Retire Today

Retire Like a Boss: 3 Steps to Your Best Life Yet with Kevin Lyles


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Discover your purpose outside of your occupation and live your best life yet in retirement.

How do you come out of your career into a retirement that fulfills all of your dreams and expectations? My guest on this week’s episode of “Retirement Revealed” is Kevin Lyles, a retired corporate attorney who took a hands-on approach to realizing his retirement dreams. After retiring at the age of 55, Kevin has found a calling in guiding others on their retirement journey. 

Let me break down our conversation and explain Kevin’s 3 essential steps to navigating retirement.

The Importance of Planning Beyond Finances

When you’re in your working years, it’s easy to get wrapped up in finances as the primary focus of retirement planning. Kevin’s experience was no different; he initially concentrated on the financial aspects, making sure he had enough saved up and all the numbers lined up for a secure future. But as he soon discovered, retirement is about more than just financial readiness—it’s about who you’ll be and what purpose you’ll serve in this new phase of life.

This is something I stress in my own practice as well. Financial security is the foundation, but it’s only part of the picture. The real excitement of retirement comes from the chance to explore new identities, roles, and interests. However, a big challenge for many, especially those who identify closely with their careers, is letting go of their professional identity. 

Crafting Your New Identity in Retirement

The key to embracing retirement is to recognize that it’s an opportunity for a fresh start. Kevin shared three essential tips for discovering who you are in retirement:

  1. Focus on your unique gifts
    Take a moment to reflect on what makes you unique, what you’ve enjoyed in life, and what qualities others admire in you. Kevin emphasized the importance of allowing certain aspects of yourself, which may have been sidelined during your career, to resurface. For instance, he’s always had a sense of humor that he couldn’t fully express in his role as a corporate lawyer. In retirement, he’s embraced this side of himself more openly.
  2. Decide on your primary purpose in retirement
    Just because you’re done working doesn’t mean you’re done contributing. Retirement allows you to choose what impact you want to make. For Kevin, this purpose became helping other retirees as a coach and member of the Rock Retirement Club, a virtual club that offers resources and community support for retirees. Whether your purpose involves volunteering, pursuing hobbies, or spending time with family, having a goal that excites you will make retirement all the more fulfilling.
  3. Find ways to use your gifts to fulfill your purpose
    Once you know who you are and what you want to do, the next step is finding ways to bring that purpose to life. Kevin highlighted the importance of continuing to use the skills you’ve built over the years—whether those are professional skills, interpersonal abilities, or even the little things that make you who you are. In Kevin’s case, he combined his experience in counseling and public speaking with his newfound mission in retirement coaching.
  4. Making the Most of Financial Freedom

    One of the great parts about retirement is the freedom you gain, both in time and resources. Yet many retirees struggle to switch from saver mode to spending mode. Kevin told me about a couple he worked with in the Rock Retirement Club who booked first-class tickets for the first time, a luxury they’d never considered before. They were thrilled to experience something new, and Kevin helped them realize that spending in retirement can be about creating joyful experiences and lasting memories.

    This is a recurring theme for my clients as well. Often, they’ve been such disciplined savers throughout their careers that they feel uneasy about spending in retirement, even when they have the means to do so. But as Kevin said, “Money is just a tool.” In retirement, it’s there to support the life you want, so give yourself permission to enjoy it!

    Handling New Dynamics with Family and Loved Ones

    Retirement also brings unique dynamics in relationships, particularly with family. Kevin shared a thoughtful insight about how he and his wife enjoy taking their adult children and grandchildren on vacations, investing in experiences rather than leaving behind a big inheritance. But he noted it’s important to ensure this doesn’t create expectations, a challenge some retirees face when family members begin to expect financial support or extravagant trips regularly.

    Open communication is crucial here. Talk to your family about your plans and set boundaries where necessary. Kevin suggested bringing family members into conversations about your financial goals and limits. Not only does this foster understanding, but it also prepares younger generations to make their own financial decisions.

    Embracing the Freedom to Reinvent

    One of Kevin’s points that resonated with me was the freedom retirees have to explore new lifestyles. You’re no longer tethered to a specific location for work, and you have the flexibility to experiment with where you live and how you spend your days. Many retirees continue living as they always have, but those who take advantage of this freedom often find greater satisfaction in retirement.

    This freedom doesn’t mean you’re making permanent choices; instead, it’s about the chance to try new things. Kevin advises retirees to approach this period with an open mind. Move to a new city if it appeals to you, or spend a few months in a place you’ve always wanted to live. Remember, the decisions you make in retirement don’t have to be set in stone; you can change and adapt as you go.

    A Fulfilling Retirement

    Retirement is a major life transition, and just like other transitions in life, it involves a period of adjustment. Kevin’s journey and insights remind us that retirement is not the end, but rather a new beginning. It’s a time to explore who you are, decide on a purpose, and make the most of the freedom you’ve earned.

    So, as you plan for retirement, don’t just focus on the numbers. Ask yourself what kind of life you want to lead, what legacy you want to leave, and how you want to feel each morning when you wake up. Embrace this chapter with intention, and remember: retirement is your time to discover the new you.

    Don’t forget to leave a rating for the “Retirement Revealed” podcast if you’ve been enjoying these episodes!

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    Additional Links:

    • Rock Retirement Club
    • Kevin Lyles – LinkedIn
    • Connect With Jeremy Keil:

      • Keil Financial Partners
      • LinkedIn: Jeremy Keil
      • Facebook: Jeremy Keil
      • LinkedIn: Keil Financial Partners
      • YouTube: Retirement Revealed
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        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.

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