Not Ready to Fully Stop? Designing Your Encore on Your Own Terms
Here’s a question worth sitting with:
Are you still working — or considering going back to some version of it — because you genuinely want to? Or because the alternative feels less defined than you’d like?
Both answers are valid. But they lead to very different decisions. And knowing which one is actually driving you is, practically speaking, the most useful thing you can figure out before you commit to anything.
The Two Very Different Reasons People Keep Working
There is a meaningful difference between working because something pulls you toward it and working because something is pushing you away from the alternative.
Working because you’re pulled toward it looks like this: there is a project, a role, a problem, or a form of contribution that genuinely interests you. You find yourself energized by it. The idea of doing it doesn’t feel like obligation — it feels like engagement. You’d probably do some version of it even if nobody was paying you, or paying you much.
Working because you’re being pushed looks different: the structure of work is what you’re actually after. The daily rhythm. The sense of being useful. The identity that comes with having somewhere to be and something to produce. The work itself is almost secondary — what you really want is what work provides.
Neither of these is wrong. But they require different responses.
If you’re being pulled toward something specific, the question is how to design that engagement on terms that fit this chapter of your life.
If you’re being pushed by a need for structure, purpose, or identity, the better question might be how to meet those needs in ways that don’t simply replicate the old career under a different name.
What an Encore Actually Is — and What It Isn’t
The word “encore” is important here, so it’s worth being precise about what it means.
An encore career, at its best, is not a continuation of your previous career with slightly different hours. It is a deliberate choice to contribute in a way that reflects who you are now — your current interests, your current energy levels, your current values — rather than who you were at the height of your professional life.
That distinction matters because the most common mistake people make when designing an encore is simply trying to replicate the old career in a smaller package.
Same industry, same pressure, same implicit expectations of themselves, just nominally part-time. The result is often a retirement that feels like a poorly negotiated version of the job they just left.
A genuine encore has different qualities. It tends to be chosen rather than defaulted into. It has clear boundaries around time and energy. It prioritizes meaning and engagement over status or income, unless income is genuinely needed. And it is held loosely enough that it can be adjusted, reduced, or set down when it stops serving you.
A Practical Framework: Four Questions
If you’re trying to figure out whether an encore is right for you — and if so, what shape it should take — these four questions will get you further than most career assessments:
What specifically am I drawn to doing, not just a field or category but an actual activity? What does the work itself look like on a Tuesday morning?
What conditions made my best work possible in the past — and which of those conditions do I want to carry forward? Which ones am I genuinely relieved to leave behind?
How much time and energy am I actually willing to give this? Not how much I think I should give — how much I genuinely want to give, on my current best day and on my current worst day?
What would have to be true for me to feel good about stepping back from this in two or three years? In other words, what does success actually look like — and is it achievable on my terms?
These questions are practical rather than philosophical because the most common encore planning mistake is operating at the level of the idea rather than the level of actual work engagement.
The idea of consulting sounds appealing. The reality of sourcing clients, managing deliverables, and showing up on someone else’s timeline is a different thing.
Getting clear on which one you actually want saves a significant amount of time and frustration.
The Shapes an Encore Can Take
For those who have worked through the questions above and still feel genuinely drawn to continued work of some kind, the range of possibilities is wider than most people initially consider.
Part-time employment in a different context. Many retirees find that a part-time role in a field adjacent to — but less pressured than — their primary career gives them the rhythm and engagement they want without the weight they’ve set down.
Project-based consulting. Defined scope, defined timeline, defined end. For people who want intellectual engagement without indefinite commitment, project consulting offers a clean structure. You choose what you take on, you deliver it, and you’re done. The boundaries are built into the model.
Board or advisory roles. Many organizations — nonprofits, community organizations, small businesses — are actively looking for experienced advisors who can contribute strategically without day-to-day operational involvement. These roles offer genuine contribution and continued relevance without the demands of a traditional position.
Passion-driven work that may or may not generate income. This is perhaps the most underexplored category. Work that is meaningful enough to pursue regardless of whether it pays well — a creative practice, a community project, a teaching role in a subject you love.
An encore is supposed to work for you
Not for your LinkedIn profile, not for the sense of staying relevant, not for the implicit approval of people who equate busyness with worth.
The most satisfying encores I’ve seen are the ones that were designed with exactly that clarity — by people who knew what they wanted, were clear about what they didn’t, and built something that fit the life they were actually living rather than the life they used to have.
That kind of design is entirely available to you. It just starts with your answer to the question at the top of this post.
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