I was never going to be CEO.” It became clear he thought I’d reached my peak at the company.
Duped by my own illusion
As I drove home that evening, I reflected on the conversation. It was the bad-boyfriend moment: You realize you’re putting everything into it, and there’s not really any commitment on the other side. I was like, “I need to figure something out, because this feels like rejection.”
I had been doing cybersecurity work, and it was super fun. I had this secret hope that eventually I would be recognized or promoted. My boss was being honest with me — and ultimately commiserating — but it was really disappointing to hear.
I felt duped by my own illusion. I wasn’t perceptive enough to see that I didn’t have much room to move up, because I liked the work and was focused on getting it done. I was the annoying coworker saying, “Hey guys, happy Monday.”
After that conversation, I decided to become a bit more mercenary about it, which sounds terrible. But if this is going to be transactional, let’s make it transactional. So I stopped volunteering for everything and getting in the middle of everything. I kept working very hard, but it wasn’t 60 hours a week anymore.
I wasn’t prepared for that, because suddenly I wasn’t putting my whole self into it and was still getting the same amount of money back. But it didn’t feel as good; it felt hollow.
So I thought, “If I worked as hard — but part-time — maybe that’s the answer.” By then, I had a different boss, and she was willing to try that with me.
It was fun at first, but after a couple of months, I felt like I was spending my time at my desk, and life was passing me by. After pulling back, I never could fall in love with it again.
Best case, I’ve got maybe 20 years of great health left. That’s like 7,000 days. That’s 1,000 weeks — 1,000 Mondays. That’s not a lot of time.
One hand on my phone
When you leave a job, it’s kind of like a retrospective at the end of a project. Looking back, I was like, “Whoa. How many vacations did I drag my computer on? How many times was I shushing my family in the background, or sneaking off to a closet in the Vrbo for a conference call?”
They weren’t things that I missed, but things that I hadn’t fully participated in because I had one hand on my phone.
I had always felt so time-impoverished. I would cook dinner and be working on whatever, or get in the shower, put my phone down, get out, and check it.
Suddenly, after leaving, I was overwhelmed. My time is not constrained. I’m not going to live forever, but today is mine. What am I going to do? I’m going to go do some yoga.
I feel like it’s a break, not retirement. I have no desire to go back to corporate, and particularly not tech. I’ve been there, and it was great. When I go back, it’s going to be something that I can love and be completely enmeshed in — when you look up, you’re like, “Oh, it’s dark again.” Maybe something nonprofit, maybe government, maybe a startup. It’s definitely the sense of purpose and greater good beyond stockholders and CEOs.
Man, this is easily top five, maybe top three best decision I’ve ever made. Could I have made it sooner? Maybe, but it was just about the right time.
Your real business
When I get up in the morning, I think if I were not here today — drinking my coffee, reading the news — I’d be scurrying back in my pajamas and slippers, trying to get caught up on something.
I don’t miss the “What did I miss? What did they find overnight? Is there anything that’s going to stop our deployment?” It’s all of that false urgency. Now, it’s like, “Oh, no. We’re almost out of half-and-half.” That’s the urgency.
Work is not your life. Your employer only buys 40 hours. Every hour they do not pay for is yours. Enjoy your work — love your work — but know your real business is life.
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