More than four years ago, I shared How to Semi-Retire, which described my plan to gradually wind down my consulting, training, and facilitation business.

To recap my semi-retirement strategy: avoid lengthy jobs (strategic plans, mergers, long-term consulting gigs) and focus on one-offs, such as workshops, webinars, retreats, and meeting facilitation. I don’t want to carry a client around in my head for six months, but I’m happy to make short-term commitments.

When I wrote that post, my intended audience was fellow Boomers nearing the end of their working lives. More broadly, I sought readers who were considering any kind of long-term work transition. Perhaps, I thought, you can learn from my experience, and we can all learn from each other.

Several years into this experiment, let’s discuss the good, the bad, and the confusing.

Semi-retirement is non-binary – and people struggle with that concept

When I first shared my plans, colleagues congratulated me on my “retirement.” What are you going to do, they asked, with all that free time? Others stopped sending requests for consulting proposals or removed me from their referral lists, assuming that I was done.

I continue to explain (often!) that I’m still working but doing it differently. When describing how I rarely set a wake-up alarm – this makes everyone smile – they begin to understand the concept.

Somewhere along the way, we Americans were trained to think of employment as binary: either you’re working – and probably working your butt off – or you’re fully retired, parked in a recliner or driving around in an RV. This is likely the residue of an earlier era that included the promise of lifetime employment and workplace pensions.

In reality, our work lives have always been complicated. Many households require multiple jobs and side hustles just to get by. Indeed, some folks will work until they die because they need the money and/or derive meaning from their work … possibly both.

Of course, the definition of semi-retirement remains somewhat slippery for me, too. When people ask what it means, my standard response is, “Not entirely clear, but I’m figuring it out.”

Years saying yes – then it’s hard to say no

After 30 years of self-employment – surfing the ups and downs of cash flow – my strong impulse is to seek out clients, respond to their requests, and prepare lots of proposals. You know the drill: Not every bid is accepted, so you need to pursue multiple opportunities as they arise.

As both a fundraising trainer and someone who supports new consultants (raise your hand if I’ve helped you launch or build your business), I believe in the power of abundance. Yes, there’s enough money for your nonprofit to thrive. Yes, there are plenty of clients. If you find the right niche, you can build a viable business. Yes, yes, yes!

However, not every bid lands. Not every client commits. Therefore, I’ve trained myself to keep multiple balls in the air and many projects in development.

In semi-retirement, juggling fewer balls – and allowing a few of them drop – is a profound change for me. And yes, it’s been a little more difficult than anticipated.

Nature – my nature – abhors a vacuum

When the previous post appeared in 2021, I had recently become board president of a local nonprofit, helping to navigate the group through COVID and other difficult moments.

More recently, I co-chaired a capital campaign for our local food co-op, then joined the board during a challenging transition for the organization. I’ve also been pulled into fundraising efforts to provide legal services for Vermont’s immigrant and refugee community.

This is all volunteer work: hours and hours of volunteering. As noted earlier, I have a hard time saying no. Therefore, some of my non-work time has been vacuumed up by volunteer commitments. And that’s OK.

To paraphrase the famous disclaimer, your experience may vary. Or maybe not.

OK, how about the best parts?

Overall, my semi-retirement experiment has been working pretty well. Here’s why and how.

Choice. I can be more selective about which jobs I accept and which I decline.

Comfort and skill. After 45 years in the nonprofit universe, including 30 as a consultant and facilitator, I can manage almost anything. Indeed, I am a little reluctant to shut it down because I continue to enjoy the work and I’m good at what I do.

Mentoring. I can support those entering the field and building their consulting practices.

More free time! In the woods and on the water, digging in the garden, going to the theater and movies, reading books, seeing friends, and hanging out with my beloved. Plus the part about sleeping late.

Finances. I’m earning less but generating enough to avoid draining our retirement account. I will qualify for maximum Social Security in two years – assuming they still have employees to process my claim (!) – so that’s the next goal.

What’s your plan?

If you’re nearing retirement – I’m talking specifically to my nonprofit lifer colleagues – how are you thinking about the transition? Any lessons you’ve learned from family, friends, or peers?

Please use the comments section below to share your questions and your wisdom.