Even the best-laid retirement withdrawal plans can’t foresee every expense that crops up. When you need extra cash for unforeseen costs, knowing where to turn can be paralyzing. After all, every financial move comes with tax implications that ripple well into your future.
Should you sell stocks in your brokerage account, or flip the family lake house? Is it time to finally get rid of the boat you keep meaning to take out, or should you drain a Roth IRA instead?
“When you need cash in retirement, it requires a balancing act,” says Patrick Marcinko, a financial advisor at Bogart Wealth. “Don’t rush. There’s a timeline and a deadline, but you really need to take an objective look at all your assets and what the tax implications are.”
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In a perfect world, you’d have a cash reserve carved out for the unexpected. But if you don’t, some assets are far better to tap than others. From brokerage accounts to lifestyle vehicles, here is a look at which assets to sell first when you need extra money.
1. Investments in your brokerage account
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When withdrawing money in retirement, Marcinko says retirees must be mindful of the potential tax hit, which is why a taxable brokerage account is typically a better first choice than a traditional 401(K) or IRA. Long-term capital gains tax rates, which top out at 20% for the highest earners, are substantially lower than ordinary income tax rates, which apply to traditional retirement account withdrawals.
Taking money from the wrong bucket can easily push you into a higher bracket, triggering higher Medicare premiums and even taxes on your Social Security benefits. To avoid this, try to minimize capital gains by employing strategies like tax-loss harvesting and avoiding selling your most highly appreciated assets, says Patrick Shope, Certified Wealth Strategist and founder of Shope + Associates. It’s better to pick and choose to ensure you aren’t creating a bigger tax event than necessary.
2. High-fee and redundant funds, stocks and investments
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If you’re tapping a brokerage account for extra cash, start by trimming the fat. Sell off high-fee funds, redundant holdings and underperforming assets that could harm your overall portfolio over the long term.
However, be mindful of timing, says Marcinko. If you sell during a down market, you risk locking in losses. This causes sequence of returns risk, leaving your remaining portfolio with a smaller base to recoup those losses, which can cause a structural shortfall later in your retirement.
3. Concentrated stocks that have done well
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Cutting back a very concentrated position may seem like a no-brainer, especially if you own big-name tech or AI stocks that have surged in value over the past few years. While it may make sense to sell the stock from a diversification perspective, you must carefully navigate the tax implications.
If the stock is held inside a traditional 401(k) or IRA, selling the asset won’t cause an immediate tax event, but withdrawing the cash from the account will subject it to ordinary income tax. Even if the stock is in a Roth 401(k) or IRA, where withdrawals are tax-free, cashing out now permanently impacts the tax-free compounding advantage that would otherwise benefit you and your heirs. If you do sell a concentrated stock position in a taxable account, Shope suggests doing it gradually to minimize your annual tax liability.
4. Unused lifestyle vehicles (boats, RVs, motorcycles, and extra cars)
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If you can’t remember the last time you took your boat out on the water or your RV has sat in the driveway for years, it is safe to put those lifestyle vehicles up for sale. Finding a buyer won’t always be a quick or easy way to get immediate cash, but it frees up significant equity.
Unused lifestyle vehicles represent unique vulnerabilities in a portfolio: they actively drain your cash flow through ongoing maintenance, storage and insurance expenses without bringing you actual joy.
Nonetheless, they aren’t usually high on financial advisers’ lists of what to tap first because they are illiquid, require work to sell, and can be emotionally hard to part with. “If it hasn’t moved off the lot in 36 months, you have to commit to having more fun (with it) or selling it,” says Marcinko.
5. Rentals or second homes
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Real estate is another asset that isn’t easy to sell. It carries substantial tax and family implications, especially if you originally planned to pass the property down to the next generation. However, it can also generate serious capital.
If you are considering selling real estate, the decision often comes down to whether the property brings you joy or stress. If it’s the latter, then selling makes the most sense.
“If every time the phone rings you think something is wrong with the house, that’s a lot of juice not worth squeezing,” says Marcinko. “You want to get out of the real estate business and start living the retirement life.”
Consider the big financial picture before selling
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When selecting assets to sell, resist the temptation to just pick the stock with the biggest run this year or the fund with the highest expense ratio. Instead, put in the work and look at your entire financial picture, considering what the sale will mean from a tax and savings perspective, both now and in the future. Will it impact your Medicare premiums and Social Security benefits today? If you withdraw the money now, will you have enough to live on tomorrow?
“One of the biggest mistakes retirees make when they need cash in retirement is to sell whatever is the easiest to sell instead of what is the smartest,” says Shope. “So much of it is around distribution planning, tax planning and Medicare planning. It’s not just about having the money. It’s about having the right money at the right time with the right tax situation.”