Time to read: 6 Minutes
Last week, one of our advisors spoke with a client who should have been celebrating. At 62, David had built a successful accounting practice, saved diligently, and according to every financial metric, was more than ready to retire. His portfolio could support his lifestyle. His health was good. His wife was excited about their travel plans.
So why did he look like he was about to throw up?
“I keep telling everyone I’m excited,” David confided, “but honestly? I’m terrified. And I feel ridiculous admitting that.”
David isn’t alone. In fact, his reaction is so common that we’ve started to recognize it as a pattern. The more successful someone has been in their career, the more frightening retirement can feel even when they’re financially prepared.
The Identity Crisis Nobody Talks About
Here’s what David was really afraid of: “If I’m not the guy who runs the accounting firm, then who am I?”
For decades, we introduce ourselves by what we do. “I’m a surgeon.” “I’m an attorney.” “I’m a CEO.” Our careers don’t just pay our bills—they define our identity, structure our days, and give us purpose. When someone asks what you do, you have an immediate, confident answer.
But what happens when that answer disappears?
David had spent 40 years being “the accountant.” He was the one people called during tax season, the one who solved financial puzzles, the one who built something from nothing. Without that role, he felt like he was losing himself.
The Freedom Paradox
“I should be excited about sleeping in,” another client told our team recently. “So why does the thought of having nothing to do make me panic?”
This is what we call the freedom paradox. We spend our entire working lives dreaming of freedom from alarm clocks, meetings, and deadlines. But when that freedom arrives, it can feel overwhelming rather than liberating.
Without structure, without goals, without the familiar rhythm of professional life, many retirees find themselves feeling lost rather than free. The days stretch endlessly ahead, and suddenly having “all the time in the world” feels more like a burden than a gift.
The Success Trap
Interestingly, the most successful people often struggle the most with retirement transitions. Why? Because they’re used to achievement, recognition, and constant forward momentum. They’ve spent decades climbing ladders, hitting targets, and pushing toward the next milestone.
Retirement, by contrast, can feel like… nothing. No promotions to earn, no deals to close, no problems to solve. For someone whose identity is built around achievement, this can feel like a kind of professional death.
The Spouse Dynamic
Here’s something else David mentioned that rang true: “My wife seems to have this all figured out. She’s already planning her garden, talking about cooking classes, excited about having time for hobbies. Meanwhile, I’m over here having an existential crisis.”
Often, one spouse adapts to retirement planning more easily than the other. This can create additional pressure and even some guilt. “Why can’t I just be excited like she is?” David wondered.
The truth is, we all process major life transitions differently. Some people are natural planners who thrive on envisioning their next chapter. Others need more time to work through the emotional aspects of leaving their careers behind.
It’s Not About the Money
What struck me most about David’s situation—and what I see with many clients—is that his fear had nothing to do with finances. He wasn’t worried about paying bills or maintaining his lifestyle. He was worried about maintaining his sense of self.
This is why purely financial retirement planning often falls short. We can run all the numbers, stress-test portfolios, and create detailed withdrawal strategies. But if we don’t address the emotional and psychological aspects of retirement, we’re only solving half the problem.
The Path Forward
So what did our advisor tell David? First, that his fears were completely normal and nothing to be ashamed of. Second, that recognizing these concerns early is actually a huge advantage; it means he can address them proactively rather than reactively.
They talked about ways to maintain structure and purpose in retirement. They discussed volunteer opportunities that could utilize his professional skills. They explored hobbies that might evolve into something more meaningful over time.
Most importantly, they acknowledged that retirement isn’t just an ending, it’s a beginning. And like any major life transition, it’s natural to feel uncertain about what comes next.
The Real Preparation
Financial preparation for retirement is crucial, but it’s not enough. The clients our team sees who thrive in retirement are those who’ve also prepared emotionally and psychologically for this transition. They’ve thought beyond the numbers to consider questions like:
- What will give my life meaning when I’m not working?
- How will I structure my days?
- What relationships will I cultivate?
- How will I stay mentally and physically engaged?
These aren’t easy questions, and they don’t have quick answers. But asking them and working through them is just as important as calculating your withdrawal rate.
You’re Not Alone
If you’re approaching retirement and feeling excited one minute and terrified the next, know that you’re in good company. The fear behind the excitement is real, valid, and more common than you might think.
The key is acknowledging these feelings rather than pushing them aside. Talk to your spouse, friends, or advisor about your concerns. Consider working with a counselor who specializes in life transitions. Most importantly, give yourself permission to feel uncertain about this major life change.
Retirement is one of the biggest transitions you’ll ever make. It’s okay to feel unsure. And it’s definitely okay to take time to figure out who you want to be in this next chapter of your life.
This topic and many others like it is explored in depth in our book “8 Things I wish I Knew Before I Retired.” While financial security is important, true retirement fulfillment comes from addressing all aspects of this major life transition and we believe this book will help you navigate not just the numbers, but the emotions, relationships, and decisions that shape your next chapter with clarity and confidence.
Download the book here: https://thetranelfinancialgroup.com/complimentary-8-things-i-wish-i-knew-before-i-retired/
All securities through Money Concepts Capital Corp. Member FINRA / SIPC. Investments are not FDIC/NCUA insured. No bank or credit union guarantee. May lose value. Money Concepts Advisory Service is a Registered Investment Advisor with the SEC. The Tranel Financial Group is an independent firm not affiliated with Money Concepts Capital Corp.
Note: This content is for informational purposes only and should not be considered financial or tax advice. Please consult with your financial or tax advisor for guidance tailored to your specific situation.