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  • Retirement Accounts

How to Self-Direct Your Retirement Account

Cattle on open ranch with rancher on horse in background, representing ong of the possible alternative investments that can be owned in a self-directed retirement account.

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Mark J. Kohler
Mark J. Kohler August 4, 2026 • 9 min
Mark J. Kohler, CPA and attorney, has helped millions of Americans improve their finances through practical, trustworthy tax and wealth strategies. Mark's mission is simple: deliver credible, actionable financial advice and guidance you can always rely on.

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What if everything you've been told about investing your retirement account is only half true?

Conventional wisdom says retirement accounts should only hold traditional Wall Street investments. The IRS says otherwise. Self-directing opens the door to a much broader range of investment opportunities and puts you back in control of where your retirement dollars go. The key is understanding how self-directing works and the rules that make it possible.

What Does It Mean to Self-Direct Your Retirement Account?

Self-directing doesn't create a new type of retirement account. It just means you're choosing how your retirement dollars are invested instead of limiting yourself to the investment options offered by a traditional brokerage.

Whether you have a Traditional IRA, Roth IRA, SEP IRA, HSA, Solo 401(k), or other eligible retirement account, the tax advantages remain the same. What changes is your investment freedom. You control the investment decisions, not your broker. A true self-directed retirement account puts you in the driver's seat. You decide where your retirement dollars go based on your knowledge, experience, and investment strategy.

Why Do So Many Investors Think They Can't Self-Direct?

One of the questions I hear most often is "If this is legal, why haven't I heard about it before?"

The answer is actually pretty simple. Most large financial institutions make their money managing traditional investment portfolios. Their business model is built around stocks, bonds, mutual funds, ETFs, and the fees generated by those investments. Self-directing doesn't fit that model.

That doesn't mean traditional investments are bad. It simply means many brokers aren't equipped to hold alternative assets, and they aren't compensated for helping clients invest outside the products their firms offer. That's so why many investors are told they "can't" buy real estate, cryptocurrency, or private investments inside a retirement account. In reality, they often can't do it with that particular brokerage.

By moving your retirement account to a custodian that specializes in self-directed investing, you gain access to investment opportunities that many traditional firms don't offer.

What Can You Invest in When You Self-Direct?

One of the biggest advantages of self-directing is the freedom to invest beyond traditional Wall Street products. Your retirement account can own a wide variety of alternative investments, including:

  • Residential and commercial real estate
  • Raw land
  • Rental properties
  • Mobile homes
  • Promissory notes and private lending
  • Tax liens and tax deeds
  • Precious metals that meet IRS requirements
  • Cryptocurrency
  • Private businesses and LLCs
  • Startup investments
  • Syndications and private funds
  • And much more

The beauty of self-directing is that you can invest in what you know best.

Maybe you've spent 20 years investing in rental properties. Maybe you've built a successful business and understand private companies better than Wall Street. Or maybe you've developed expertise in cryptocurrency or private lending.

Self-directing gives you the flexibility to put your retirement dollars into investments that align with your knowledge and experience, not just the products available through a traditional brokerage.

Strategic Strategies With A Self-Directed IRA

What Can't You Invest In?

The list of prohibited investments is surprisingly short. In general, retirement accounts can not invest in:

  • Collectibles, including artwork, antiques, most coins, stamps, and alcoholic beverages
  • Life insurance contracts
  • S corporation stock
  • Investments that violate federal law
  • Transactions that violate the IRS prohibited transaction rules

That's it. Most investors are shocked to learn that the list of prohibited investments is far shorter than the list of investments they're actually allowed to own.

The real limitations usually aren't the investments themselves. They're the rules governing how your retirement account invests and who it can transact with.

What Is a Prohibited Transaction?

If you've spent any time researching self-directed retirement accounts, you've probably heard someone warn you about prohibited transactions.

In fact, this is usually the first objection I hear from traditional financial advisors. They'll tell you self-directing is risky because of the IRS rules. They may even suggest you'll be audited, face massive penalties, or lose your retirement account altogether. Don't let those scare tactics stop you.

The prohibited transaction rules are real, and they're important, but they're often misunderstood. Investors have been successfully self-directing their retirement accounts for decades by simply understanding and following the rules.

One of the biggest misconceptions is that prohibited transaction rules limit what you can invest in. They don't. Instead, they primarily regulate who your retirement account can do business with. The rules are found in Internal Revenue Code Section 4975 and the Employee Retirement Income Security Act (ERISA). While the law is detailed, the basic concept is straightforward: Your retirement account can't engage in certain transactions with you or other "disqualified persons."

Once you understand that principle, the rules become much easier to navigate.

Self-Directed IRA Prohibited Transaction Rules

Who Is a Disqualified Person?

A disqualified person is someone the IRS says cannot personally benefit from the assets held inside your retirement account.

Disqualified persons generally include:

  • You, the account owner
  • Your spouse
  • Your parents
  • Your children and their spouses
  • Certain fiduciaries and investment advisors
  • Businesses you or other disqualified persons control

Notice who isn't on that list.

  • Your siblings.
  • Your cousins.
  • Your aunts and uncles.
  • Your nieces and nephews.
  • Your friends.

Those relationships often surprise people.

Here's a simple example. Let's say your father owns a rental property. Your self-directed IRA cannot purchase that property because your father is a disqualified person. However, your IRA may be able to purchase a rental property owned by your cousin or an unrelated third party because they aren't considered disqualified persons under the IRS rules. The same rule applies if your self-directed IRA owns a rental property. You can't live in it, vacation in it, or personally benefit from it. The property must be held strictly as an investment until it is distributed from the retirement account.

That's the real purpose behind the prohibited transaction rules. Congress wanted to prevent taxpayers from using tax-advantaged retirement accounts for immediate personal benefit while still allowing those accounts to grow for retirement. They're simply the guardrails that keep retirement investing fair and compliant.

Real Examples of Self-Directed Investing

One of the things I enjoy most about self-directing is seeing investors use their own knowledge and experience instead of relying solely on traditional Wall Street investments.

One client used a Roth IRA to purchase and sell mobile homes. They started with a relatively modest retirement account and used those funds to purchase several mobile homes. Over the next three years, they grew the account from approximately $40,000 to more than $200,000, while also building a portfolio of installment notes from mobile home sales.

I've always believed in practicing what I teach, which is why I self-direct many of my own retirement accounts.

Over the years, I've used self-directed accounts to:

  • Invest an HSA in a livestock operation in Utah.
  • Invest a Roth IRA in a cryptocurrency mining operation.
  • Hold rental real estate inside a retirement account for nearly a decade.

I want to make sure I'm implementing the same wealth-building strategies I see my most successful clients using every day.

The point isn't that everyone should buy mobile homes, cryptocurrency, or livestock. The point is that self-directing gives you the freedom to invest in what you know best, while still enjoying the tax advantages of a retirement account.

How Do You Get Started?

Getting started is often much easier than you might think. You can fund a self-directed retirement account through:

  • Annual contributions
  • A transfer from an existing IRA
  • A rollover from a former employer's 401(k) or other qualified retirement plan

Screenshot 2026-08-06 at 4.52.05 PM

The exact process depends on the type of retirement account you currently have and the type of account you want to open. Choosing the right account and properly funding it from the beginning can help you avoid unnecessary taxes, penalties, and delays.

The Bottom Line

Self-directing gives you the freedom to build a retirement portfolio around the investments you know and understand. You decide where your retirement dollars go. When you understand the rules and structure your investments correctly, self-directing can become one of the most powerful wealth-building strategies available.

My team at Directed IRA specializes exclusively in self-directed retirement accounts. Whether you're rolling over an old 401(k), transferring an existing IRA, or opening your first self-directed account, they can help you choose the right account, complete the funding process, and confidently begin investing beyond traditional Wall Street products. Book a free call with Directed IRA today and find out how to open your account and start taking control of your retirement future.

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Frequently Asked Questions

What Is a Self-Directed Retirement Account?

A self-directed retirement account is an IRA, HSA, Solo 401(k), or other qualified retirement account that allows you to invest in a much broader range of assets than a traditional brokerage typically offers. The tax advantages remain the same, but you control the investment decisions.

What Is a Prohibited Transaction?

A prohibited transaction occurs when your retirement account engages in certain transactions with a disqualified person or provides you with an immediate personal benefit. These rules are designed to preserve the tax-advantaged status of your retirement account.

Who Is a Disqualified Person?

Disqualified persons generally include:

  • You, the account owner
  • Your spouse
  • Your parents
  • Your children and their spouses
  • Certain fiduciaries
  • Businesses controlled by you or other disqualified persons

Can I Roll Over My Existing 401(k) or IRA?

In many cases, yes. Retirement funds can often be transferred or rolled over into a self-directed account without triggering taxes or penalties when handled properly. The exact process depends on your current retirement plan and employment status.

Do I Need a Special Custodian to Self-Direct?

Yes. Most traditional brokerage firms don't hold alternative assets like real estate or private investments. You'll need a custodian that specializes in self-directed retirement accounts to administer the account and process investments.


 


Related Topics
  • Retirement Accounts
  • Self-Directing
  • Directed IRA
  • Roth IRA
  • Alternative Investments
Mark J. Kohler
Mark J. Kohler

Mark J. Kohler, CPA and attorney, has helped millions of Americans improve their finances through practical, trustworthy tax and wealth strategies. Mark's mission is simple: deliver credible, actionable financial advice and guidance you can always rely on.

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