Transitioning to Retirement Is Like Moving to a New World – Bring a Map
To truly be ready to retire, you need to fully explore the unfamiliar territory ahead. Your retirement future can be broken down into five distinct "worlds," each with its own danger zones that you need to navigate.
Maybe you managed to pull together a down payment for your first house without some sort of formal savings plan. Many people do.
Maybe you even got your kids through college without any real strategy for how to pay for it. It happens.
So maybe you think you can lick this retirement savings thing, too. Perhaps with a buy-and-hold investment strategy, or simply figuring it out as you go, you’ll hoist yourself over one last financial hurdle before you hit the finish line. Good luck.
From just $107.88 $24.99 for Kiplinger Personal Finance
Become a smarter, better informed investor. Subscribe from just $107.88 $24.99, plus get up to 4 Special Issues
Sign up for Kiplinger’s Free Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
Retirement isn’t the finish line; it’s the starting line for a whole new way of life. One without a paycheck.
You’ll be living off relatively fixed finances, on an income you determine yourself. So, the decisions you make as you transition from working to retirement will help establish how long your money will last and how comfortable you’ll be. To make the journey to and through retirement without some sort of plan just might be the most daunting endeavor you could ever take on.
Yet, people try it. Some without even realizing how unprepared they are. Like a married couple I met with recently in my office: Mid- to late-50s. All assets focused on growth. No income plan, really, just a hodgepodge of investments that meant they’d do well when the market is up and have to live leanly when it’s down.
They had a portfolio. They needed a plan.
Over the years, we’ve seen investors in this same situation over and over again. Some are worried, some unaware, some simply naïve about what they’ll need for the retirement lifestyle they want. All are vulnerable — even if they’ve worked hard at saving — because they’re traveling new territory without a map.
So we talk about the obstacles they might encounter that could keep them from experiencing the retirement they want. There are the obstacles they know about — and those are typically the concerns they come in with — but there are also barriers they don’t foresee that could keep them from enjoying their wealth to the fullest.
Wealth has two sides: lifestyle and legacy. If you could wave a magic wand and have anything you wanted, what would that look like? Think of it like pulling up Google Maps: You put in the destination first and then find your way.
We call our process the “Retirement Navigator,” and it takes each client through five “worlds” they should explore before and during their retirement.
World No. 1 – Income
Maybe you’ll have a pension, and, of course, there’s your Social Security benefit. But you’ll likely need to use your nest egg to make sure an adequate retirement paycheck keeps coming month after month. The first step for most is to change focus from accumulation to preservation. When you retire, the rules change. You can’t just ride the market up and down the way you did when you were younger and had time to recover from a loss. You’ll want to include strategies that provide consistent income, so you can have the lifestyle you want no matter what happens in the market. These strategies might include income-producing real estate, guaranteed annuities, CDs and/or bonds.
World No. 2 – Growth
The challenge here is to put together a portfolio that’s less vulnerable to volatility but still includes investments that will help offset inflation. This could include a more focused approach — an institutional portfolio or actively managed account — to help minimize risk and take advantage of growth opportunities. You also might want to consider alternative investments such as commodities or real estate.
World No. 3 – Tax-efficiency
Of course, your income and investment plans won’t be worth much if you end up giving most of your money back to Uncle Sam. So you’ll want to make sure all the pieces of your plan are working in the most tax-efficient way. It seems as if many Americans’ CPAs are on one side of town and their financial advisers are on the other; they might talk once a year or not at all. Why not bring the two together when building and modifying your overall plan? That way you can be sure you’re not only making the best moves year to year but also through your entire retirement and even to the benefit of your beneficiaries. Consider tax-favored investments or insurance products that can minimize your tax bill in retirement.
World No. 4 – Health and Long-Term Care
According to one report from the U.S. Senate, the cost of seniors’ most commonly used brand-name drugs is increasing at 10 times the rate of inflation. The U.S. Centers for Medicare and Medicaid Services projects health care spending will rise 5.5% annually, on average, from now until 2026. Long-term care costs are just as daunting; Genworth’s “2018 Cost of Care Survey” reported annual median costs of long-term care support services increased an average of 3% from 2017 to 2018, with some categories surpassing by two to three times the 2.1% U.S. inflation rate . The insurance industry is creating more products aimed at long-term care, including life insurance that allows you to access the death benefit under certain circumstances. The important thing here is to explore all your options before you need care.
World No. 5 – Leaving a Legacy
This is another often-ignored piece of retirement planning. A 2017 Ameriprise study found that most survey participants (83%) want to leave money or assets to a loved one; however, only 64% feel they’re on track to leave an inheritance, and even fewer (50%) have a formal plan in place. It’s possible to design a plan that helps accomplish your income goals first, while allowing room to leave a legacy. This is also an area where there can be a disconnect among advisers, so make sure your financial adviser, CPA and attorney are on the same page regarding your wishes.
Having a navigation process can help you maneuver past the obstacles on the way to retirement and allow you to enjoy yourself more once you get there. You won’t have to monitor the stock market or worry about which world events might affect your nest egg. Instead, you can put your energy into crossing off the items on your bucket list.
Fee-based financial planning and investment advisory services are offered by Ladin Financial Group, a Registered Investment Advisor in the State of Florida. Insurance products and services are offered through Ladin Consulting Group. Ladin Financial Group and Ladin Consulting Group are affiliated companies. Investing involves risk, including the potential loss of principal. Any references to guarantees generally refer to fixed insurance products, never securities or investment products. Insurance and annuity product guarantees are backed by the financial strength and claims-paying ability of the issuing insurance company. Our firm does not provide, nor is any statement contained here in intended to provide tax or legal advice, all individuals are encouraged to consult with qualified professionals prior to making any decisions about their personal situation.
Kim Franke-Folstad contributed to this article.
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.

Michael Ladin is founder and CEO of Ladin Tax & Financial Group, a firm that focuses on assisting Florida business owners, Baby Boomers and retirees with retirement income strategies that work in a tax-efficient way.
-
7 Retirement Planning Trends: What They Mean for You in 2026From government shutdowns to market swings, the past 12 months have been nothing if not eventful. The key trends can help you improve your own financial plan.
-
What Defines Wealth? A Christmas Tale of Legacy vs PossessionThe tale of Good King Wenceslas shows that true wealth is built through generosity, relationships and the courage to act kindly no matter what.
-
5 Moves to Ensure the Markets Work Hard for You in 2026After a strong 2025 in the stock market, be strategic by rebalancing, re-investing with a clear purpose and keeping a disciplined focus on your long-term goals.
-
7 Retirement Planning Trends in 2025: What They Mean for Your Wealth in 2026From government shutdowns to market swings, the past 12 months have been nothing if not eventful. The key trends can help you improve your own financial plan.
-
What Defines Wealth: Soul or Silver? Good King Wenceslas' Enduring Legacy in the SnowThe tale of Good King Wenceslas shows that true wealth is built through generosity, relationships and the courage to act kindly no matter what.
-
An Investing Pro's 5 Moves to Help Ensure 2025's Banner Year in the Markets Continues to Work Hard for You in 2026After a strong 2025 in the stock market, be strategic by rebalancing, re-investing with a clear purpose and keeping a disciplined focus on your long-term goals.
-
Introducing Your CD's Edgier Cousin: The Market-Linked CDTraditional CDs are a safe option for savers, but they don't always beat inflation. Should you try their counterparts, market-linked CDs, for better returns?
-
How to Protect Yourself and Others From a Troubled Adult Child: A Lesson from Real LifeThis case of a violent adult son whose parents are in denial is an example of the extreme risks some parents face if they neglect essential safety precautions.
-
To Build Client Relationships That Last, Embrace SimplicityAs more automation becomes the norm, you can distinguish yourself as a financial professional by using technology wisely and prioritizing personal touches.
-
Client Demand Is Forcing Financial Advisers to Specialize: How to DeliverThe complexity of wealthy clients' needs — combined with AI and consumer demand — suggests the future of financial planning belongs to specialized experts.
-
A Financial Planner Takes a Deep Dive Into How Charitable Trusts Benefit You and Your Favorite CharitiesThese dual-purpose tools let affluent families combine philanthropic goals with advanced tax planning to generate income, reduce estate taxes and preserve wealth.