How to Turn Your Investments into Paychecks That Never Stop

When you’ve reached CoastFI, your retirement accounts are on autopilot, and you’ll live off your taxable brokerage for the next couple of decades, does the “never hold bonds in taxable” rule still apply?

That’s the dilemma facing Brandon, a listener whose investment strategy has shifted from accumulation to decumulation. He’s about to coast for 20 years, spending exclusively from his taxable account while his retirement funds remain untouched. But if all withdrawals come from that one account, where should his bonds live, and how does he generate stability without sabotaging tax efficiency?

We unpack the trade-offs between asset location theory and real-world spending needs. While conventional wisdom says to stash bonds in tax-advantaged accounts, Paula explains why that rule breaks down when your taxable account is also your spending bucket.

We reveal how to balance growth, risk, and liquidity when the traditional playbook no longer fits.

Then we turn to two fascinating money dilemmas that take the conversation in unexpected directions.

One listener faces a tricky balance between generosity and boundaries while helping a parent retire through shared home ownership. Another wants to know whether it’s possible to turn a stock-heavy portfolio into a reliable income stream using covered-call strategies.

Both stories reveal how flexible, creative thinking can solve complex financial puzzles.

Listen to the full episode to hear how these situations unfold, and to discover what Paula recommends when family, housing, and investing all collide.


Key Takeaways
The “no bonds in taxable” rule isn’t universal. When you’re drawing solely from taxable accounts for many years, that account needs to function as its own mini-portfolio, including bonds or cash for stability.


Asset location follows purpose, not dogma. Tax efficiency matters, but liquidity and risk management take priority when the account funds your life.


Think in terms of buckets. Your retirement accounts can stay growth-oriented while your taxable account carries the ballast for spending.


Plan ahead for rebalancing. When taxable balances decline, know how and when to refill your bond/cash sleeve from other sources to keep your glidepath intact.


The transition to CoastFI is a mental shift. You’re no longer optimizing for maximum returns, you’re designing for peace of mind and steady withdrawals.



Chapters
Note: Timestamps will vary on individual listening devices based on dynamic advertising segments. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.
(0:00) Introduction and overview of listener questions
(1:28) Brandon’s CoastFI question: bonds in taxable when withdrawals start now
(3:56) Why “no bonds in taxable” is a rule of thumb, not a law
(12:42) How to treat taxable as a stand-alone portfolio
(18:31) Balancing tax efficiency with cash-flow reality
(24:24) Andrew’s question: Helping a parent retire through shared property ownership
(49:26) Chandan’s question on whether covered-cal EFTs help generate income
(67:24) Covered calls explained simply, income with a ceiling

Resources & Links
Asset Location Cheat Sheet (free): affordanything.com/assetlocation
Guide to Double-I FIRE (free): affordanything.com/fiire

Glossary
CoastFI: The point at which your invested retirement savings can grow to fund your future without further contributions, allowing you to “coast” by covering only current expenses through work you enjoy.


Asset Location: The strategy of placing specific asset types (stocks, bonds, REITs, etc.) in different account types for tax efficiency.


Bond Placement: Deciding which account should hold your fixed-income investments — often reconsidered during drawdown phases.


Taxable Account: A brokerage account where investment gains are taxed annually; more flexible than retirement accounts but less tax-sheltered.



Listen, Share, Subscribe
If you’re transitioning from saving to spending, or wondering how to structure your taxable portfolio during CoastFI, this episode is for you. Listen now, share it with a fellow FI enthusiast, and download the free Asset Location Cheat Sheet for a quick-reference guide to smarter portfolio design.

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Subscribe via Apple Podcasts: https://affordanything.com/applepodcasts
Full show notes for the episode: https://affordanything.com/episode
Get our show notes in your inbox: https://affordanything.com/shownotes


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