Should You Borrow Against Investments Instead of Selling Them for a Retirement Expense?

Ross Marino |

Your home renovation has a firm payment date. You could sell appreciated investments to pay for it, but a lender offers another route: borrow against your taxable portfolio and repay when money expected later arrives.

That may preserve your investments for now. Before accepting, follow the money through repayment—including a delay. The useful question is whether this expense can stay manageable without asking your retirement spending to absorb an obligation you cannot control.

What would paying for the expense actually require?

Start with the amount due, its payment date, and cash already available after protecting ongoing spending and emergency needs. Money set aside for an unexpected expense has a different job from money available for this project.[1]

Then identify what you would sell and estimate the tax alongside the proceeds. A capital gain generally reflects the sale proceeds minus adjusted basis, rather than the entire amount sold. Holding period and your broader tax picture affect the treatment.[2] Compare enough cash to cover the expense and any resulting tax with the full borrowing cost.

What changes when investments secure the loan?

The pledged investments become collateral: assets the lender can reach under the agreement. You still owe the borrowed amount, and interest payments do not necessarily reduce it. Rates may vary, so a longer bridge can cost more than expected.[3]

A decline can trigger a maintenance call requiring additional collateral or repayment, potentially within days. The lender may sell pledged investments if requirements are not met. Demand provisions can also permit repayment to be called at any time. Your expected repayment date does not bind the lender.[3]

Use the actual agreement to confirm what you could owe: rates, fees, and demand provisions. Establish how collateral eligibility could change and how quickly a maintenance call requires action. Confirm when the lender can sell, what notice you receive, and whether your expense is a permitted use. This example concerns taxable investments for a noninvestment expense. It does not extend the arrangement to IRA assets or borrowing to buy investments.

What if the expected money arrives late?

Suppose proceeds from selling another asset are intended to repay the renovation loan. If those proceeds arrive as expected, identify the amount left after taxes, selling costs, and other commitments. That net amount must cover the loan and its carrying cost.

Now move the receipt date later. Name the cash that would cover interest in the meantime and the assets available if repayment is demanded sooner. A hoped-for sale price or a second borrowing offer is not money already available. Neither is a future portfolio recovery.

Can the bridge survive a change?

Expected repayment arrives

Borrow against investments

Cash: principal plus interest and fees.

Sale exposure: pledged holdings remain at risk until repayment.

Response: repay from the net proceeds.

Sell enough now

Cash: expense and tax funded now.

Sale exposure: chosen investments sold now.

Response: later proceeds remain available for other needs.

Repayment is delayed

Borrow against investments

Cash: continuing interest; principal if called.

Sale exposure: investments may fund the shortfall.

Response: use a separate reserve or make a planned sale.

Sell enough now

Cash: no loan payment for this expense.

Sale exposure: no collateral sale obligation.

Response: adjust plans for the delayed proceeds.

Collateral falls before repayment

Borrow against investments

Cash: paydown may be required quickly.

Sale exposure: lender may sell pledged holdings.

Response: provide acceptable collateral or repay on time.

Sell enough now

Cash: no collateral top-up for this expense.

Sale exposure: remaining investments still face market loss.

Response: review the portfolio without this loan deadline.

Read down each path. Which response could you actually carry out while continuing ordinary retirement spending? Your borrowing limit should come from that answer. The lender’s credit limit measures something different.

Dovetail Principle: Planning Helps You Decide When the Future Is Unclear

You do not need certainty about the arrival date to make a decision. You do need a response you can afford if that date changes. Planning tests the bridge against the resources and choices you would still have, rather than relying on the outcome you prefer.

When can selling be the stronger choice?

Borrowing postpones a sale; it does not erase the expense or promise a lower lifetime tax bill. If repayment ultimately requires selling investments, you may face a sale plus interest. Keeping investments also preserves their exposure to losses. Do not assume their returns will exceed the borrowing rate.

Nor does investment collateral make the interest deductible. The use of the borrowed money matters. Have your tax professional determine the treatment before counting any deduction in the comparison.[4]

Ask your advisor to compare both paths within the retirement plan, including what each leaves available for future spending. Evaluating alternatives against your circumstances is part of financial planning, rather than a contest to produce the smallest current tax bill.[5]

What would make the bridge supportable?

Set a borrowing amount, a credible repayment source, and a fallback that remains workable after a delay or decline. Agree who will monitor the loan and what changes require action; ongoing review responsibilities should be explicit.[6]

If the fallback would consume essential spending reserves or require favorable markets, reduce the borrowing, sell enough now, or redesign the expense. A sale can be the stronger choice even when it creates tax today. The financing should support the life the expense is meant to improve.

For the sale side of this decision, read How Should You Manage a Taxable Account With Large Embedded Gains? It explores the tradeoff between keeping appreciated holdings and changing their role in your plan.

About the author

Ross Marino, CFP®, CeFT®, is the Founder & CEO of Dovetail Financial and creator of Human-First Financial Guidance®. He helps people nearing or living in retirement connect their lives and wealth so that financial decisions become clearer, more personal, and easier to navigate.

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Notes

  1. Financial Foundations, FINRA.
  2. Topic no. 409, Capital gains and losses, Internal Revenue Service.
  3. Securities-Backed Lines of Credit Explained, FINRA.
  4. Publication 550 (2025), Investment Income and Expenses, Internal Revenue Service.
  5. Code of Ethics and Standards of Conduct, CFP Board.
  6. Roadmap to the Code of Ethics & Standards of Conduct, CFP Board.

Disclosure

This content is provided by Dovetail Financial Group LLC (“Dovetail Financial”) for informational and educational purposes only. It is not intended as, and should not be construed as, individualized investment, tax, legal, or accounting advice; a recommendation to buy or sell any security; or a recommendation to adopt any investment strategy. Because each person’s situation is unique, readers should consult their own financial, tax, and legal professionals before taking action based on this content. Information contained herein is believed to be reliable, but its accuracy or completeness is not guaranteed. Any opinions expressed are current as of the date of publication and are subject to change without notice. All investing involves risk, including the possible loss of principal. Asset allocation and diversification do not guarantee profits or protect against losses in declining markets. Past performance is not a guarantee of future results. Dovetail Financial Group LLC is a registered investment adviser. Registration does not imply a certain level of skill or training. Additional information about Dovetail Financial Group LLC, including Form ADV Part 2A and Form CRS, is available at adviserinfo.sec.gov. © 2026 Dovetail Financial Group LLC. All rights reserved.