5 Reasons To Start A Side Gig After 50: Building Wealth, Connection & Purpose
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Retirement doesn’t have to mean stepping away from work entirely. For many over 50, starting a side gig has become an excellent way to supplement income, boost retirement savings, build meaningful relationships, and find new fulfillment—or simply to enjoy doing something they love. Whether your goal is to grow your wealth, meet new people, or give back, the right side gig could be your next exciting chapter.
Starting a side gig has been an incredible journey for me personally. I’ve been reselling for over 25 years, and what began as a way to make a little extra money while my girls were young, quickly turned into a passion. What I love most about it is the math—it’s like solving a puzzle. Target specific items, know your niche, and you can create real profits. When I first started, I focused on designer handbags. With a little research and careful purchasing from local outlets, I found I could net a profit of $100 or more per handbag. That, I thought, was worth my time. Soon enough, I expanded to other high-margin items that could also net $100 per sale. I had found my niche. Over time, it became a simple equation: how many items could I sell in a week, and how much could I earn? This approach not only made it enjoyable but also made my earnings feel entirely within my control.
One of my favorite recent finds was a few pairs of Gucci earrings in the clearance section of a local TJ Maxx. While I was not in my reseller mode, they caught my eye as they were attractive and could be worn by many, and yes, were substantially marked down. After a quick internet search, I discovered that these particular earrings were also sold out on most sites. This is a moment when you truly can’t wait to whip out a credit card and buy as soon as possible! Not to mention, I made over $1,000 on each pair and they sold quickly. Not every find is as big of a payout, but with experience – it’s possible for it to happen more often than not.
Let’s review some additional opportunities for side hustles that may be a good fit for you…
What Are The Benefits Of Starting A Side Hustle After 50?
A side gig can be a practical and rewarding way to navigate life’s next phase. Here are five key reasons to consider taking on a side hustle:
1. How Can a Side Gig Help You Grow Retirement Savings?
Many people over 50 worry about whether their retirement savings will be enough. A side gig offers an opportunity to grow your wealth, create a financial safety net, or simply enjoy additional financial freedom.
2. What Are the Best Ways to Earn Extra Income After 50?
Whether you’re semi-retired or still working, a side hustle can help cover rising expenses or fund the things you enjoy—travel, hobbies, or family activities.
3. How Can a Side Hustle Help You Stay Engaged with Purpose?
A side gig allows you to stay active, contribute meaningfully, and explore new passions. If you are considering transitioning away from full-time work, consider the potential of feeling a loss of identity, this may be an answer for you.
4. How Can a Side Gig Connect You with Others?
Side gigs often involve meeting like-minded individuals—whether clients, customers, or a supportive community of fellow gig workers.
5. What Hobbies or Skills Can You Turn Into a Side Gig?
Sometimes, it’s not about money at all. A side gig lets you share a passion or hobby while creating something valuable for others. Imagine how fulfilling it could be, to turn your favorite pastime into a source of income.
Make Money Doing What You Love: Top Side Gigs
While there are countless options for side hustles today, here are the top five to consider for your next chapter. These side gigs offer the best financial opportunities with a faster path to profitability and an investment that most can afford – all while aligning with the core values of Well Wise Wealth:
Wealth: Build or supplement your financial resources to enhance retirement security.
Wellness: Engage in meaningful activities that keep you mentally and physically active.
Wisdom: Leverage your life experience and skills to make a lasting impact.
1. Resale Business
What It Is: Buying and selling items on platforms like eBay, Poshmark, Etsy, or Facebook Marketplace. This gig is ideal for anyone who loves bargains, thrifting, antiquing, or crafting.
Why It Works: Resale combines creativity with entrepreneurship. Plus, it’s flexible and can be scaled up or down depending on your goals.
How It Adds Value:
Wealth: Flip thrift store finds, unused household items for profit, or practically anything for a profit. The list is infinite as to what can be bought, found and then sold.
Relationships: Connect with buyers and other resellers in online communities.
Purpose: Turn your love of hunting for hidden treasures into a meaningful venture.
IS A STARTING A RESALE BUSINESS RIGHT FOR YOU? | RATING: 1= LOW, 5 = HIGH
Investment To Start
2 – Initial costs for inventory or supplies.
Earning Power
4 – Potential for steady income with high-demand items.
Effort
3 – Requires sourcing, listing, and customer service.
Time To Profitability
2 – Can take weeks to months depending on inventory turnover.
Difficulty Level
3 – Learning SEO, pricing strategies, and platform algorithms is key.
Getting Started:
Platforms: eBay, Poshmark, Etsy, Facebook Marketplace and more.
Tools: Invest in shipping supplies, scales, and inventory management tools.
Once you become comfortable with a niche or develop expertise in researching products and brands, you’ll discover a wide range of profitable opportunities. While I often rely on traditional sourcing methods—such as discount or closeout stores, Goodwill, Salvation Army, and Savers thrift stores, as well as estate sales—I’ve also found incredible success in less conventional avenues. Designer pop-up sales, specialty Facebook groups, and local platforms like OfferUp and Craigslist have all yielded profitable finds.
One of my favorite hacks is capitalizing on seasonal online sales to scoop up bargains and flip them for a quick profit. I review emails that come directly to my inbox before and after holidays, seasons, and cyclical sales by store or designer. Not only does this strategy maximize my earnings, but it also saves gas money and precious time. In the world of reselling, creativity truly pays off—and thinking outside the box can make all the difference in growing your profits.
2. Freelance Writing or Editing
What It Is: Writing articles, blogs, or editing content for businesses, online publications, or self-published authors.
Why It Works: If you have a knack for storytelling or a strong grasp of grammar, this gig lets you work from home and at your own pace.
How It Adds Value:
Wealth: Earn per word or per project. Rates can grow as you build your portfolio.
Purpose: Share your voice or help others bring their ideas to life.
Enjoyment: Work in niches that align with your passions.
IS FREELANCE WRITING OR EDITING RIGHT FOR YOU? | RATING: 1= LOW, 5 = HIGH
Investment To Start
1 – Minimal (computer and internet).
Earning Power
3 – Rates vary; higher for specialized niches.
Effort
3 – Requires research, writing, and revisions.
Time To Profitability
2 – Can start earning within weeks after finding clients.
Difficulty Level
2 – Lower if you’re skilled in writing or editing.
Getting Started:
Platforms: Upwork (waiting for aff. Approval), Fiverr, ProBlogger.
Tools: Grammarly, Hemingway Editor, or Scrivener for drafting and editing.
Practical Tip
I’ve seen firsthand how writing can open doors to unexpected opportunities. A friend of mine, who had never considered herself a “writer,” started freelancing by offering editing services on a whim. Her first client was so impressed that they referred her to others, and within a year, she was making a full-time income from writing and editing gigs. The key? Start small and focus on areas you’re passionate about. Whether it’s crafting engaging blog posts, editing someone’s novel, or writing product descriptions, every word you write builds your skills and reputation. Remember, the first step is just putting yourself out there—you never know where your words might take you.
3. Consulting or Coaching
What It Is: Offering expertise in your career field or a passion, such as business strategy, financial planning, or life coaching.
Why It Works: You can leverage decades of professional experience to help others achieve their goals while working on your own schedule.
How It Adds Value:
Wealth: Consulting gigs can command high hourly rates. The average hourly rate for a business consultant in the U.S. ranges from $100 to $300, depending on expertise.
Purpose: Share hard-earned knowledge to help others succeed.
Relationships: Build meaningful connections with clients.
IS CONSULTING OR COACHING RIGHT FOR YOU? | | RATING: 1= LOW, 5 = HIGH
Investment To Start
2 – May need certifications or a website.
Earning Power
5 – High, depending on niche and clientele.
Effort
4 – Requires client management and prep time.
Time To Profitability
3 – May take weeks to establish clients.
Difficulty Level
3 – Moderate if you’re building from scratch.
Getting Started:
Platforms: LinkedIn (aff approval), Clarity.fm, or directly through your own website.
Tools: Use scheduling software like Calendly and video conferencing tools like Zoom.
Practical Tip
When I started consulting, I worked with a small business owner struggling to scale their operations. They had great products but lacked the systems to manage growth. Through our sessions, we identified key inefficiencies, streamlined their processes, and developed a simple yet effective financial plan. Within six months, their revenue increased by 30%, and they felt more in control of their business than ever before. The best part? Seeing their confidence grow alongside their success. Consulting isn’t just about offering advice—it’s about empowering someone to achieve their full potential.
4. Driving or Delivery Services
What It Is: Working with companies like Uber, Lyft, DoorDash, or Instacart to provide rides or deliver food and groceries.
Why It Works: Flexible hours and low startup costs make this a popular choice for semi-retired individuals.
How It Adds Value:
Wealth: Earn consistent income with opportunities for tips.
Relationships: Interact with a variety of people every day.
Purpose: Provide a valuable service to your community.
IS DRIVING OR MAKING DELIVERIES RIGHT FOR YOU? | | RATING: 1= LOW, 5 = HIGH
Investment To Start
3 – Requires a reliable vehicle and insurance.
Earning Power
4 – Good earning potential with consistent hours.
Effort
3 – Time-intensive, but straightforward tasks.
Time To Profitability
1 – Immediate after onboarding.
Difficulty Level
2 – Low; mostly physical effort.
Getting Started:
Platforms: Uber, Lyft, DoorDash, Instacart.
Tools: Use apps for route optimization and gas discounts.
Practical Tip
While I don’t have direct experience with delivery driving, I’ve learned a lot from my daughter, her boyfriend, and their friends who work in this gig. One of the best tips they’ve shared is to focus on peak hours and high-demand areas to maximize earnings. For example, timing shifts around lunch and dinner rushes or targeting busy neighborhoods can significantly boost income. They also swear by apps that optimize delivery routes, saving time and gas money. A little planning can make a big difference in turning delivery driving into a profitable and efficient side hustle.
5. Teaching or Tutoring
What It Is: Sharing your knowledge with others, whether it’s academic subjects, music lessons, or specialized skills like knitting or photography.
Why It Works: Teaching is fulfilling and flexible, and there’s always demand for personalized instruction.
How It Adds Value:
Wealth: Earn hourly rates for private sessions or group classes.
Purpose: Help others learn and grow.
Relationships: Build a loyal base of students and their families.
IS TEACHING OR TUTORING RIGHT FOR YOU? | RATING: 1= LOW, 5 = HIGH
Investment to Start
1 – Minimal if teaching online or in local areas.
Earning Power
3 – Depends on subject and location; high for specialized skills.
Effort
3 – Requires preparation and scheduling.
Time to Profitability
1 – Immediate once students are found.
Difficulty Level
2 – Lower if leveraging existing expertise.
Getting Started:
Platforms: VIPKid, Wyzant, or advertise locally.
Tools: Use Zoom for virtual sessions and Canva to create lesson materials.
Practical Tip
If you’re looking to find students for teaching or tutoring gigs, start by leveraging your existing network. Reach out to friends, family, and local community groups—word of mouth can work wonders. My friends have built their tutoring businesses by simply posting in local Facebook groups and on neighborhood apps like Nextdoor. Libraries, community centers, and even local coffee shops often have bulletin boards where you can advertise your services. Offering an introductory session at a discounted rate is another great way to attract students and build trust. Once you get started, referrals often come naturally.
How To Choose The Right Side Gig For You
Choosing the perfect side gig depends on your goals and interests. Ask yourself:
Do I want to earn more income or simply stay engaged?
How much time can I commit?
What skills or passions can I leverage?
Am I looking for social interaction or something I can do independently?
Start small and scale up as you gain experience. The beauty of side hustles is their flexibility—you’re in control of how far you take them.
In my experience, starting small was the best decision I made when building reselling business. It allowed me to learn the ropes, test what worked (and didn’t!), and build confidence without feeling overwhelmed. I remember starting with just a few items to resell—carefully chosen designer handbags—and focusing on understanding the market. Over time, I expanded my inventory, increased my expertise with the goal of learning five new brands each time I entered a retail store, and streamlined my processes, growing at a pace that felt manageable. The beauty of starting small is that every step forward builds momentum, and before you know it, you’re achieving goals you once thought were out of reach.
Final Thoughts
A side gig isn’t just about making money—it’s about creating a richer, more fulfilling life in retirement. Whether you’re looking to boost your wealth, connect with others, or share your talents with the world, the possibilities are endless. Start exploring today, and who knows? Your side gig could become your next great passion.
What will you begin today?