Massive Passive Income? ̄\_(ツ)_/ ̄

You’ve survived Y2K, dial-up internet, and the emotional trauma of Blockbuster’s demise (I am pretty sure that I still owe them late fees…). But, you aren’t ready to sit in your rocking chair quite yet, you aren’t jonesin’ for a big grind, and your 401(k) is giving off strong "meh" vibes. Hustling isn’t something that you want to jump into — so maybe think about some passive income ideas that actually pay. Here's your no-BS, chapterneXt guide to creating some cash flow w/o selling out (well, maybe a little bit…). Please note that none of this is investment advice - just ideas.

What it is: Buy a slice of boring, stable companies. Get paid just for existing.

Think of this like getting a participation trophy from the stock market, except the trophy is cash. Pro tip: Don’t chase those 14% dividend yields from weird offshore shipping companies unless you're also planning to buy a parrot and live on a tugboat.

What it is: You want real estate income without ever plunging a toilet.

Buy REITs (public or private) and rake in rental income from someone else’s office park, apartment building, or data center. It’s like being a landlord without the land, or the lordliness. Public REITs are like stocks, private ones are like a group project with strangers and a five-year lockup.

What it is: Real estate investing for people with $100 and commitment issues.

Platforms like Fundrise or Arrived let you buy tiny slices of homes or apartment deals. It’s Monopoly for adults with less drama and more monthly payouts. Just don’t expect to flip a house like it's 2006. You’re here to collect rent and chill.

What it is: You, but as a venture capitalist.

Drop $100 on a random beverage startup that claims it's the next Liquid Death. Maybe it 100x-es. Maybe it burns out in a blaze of overpriced branding. Welcome to Wefunder or StartEngine, where returns are imaginary until proven otherwise.

What it is: Be the bank, minus the suit. (Tho, really, wear whatever you want…)

Lend money to strangers on the internet and hope they pay you back. Platforms like Prosper or Honeycomb promise 7–12% returns if Karen’s Cupcake Co. doesn’t implode. This is capitalism with a side of gambling.

What it is: Own a piece of someone else's Subway without smelling like bread all day.

FranShares lets you invest in a franchise portfolio. You sit back, they run the business, you (hopefully) get checks. Feels like Shark Tank with training wheels and fewer awkward product demos.

What it is: Get paid every time someone streams music you didn’t write or buys mouthwash you didn’t invent.

Yes, you can invest in royalties like a washed-up rock star. David Bowie securitized his music. Some guy did it with Listerine. Find a platform, buy in, collect tiny payments while humming your way to profit.

What it is: Investing for people who check their blood pressure voluntarily.

Treasuries, CDs, annuities. Yields are finally above "sad." You won’t get rich, but you’ll sleep at night. Also a great way to feel smug when the market tanks and you’re still getting your 5%.

What it is: Buy a cash-flowing business online and let someone else run it.

You’re the silent partner, they do the work. Kind of like being in a band but only showing up for the royalties. Vet carefully, or you’ll end up owning a dropshipping store selling LED cat hats to zero customers. You can find opportunities at places like Flippa or Acquire.com

What it is: Stake your crypto and earn yield while doing literally nothing.

Crypto staking is like earning interest for believing in magic internet money. ETH, SOL, etc. — lock it up, watch your balance grow. Just remember, the underlying asset could go full rug pull while you nap.

Passive income isn't just for boomers with apartment buildings or YouTubers with course funnels. With a little cash and a lot of curiosity, Gen Xers can finally make their money do the heavy lifting.

Pick your flavor —> conservative, wild, or somewhere in between. Then put your cash to work so you can finally get floor seats for Def Leppard.

chapter neXt is a newsletter/community/guide for entrepreneurial folks in their 50s and beyond. It is published by Julia Kelahan (check her out on LinkedIn, her amazing strength-based learning center & her ADHD & Executive Function coaching business) and Tim Kilroy (check him out on LinkedIn & his agency growth business & his agency-focused newsletter). They are the proud parents to 5 kids, they live near Boston & their dog’s name is Fred. Our ads are ads - duh. But some of the publishers that we link to in our content may offer us a commission if you buy something from them - that doesn’t influence what we link to, nor does it influence what we say about it.