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Retire while Trump is president if you can answer ‘yes’ to these 5 questions — you're closer to freedom than you think
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Moneywise and Yahoo Finance LLC may earn commission or revenue through links in the content below. For Americans hoping to retire within the next few years, some of the most important financial decisions may need to happen before their final day of work. And for those planning to retire before January 2029, those decisions could become even more important. That's when Donald Trump's presidential term ends, and changes coming out of Washington during his presidency could directly affect how much retirees spend, save and ultimately have to live on. Jeff Bezos backs a platform that lets anyone invest in rental homes for as little as $100 — 6 ways to build wealth like a landlord without actually being one JPMorgan sees gold hitting $5,000/oz by Q4 — and savvy investors are protecting their wealth with a tax-advantaged Gold IRA. Get your free guide from Priority Gold The tax breaks in Trump's 'big beautiful bill' expire after 2028. Here are 4 moves to make before the window closes Trump has already signed a sweeping overhaul of the tax code, while his tariff policies have contributed to uncertainty over prices and inflation. At the same time, questions are looming over the long-term finances of Social Security, a program millions of retirees depend on for income. But if leaving the workforce before January 2029 is already your goal, you don't necessarily need to wait for the political or economic picture to become clearer. What matters is whether your finances are prepared to withstand it. If you can answer "yes" to the following five questions, you may already be closer to retiring during Trump's presidency than you think. The median retirement savings for someone in their 60s is $568,116, while the average is $1,228,196, according to Empower's March 2026 data (1). In other words, if you've crossed the seven-figure mark you're probably doing better than the average sexagenarian. Of course, $1 million isn't a magic number that guarantees a comfortable retirement. How far your savings will stretch depends on your spending, location, retirement age and other sources of income. But if you've accumulated seven figures and determined that it's enough to cover your expected retirement expenses, you may be closer to leaving the workforce than you think. If you're falling behind your target, you could leverage expert advice on investments to help you catch up quickly. Moby offers expert research and recommendations to help you identify strong, long-term investments backed by advice from former hedge fund analysts. In four years, and across almost 400 stock picks, their recommendations have beaten the S&P 500 by almost 12% on average. They also offer a 30-day money-back guarantee. Moby's team spends hundreds of hours sifting through financial news and data to provide you with stock and crypto reports delivered straight to you. Their research keeps you up-to-the-minute on market shifts, and can help you reduce the guesswork behind choosing stocks and ETFs. Plus, their reports are easy to understand for beginners, so you can become a smarter investor in just five minutes. Read More: Millionaires under 43 hold only 25% of their wealth in stocks. Here's where their money is actually going According to a letter from the Chief Actuary of the Social Security Administration sent to the Senate Finance Committee in 2025 (2), Trump's "One Big Beautiful Bill Act" (OBBBA) may have accelerated the timeline for depletion of Social Security's underlying trust fund. The fund is now expected to be insolvent by the fourth quarter of 2032 (instead of the first quarter of 2033), at which point benefits will be slashed by 22%, according to the SSA Trustees' report (3). There are several policy ideas on the table to prevent this. But if lawmakers are unable to find consensus by the deadline, benefits could drop for all seniors on the program. With that in mind, it makes sense to stress-test your retirement plan for Social Security at 78 cents on the dollar. If your retirement plan can withstand that potential reduction, you may not need to postpone retirement simply because Social Security's future remains uncertain. For the 12-months ended July 2026, inflation was at 3.4%, according to the Bureau of Labor Statistics (4). That's significantly higher than the Federal Reserve's 2% target (5). Trump's ongoing trade wars and the Iran conflict could keep prices volatile and unpredictable for the remainder of his term. Simply put, retiring before Trump leaves office means being prepared for inflation to remain unpredictable. If your budget has enough room to absorb higher prices, inflation alone may not be a reason to postpone your plans. Many investors turn to gold as a safe haven during uncertain times. The precious metal is widely considered a hedge against inflation. A gold IRA is one option for building up your retirement fund with an inflation-hedging asset. Opening a gold IRA with the help of Goldco allows you to invest in gold and other precious metals in physical forms while also providing the significant tax advantages of an IRA. With a minimum purchase of $10,000, Goldco offers free shipping and access to a library of retirement resources. Plus, the company will match up to 10% of qualified purchases in free silver. If you're curious whether this is the right investment to diversify your portfolio, you can download your free gold and silver information guide today. Seniors across the country carry between $95,000 to $172,000 in debt, according to Federal Reserve data analyzed by MarketWatch (6). The top three biggest drivers of this senior debt are credit cards, unpaid medical bills and mortgages. Managing monthly payments is rarely easy, but it's especially difficult when you're on a fixed income in retirement. If you're debt-free — particularly when it comes to high-interest debt — that's another expense you won't have competing for your retirement income. If you still have balances, consider using your remaining working years to bring them down. Two common approaches are the debt avalanche, which directs extra payments toward the debt with the highest interest rate first, and the debt snowball, which targets the smallest balance first before moving on to the next. You don't necessarily have to eliminate every dollar of debt before retiring. But if your remaining payments comfortably fit within your retirement budget — or you've eliminated them altogether — you may be in a much stronger position to stop working before January 2029. Your tax situation completely changes when you stop collecting employment income and start relying on pensions, benefits and withdrawals. And with Trump's recent overhaul of the tax code, there are several new deductions and strategies available to help you save money. If you've accounted for your retirement tax bill and have a strategy for drawing from your accounts efficiently, that's the final piece of the puzzle. Combined with sufficient savings, a Social Security stress test, protection against inflation and manageable debt, it could mean you don't have to wait until Trump leaves the White House to leave the workforce. A professional advisor can be especially helpful in this situation. If you have a portfolio of $250,000 or more, platforms like WiserAdvisor can connect you with vetted professionals who specialize in this kind of planning. Simply answer a few questions about your savings, retirement timeline and overall investment portfolio. From there, WiserAdvisor reviews its network to match you — for free — with up to three vetted, reputable advisors aligned with your specific needs. You can then schedule no-obligation consultations with your matches to determine who is the best fit for your long-term goals. WiserAdvisor is a matching service and does not provide financial advice directly. All matched advisors are third parties, and specific financial results are not guaranteed. A single line on your car insurance policy could be inflating your premium by up to 30% — here's what to change Dave Ramsey warns nearly 50% of Americans are making 1 big Social Security mistake. Here's what it is and 3 simple steps to fix it ASAP Robert Kiyosaki says China is 'dumping' the US as America piles on debt. Fortify your riches with 4 key assets Here are the 7 top habits of 'quietly wealthy' Americans. How many do you follow? Join 250,000+ readers and get Moneywise's best stories and exclusive interviews first — clear insights curated and delivered weekly. Subscribe now. We rely only on vetted sources and credible third-party reporting. For details, see our ethics and guidelines. Empower (1); United States Senate Committee on Finance (2); Social Security Administration (3); Bureau of Labor Statistics (4); U.S. Federal Reserve (5); MarketWatch (6) This article provides information only and should not be construed as advice. It is provided without warranty of any kind.
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