How to Turn Your Retirement Dreams into Reality (Despite Your Fears)
Stressing over shrinking savings, rising healthcare costs, or losing your purpose can give you chills, but smart money moves can lead to financial freedom and a happy retirement.
Retirement marks a pivotal chapter in everyone’s life, filled with both promise and uncertainty, where dreams of ditching the daily hustle collide with nagging fears about the future. Retirees often fantasize about travel, hobbies and spending more time with family.
Yet, the reality can be less rosy — loss of a predictable income, fears of outliving savings and skyrocketing healthcare costs can weigh you down, squashing your dreams of fun and relaxation. And, the closer you get to retirement, the more daunting this turning point in your life can become.
Below, we explore several common retirement dreams and fears — things that keep you up at night or help you sleep like a baby.
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.
First, the good news.
Retirement Dreams
Across the workforce, workers’ top three retirement dreams are traveling (65%), spending more time with family and friends (57%), and pursuing hobbies (49%), according to the 25th Annual Transamerica Retirement Survey, Retirement in the USA: The Outlook of the Workforce. Other wishes and goals, include:
Financial Freedom and Security: You may dream of having enough savings to live comfortably without financial stress. Freedom from financial stress allows you to enjoy your time, whether splurging on a cruise or dining out with friends.
Read: Retirement Calculator: How Much Do I Need to Retire?
According to Charles Schwab’s 2025 Modern Wealth Survey, Americans believe it takes $839,000 to be “financially comfortable.” This is up from $778,000 reported last year, but down from the $1 million Americans cited in 2023. Adding more pressure, the 2025 Planning & Progress Study by Northwestern Mutual puts that figure at $1.26 million. On the whole, retirees simply crave enough savings to live comfortably, covering essentials and extras.
Travel and Adventure: Retirement also offers time to dive into interests like painting, gardening, golf, or volunteering, which brings joy, connection, and a sense of accomplishment. Maybe you envision paying off your home and having a nest egg that enables you to check off bucket-list destinations or visit family without work constraints. It’s a reward for decades of saving.
Pursuing Passions and Hobbies: Retirement offers time for learning new skills, like mastering pottery or mentoring a local youth baseball team, keeping you engaged and fulfilled. Hobbies can replace work’s purpose, boost mental health and foster community.
Spending time with family and friends: One of the best aspects of retirement is the opportunity to strengthen bonds with loved ones, from hosting family gatherings to babysitting grandkids or reconnecting with old friends.
Simplifying life and downsizing: Maybe you dream of moving to a smaller home or a vibrant retirement community to reduce your essential expenses. A simpler lifestyle frees up time and money for enjoyment, and communities offer social activities and the prospect of making new friends. You might also picture a cozy condo near the beach, with no yard work and a community pool for socializing.
Per the Transamerica retirement study, almost one-third of workers dream of doing some form of paid work in retirement – with self-employed (37%) and employed workers (33%) being more likely than unemployed workers (23%) to dream of doing so.
A striking 17% of unemployed workers say they have no retirement dreams at all.
Retirement Fears
Although 11,000 Americans will turn 65 every day through 2027, only around half of all boomers and Gen Xers believe they’ll be financially ready for retirement when the time comes, per the 2025 State of Retirement Planning study by Fidelity.
Running out of money: It's an understatement to say that the fear of outliving savings is a top concern, especially with people living longer, and rising expenses like healthcare (In 2025, that number is $315,000 on average for a couple’s healthcare in retirement per Fidelity).
The Transamerica Retirement survey found 40% of retirees worry about depleting their savings. Inflation and market volatility can erode nest eggs. Social Security’s future is also uncertain, with potential benefit cuts by 2035 without reform. If your 401(k) runs dry, you may worry about the need to trim down your lifestyle or rely on your family. These concerns are real and keep many pre- and current retirees up at night.
Healthcare costs and declining health: As you age, the fear of escalating medical bills and losing physical or mental independence can add to your retirement fears. Chronic conditions, cognitive decline, dementia, or Alzheimer’s disease (33%), possible long-term care costs (31%), and losing independence (30%) were also listed as fears in the Transamerica Retirement survey.
Medicare doesn’t cover everything, and out-of-pocket costs can balloon. Declining health also threatens quality of life; Concerns over a diagnosis that requires expensive treatments or fear of becoming a burden to loved ones can be overwhelming.
Loss of purpose: Leaving the workforce can lead to feelings of a lack of purpose, especially if your identity was tied to work. A 2025 AARP study noted that 25% of retirees struggle with finding purpose post-career. Without the structure and social connections from work, you may feel isolated or even irrelevant, potentially leading to boredom or depression.
Inability to support family or leave a legacy: Maybe your biggest fear is wondering if you’ll have enough money left to help your children and grandchildren and leave an inheritance. Unexpected expenses can drain savings you put aside for gifting or helping fund your grandkids’ education.
Housing and lifestyle costs: Rising housing costs, property taxes, or maintenance expenses can strain fixed incomes. Redfin’s May 2025 data shows the U.S. median home price is $440,892, making downsizing tricky in some markets. That means that selling your home may yield less profit than expected, and renting or relocating can be costly and emotionally draining. Lifestyle inflation can also creep in.
How to bridge the gap between dreams and fears
Bridging the gap between retirement dreams and fears involves taking a hard look at both the emotional and practical aspects of planning for your future. Here are a few actionable strategies to consider:
Specify your vision for retirement. Having a clear vision of what retirement looks like can alleviate any fears you may have and provide a clear direction for your retirement. Start by writing down some specific goals, such as traveling, spending time with your family, or even driving for Uber two days a week. Having a vision counters the fear of not knowing what lies ahead in retirement.
Assess your finances: When you’ve got a handle on your finances, uncertainty takes a back seat. For example, knowing you need $70,000 annually and have $30,000 from Social Security highlights a gap to plan for. Ditto in reverse. Calculate your retirement income and projected expenses to help address the fear of running out of money.
Create a flexible financial plan: Develop a savings plan with multiple income sources, such as part-time work, rental income, stocks, or annuities, that provides security and flexibility. For instance, saving an extra $500 per month for 10 years at a 5% return could grow to over $75,000. This can reduce the fear of unexpected expenses by building a buffer.
Consider health concerns: Healthcare costs are a major retirement fear. But planning for medical expenses can help ensure health issues don’t derail your retirement dreams. Remember, Medicare doesn’t cover long-term care, so explore health savings accounts (HSAs), long-term care insurance, and invest in your health now.
Discover your retirement lifestyle: Exploring your retirement goals can help refine your dreams and identify any gaps, such as needing more money for travel but less for hobbies. Recognizing your ideal retirement now can ensure you are fulfilled without the fear of losing purpose. While you’re at it, strengthen relationships with your family and friends so you don’t feel isolated in retirement.
Plan for the unexpected: Preparing for surprises now can help reduce the fear of the unforeseen later on. Create an emergency fund for three to six months of expenses — just in case.
Seek professional advice: Consult a certified financial planner or retirement coach to create a personalized retirement plan. This can help alleviate the fear of "making mistakes."
Connecting Fears and Dreams
Retirement is a big shift where your worries and hopes can get all tangled up. Fears like running out of money, unexpected healthcare costs or losing purpose can obscure dreams of financial freedom, travel or pursuing your passions. By addressing these fears with practical strategies, such as reaching out to a financial professional, while nurturing aspirations, retirees can create a balanced, happy retirement.
Related Content
-
The Wealth Equation: Balancing Money and StressSponsored Don’t let assets be a liability that strains your family.
-
Is Your Emergency Fund Running Low? Here's How to Bulk It UpIf you're struggling right now, you're not alone. Here's how you can identify financial issues, implement a budget and prioritize rebuilding your emergency fund.
-
Guide to How All-Assets Planning Offers a Better RetirementAn "all-asset" strategy would integrate housing wealth and annuities with traditional investments to generate more income and liquid savings for retirees.
-
An Expert Guide to How All-Assets Planning Offers a Better Retirement
An "all-asset" strategy would integrate housing wealth and annuities with traditional investments to generate more income and liquid savings for retirees.
-
Forget FIRE: Why ‘FILE’ Is the Smarter Move for Child-Free DINKsHow shifting from "Retiring Early" to "Living Early" allows child-free adults to enjoy their wealth while they’re still young enough to use it.
-
7 Tax Blunders to Avoid in Your First Year of Retirement, From a Seasoned Financial PlannerA business-as-usual approach to taxes in the first year of retirement can lead to silly trip-ups that erode your nest egg. Here are seven common goofs to avoid.
-
How to Plan for Social Security in 2026's Changing Landscape, From a Financial ProfessionalNot understanding how the upcoming changes in 2026 might affect you could put your financial security in retirement at risk. This is what you need to know.
-
Healthy to 100: Secrets from Countries Where Retirees Age BestLongevity is a team sport, according to author Ken Stern. Here's the secret sauce for living long, healthy lives from countries like Italy and Japan.
-
6 Overlooked Areas That Can Make or Break Your Retirement, From a Retirement AdviserIf you're heading into retirement with scattered and uncertain plans, distilling them into these six areas can ensure you thrive in later life.
-
I'm a Wealth Adviser: These Are the 7 Risks Your Retirement Plan Should AddressYour retirement needs to be able to withstand several major threats, including inflation, longevity, long-term care costs, market swings and more.
-
High-Net-Worth Retirees: Don't Overlook These Benefits of Social SecurityWealthy retirees often overlook Social Security. But timed properly, it can drive tax efficiency, keep Medicare costs in check and strengthen your legacy.
