Let’s face it — retirement isn’t what it used to be. You can’t just plop your nest egg into a savings account and coast on interest. You need income. Reliable, fat, juicy, wallet-plumping income. And with inflation doing cartwheels, Social Security wobbling like a Jenga tower, and the market more bipolar than your ex, finding dependable high yield is no longer just smart — it’s survival.
So, I asked myself: If I had to retire tomorrow and could only pick three high-yield investments to generate income, which ones would make the cut? Which would let me sleep at night while still paying the bills, spoiling the grandkids, and sipping something expensive on a Tuesday afternoon?
This isn’t just theoretical. This is war-tested, dividend-obsessed, call-the-lawyers-if-it-cuts-its-payout investing. Let's walk through the process, the reasoning, and ultimately — the three high-yield beasts I'd retire with if the market shut its doors tomorrow.
The Criteria: No Dividend Clowns Allowed
Before we name names, let’s set the ground rules. High yield doesn’t mean "whatever pays the most." That’s how you end up with yield traps, dividend cuts, and deep regret.
Here's what I looked for:
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Yield north of 6% — because 2-3% won’t cut it in retirement.
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Dividend safety — payout ratio must be sustainable, backed by cash flow or FFO (Funds From Operations for REITs).
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Business quality — no zombie companies or fads. I want assets that people need, not just like.
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Recession-resilient — because I don’t want to time the economy. I want to crush it regardless.
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Optional upside — I’m here for income, but capital appreciation is always welcome.
So let’s get to it. If I could only retire with three high yields right now, here’s who’s riding shotgun.
1. Enterprise Products Partners (EPD) – Yield: ~7.2%
Sector: Energy Midstream
Structure: MLP (Master Limited Partnership)
Yes, it’s boring. No, it’s not flashy. But that’s exactly why I love it.
Enterprise Products Partners is the undisputed king of midstream infrastructure. They transport and process natural gas, NGLs, crude oil, and petrochemicals through an empire of pipelines and terminals. Their cash flow isn’t dependent on commodity prices — they’re the toll booth of the energy world.
Why It Makes the Cut:
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Distributable cash flow covers the payout comfortably — in 2024, EPD had a coverage ratio of over 1.7x.
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Insider ownership is massive — over 30% is held by management. Their incentives are your incentives.
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Inflation protection — many of EPD’s contracts are indexed to inflation.
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Long-term contracts and customer stickiness make revenue very stable.
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26 consecutive years of distribution increases.
The Risk:
MLPs can be tax-ugly in a retirement account. You'll get a K-1, and there are UBTI considerations for IRAs. But for a taxable account? This thing is a yield machine.
The Bottom Line:
If you want your retirement income gushing like an oil well in Texas — but with the steadiness of a municipal bond — EPD is your guy. Just don’t expect meme-stock excitement. This is a tortoise that crushes hares in the long run.
2. Realty Income Corporation (O) – Yield: ~5.8%
Sector: REIT (Retail Real Estate)
Structure: Monthly Dividend Stock
“The Monthly Dividend Company.” That’s not just a slogan — it’s a promise. And Realty Income has been delivering on it since long before TikTok investors were born.
This REIT owns over 13,000 commercial properties across the U.S. and Europe. We're talking Dollar General, Walgreens, 7-Eleven, and other fortress tenants that pay rent like clockwork.
Why It Makes the Cut:
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Monthly dividend — your bills come monthly, and now your income can too.
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A 5.8% yield backed by 25+ years of dividend increases.
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Occupancy rates near 99%, even in recessions.
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Long-term net leases — meaning tenants pay taxes, maintenance, and insurance.
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Global expansion into the UK and Europe adds diversification.
The Risk:
Retail apocalypse, you say? Maybe for malls. But O doesn’t do malls. They stick with essential service retail. People still need groceries, pharmacies, and convenience stores in a recession — if anything, even more so.
And yes, rising interest rates do pressure REITs. But Realty Income has one of the best balance sheets in the industry, with fixed-rate debt and smart refinancing strategies.
The Bottom Line:
It’s not the highest yielder on the block, but it’s the sleep-easy, check-it-once-a-year kind of income play. The kind that’ll be paying you long after that banana-shaped crypto token you bought is delisted.
3. Main Street Capital (MAIN) – Yield: ~6.8% + Special Dividends
Sector: Business Development Company (BDC)
Structure: Regulated Investment Company
Main Street Capital is like Warren Buffett if he focused solely on small businesses and paid you monthly.
This BDC invests in the backbone of America — profitable private companies with solid growth prospects that just need capital. Think mezzanine loans, equity stakes, and senior secured debt. They do it all, and they do it with discipline.
Why It Makes the Cut:
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Monthly dividends + semiannual specials — yes, you read that right.
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Internal management — which means no fat management fees sucking the lifeblood out of your returns.
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ROE over 15% — they know how to make money.
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Track record of NII (Net Investment Income) exceeding dividend payouts — that’s crucial for safety.
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Direct equity investments provide upside, while the debt side anchors stability.
The Risk:
It’s still a BDC. If the economy tanks and small businesses default, MAIN could take some hits. But they’ve navigated 2008 and 2020 like pros, with minimal dividend disruption.
They also manage risk by keeping loan-to-value ratios conservative and sticking to industries with recurring revenue.
The Bottom Line:
MAIN offers a blend of income, growth, and monthly predictability. It's like combining a hedge fund with a piggy bank — only the piggy bank actually pays you.
The Income Numbers Don’t Lie
Let’s assume a $1 million retirement portfolio split evenly among the three.
*Doesn’t include special dividends, which can add another $1,000–$2,000/year.
That’s $5,500 per month in passive income, not touching principal. And not one of those companies has cut its dividend in a crisis. In fact, two of them raised during COVID.
You want dignity in retirement? You want to live off the grid, off the clock, and off your boss’s radar forever?
That’s how you do it.
But What About…
You might be wondering: Why not go for 10%+ yielders? Or throw in some junk bond ETFs? Or closed-end funds with monster payouts?
Because I’m not building a yield illusion. I’m building a fortress. I want high yield, but I want it sustainable, backed by real assets and cash flow — not smoke and mirrors.
I’ll take 7% I can count on over 12% that collapses when the Fed hiccups.
The Retirement Sweetener: Compounding Early
Here’s the real kicker: if you’re not retiring yet, and you reinvest these payouts for a few years, the compounding effect turns your income machine into a monster.
Let’s say you’re 55, planning to retire at 65. With $500,000 invested today and all income reinvested, here’s what the portfolio could look like in 10 years, assuming modest capital appreciation:
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EPD grows 3% annually, reinvested yield 7.2%
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O grows 2% annually, reinvested yield 5.8%
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MAIN grows 4% annually, reinvested yield 6.8%
Your $500K turns into roughly $1.1 million, and your retirement income at that point is $60,000–$70,000/year. All passive. All from three tickers.
This is how retirees win.
Final Thoughts: The Art of Fewer, Better Bets
You don’t need 40 stocks to retire.
You don’t need 17 ETFs and 28 newsletters and a PhD in macroeconomics.
You just need a few great companies that return capital reliably, predictably, and without drama.
So if I had to retire tomorrow with only three high yields, I’d roll with:
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Enterprise Products Partners (EPD) — for inflation-proof energy tollbooth income.
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Realty Income (O) — for dependable, monthly real estate cash flow.
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Main Street Capital (MAIN) — for diversified, high-octane lending income with equity upside.
These three aren’t just high yielders — they’re high conviction.
They’re the foundation of a retirement that doesn’t beg the market for mercy.
And that, dear reader, is a portfolio you can toast to — every month.
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