The Emotional Side of Retiring: Six Steps to Help You Move On

An older couple sits on a beach cuddling, with the woman looking back at the camera, smiling.

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A happy retirement hums right along when you’ve got the right mindset — beyond having plenty of cash and waving goodbye to the daily grind. But retirement can mark a significant life transition, triggering both optimism and uncertainty.

In a long-running Harvard study on happiness (that has tracked the same group of men since they were teenagers in 1938), researchers asked participants as they entered their golden years what they worried about most in retirement, beyond financial concerns. The answer? How to find new social ties to replace the work connections they leaned on for so many years.

More recently, research from the Financial Planning Association (FPA) shows that only 11% of financial planners think their clients are emotionally prepared for retirement, despite over 50% rating clients as financially prepared.

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Why making peace with the mental side of retiring is so hard

Retiring isn’t just about clocking out of work for good, it’s a major life shift that can mess with your head in ways you might not expect.

Loss of purpose: Many retirees feel that work defines who they are. Without a job title, daily responsibilities, and projects, many might feel they’ve lost their “why” in life. For example, a manager who supervised people for 30 years might struggle to feel relevant without that role.

Missing social connections at work: A 2024 Transamerica survey found that 17% of retirees feel lonely, and many struggle to replace the support from co-workers, including daily chats, shared goals and a sense of belonging.

Lack of a routine: Work, especially a 9-to-5 schedule, can provide a rhythm that becomes a daily habit. Without a schedule or routine, retirees can feel lost. The Transamerica survey says 27% feel unmotivated or overwhelmed, struggling to build a new routine outside of work that feels meaningful. Besides that, the idea of waking up to an empty calendar can be freeing at first, but turns paralyzing without a daily regimen.

Fear of irrelevance: Many retirees feel like they’ve been sidelined for the rest of the game. The FPA survey highlights these fears, such as becoming a burden or losing social value, especially when work was a source of influence or respect.

Expectations vs. reality: The Employee Benefit Research Institute (EBRI) 2024 Spending in Retirement survey reveals that retirees’ life satisfaction is lower than expected, partly because dreams of travel (59% aspire to travel but only 36% actually do) or hobbies don’t always pan out, so the gap between expectations and reality grows.

Health worries: The fear of declining health or needing long-term care can weigh heavily on your retirement plans. Worrying about losing independence or burdening family (48% plan to rely on loved ones) adds stress, per the Transamerica study.

To make retirement work on your terms and ensure a smooth transition into your next chapter, take a look at these six practical ways to rethink your approach to retirement.

1. Redefine your identity

This may be more challenging for some people because they feel their job defines who they are. But one way to redefine your identity is to think about who you are beyond your job title. List your passions and goals. Learn a new skill or hobby, or try out a side hustle. You may uncover a new side of yourself you didn’t realize existed. The FPA 2025 survey noted that only 11% of retirees are emotionally ready, often because work defined their identity. Shifting focus to personal strengths can help you see who you are now.

Making friends outside of work can help keep you mentally young and healthy. Consider volunteer positions, joining a recreational sports league, or a professional organization to meet new friends. You might even consider building new relationships long before you retire. Transamerica’s 2024 data showed that 17% of retirees feel lonely, missing workplace bonds. Prioritizing meeting new people can help replace workplace connections, which can reduce feelings of isolation.

3. Find a new purpose

Explore activities that help give you a new purpose, like part-time work or learning something new. Ask yourself what gets you excited to wake up in the morning. The loss of work’s purpose hits hard. That’s why setting new goals can help keep you engaged and combat the “what now?” feeling so many retirees experience.

4. Tackle health fears

Research health care options, such as Medicare and secondary health insurance plans, eat right, and stay active with exercise to boost both your mental and physical health. You may also want to look into long-term care options, make sure your will is up-to-date, and that you've talked with family about the management of your inheritance. The Transamerica study emphasizes the fact that 37% of retirees fear a decline in their health as they grow older.

5. Adjust your expectations gradually

Start small when defining your retirement dreams. Try a weekend trip before a world tour or a single hobby before overloading your schedule. Test out a local art class before committing to a full online painting course that costs a tidy sum.

6. Prepare for the worst (expect the best)

Not to be a buzzkill, but retirement is full of ups and downs, good times and bad. So, it’s best to prepare yourself before retirement for both the golden moments and rough patches. Set your expectations high and pursue your next adventure with a positive mindset to ensure your golden years are truly golden.

Retirement can be a way of redefining your purpose

Retirement isn’t just about finances and leaving a job. it’s a chance to redefine your purpose, embrace new routines and set out on a new and fulfilling chapter filled with exciting possibilities. Prepare for the worst — but never lose sight of the freedom and opportunities retirement can offer.

For the past 18+ years, Kathryn has highlighted the humanity in personal finance by shaping stories that identify the opportunities and obstacles in managing a person's finances. All the same, she’ll jump on other equally important topics if needed. Kathryn graduated with a degree in Journalism and lives in Duluth, Minnesota. She joined Kiplinger in 2023 as a contributor.