Why You Should Start Exploring Your Encore Career Before Retirement

In my recent article,“Four Questions Answered About Encore Careers,” I discussed how encore careers are less about starting over and more about building forward into work that feels purposeful and aligned with who you are today.

What I loved most after the article was published were the responses from the community.

One woman shared that she found her encore career as a caregiver. Another retired from a demanding healthcare role and now teaches lipreading classes on her own schedule, combining purpose, flexibility, and fulfillment. Others expressed a desire for stimulating work that supports their lifestyle, energy, and personal well-being.

What stood out to me most was this: many of you are not waiting until retirement to begin exploring what comes next. You are experimenting, testing ideas, and slowly building your next chapter while you are still working.

And honestly, that may be the best approach.

An Encore Career Does Not Need to Begin the Day You Retire

Starting earlier gives you time to thoughtfully explore possibilities without pressure. Instead of feeling rushed to figure it all out later, you can begin now in small, manageable ways.

This exploration might look like volunteering for a cause you care about, mentoring someone in your field, teaching a class, freelancing, consulting, or turning a hobby into a small side business. Sometimes what people truly want is not necessarily another full-time job, but more flexibility, creativity, connection, or meaning in how they spend their time.

The beauty of starting early is that you give yourself permission to experiment.

Small experiences often lead to surprising discoveries. One conversation may spark an idea. One volunteer opportunity may uncover a hidden talent. One small class or project may eventually become your next chapter.

As a Career and Life Coach, I help women take those first steps toward exploring what is possible next. Often, the hardest part is not making the change itself, it is simply giving yourself permission to begin exploring. Sometimes having someone beside you who can gently challenge your thinking, encourage curiosity, and provide accountability can make all the difference. You do not have to figure it all out alone. In fact, collaboration and conversation are often what help uncover possibilities you may not have considered on your own.

If you are wondering where to start, here are three questions to ask yourself:

1. What Activities Make Me Lose Track of Time?

Pay attention to what energizes you naturally. Your interests often leave clues about where your next chapter may lead.

2. What Skills or Experiences Do People Consistently Come to Me For?

Sometimes your encore career grows from strengths you already use so naturally that you overlook them.

3. What Kind of Lifestyle Do I Want Moving Forward?

More flexibility? Less stress? More creativity? More connection? Your next chapter should support the life you want now, not the life you had 20 years ago.

Perhaps most importantly, exploring an encore career before retirement can help ease the emotional transition many people experience when leaving long-term work. Careers often provide structure, identity, purpose, and connection. Beginning to build something meaningful ahead of time creates a smoother bridge into what comes next.

You do not need a perfect plan.

You do not need all the answers.

You simply need to stay curious enough to take the first small step.

Your encore career may unfold one conversation, one experiment, and one opportunity at a time. And that is perfectly okay.

Let’s Get the Conversation Started:

Have you already started exploring your encore career while still working? What have you discovered so far? I’d love to hear about your experiences, ideas, or even the small steps you are considering taking next. Share your thoughts in the comments below, and let’s encourage one another as we explore what’s possible in this next chapter.