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3 smart crypto tax moves to consider — whether prices go up or down

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It is nearly impossible to predict future cryptocurrency prices amid political and economic uncertainty, but you can still make some smart tax moves, experts say.

As investors brace for interest rate news from the Federal Reserve and weigh policy proposals from former President Donald Trump, the price of bitcoin was at $65,856 around midday Tuesday, while ether bitcoin was trading at $3,310.97, according to Coin Metrics. 

The price of bitcoin dipped to a two-month low in early July after the Fed indicated it was not yet ready to cut interest rates.

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Whether prices move up or down, here are some key crypto tax strategies to consider, according to experts.  

1. Weigh ‘tax-gain harvesting’

Despite recent dips, many longtime crypto investors could have significant gains. The price of bitcoin was still up about 49% year to date, while the price of ether has grown about 40%, as of midday on July 30.

If you are expecting a lower-income year for 2024, it could be a chance for tax-gain harvesting, or strategically selling profitable crypto while in the 0% long-term capital gains bracket. Long-term capital gains rates apply to assets owned for more than one year.

These rates apply to your “taxable income,” which you calculate by subtracting the greater of the standard or itemized deductions from your adjusted gross income.

“Tax gain harvesting is one of the best strategies,” to spread earnings across multiple years, according to Andrew Gordon, a tax attorney, certified public accountant and president of Gordon Law Group.

Of course, you will need to weigh the tax consequences of boosting your adjusted gross income with crypto gains, which can affect other tax breaks.

2. Reset your purchase price

3. Consider the crypto wash sale ‘loophole’

If you are sitting on crypto losses, you could consider tax-loss harvesting, which allows you to offset other investing profits. Once losses exceed gains, you can use the excess to reduce regular income by up to $3,000 per year.

Although tax-loss harvesting often happens at year-end, it is better to harvest crypto losses over time because “those losses may no longer exist” by year-end, Gordon explained.

Trump stops short of delivering crypto monetary policy commentary during Bitcoin 2024 keynote

Typically, investors are subject to the wash sale rule, which blocks you from claiming the tax break if you repurchase a “substantially identical” asset within a 30-day window before or after the sale.

However, the wash-sale rule currently does not apply to cryptocurrency, meaning you could harvest losses and immediately repurchase to maintain your position.

The IRS gives us this loophole. We may as well take it.

Adam Markowitz

Enrolled agent at Luminary Tax Advisors

“The IRS gives us this loophole,” Markowitz said. “We may as well take it.” 

While previous Congressional efforts to repeal the crypto wash sale rule have failed, changes could still happen.

Without action from Congress, trillions of tax breaks enacted by Trump will expire after 2025. The crypto wash sale rule could be revisited as lawmakers seek funding to extend key provisions, experts say.

“It may make sense to utilize it now before it goes away,” Gordon added.

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Millions of older workers lost jobs during Covid. Prospects have improved

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Millions of older workers lost their jobs during the Covid-19 recession.

Between March and April 2020, 5.7 million workers ages 55 and up lost their jobs, according to the Economic Policy Institute’s analysis of federal data.

Now, five years since the onset of the pandemic, some older workers may be benefitting from policies that help them extend their careers.

“We’re seeing more and more employers putting in benefits and programs that help retain some of that older workforce,” said Carly Roszkowski, vice president of financial resilience programming at AARP.

These programs include phased retirement plans, part-time schedules and remote or hybrid work options, Roszkowski said.

Money is still the main reason why people want to stay in the workforce longer, particularly as inflation has pushed prices higher, according to Roszkowski. But there are also other motivators, including social connections, a sense of purpose or meaningful work that may help inspire individuals to continue to work.

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Working remotely may help extend careers

One lasting impact of the pandemic — increased flexibility to work remotely — may be helping some older workers delay retirement, according to new research from the Center for Retirement Research at Boston College.

The research finds that an individual who is working remotely is 1.4 percentage points less likely to retire than a worker in an otherwise comparable situation.

Based on those results, that could enable workers to extend their careers by almost a full year.

“If they delay claiming Social Security for that year, or delay digging into their 401(k) for that year, or contribute to their 401(k) for that year, that’s all going to be good for their finances,” said Geoffrey Sanzenbacher, a research fellow at the Center for Retirement Research and professor of the practice of economics at Boston College.

73% of Americans are financially stressed

Whether or not individuals can work remotely comes down to employer preference. For example, some companies — JPMorgan, AT&T, Amazon and Dell — have moved to five-day in-office policies. The federal government, which has a workforce that skews older, has also moved to enforce in-person work policies under President Donald Trump.

Research suggests older workers benefit from remote work. In particular, the employment rate of older workers who have a disability increased by 10% following the pandemic, according to the Center for Retirement Research.

To be sure, not all careers may allow for remote work.

What career experts say to do now

Career experts say there are certain ways older workers can help extend the longevity of their working years.

Older workers should focus on upscaling — gaining new skills or boosting their current skill set — to help show off their skills to employers, said Vicki Salemi, career expert at Monster.  That may be through a certification, online class or volunteering, she said.

Having a foundational, basic understanding of technology tools used in the workplace is also essential, said Kyle M.K., a talent strategy advisor at Indeed.com.

Older workers may also want to show off their relationship building skills, which can set them apart from younger generations that are more digitally inclined, according to Salemi.

Mentoring, conflict resolution or other interpersonal skills are highly sought after skills that should be highlighted, where possible, M.K. said.

By keeping digital profiles up to date on job search sites, older workers can emphasize their skills and experience, he said.

“Digital presence is sometimes the very first introduction that the employer will have with you,” M.K. said.

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Here’s what your student loan bill could be under a new GOP plan

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U.S. Secretary of Education Linda McMahon smiles during the signing event for an executive order to shut down the Department of Education next to U.S. President Donald Trump, in the East Room at the White House in Washington, D.C., U.S., March 20, 2025. 

Carlos Barria | Reuters

House Republicans have a plan to drastically change how millions of Americans repay their student debt.

Under the GOP’s new proposal, known as the Student Success and Taxpayer Savings Plan, there would be just two repayment options for those with federal student loans. Currently, borrowers have about 12 ways to repay their student debt, according to higher education expert Mark Kantrowitz.

If the GOP plan is enacted, borrowers would be able to pay back their debt through a plan with fixed payments over 10 to 25 years, or via an income-driven repayment plan, called the “Repayment Assistance Plan.”

Under the RAP plan, monthly bills for borrowers would be set as a share of their income, said Jason Delisle, a nonresident senior fellow at the Urban Institute. The percentage of income borrowers’ would have to pay rises with their earnings, starting at 1% and going as high as 10%.

House Republicans unveiled their agenda to overhaul the student loan and financial aid system at the end of April, in an effort to tout savings for President Donald Trump’s planned tax cuts.

Here’s what monthly bills for student loan borrowers could be if the proposal becomes law.

What’s new about the GOP student loan payment plan

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This lesser-known 401(k) feature provides tax-free retirement savings

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If you’re eager to increase your retirement savings, a lesser-known 401(k) feature could significantly boost your nest egg, financial advisors say. 

For 2025, you can defer up to $23,500 into your 401(k), plus an extra $7,500 in “catch-up contributions” if you’re age 50 and older. That catch-up contribution jumps to $11,250 for investors age 60 to 63.

Some plans offer after-tax 401(k) contributions on top of those caps. For 2025, the max 401(k) limit is $70,000, which includes employee deferrals, after-tax contributions, company matches, profit sharing and other deposits.

If you can afford to do this, “it’s an amazing outcome,” said certified financial planner Dan Galli, owner of Daniel J. Galli & Associates in Norwell, Massachusetts.    

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“Sometimes, people don’t believe it’s real,” he said, because you can automatically contribute and then convert the funds to “turn it into tax-free income.”

However, many plans still don’t offer the feature. In 2023, only 22% of employer plans offered after-tax 401(k) contributions, according to the latest data from Vanguard’s How America Saves report. It’s most common in larger plans.

Even when it’s available, employee participation remains low. Only 9% of investors with access leveraged the feature in 2023, the same Vanguard report found. That’s down slightly from 10% in 2022.

How to start tax-free growth

After-tax and Roth contributions both begin with after-tax 401(k) deposits. But there’s a key difference: The taxes on future growth.

Roth money grows tax-free, which means future withdrawals aren’t subject to taxes. To compare, after-tax deposits grow tax-deferred, meaning your returns incur regular income taxes when withdrawn.

That’s why it’s important to convert after-tax funds to Roth periodically, experts say.

“The longer you leave those after-tax dollars in there, the more tax liability there will be,” Galli said. But the conversion process is “unique to each plan.”

Often, you’ll need to request the transfer, which could be limited to monthly or quarterly transactions, whereas the best plans convert to Roth automatically, he said.

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Focus on regular 401(k) deferrals first

Before making after-tax 401(k) contributions, you should focus on maxing out regular pre-tax or Roth 401(k) deferrals to capture your employer match, said CFP Ashton Lawrence at Mariner Wealth Advisors in Greenville, South Carolina.

After that, cash flow permitting, you could “start filling up the after-tax bucket,” depending on your goals, he said. “In my opinion, every dollar needs to find a home.” 

In 2023, only 14% of employees maxed out their 401(k) plan, according to the Vanguard report. For plans offering catch-up contributions, only 15% of employees participated. 

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