Avoiding 3 High-Achieving Career Retirement Mistakes

Exploring how to transition from an achievement-based career to a fulfilling retirement lifestyle with author Elizabeth Zelinka Parsons.

I’ve worked with people from all walks of life, and I can confidently say that every retirement has its own unique challenges. My guest on this week’s episode of Retirement Revealed, Elizabeth Zelinka Parsons, wrote an interesting book aimed at people who are transitioning out of high-leverage careers into retirement. 

These are the doctors, lawyers, executives, and business owners who have built careers on success, productivity, and pushing themselves to be the best. So what happens when the structure of a career disappears? What replaces the status, the goals, and the intellectual stimulation? 

In this episode, Elizabeth and I dive into 3 common mistakes these people make and explore some strategies to address them in retirement.

Elizabeth brings a unique perspective to the retirement discussion. After a high-powered legal career on Wall Street, she made the tough decision to step away to focus on family. She called it “borrowing from retirement,” but quickly realized she was wholly unprepared for the identity shift that came with leaving the career she had wrapped so much of her self-worth around.

This is where many high achievers find themselves in retirement. They’ve done a great job saving and investing. But when work ends, it’s not just about how much money they have — it’s about what they’re retiring to. And as Elizabeth shared, that might not be something you can put a price tag on.

Mistake #1: Believing Money Alone Will Make Retirement Fulfilling

Many successful professionals assume that if they’ve saved enough, retirement will take care of itself. But Elizabeth learned firsthand that without a clear plan for how to spend your time and define your new identity, retirement can feel like a vacuum.

“It wasn’t just losing a job,” Elizabeth said. “I lost my identity, my community, my intellectual engagement — everything I had invested myself in.”

This is especially tough for high achievers who have always thrived on goals and external validation. So, how do you replace that? Elizabeth posits one strategy: learn to become the creator of your next phase — not the reactor to what others need from you. And that takes intentionality.

Mistake #2: Assuming Retirement Will Be One Long Vacation

We all dream of endless leisure, but as Elizabeth puts it, “365 Saturdays in a row” gets old fast. High achievers need challenge, engagement, and a sense of contribution. Elizabeth explains that leisure only feels fulfilling when it’s paired with purpose.

That’s why we encourage retirees to think of retirement not as an endpoint but as another graduation. It’s a transition into a new chapter, and like any big life change, it requires new structure. Elizabeth calls it creating a “mosaic” — intentionally designing your life with the people, hobbies, and causes that light you up.

Mistake #3: Struggling to Transition from Saver to Spender

One of the most common psychological hurdles I see, especially in the clients we work with at Keil Financial Partners, is the fear of spending in retirement. High achievers are often exceptional savers — that discipline helped them succeed professionally and financially. But now that it’s time to enjoy what they’ve saved for, they often feel guilty.

Elizabeth reframes it beautifully: “You’re not spending, you’re investing in your life.” Whether it’s travel, supporting your children, or giving to causes you care about, money gains meaning for many people when it’s deployed intentionally. 

I also encourage people to stop labeling themselves “savers” or fearing the word “spender.” You’re a planner — and good planning means using your resources wisely over your lifetime. That next tactic may simply involve drawing from what you’ve built to live the life you envisioned.

Thriving in Retirement

If you’re a high achiever approaching retirement, consider these steps:

1. Redefine success. Ask yourself what fulfillment looks like outside of your career.
   
2. Build new structure. Without work as your scaffolding, create a schedule and identity around what matters most to you.
   
3. Invest your time and money in purpose. Consider what energizes you and use your resources accordingly.
   
4. Talk to others. Reach out to peers who’ve retired and seem to be thriving. You’ll be surprised how much you can learn from a few honest conversations.
   

As Elizabeth emphasized, retirement doesn’t mean disappearing from relevance — it can be about creating a new form of it. 

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Additional Links:

• Elizabeth Zelinka Parsons on LinkedIn https://www.linkedin.com/in/elizabeth-zelinka-parsons-3b58a52/ 
• Elizabeth Zelinka Parsons Website: https://www.highachieverretirement.com/
• “Encore: A High Achiever’s Guide to Thriving in Retirement” – Elizabeth Zelinka Parsons https://www.amazon.com/dp/B0DCG8MVF1 
• How Middle-Income Retirees Are Winning at Retirement with Jean Chatzky – Retirement Revealed, guest Jean Chatzky
• Dr. Jordan Grumet Discovered “The Purpose Code” – Retirement Revealed, guest Dr. Jordan Grumet

Connect With Jeremy Keil:

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• YouTube: Retirement Revealed
• Book an Intro Call with Jeremy’s Team

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