If a 2027 retirement date is circled on your calendar, your financial life is about to change forever. The final 12 months before retirement are less about the "if" and entirely about the "how."
Your window for major course corrections is closing, and the transition from wealth builder to wealth spender is about to begin. This is arguably the biggest financial transition of your life, and not one to approach on a wing and a prayer.
Think of 2026 as your pre-flight checklist: a time to move beyond vague projections and into hard-coded reality. While the excitement of a wide-open calendar is on the horizon, the math of your first year of retirement requires an objective, clinical audit. From reviewing and stress-testing your portfolio to giving your emotional state an intimate look, here is your portfolio checklist if you are planning to retire in 2027.
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1. Review and consolidate your portfolio
Anytime you're planning for the future, the first step is often to assess where you are at in the present. For near-retirees, this means reviewing your portfolio to understand how it's set up and using that information to help plan your withdrawal strategy.
"Too often, I run into investors nearing retirement who have accounts at many different financial institutions with little idea what's in each account," says Mike McCulloch, a certified financial planner and managing director at Hunter Associates. To combat this, he suggests considering consolidating your accounts. This will help you get a clearer picture of what you own, and from that, create an income strategy in retirement.
"A good first step is to create an inventory of retirement and investment accounts and consider consolidating accounts with similar tax treatment for ease of administration," says Ashley Weeks, a wealth strategist for TD Wealth.
McCulloch cautions against immediately taking distributions from your Roth accounts after you retire. This would mean you're "taking from an account that could continue to sit and grow tax-free," he says. "It may make more sense to start by drawing from a non-retirement account or a traditional IRA prior to the Roth IRA."
2. Finalize and stress test your withdrawal rate
Once you've consolidated your accounts, it's now time to stress test your retirement withdrawal rate. The 4% Rule — where you withdraw no more than 4% of your portfolio the first year of retirement, then adjust that dollar amount for inflation each year — is a common guideline, but it isn't for everyone. A portfolio's "safe" withdrawal rate is highly dependent on the market valuations at the moment you stop working.
Your 2027 retirement plan requires precision. One way to get this is through Monte Carlo simulations. These test your portfolio against thousands of market scenarios to see the probability of your money lasting through retirement. Many brokerage firms, including Fidelity, Charles Schwab and Vanguard, offer Monte Carlo simulations for clients.
A success rate of at least 80% to 95% is often recommended, but the appropriate level will vary by individual and the variability of your income in retirement. If the confidence level isn't where you'd like it, you may want to consider postponing retirement or looking for other income sources in retirement.
3. Reduce portfolio risk
If you're planning to retire in 2027, you're deep in the "red zone" of retirement planning. This is the five years before and after you retire, when your portfolio is at its most vulnerable.
"The years immediately before and after retirement can pose the greatest threat to retirement security due to sequence risk," Weeks says. "A major portfolio decline in this period could require selling into the loss to cover spending needs instead of riding out the recovery." And this, he adds, can have "an outsized impact on long-term portfolio solvency."
When you are decades away from retirement, a bear market is a buying opportunity; when you are one year away, it is a threat to your lifestyle.
To mitigate this risk, it's generally recommended to reduce your portfolio risk in the years leading up to retirement. You can do this by increasing the proportion of bonds and fixed income relative to stocks in your portfolio. Diversification is also your friend now more than ever. "Concentration may build wealth, but diversification may help preserve it," McCulloch says.
Also, ensure you have adequate liquidity in cash or cash equivalents, so you won't need to tap investments for short-term cash flow. This will give you a buffer so you can hopefully avoid large withdrawals during market downturns.
4. Strategize Social Security
Your investments probably won't be the only income source you have in retirement. Social Security is often a key and important ingredient because it can provide a fixed income stream. But when you start claiming your benefits has a crucial impact on how much income you can count on.
The best way to strategize your benefits is by creating a free account at SSA.gov and pulling your individual projection, Weeks says. This "provides estimates for monthly payment depending on your filing age."
You can start receiving Social Security benefits as early as age 62, but claiming before your full retirement age will reduce your monthly benefit amount. The longer you wait until the age of 70 to start claiming, the larger your benefit will be. There is no change to your benefits beyond the age of 70.
If you plan to delay taking Social Security, make sure you have a clear plan for where your income will come from in the meantime, McCulloch says.
There are other important Social Security rules to be aware of, too. For instance, you can claim benefits and continue to work. However, if you earn above a certain amount before reaching full retirement age, your benefits will be reduced.
You should apply for benefits about four months before the date you want to start receiving them.
5. Pay down high-interest debt
The amount of debt you carry in retirement is a personal preference. Some folks prefer a clean slate, which makes budgeting easier. Others don't mind having some low-interest debt. One universal rule, however, is to pay off as much of your high-interest debt as possible leading up to retirement.
"It can help to frame the decision by comparing the interest you're paying to what that money could realistically earn elsewhere," McCulloch says.
For example, if you have a 6% mortgage but are earning 8% per year in the stock market, it generally makes more sense to focus on investing. If your portfolio is only earning 5% per year, however, you're probably better off paying down the mortgage first.
6. Your next step
The transition from "Saver" to "Spender" is as psychological as it is mathematical. While you're fine-tuning and stress-testing your portfolio, don't forget to assess your emotional readiness, too.
"Employment provides a slew of benefits beyond income, including social interactions, camaraderie and shared goals with colleagues," Weeks says. If you aren't intentional about cultivating relationships beforehand, "retirement can be a social vacuum."
He recommends taking time to identify three to five specific personal goals you have for the first two years of retirement. This can help give you avenues for finding purpose, engagement and social interaction to ensure your retirement is both financially secure and emotionally fulfilling.
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