Encore Career vs. Side Hustle: What’s Right for You in Retirement?

purposeful living May 07, 2025

Not All Retirement Work Is the Same

You’ve wrapped up your first career, but that doesn’t mean you’re done working. Maybe you want extra income or miss the sense of purpose. Perhaps you’re just not ready to sit still. That’s where your second act begins.

But here’s the truth: not all post-retirement work is created equal.

Some retirees feel called to make a difference, others want more money and flexibility, and many want a little of both. Whether you're driven by impact or side income (or still figuring it out), there are two main paths to explore: the encore career and the side hustle.

This guide will help you:

Understand the difference between purpose-driven encore careers and flexible side hustles
Compare the pros, cons, time commitments, and income potential of each
Reflect on your goals to choose a path that fits your lifestyle

💬 Hint: There’s no wrong choice. There’s only what works for you, and it can evolve.

Let’s explore the options so you can start your second act with confidence and clarity.

👉 Encore Careers for Retirees

What Is an Encore Career?

An encore career is a purpose-driven role you pursue after your primary career ends, often serving something bigger than yourself. It’s not just about staying busy or earning a paycheck. It’s about making an impact with the experience and wisdom you’ve already earned.

Think of it as the next meaningful chapter that aligns with your values, not just your résumé.

Key Traits of an Encore Career

Purpose first, income second – It’s driven by what matters to you
Leverages life experience – You bring decades of insight to a cause
Found in mission-based roles – Common sectors include education, healthcare, nonprofits, and mentorship
Often starts informally – Many encore careers begin as volunteer work, part-time teaching, or passion projects

Encore careers are often people-focused, community-oriented, and emotionally rewarding.

Pros of an Encore Career

Deep fulfillment and sense of impact
Alignment with legacy goals or personal mission
Flexible formats—part-time, project-based, or seasonal
Opportunities to mentor, teach, or give back

For many, this work feels more meaningful because it connects directly with their values.

Considerations Before You Dive In

Time and energy – Encore careers often require consistent effort and emotional investment
Lower pay – Nonprofits and purpose-driven roles may pay less than corporate gigs
Clarity required – You'll want to reflect on your “why” and decide who you truly want to serve

💬 “I thought I was done working, but wasn’t done contributing. My encore career helped me feel needed again.” — Retirepreneur reader, age 66

What Is a Side Hustle?

A side hustle is a flexible, income-generating activity you do alongside retirement, often part-time, digital, or based on a hobby or skill. It’s less about legacy and more about lifestyle. And it’s a great option if you want freedom, extra cash, or a fun project to focus on.

Side hustles can range from selling handmade goods to driving for a delivery app, managing social media for a local business, or launching a small freelance service.

Key Traits of a Side Hustle

Income-first, passion optional – It’s often about supplementing your lifestyle
Built around what you already have – Monetize a hobby, skillset, or even spare time
Low barrier to start – Many require little to no upfront investment
Often online or local – Think Etsy, Uber, eBay, coaching, or digital content

A side hustle can be scaled to fit your goals, whether you want $300/month or $3,000/month.

Pros of a Side Hustle

Flexible schedule and work style
Wide range of income potential
No résumé required—just results
Can start small and grow gradually

It’s the perfect blend of freedom, fun, and financial boost for some retirees.

Considerations Before You Start

Can feel transactional – Side hustles often prioritize productivity over purpose
May lack deeper fulfillment – If you’re craving meaning, it might not fully satisfy
Income varies – Some side hustles take time to build or are inconsistent month to month
Requires some trial and error – Not every idea will stick, and that’s okay

💬 “Driving for Instacart gave me structure and income after I retired. It wasn’t glamorous, but it paid the bills and kept me active.” — Retirepreneur reader, age 70

Encore Career vs. Side Hustle: Key Comparison Points

Which path is right for your retirement lifestyle? Use these side-by-side comparisons to clarify what matters most to you—purpose, profit, or a bit of both.

1. Primary Focus

Encore Career: Purpose, impact, and making a difference
Side Hustle: Income, flexibility, and lifestyle control

2. Time Commitment

Encore Career: Medium to high (10–30 hours/week)
Side Hustle: Low to medium (5–15 hours/week)

3. Startup Path

Encore Career: Reflect on your skills, values, and service-driven goals; often starts with volunteering or training
Side Hustle: List your service on a platform, monetize a hobby, or pick up a digital gig

4. Income Potential

Encore Career: Typically modest but steady; designed for sustainability
Side Hustle: Varies widely, from a few hundred dollars a month to full-time income, depending on effort and model

5. Common Examples

Encore Career: Nonprofit staff, tutor, coach, mentor, community organizer
Side Hustle: Etsy shop, freelance writing, pet sitting, selling crafts, rideshare driving

6. Best For

Encore Career: Retirees seeking meaning, contribution, and lasting impact
Side Hustle: Retirees who want quick wins, light work, or to test out new income streams

💬 “Think of an encore career as legacy work—and a side hustle as lifestyle work. Both are valid, and some people do a little of each.” — Curt Roese, Founder of Retirepreneur

📌 Want a visual version of this comparison? Stay tuned—Retirepreneur will release a downloadable graphic soon.

How to Decide What’s Right for You

You don’t need to pick the “perfect” path—you need to choose the one that aligns with your current season of life. For some, that’s diving into purpose. For others, it’s about enjoying extra income without the pressure. Many retirees find a mix that works.

Start by reflecting honestly on your goals, energy, and values.

Reflection Questions

Ask yourself:

Do I need income, or want meaning? If you need money, a side hustle may be the faster route. If you want to make a difference, an encore career may be more fulfilling.
Do I enjoy people-focused work, or prefer solo projects? Encore careers often involve collaboration and community. Side hustles can be done solo, at your own pace.
Do I want a new identity—or just a new income stream? An encore career might reshape how you introduce yourself. A side hustle can stay behind the scenes.
Am I looking to contribute, or stay active? Knowing your deeper motivation makes it easier to commit to the right path.

Hybrid Options to Consider

You don’t have to choose just one path. Many retirees blend purpose and income through hybrid approaches like:

Freelancing for mission-driven clients – Offer your services to nonprofits, schools, or community orgs
Turning volunteer roles into paid ones – Start with service, then explore part-time project opportunities
Coaching or mentoring – Help others navigate their careers, transitions, or skills development.
Workshops and teaching – Share your knowledge in a way that inspires and earns

💡 Tip: If you’re torn between paths, start with a short trial of each—test, learn, and adjust as you go.

Real-Life Examples of Each Path

Need some inspiration? Here’s how real retirees turned their experience, interests, and goals into second-act success—each on their terms.

🎓 Encore Career Example: Helen, 64

Former Role: Public school teacher

Encore Path: Online tutor for underserved youth through a nonprofit

Why It Worked: Helen missed teaching but didn’t want the full-time grind. Now, she tutors students in reading and math twice weekly via Zoom and says it’s “the most rewarding work I’ve ever done.”

“I still get to make a difference—just without the bells and faculty meetings.”

🧰 Side Hustle Example: Ray, 67

Former Role: Retired contractor

Side Hustle: Turned his woodworking hobby into a side business selling handmade furniture and home decor at local markets and on Etsy

Why It Worked: Ray set his schedule, kept things simple, and now brings in $800–$1,200/month doing something he enjoys.

“It’s not about getting rich—it’s about staying sharp and making something with my hands.”

💼 Hybrid Example: Lisa, 60

Former Role: Corporate HR executive

Encore + Hustle: Became a part-time career coach for recent college grads and leads paid LinkedIn workshops online

Why It Worked: Lisa blends purpose and income, supporting young professionals while building a personal brand and generating flexible revenue.

“It’s the best of both worlds—impact and independence.”

These stories show no single “right way” to work after retirement. Your second act can look exactly how you want it to.

Final Thoughts: There’s No One-Size-Fits-All Second Act

Retirement isn’t a finish line—it’s a reset. And what comes next is entirely up to you.

Whether you choose the meaningful mission of an encore career, the flexible income of a side hustle, or a creative blend of both, what matters most is that it fits your life, goals, and values.

You’ve earned the right to design your second act on your terms.

Let’s recap your path forward:

Compare your options: Understand the difference between impact-driven and income-driven work
Reflect on your goals: What do you want from this next chapter?
Start small and stay flexible: Test the waters, pivot as needed, and grow from there.

💬 “You don’t need a business card to have a purpose. You need to say yes to what excites you next.” — Curt Roese, Founder of Retirepreneur.

You're not starting over—you’re starting with clarity. And Retirepreneur is here to guide you every step of the way.

✅ Frequently Asked Questions

What’s the difference between an encore career and a side hustle?

An encore career is purpose-driven and often mission-based, while a side hustle is typically income-focused and flexible. Encore careers may involve more structure and long-term commitment.

Which is better for retirees: encore career or side hustle?

It depends on your goals. If you want meaning and contribution, an encore career may be the better fit. If you prefer extra income with flexibility, a side hustle is ideal.

Can I start with a side hustle and turn it into an encore career?

Absolutely. Many retirees begin with part-time gigs and grow them into more fulfilling, structured encore careers as they gain confidence and experience.

Do encore careers require more time than side hustles?

Typically, yes. Encore careers often involve more planning, hours, and dedication. Side hustles are usually easier to start and pause, making them ideal for low-commitment income.