What can you expect in the early days and weeks of stepping away from full-time work? Whether you choose to quit abruptly or ease into semi-retirement, managing your time and setting firm boundaries can be surprisingly challenging.

Back when I was a teenager, pop singer Neal Sedaka sang, “Breaking Up Is Hard to Do.” Now, after more than three months of being a “somewhat retired” lawyer, I can confirm that stepping away from a long-time career is indeed tough. I still struggle to give anything less than my full attention to the clients I’ve kept on.

Logging In… Way More Than I Thought I Would

Aside from a few brief vacations, I’ve barely missed a day (weekends included) of logging in to the office since the start of the year—pretty much the same routine I had when I was working full-time.

I’m glad I opted to scale back instead of quitting completely, because now I realize I couldn’t have just walked away without a gradual transition.

So now I find myself trying to define what retirement—or semi-retirement—really means. While retirement sounded great in theory, I’m still working on making it a reality I enjoy. Those little breaks I’ve taken have been fantastic (check out Camille Stell’s “5 Ways a Sabbatical Can Help You Assess Retirement”).

Truth is, I still really enjoy representing people—more than I expected.

Semi-Retirement Isn’t as Effortless as It Sounds

I have full control over my caseload and my hours, but old work habits are hard to shake. I’m putting in the effort to scale back, even though it feels counterintuitive at times.

Ultimately, I’m reassured that I made the right choice to gradually reduce my workload rather than making a clean break. I still enjoy the legal work—especially when it’s free from office-related stress like commuting.

It’s not that I lack hobbies or other interests. I do want to spend more time volunteering. And I’ve made some fun discoveries—like how quiet stores are during weekday afternoons, or how relaxing it is to read a book in the middle of the day with sunlight pouring in, instead of nodding off over a novel at bedtime.

But still, I can’t seem to stop checking in on work.

Maybe that’s not all bad. It reminds me of the old interview cliché—“I care too much”—and maybe that’s just how I’m wired.

Looking back, I know I made my decision at the right time. I didn’t want to wait until burnout forced my hand. I spent a lot of time thinking it through, and I still believe I chose well. But I may have overestimated how ready I was to quit entirely. So, I’ll keep easing out, bit by bit.

Tip: Give Yourself Something to Look Forward To

Leaving a fulfilling career behind is no small feat. The best advice I can offer is to start planning early. Cultivate interests beyond your profession, and let those passions grow. When it’s time to walk—or run—away from your career, having something else to pursue makes the transition much smoother. And don’t be afraid to look back when you need to. (For more, read “Prepare Yourself for a Happy Retirement” by Ida O. Abbott.)

I hope to keep moving forward, away from full-time law practice, while still enjoying the clients I choose to work with. And maybe, just maybe, when I travel to Green Bay for all nine Packers home games this season, I’ll manage to leave the laptop at home for at least one or two of them.

Just like a truly retired person would.

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