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How to Prepare for a Happy Retirement

It’s time to prioritize what matters most to you

By Sam Zimmerman and Sagewell Financial
Two retired friends laughing after playing tennis. Next Avenue
Credit: Getty

If you ask 10 older Americans what retirement means to them, you'll likely get 10 different answers. That's because retirement is personal and enjoying this next phase of life is not a one-size-fits-all proposition.  

"More and more, we are finding that retirement is much more of a new beginning for people than anything else," said Elisabeth Larson, a financial adviser at Edward Jones in Amherst, N.H.  

In June 2021, Edward Jones and Age Wave released a study called "The Four Pillars of the New Retirement: What a Difference a Year Makes." In this report, four pillars ⏤ health, family, purpose and finances ⏤ "are highly intertwined and critically influential in shaping retirees' overall quality of life," Larson said.  

And, while there's no cookie-cutter way to retire, older Americans seem united in wanting to live life on their own terms. As the report states: "Retirees tell us they are free from the responsibilities and stresses often associated with work, such as commuting, deadlines and office politics. The joys and challenges of raising a family have also been largely fulfilled. Now they are free to do the things that they always dreamed of doing, such as spending more time with loved ones, engaging in projects and activities that provide them with a sense of purpose and traveling on their own time." 

With this in mind, we talked to financial experts and older Americans to gather their best tips for a happy retirement. Read on to learn more.  

Live Where You Want

For Julie Eisenberg, 60, retirement meant the chance for new adventures. So, Eisenberg and her partner Glen, 68, moved from Washington D.C. to Lisbon, Portugal in the summer of 2021. 

Eisenberg, formerly owner of a yoga studio, first laid eyes on Lisbon in 2017 when she visited the city for a brief four days. She fell in love with Lisbon and in 2018, purchased an apartment there. In 2020, due to the pandemic, she spent more time in Lisbon than expected and this expedited her plans to retire to Portugal.  

"I'm a city person, but D.C. is so big and congested. Lisbon is a small, beautiful city with an excellent health care system and a government that puts people first," Eisenberg  said. "I love that people are not working themselves to death here, and there's a strong sense of community. Moving here came down to the right vibe."  

Of course, money matters, too. To help speed up her retirement, Eisenberg sold both her house and business, while her partner sold his home-improvement contracting business. Eisenberg also has a 401k to fall back on. She also sought out advice from financial experts in both D.C. and Portugal.  

Connect With Other People

Spending more time with family and friends is often a top priority for older Americans. According to the Edward Jones and Age Wave study, 77% of U.S. retirees said "having family and friends that care about me" is key to achieving optimal well-being. 


"Almost all of our clients' ears perk up when I ask them: 'Do you want to be near your kids or grandkids when you retire?" said Joseph Finn, director of business development at Argent Wealth Management in Waltham, Mass.  

Connection to friends and community, however, can be just as important as living near your family. For Kathy Lilli, 68, being involved in her community and social circles was a key priority when she retired at 62. Lilli, who lives in Iowa City, Iowa, spent her career working as a registered nurse. She was burned out and wanted to spend her next phase of life being with friends and giving back to her community. 

Lilli, who lives on her own, participates in a book club, volunteers at a local hospice home and spends a lot of time with friends. "I get the most joy from connection with other women," she said.  

Find Purpose

This one can be a doozy. According to the Edward Jones and Age Wave report, almost one-third of older Americans report struggling to find purpose in retirement. And although only 24% volunteer, 87% wish there were more ways to help in their communities.  

To help you find your purpose and not feel so lost when you begin your next phase, Larson suggests engaging in groups before you retire.  

"This not only helps establish relationships, but it helps you 'try on' what life might look like in retirement," she said. 

Some suggestions: take some classes, join organizations or volunteer. You may, in fact, meet like-minded people and find something you really love. Take Lilli, for example. She has a busy life already, but also volunteers for political candidates and causes she believes in.  

After years of working in hospitals with very little spare time, "getting involved in politics is my chance to pay it forward and make a difference," said Lilli. 

Focus on Health

If you're worried about your health as you grow older, you're not alone. In fact, according to the Edward Jones and Age Wave report, 85% of retirees said having good physical/mental health is an important element to achieving optimal well-being. 

"It's important to be prepared for anything ⏤ including a serious physical illness or the onset of some type of mental incapacity, such as Alzheimer's disease," said Larson. 

Finn at Argent agreed, saying that taking care of yourself now is important, but so is being able to afford your health care in the future.  

For starters, it's critical to understand your current health coverage, and make adjustments to ensure you have what you need, he said. 

According to Sagewell, a personalized financial platform that offers banking services exclusively for older Americans, health care can be a daunting process ⏤ often more confusing when you get solicitations from many different providers. To help you better prepare for health and wellness as you age, a Sagewell advocate will help you navigate healthcare challenges like:  

  • Medicare enrollment support and advice 
  • A Medicare Advantage plan vs. Traditional Medicare 
  • Comparing health insurance policies and price quotes 
  • Finding low-cost options for your prescription drugs 

Better yet, a free, dedicated Sagewell advocate will also help you navigate the complex details of retirement and find hidden discounts and savings along the way. 

While you navigate your health insurance, Larson also recommends updating your power of attorney and healthcare directive.  

Also important: talk to an insurance expert about long-term care insurance, especially since the cost of long-term care can be very expensive. In fact, the median annual cost for a private room in a nursing home is about $105,000, and it's almost $55,000 for home health aide services, according to the insurance company Genworth. 

"Someone turning age 65 today has almost a 70% chance of needing some type of long-term care services and supports in their remaining years," according to the U.S. Department of Health & Human Services.  

Craft Your Own Best Retirement

While there's a lot to think about when preparing to retire, just remember: this is your time. Besides getting your financial house in order, "a little bit of soul searching about what you want out of life can go a long way to crafting the retirement you have envisioned," said Larson.  

Sam Zimmerman is the CEO and Cofounder of Sagewell, where he's focused on building financial products that help take the guesswork out of retirement. Sam spent the last nine years in financial technology having worked as a quantitative analyst and most recently as the cofounder of Freebird, a travel insurance company that was sold to Capital One. Sam has also worked at MIT and NASA in research roles in cybersecurity, statistics and cognitive science. Read More
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By Sagewell Financial

Sagewell is the only one-stop-shop financial platform built using modern technology exclusively for older adults. We use innovative financial products and human support to help older adults get the most out of their retirement savings and entitlements.   

We take the guesswork out of retirement by putting all of the key retirement-related financial and health products under one roof. As a result, our retirees make more confident aging related decisions, worry less about financial exploitation and get more out of their retirement. 

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