How I Knew It Was Time for Me To Retire

Shot of a joyful senior couple enjoying the sunset during a roadtrip.
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Inflation, high interest rates and an increased cost of living have taken a toll on consumers’ wallets and savings, and in turn hindered many Americans’ retirement plans. The data is worrisome — for example, an Allianz Life survey recently found that 61% of Americans are more afraid of retirement than dying.

While the conventional wisdom is to decide to retire when one achieves a specific milestone — often linked to when a bank account or a retirement fund has reached a specific amount — some Americans have taken a different approach and decided to retire early, favoring other criteria.

That was the case for James Allen, CPA, CFP and founder of Billpin.com, who retired from his role in financial planning at 46, after 19 years in that job.

“Retirement isn’t just about reaching a certain age or financial milestone,” Allen said. “It’s an emotional journey, a transition as significant as any other life-altering event.

“I knew it was time for me to retire when my work, which I once loved, began to feel like an obstacle rather than a passion. I found myself daydreaming about the freedom of retirement, the opportunity to explore new interests, and the chance to spend more time with my loved ones. It was as if work was standing in the way of my personal goals, and that was a clear signal that my priorities were shifting.”

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‘Preparing for a Long Voyage’

Allen explained that preparing for retirement was “like preparing for a long voyage.”

In turn, he said, he had to ensure he was financially fit for the journey. He sat down with his financial advisor to chart a course, taking into account his savings, estimated Social Security benefits and retirement budget.

“It was crucial to have a strong financial foundation, to alleviate any worries about the voyage ahead,” Allen said.

Yet, Allen also emphasized that retirement isn’t just about financial planning — it’s also about emotional preparation.

“I liken it to standing on the edge of a diving board, looking into the pool of retirement,” he said. “It’s a mix of anticipation and fear.”

So, to ease this transition, he began focusing on his relationships outside of work, cultivating social interactions that would continue into his retirement. In addition, he said he started to explore his interests outside his career, “allowing myself to dream about the possibilities that lay ahead.”

“In the end, retirement is not an ending, but a new beginning,” Allen said. “It’s a chance to redefine your identity outside of your career and to embark on new adventures. It’s a journey that requires preparation, self-compassion and a willingness to embrace change. And when you’re ready, you’ll know. It’s like hearing a song that stirs your soul, and you can’t help but dance. That’s when you know it’s time to retire.”

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Passing Along Financial Wisdom

Since retiring, Allen said he’s on a journey of exploration and giving back.

“I’ve been using my CFEI [certified financial education instructor] certification to mentor young, upcoming financial planners,” he said. “It’s been a rewarding experience to pass on the wisdom I’ve gathered over the years and to see the next generation of financial minds grow and develop. I like to think of it as my way of ensuring the financial world remains in good hands.”

He added that he also has been investing time in his personal growth, taking up painting — a hobby he always wanted to explore but never had the time for.

“It’s been a fascinating journey of self-expression and creativity,” he added. “I’ve found it to be a great way to unwind and reflect on my experiences.”

Traveling has been another significant part of his retirement and included places he has always wanted to see but never had the time to, such as Japan and New Zealand.

Finally, Allen said that volunteering has also been a part of his retirement.

“I’ve been working with a local charity that provides financial education to underprivileged communities,” he said. “It’s been a humbling experience to use my skills to give back and make a difference.”

What Do Experts Say?

Experts note that determining when it’s time to retire is a highly personal situation, but there are some steps pre-retirees should take into account to make the transition smoother.

These include financial readiness and a clear assessment of your savings, investments and pension plans to determine whether you have accumulated enough funds to sustain your desired lifestyle throughout retirement.

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“Consulting with a financial advisor can help you evaluate your financial situation and develop a comprehensive retirement plan,” said Cameron Burskey, managing director at Cornerstone Financial Services.

In addition, of course, health considerations are also important, as well as lifestyle goals.

Retirement is a significant life transition that allows individuals to pursue their passions, hobbies and interests. Considering your personal goals and aspirations can help you determine the right time to retire, Burskey said. Some people may want to travel, spend more time with family, engage in volunteer work or pursue new entrepreneurial ventures. Reflecting on what you want to achieve in retirement can provide clarity on when to make the leap.

Finally, Burskey — echoing Allen’s sentiment — said it’s important to consider emotional readiness, as retirement is not solely a financial decision.

“Remember that retirement is a highly personal decision, and what works for one person may not necessarily work for another,” Burskey said. “It’s important to assess your individual circumstances, goals and financial situation carefully. Seeking advice from retirement and financial experts can provide valuable insights tailored to your specific needs and aspirations.”

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