Five strategies to plan for a fulfilling retirement

Five Strategies to Plan for a Fulfilling Retirement

May 13, 20263 min read

I recently sat down with Alex Holley and Mike Jerrick, hosts of “Good Day Philadelphia,” to discuss how to thrive in retirement.

Research shows that retirees who planned early are more fulfilled in retirement.

Any life change, positive or negative, can kick off a grieving process: losing a job, moving, getting married, and death of a loved one. Simply put, we feel grief when things change because change is a perceived loss as we're leaving something behind.

The thought of retirement often brings conflicting feelings, from excitement about managing our own time to despair over losing identity and purpose.

Since we all must eventually stop working, planning early is essential. While we're taught to save and invest for retirement, what we'll actually do with ourselves is often an afterthought. This lack of purpose can drive people to delay retirement or struggle when they stop working.

Watch the video:


How do I find my purpose in retirement?

If you're worried about retirement, first define retirement by asking yourself:

  • What purpose will retirement serve me?

  • What will be fulfilling in retirement?

  • How do I envision myself as a retiree?

Then, if any anxious feelings come up, identify what exactly is causing the anxiety around retirement.

If it’s anxiety over finances, think about the practical steps you can take to feel financially secure. Find a certified financial planner and share your retirement goals. They will run financial projections to estimate how much you’ll need for retirement and develop an investment plan. Ask friends and family to recommend a financial advisor that they trust.


Five action steps to plan for a more fulfilling retirement

Once you know your purpose and values, think through a plan to make your next life phase more fulfilling than your career.

  1. Create a life adventure list: List things you want to do -- no matter how big or small -- that you can’t do while working. Maybe it’s to practice a hobby more often, learn a new skill or language, live abroad temporarily, travel for a year, or be a snowbird (that's my goal - I can't stand winter!)

  2. Find like-minded people: The antidote to grief is community and connection. Talk to other retirees to know how they created a fulfilling retirement. Find local groups and clubs dedicated to topics and causes you care about while you're still working so that you are cultivating relationships that aren’t tied to your workplace.

  3. Test drive retirement: Instead of going on vacation, take a staycation but with a plan to do things locally and at home that you envision yourself doing in retirement. Once the staycation is over, check in with yourself and see how you feel.

  4. Share your wisdom: Your experience and knowledge are valuable. Join a board, volunteer, or mentor others. Use your wisdom and experience to help others grow personally or professionally.

  5. Part-time work: If you want to still work, but less hours, look into consulting, freelance and fractional C-suite roles before retiring. Due to budget restrictions, many small businesses and start-ups hire "fractional" executives to work a few hours each week or month providing strategic advice. In this way, you'll be helping a small business grow.

One final note: remember, everything is temporary! You are allowed to change your mind at any time. You can go back to work, you can find new hobbies and new social circles. Think of retirement as your life's playground. For example, my father retired and after 6 months he missed working. He then found a flexible role at a smaller company that needed and valued his experience in order to grow. After 4 years, he felt fulfilled having helped this company and finally retired as he wanted to spend more time on his hobbies and travel.

If you're reading this and could use some help in reimagining what life could look like in retirement, contact me for a free strategy session. Let's see what's possible!


I work with mid-career professionals who want to reimagine their lives and careers but feel stuck, pressed for time, or unsure where to start.
Having navigated my own career shifts—from nonprofit work, to corporate, to becoming an entrepreneur—I know firsthand how confusing and overwhelming change can feel. That’s why I bring empathy, clarity, and accountability to every step of the process.
My Reimagine → Believe → Build framework makes change simple, helping you align your career and life with what truly matters to you.

Lia Daniels

I work with mid-career professionals who want to reimagine their lives and careers but feel stuck, pressed for time, or unsure where to start. Having navigated my own career shifts—from nonprofit work, to corporate, to becoming an entrepreneur—I know firsthand how confusing and overwhelming change can feel. That’s why I bring empathy, clarity, and accountability to every step of the process. My Reimagine → Believe → Build framework makes change simple, helping you align your career and life with what truly matters to you.

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