The 10 Hottest “Encore Careers” That Don’t Feel Like Work? Not.

Many people reach a point in their career when they start wondering what comes next. Some think they can just retire or pivot to a so-called “encore career” for personal fulfillment. But let me tell you, this idea of an encore career isn’t the easy, rewarding shift you might expect. It’s not a simple way to stay active or follow your passions without feeling like you’re working—it’s often just as demanding as any job, if not more so.

Switching to a new career is daunting. It’s a risky leap that can leave you frustrated and drained. The options out there aren’t as accessible or fulfilling as people claim, and using your existing skills or learning new ones doesn’t guarantee success or satisfaction. I’ve put together a list of ten so-called “hot” encore careers, but I’m skeptical about how great they really are—here’s why they’re not as rewarding as you might think.

1. Garden Designer: Not Just Planting Flowers

Turning a love for plants into a job sounds nice, but it’s not a walk in the park. Garden design demands physical stamina, technical knowledge, and dealing with picky clients. Creativity? Sure, but you’re also battling unpredictable weather, tight budgets, and endless revisions. No degree might be required, but without serious experience or costly courses, you’re likely to struggle. The idea that this is more rewarding than a desk job is oversold—expect sore muscles and stress, not just pretty flowers.

• Not for those who think gardening is just a relaxing hobby.
• Hours aren’t as flexible as they seem; clients dictate your schedule.
• Going solo or joining a firm both come with high pressure and low pay.
  The “immediate results” are overstated—projects take months, and the mental and physical toll isn’t worth it for most.

2. Tour Guide: More Work Than Storytelling

Showing off your city sounds fun, but being a tour guide is exhausting, not a casual stroll. You’re on your feet for hours, dealing with demanding tourists and memorizing endless facts. Enthusiasm isn’t enough—public speaking skills and thick skin are crucial, and even then, it feels like work. Part-time? Sure, but unpredictable schedules and low pay make it less appealing. The idea that you’re just “sharing what you know” ignores the prep and hassle involved.

• Training isn’t just “informal”; it’s often rigorous and ongoing.
• Specializing in tours doesn’t make it easier—every niche has fierce competition.
• Staying active sounds nice, but it’s physically and mentally draining.
  The novelty of meeting new people wears off when you’re repeating the same stories daily, and “discovering new details” is more about constant research than excitement.

3. Exotic Pet Sitter: Not a Vacation with Lizards

Caring for exotic pets might seem quirky and fun, but it’s a logistical nightmare. Reptiles aren’t cuddly, and their needs are complex—special diets, habitats, and health risks aren’t for amateurs. Flexible? Maybe, but clients expect you to be on call, and building a client base takes way more than word of mouth. Platforms like Rover are oversaturated, and international gigs are rare and risky.

• Not for casual pet lovers; you need serious expertise with exotics.
• Long-term assignments sound cool but often mean isolation and liability.
  This isn’t a “low-commitment” gig—you’re stuck with high-stakes responsibilities and little payoff.

4. Event Planner: Stress, Not Celebration

Event planning sounds glamorous, but it’s a grind, not a party. Your organizational skills are tested by chaotic clients, tight deadlines, and endless last-minute changes. It’s not about creativity; it’s about managing stress and egos. The idea that it “never feels like work” is nonsense—every event is a high-pressure puzzle. Certifications help, but the real hurdle is the emotional and physical toll.

• Multitasking under pressure isn’t fun; it’s exhausting.
• Specializing doesn’t simplify things; every event type has its own headaches.
• Learning by doing means unpaid hours and costly mistakes.
  Variety sounds nice, but the constant chaos leaves little room for enjoyment or personal flair.

5. Art Instructor: More Than Just Sharing Passion

Teaching art might seem rewarding, but it’s not just about inspiring creativity. You’re managing diverse skill levels, difficult students, and low pay. Passion alone doesn’t cut it—you need patience and business savvy to make it work. Community centers and online platforms sound great, but they’re competitive, and the prep work eats up your energy. Feeling energized after a class? More like drained from constant problem-solving.

• Virtual or in-person, you’re juggling tech issues or classroom chaos.
• Flexible schedules are a myth when you’re tied to bookings.
• Seeing students grow is rare; most just want a quick hobby.
  This isn’t about nurturing creativity—it’s about managing expectations and scraping by financially.

6. Freelance Writer/Editor: Not as Free as It Sounds

Freelance writing sounds like freedom, but it’s a hustle with inconsistent pay and brutal deadlines. Platforms like Upwork are crowded with lowball offers, and networking is a full-time job itself. No prior experience? Good luck building a portfolio while competing with pros. The idea of working from anywhere ignores the stress of unreliable clients and feast-or-famine income.

• Remote work means isolation, not freedom.
• Writing about your passions is rare; you take what pays.
• Flexible hours come with the pressure of constant hustling.
  Blogging or self-publishing sounds nice, but it’s a money pit with little return for most.

7. Personal Coach: Not Just Giving Advice

Coaching sounds fulfilling, but it’s not just helping people grow—it’s a business with high emotional and financial costs. Training programs aren’t cheap, and empathy doesn’t pay the bills. Finding clients is tough in a saturated market, and the pressure to deliver results is relentless. Your own experience? It’s not enough without serious marketing and credentials.

• Specializing in your experience sounds good but limits your client pool.
• Virtual or in-person, you’re on call for clients’ crises.
• Job satisfaction fades when clients don’t follow through.
  Helping others sounds noble, but it’s a grind that often leaves you burned out.

8. Handyperson: More Hassle Than Pride

Fixing things might seem satisfying, but handyman work is physically demanding and rarely relaxing. Clients expect perfection on a budget, and the skills you need take years to master. Demand is there, but so is competition, and you’re often underpaid for the effort. The “immediate results” are overshadowed by long hours and liability risks.

• Hands-on work sounds fun until you’re fixing someone else’s mess.
• Job variety means unpredictable challenges, not excitement.
• Setting your own rates? Clients will haggle you down.
  Being handy is less about pride and more about endless demands and little appreciation.

8. Museum Docent: Not Just Sharing Knowledge

Being a museum docent sounds cultured, but it’s not all storytelling and learning. You’re on your feet, dealing with uninterested crowds or tough questions, often for little or no pay. Training is intense, and the “flexible” schedule means fitting into the museum’s needs, not yours. The social aspect? It’s more about managing groups than making friends.

• Lifelong learning comes with pressure to know everything.
• Flexible schedules are limited by museum hours.
• Connecting with like-minded people is rare when you’re always on duty.
  This role feels less like cultural engagement and more like unpaid labor with high expectations.

10. Nonprofit Board Member: Impact Isn’t Guaranteed

Giving back sounds noble, but nonprofit work is often bureaucratic and thankless. Board roles demand serious time and expertise, with little financial reward. Volunteering? It’s emotionally draining when you see systemic issues you can’t fix. The idea of using your skills for good is overshadowed by meetings, fundraising pressure, and slow progress.

• Your expertise often gets lost in red tape.
• Flexible? Only if you can commit to unpredictable demands.
• Staying active in the community feels more like obligation than joy.
  The “big changes” you hope for are slow, and the personal cost often outweighs the impact.

How to Find the Right Encore Career?

Finding a so-called “perfect” encore career isn’t as simple as listing hobbies or asking friends for advice. Volunteering or shadowing might sound like a start, but they often lead to dead ends or unmet expectations. Resources like Encore.org or AARP’s job boards aren’t magic solutions—many roles are oversaturated. Trial and error? That’s code for wasting time and energy.

I’ve seen people dive into encore careers expecting a fun second act, only to find stress and disappointment. These paths aren’t the easy, fulfilling shift they’re made out to be. If you’re thinking about an encore career, brace yourself—it’s not the hobby-like dream job you’re hoping for.