3 Reasons You Might Regret Retiring Early

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Individuals who are able to retire early work hard and plan ahead to enter into the next chapter of their life.

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Transitioning into retirement, however, is not a one-size-fits-all situation. Some people adapt quickly while others struggle with the changes. Here are a few of the most common feelings people experience when they retire in their 40s and 50s. 

Guilt and Lack of Identity

In June 2022, George Jerjian shared with CNBC the story of “un-retiring” at age 67. Jerjian surveyed more than 15,000 retirees over the age of 60 to learn about their biggest retirement challenges. One of the most cited challenges surrounded identity. Some individuals responded by saying they feared losing an identity that was created over a lifetime or simply not being seen anymore.

Aimee Bond was a former senior financial analyst at McLaren Hospital from 2001 until 2020. Bond retired at age 58 after 35 years in the workforce in July 2020. Even with COVID-19 restrictions, 2020 had been the best year of Bond’s life. 

Initially, Bond struggled with nightmares plagued with guilt for retiring early. 

“I had wonderful bosses and coworkers and I still miss them very much. In some of my dreams, I was called back to work because they really need me,” Bond wrote on Quora. “In the dreams, I think ‘Oh, I am so happy to be needed. I will work forever.’ Then I wake up and realize they didn’t need me after all. I feel a little empty and sad upon awakening.”

Are You Retirement Ready?

Bond never realized there would be feelings of guilt and a lack of purpose in retirement. This said, however, Bond is not unhappy with the decision.

“I think overachievers and Type A personalities may have the hardest time in retirement,” Bond wrote. “I am trying to just appreciate the simple things.”

The Rest of Your World Stays the Same

Retirees are often taught to anticipate the unexpected in retirement. What happens, however, if you were not planning to retire early? 

David Dean was a self-service wealth manager. Dean retired in his early 40s after 20 years of employment. Despite being a meticulous planner, Dean didn’t expect to retire early. It was simply an available opportunity.

“The problem with retiring young is the rest of your world will continue unchanged,” Dean wrote on Quora. “Siblings, friends, perhaps your spouse will continue their careers. Kids will continue their schooling. It’s wonderful to have a strong social network but you will be the odd one out.”

Despite being the odd one out, Dean has no regrets about early retirement. Dean has been able to fulfill goals including spending more time with family and helping family members when they get sick thanks to early financial independence. 

Early retirement, Dean wrote on Quora, is not necessarily about sipping margaritas on the beach or traveling the world. Nor is it even about self-improvement or finding one’s passion. 

Are You Retirement Ready?

“Sometimes it’s just about spending time with loved ones during the times they need you the most and the peace of mind I can overcome almost any unexpected financial challenge.”

Lacking a Day-to-Day Plan

A former engineer in the defense industry, who went by the pseudonym Jack Smith on Quora, initially regretted retiring early.

Smith retired at age 54 after working hard to ensure a comfortable early retirement. The only issue moving forward was more about what Smith planned to do during retirement. 

“I really enjoyed working and nearly all my social life revolved around my working friends,” Smith wrote on Quora. “My problem is I never put much thought into what I would do in retirement and felt a bit lost. There’s only so many home projects and I had to find something to fill my day every day.”

What helped, aside from traveling in an RV, was doing occasional contract work. Now, it’s impossible for Smith to imagine going back to work. Smith recommends those interested in retiring early to carefully plan what they’ll do with themselves during these years. 

Find Your ‘Why’ for Early Retirement

The majority of stories we read from early retirees said they did not regret the decision to retire early. Some cited health issues and stressors in the workplace, which would have worsened had they continued working. Others said we only have a short amount of time on this earth and planning early was worth it. Those who retire early, with careful planning and hard work, enjoy living their lives by creative design and on their own terms.

Are You Retirement Ready?

Take a moment to figure out your “why” for retiring, especially if you plan on doing it early. Answering these questions can help you develop a sense of purpose. 

  • How will you spend your time? 
  • Who will you spend it with? 
  • Will you travel? 
  • Are there charitable organizations you can share your gifts and skills with? 

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