Make Money in Your Pajamas Without Learning TikTok Dances
Let’s get one thing out of the way: I’m not against traditional retirement activities. I think jigsaw puzzles are a noble pursuit, I’ve done more than my fair share of yelling at squirrels, and I once played golf for 14 days straight until my hips staged a protest and I had to sleep in a recliner for a week.
But after a few months of this golden-idleness, I realized something shocking: I missed working. Or at least the parts of it that didn’t involve fluorescent lighting, HR memos, or Steve from Accounting.
More importantly, I missed earning money—real money, not the three bucks I once found behind the couch cushions while looking for the remote.
And that’s when I discovered the magical, coffee-fueled, bathrobe-friendly world of freelancing online.
You Already Have What You Need (Except Maybe a Strong Password)
Here’s the first beautiful truth: You already know something valuable.
Seriously. You’ve spent decades working, learning, managing people, fixing things, explaining things, or doing something more productive than most 20-year-olds can manage between avocado toast sessions. You don’t need a new degree, a ring light, or a TikTok account with 10,000 followers. You just need:
- A computer
- An internet connection
- A willingness to click around until something makes sense
The online world is desperate for skills like yours—especially if you can write, edit, coach, organize, tutor, translate, or do anything besides post duck-face selfies.
What Can You Freelance?
Glad you asked. Here’s a menu of options, served with a side of common sense:
1. Writing and Editing
Can you string a sentence together without confusing “your” and “you’re”? Congratulations, you’re already more qualified than half the internet.
- Write blog posts, web copy, product descriptions, or newsletters
- Edit books, articles, or awkwardly written resumes
- Help people untangle their grammar like a pair of earbuds from 2006
Platforms to explore: Upwork, Fiverr, Freelancer, and Reedsy (for books)
2. Tutoring and Teaching
Do you remember algebra? I don’t either. But if you do, you could be tutoring students online from the comfort of your couch.
- Teach English to students in other countries
- Tutor high school or college kids in subjects you still vaguely understand
- Host adult learning sessions (e.g., “Excel Basics” or “How Not to Cry During Tax Season”)
Sites to try: Wyzant, VIPKid, Preply, Outschool
3. Virtual Assistant Work
This is just a fancy term for “someone who helps businesspeople get their act together.” And honestly, who better than someone with a lifetime of experience bossing people around in a gentle, helpful way?
- Manage emails, calendars, data entry, travel planning
- Schedule meetings and tell people politely that they’re late for them
Try: Belay, Time Etc, Fancy Hands
4. Bookkeeping and Administrative Help
If you’re good with numbers, receipts, or anything involving spreadsheets, there are overwhelmed entrepreneurs everywhere who would love your help.
- Handle basic accounting
- Keep records tidy
- Refrain from yelling “You’re overspending again!” (unless asked to)
Sites: QuickBooks ProAdvisor, Paro, Upwork
5. Consulting and Coaching
This is where your real-life experience becomes golden. If you’ve worked in management, HR, finance, marketing, or pretty much any field ending in “-ing,” someone out there is willing to pay for your insight.
- Business coaching
- Career advice
- Life coaching, if you’ve figured out how to get teenagers to clean their room or how to make Brussels sprouts taste good
Try: Clarity.fm, LinkedIn, your own website
How to Get Started Without Accidentally Joining a Cult
Here’s the simplified, no-nonsense game plan:
- Pick one skill you already have or enjoy. Don’t overthink this. If you were a teacher, tutor. If you worked in finance, offer help with budgeting or taxes. If you’re a grammar wizard, edit.
- Set up a profile on a freelancing site (Upwork, Fiverr, etc.). Be honest, friendly, and upload a photo that doesn’t look like you’re in witness protection.
- Start small. Your first job might pay $30 or $50. That’s okay. Think of it as proof that you’re not invisible and can still earn money in your pajamas.
- Collect reviews like seashells. The more happy clients you get, the easier it becomes.
- Raise your rates as you go. Once someone pays you $100 to fix their newsletter, you’ll never look at your old hourly wage the same way again.
Real Life Example: Me and the Case of the Nervous Novelist
True story: My first online freelance job was editing a novel for a woman who had accidentally written 112,000 words without a plot. I fixed the punctuation, gently suggested that something should probably happen by page 75, and got paid $250.
I did the entire thing while sitting in a worn bathrobe and sipping tea. The novel never hit the bestseller list, but I earned enough to buy an air fryer, which now holds a sacred place in my kitchen.
Why Freelancing Works for Retirees
- Flexible hours – Work when you want, nap when you want. Bliss.
- No commute – Unless you count the shuffle from the bedroom to the laptop.
- Low to zero startup cost – No storefront, no inventory, no weird pyramid schemes.
- You’re the boss – Fire yourself if you get too annoying.
- You stay sharp – You keep your mind active and your skills fresh, even if your joints make mysterious sounds.
A Few Final Words of Encouragement
Freelancing isn’t just for 23-year-olds with ring lights and opinions about cryptocurrency. It’s for anyone who wants to earn extra income, stay engaged, and feel like they’re contributing—without ever leaving home.
You’ve already done the hard part: learning the skills, gaining the experience, and surviving at least two recessions, a pandemic, and Steve from Accounting. Selling your skills online isn’t a leap—it’s a natural next step. And if you can navigate a smartphone menu and remember a strong password, you’re already halfway there.
This blog post is adapted from my book:
Extra Income Over 60: 48 Ways to Boost Your Retirement Income Today, available at Amazon.com in paperback and eBook format. It’s packed with real-life ideas, strategies, and gentle nudges for retirees who want more income, less boredom, and zero nonsense.
Disclaimer:
This post is for informational and entertainment purposes only and does not constitute financial, tax, or career advice. Always consult your inner voice—or a trusted advisor—before starting a new venture, quitting your day job, or buying an air fryer with your first freelance check.