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Listen "Avoiding 3 High-Achieving Career Retirement Mistakes"
Episode Synopsis
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:
Redefine success. Ask yourself what fulfillment looks like outside of your career.
Build new structure. Without work as your scaffolding, create a schedule and identity around what matters most to you.
Invest your time and money in purpose. Consider what energizes you and use your resources accordingly.
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.
Don’t forget to leave a rating for the “Retirement Revealed” podcast if you’ve been enjoying these episodes!
Subscribe to Retirement Revealed to get new episodes every Wednesday.
Apple Podcasts: https://podcasts.apple.com/us/podcast/retirement-revealed/id1488769337
Spotify Podcasts: https://bit.ly/RetirementRevealedSpotify
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:
Keil Financial Partners
LinkedIn: Jeremy Keil
Facebook: Jeremy Keil
LinkedIn: Keil Financial Partners
YouTube: Retirement Revealed
Book an Intro Call with Jeremy’s Team
===
Disclosures
Videos/Podcasts/Blogs (media) published prior to June 30, 2025, were recorded and approved while the advisor was affiliated with Thrivent Advisor Network. These media reflect the advisor’s views and interpretations at that time. The information and disclosures contained in those media were believed to be accurate and complete as of the date of recording, but may not reflect current market conditions or Alongside, LLC, policies.
All content is provided for educational purposes only and does not constitute personalized investment advice. Read below for current disclosures and potential conflicts of interest.
This media is provided for informational and educational purposes only and does not consider the investment objectives, financial situation, or particular needs of any consumer. Nothing in this program should be construed as investment, legal, or tax advice, nor as a recommendation to buy, sell, or hold any security or to adopt any investment strategy.
The views and opinions expressed are those of the host and any guest, current as of the date of recording, and may change without notice as market, political or economic conditions evolve. All investments involve risk, including the possible loss of principal. Past Performance is no guarantee of future results.
Legal & Tax Disclosure
Consumers should consult their own qualified attorney, CPA, or other professional advisor regarding their specific legal and tax situations.
Advisor Disclosures
Alongside, LLC, doing business as Keil Financial Partners, is an SEC-registered investment adviser. Registration does not imply a certain level of skill or expertise. Advisory services are delivered through the Alongside, LLC platform. Keil Financial Partners is independent, not owned or operated by Alongside, LLC.
Additional information about Alongside, LLC – including its services, fees and any material conflicts of interest – can be found at https://adviserinfo.sec.gov/firm/summary/333587 or by requesting Form ADV Part 2A.
The content of this media should not be reproduced or redistributed without the firm’s written consent. Any trademarks or service marks mentioned belong to their respective owners and are used for identification purposes only.
For important disclosures visit: https://keilfp.com/disclosures/
===
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:
Redefine success. Ask yourself what fulfillment looks like outside of your career.
Build new structure. Without work as your scaffolding, create a schedule and identity around what matters most to you.
Invest your time and money in purpose. Consider what energizes you and use your resources accordingly.
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.
Don’t forget to leave a rating for the “Retirement Revealed” podcast if you’ve been enjoying these episodes!
Subscribe to Retirement Revealed to get new episodes every Wednesday.
Apple Podcasts: https://podcasts.apple.com/us/podcast/retirement-revealed/id1488769337
Spotify Podcasts: https://bit.ly/RetirementRevealedSpotify
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:
Keil Financial Partners
LinkedIn: Jeremy Keil
Facebook: Jeremy Keil
LinkedIn: Keil Financial Partners
YouTube: Retirement Revealed
Book an Intro Call with Jeremy’s Team
===
Disclosures
Videos/Podcasts/Blogs (media) published prior to June 30, 2025, were recorded and approved while the advisor was affiliated with Thrivent Advisor Network. These media reflect the advisor’s views and interpretations at that time. The information and disclosures contained in those media were believed to be accurate and complete as of the date of recording, but may not reflect current market conditions or Alongside, LLC, policies.
All content is provided for educational purposes only and does not constitute personalized investment advice. Read below for current disclosures and potential conflicts of interest.
This media is provided for informational and educational purposes only and does not consider the investment objectives, financial situation, or particular needs of any consumer. Nothing in this program should be construed as investment, legal, or tax advice, nor as a recommendation to buy, sell, or hold any security or to adopt any investment strategy.
The views and opinions expressed are those of the host and any guest, current as of the date of recording, and may change without notice as market, political or economic conditions evolve. All investments involve risk, including the possible loss of principal. Past Performance is no guarantee of future results.
Legal & Tax Disclosure
Consumers should consult their own qualified attorney, CPA, or other professional advisor regarding their specific legal and tax situations.
Advisor Disclosures
Alongside, LLC, doing business as Keil Financial Partners, is an SEC-registered investment adviser. Registration does not imply a certain level of skill or expertise. Advisory services are delivered through the Alongside, LLC platform. Keil Financial Partners is independent, not owned or operated by Alongside, LLC.
Additional information about Alongside, LLC – including its services, fees and any material conflicts of interest – can be found at https://adviserinfo.sec.gov/firm/summary/333587 or by requesting Form ADV Part 2A.
The content of this media should not be reproduced or redistributed without the firm’s written consent. Any trademarks or service marks mentioned belong to their respective owners and are used for identification purposes only.
For important disclosures visit: https://keilfp.com/disclosures/
===
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