If you’re retired (or almost retired) and you’re thinking, “Okay… now what?”, you are not alone. The fastest way to find an encore career (a second act career) that brings real purpose in retirement and makes you happy is to get clear on your hard-wired talents, your core values, and what you actually want your days to look like.
Retirement is sold to us like a permanent vacation. Golf. Cruises. Netflix. Long lunches. No alarm clock. Bliss!
And then… for a lot of people… it turns into Tuesday. Followed by Wednesday. Followed by Thursday. And you start to feel a little strange. Not because you’re ungrateful. But because you miss meaning. You miss structure. Feeling useful. That little spark that comes from being engaged in life. (And yes, sometimes you even miss the office gossip; don’t worry, I won’t tell anyone.)
I’ve watched this happen with clients over and over. They don’t want to go back to a soul-sucking 40–60-hour week. And they don’t want to “start over” in a painful way. They just want to wake up and feel happy. Purposeful. Energized. And that’s where retirement careers, or encore careers, come in.
The Truth About Work After Retirement
Here’s what I’ve noticed: the happiest retirees aren’t necessarily the wealthiest. They’re the ones who are actively engaged in life. They have something to do that matters to them. Something that uses their brain. Something that lets them contribute.
It could be part-time work. Consulting. Mentoring. A small lifestyle business. Volunteering that turns into a paid role. A creative project. Teaching. Coaching. That’s why people search for jobs after retirement, semi-retirement jobs, and career change after 50 like their life depends on it. Because in a way, it does. They aren’t trying to escape work. They’re trying to escape work they don’t love.
A Client Story: Brian’s “Retired… Now What?” Moment
Let me tell you about Brian. Brian was the classic high-achiever. Smart, reliable, the guy everyone leaned on. He had a long career, did the right things, saved, planned, and finally retired. And for the first few months? He loved it.
Then the shine wore off. He told me, “Talane, I feel ridiculous saying this, but I’m bored… and I don’t like who I am when I’m bored.”
That line hit me. Because boredom isn’t always about needing something to do. Sometimes boredom is grief. It’s identity loss. It’s the quiet fear that your best years are behind you.
Brian started searching for retirement job ideas and encore careers, but everything felt either too small (“greeter at a store”) or too exhausting (“start a business from scratch”). So we did what I always do; we stopped chasing “a job” and started chasing happiness.
We looked at what had always lit him up. Not what he did for work, but what he loved doing inside his work. The parts that made him feel alive.
It turned out Brian loved mentoring younger people. He loved simplifying complicated problems, and he loved being the calm voice in the storm. He was a natural coach; he just never called it that.
Instead of jumping into something huge, he ran tiny tests. He started volunteering with a local program that supported people transitioning careers later in life. He offered workshops. One hour, then two. Then a small group. And here’s what happened… people started asking him, “Do you do this privately?” That’s the moment. That’s the clue.
Within a few months, Brian had a simple part-time practice; three days a week, mornings only. He wasn’t trying to build an empire; he was building a life. He told me, “I don’t feel retired anymore. I feel like I’m doing what I was always meant to do.”
That’s an encore career. Not a desperate attempt to stay busy, but a second act that fits who you are now.
My Own “Second Act” Started Early… and Taught Me Everything
I left my full-time banking career to become a coach when I was still young (around 30), and I’ve never looked back. I’ve worked part-time ever since, building a coaching company, writing books, and doing the work I genuinely love.
But the feeling that drove me? The feeling of, “There has to be something better than this.” That feeling is ageless. So if you’re 55, 62, or 70 and you feel that tug, trust it. It’s not a problem. It’s a clue.
Step 1: Stop asking “What job should I do?” and start here
Most people start with: “What would be a good retirement job?” I want you to start with: “What would make my days feel happy?” Because an ideal career supports an ideal life, not the other way around.
Ask yourself:
*What do I want my mornings to look like?
*How social do I want my work to be?
*Do I want to travel? Stay local? Work from home?
*Do I want a steady schedule, or freedom?
*Do I want to help people? Create things? Solve problems? Lead? Teach?
This is how you find an encore career that actually fits you.
Step 2: Identify your hard-wired talents (this is where most people guess wrong)
Here’s the frustrating part: most people don’t actually know what they’re naturally designed to do. You might think you do, but you’re too close to yourself to see it objectively. And your friends can’t always see it either.
That’s why I love strong assessments. They can reveal hidden abilities that have been sitting on the shelf for decades, unused, while you wonder why you feel restless.
My Career Change Coaching Kit includes computerized assessments to help you identify your inherent abilities and motivations, so you can stop guessing and start building your retirement career around what you’re naturally good at.
When you’re using your natural talents, work becomes play. When you’re not, you feel dissatisfied, even if the job looks good on paper.
Step 3: Create a “tiny test”
One of my favorite coaching principles is: make it real now, in a small way.
If you think you want to teach, don’t sign up for a two-year program immediately. Run a small workshop. Tutor. Volunteer once a week. If you want to write, join a writing group. If you want to coach, start practicing. Small projects give you clarity fast.
A lot of retirement career change stress comes from the fear of making a big mistake. So don’t make a big move yet. Make a small move that gives you data.
Step 4: Don’t ignore the emotional side (it runs everything)
Sometimes what people really want in retirement is not “a job.” They want respect. Connection. Peace. Freedom. Purpose. Security. Appreciation. Those are emotional needs, and if they’re unmet, you’ll feel unhappy no matter how perfect your retirement plan looks.
(If you want a quick insight into your own emotional needs, take my free Emotional Index Quiz.)
Step 5: Make it financially smart (so you feel free, not trapped)
A lot of people want an encore career because they want extra income, or they want to take pressure off their retirement savings. Great. But I also want you to feel choice.
If financial freedom is part of your retirement happiness plan, my Financial Independence, Retire Early Course can help you get there faster.
Because the real goal isn’t “never work again.” The real goal is: you don’t have to work unless you want to.
The Bottom Line
If you’re retired and feeling a little adrift, you’re not broken.; you’re simply ready for your next chapter. And it gets to be your chapter. On your terms. With work that fits your energy, your values, your personality, and the life you actually want to live.
That is an encore career. That is the new retirement.
If you want a clear path to your encore career / second act career, start here:
- Career Change Coaching Kit (discover your hard-wired talents + best-fit paths)
- Financial Independence, Retire Early Course (create freedom + options)
- Raise Your Emotional IQ Course (learn what you truly need to feel happy)
- And if you want a great companion resource, explore my books.
