Whether you plan to retire at 55 or 75, the decade leading up to retirement is a critical investing and decision-making time. Lifestyle and portfolio choices made during these ten years determine how much financial comfort, personal fulfillment, leisure time and the possible “second acts” (whether that means continuing to work for money but in a different capacity, or pursuing volunteer or philanthropic work) available in retirement.

Advisors say several common themes emerge in conversations with their clients in the run-up to retirement. First and foremost: The sufficiency question.

“Most people wonder ‘Will I have enough?’” says Erik Olson, a CFP with Arete Wealth Management in Chicago, Illinois, for whom 25% of clients are in the decade leading to retirement. “Many aren’t confident or are unsure about how comfortable they’re going to be.”

10 years out: Sufficiency, course-correction, daydreaming

For investors ten years out from retirement, sufficiency is the big theme, say Olson and Aaron Rubin, a CFP at Werba Rubin in San Jose, California. Many investors know they have enough to retire, but aren’t sure whether their lifestyle will be diminished significantly or not. Running scenarios for investors at this stage is a common activity, Olson and Rubin say. If an investor needs more than they thought to retire, a decade provides sufficient time to course-correct, says Rubin. For a shorthand model of your sufficiency outside an advisor’s office, try AARP’s retirement calculator.

Since future retirees will want to save sufficiently to outrun the future cost of inflation, Rubin says he generally advocates that most of his investors keep at least half their investments in the market (in the form of funds, ETFs, or stocks) and assume a 4-5% return. Those concerned with sufficiency can shift their investment and savings approach while still in their working years. A decade, Rubin says, is a healthy chunk of time from an investment perspective.

“You can’t control the market, but if you’ve been working in the same company or profession for awhile, you do know your compensation structure and you can adjust your savings and investment approaches,” Rubin says. “You can also look at additional sources of income—consulting, renting space in your own home or a second home, downsizing your footprint.”

Investors who own a business need to begin thinking about their exit at least a decade before retirement, Olson says. Whether they plan to sell the business to a to-be-determined buyer, or via a succession to existing management, it’s important to engage a business valuation advisor who can help forecast the business’s future price and its founder’s take from a sale.

For investors who aren’t losing sleep over sufficiency, Olson says, they need to think about their vision for life in retirement. How do they want to spend time, where do they want to live (if outside of their current geographic area), and what will feel fulfilling in retirement? The happiest clients, he says, leverage the skills and experience they gained in their working years and apply them to new passions.

An expat energy consultant who retired comfortably in his 50s, with a vacation home, decided with his wife to devote his life to overseas Christian ministry and rent his vacation home at favorable rent to a local pastor—leveraging his expat familiarity and real estate assets to support a faith-based lifestyle.

“They really planned ahead, and were crystal clear on what they wanted to do,” Olson notes.

5 years out: Real estate decisions, portfolio tweaks, tax planning

At five years out, both advisors say, investors need to begin thinking about whether they wish to age in place, move locally (perhaps downsizing), or move elsewhere—near adult children or to a retirement-friendly market.

Depending on their decisions, running the numbers on sufficiency may adjust in a need to make portfolio changes. And, for some investors, a decision to move could unlock equity that can help a household balance sheet or even allow an earlier retirement.

Depending on an investor’s financial condition, they may also assess whether to pay off a mortgage early versus continue to keep this low-interest debt open. Investors trying to reap returns, if willing to invest somewhat aggressively, could keep up to 60% in stocks and funds.

Five years out is also a good time to model the tax impacts of an investor’s current financial plan, and whether to move funds or place ongoing investments into particular account types in order to create the optimum situation in retirement.

2 years out: Insurance assessment, simplify accounts, rethink how to spend time

Adults who plan to retire before age 65 will need to look at “gap” planning for health insurance coverage. Middle-aged and early-retired adults will find that independently-purchased insurance is very expensive, while at 65 Medicare and Social Security eligibility improve the healthcare purchasing picture significantly, Rubin notes. Those planning to bow out of their full-time job before 65 will need to research the costs of insurance for the years they’ll need to invest in it.

This is also a good time to review your overall insurance mix. Are you over-insured? (For instance, disability insurance funds lost wages at a full-time job. Do you need it if retired?) Under-insured? Reassigning insurance coverage can save money both now and later. Do you need long-term care insurance (probably) and how much? The sooner the latter is purchased, the less costly it is.

Olson and Rubin both say that it may be wise to consolidate accounts at this stage, too. Keeping future caregivers and estate plans in mind, the fewer financial institutions and products housing assets the better.

1 year out: Insurance, debt, make real estate moves

One year from retirement is a good time to make major real estate moves. If aging in place, it may make sense to refinance a mortgage or open a home equity line of credit while you’re still working. If relocating to a cheaper or more relaxing area, finish doing homework—and model the impacts of state taxes on a new home location—by going on field trips and touring homes. If you haven’t been traveling to potential new markets or at least using online and other resources to do research, devote time to that now. For instance, read articles like this one, reviewing all 50 states based on common retirement metrics, and factor such research into conversations with a planner.

“Usually the conversations I’m having at this point start with a remark like this: ‘I want to retire, but I’m living in a $2 million home. How soon can I retire if I sell and downsize?” says Rubin.

His California clientele often opt to move further from the San Francisco Bay area or to the Pacific Northwest, where their cost of living will be slightly cheaper.

Olson says that many of his retiring clients want to pay off their mortgage for psychological reasons, and if they’ve saved sufficiently, that is fine. However, if their mortgage interest rate was initiated at a low, fixed rate, it may make more sense to keep growing money in the market. While it’s vital to eradicate consumer debt (credit cards, higher-interest loans on items like cars, boats, etc.) mortgage debt has lately been so low-interest, he says, it almost always makes sense to keep money in the market rather than get rid of the mortgage.

You can also always pay above your current mortgage payment to accelerate the end of the mortgage without devoting a large lump to an early payoff: Consider running the numbers on an amortization calculator.  

Real estate maneuvers may be in order for investors in residential rental properties, Olson notes. These folks may want to take this time to use a 1031 Exchange and trade their residential investments for purely commercial property, which may deliver higher returns and better cash flow during their retirement years.

The years before retirement assume a “crescendo effect,” Olson says, with decisions water-falling one over the other to result in an investor’s lifestyle in their later years. How happy investors are financially and personally is often determined by the moves and decisions they made before they left the workforce (or a prior career).


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Jane Hodges

Jane Hodges

Jane Hodges is the author of Rent Vs. Own (Chronicle Books) and has written about real estate and personal finance for The Wall Street Journal, New York Times, Seattle Times, Fortune and many other publications. Follow Jane on Twitter and Google+