When Should You Partner with a Retirement Coach? The Answer Might Surprise You..

As a Retirement Coach, one of the most frequent questions I hear is: “When is the right time to start working with you?” My answer? It depends.

While that might sound like a dodge, it’s the honest truth. The ideal time to connect with a retirement coach isn’t a one-size-fits-all scenario. It hinges on where you are in your life journey, both in relation to retirement and in your personal aspirations for this next chapter.

Are You Approaching the Finish Line (or Just Peeking Over It)?

One key factor is your proximity to retirement. Are you still years away, diligently saving and planning? Perhaps you’re just a few months out, navigating the final paperwork and anticipating the big transition. Or maybe you’ve already celebrated your retirement and are settling into this new phase of life.

• Years Away: Engaging a retirement coach early can be incredibly beneficial for long-term planning. We can help you clarify your vision for retirement, align your financial goals with your desired lifestyle, and address potential roadblocks well in advance. This proactive approach allows for more flexibility and can alleviate stress as retirement draws closer.
• Months Away: As retirement looms, the focus often shifts to the practicalities of the transition. A retirement coach can provide invaluable support in navigating the emotional aspects of leaving your career, developing a fulfilling daily routine, and ensuring your financial plans are robust enough to support your goals.
• Already Retired: It might seem counterintuitive, but it’s never too late to work with a retirement coach. Many individuals find that the reality of retirement differs from their expectations. A coach can help you rediscover purpose, navigate social changes, explore new interests, and ensure your retirement remains a vibrant and fulfilling experience.

Beyond the Timeline: Building the Life You Want

More important than timing is your desire to bring intention to your retirement. Are you looking to create a lifestyle that reflects your values, passions, and goals? Or are you feeling stuck, unsure how to use your newfound time?

A fulfilling retirement doesn’t just happen. It often requires thoughtful consideration across various dimensions:

• Emotional Well-being: How will you find purpose and identity outside of your career? 
• Physical Health: How will you maintain an active and healthy lifestyle? 
• Social Connections: How will you nurture existing relationships and build new ones? 
• Spiritual Fulfillment: How will you connect with your values and find meaning?

If you’re seeking clarity in any of these areas, working with a retirement coach can offer structure, support, and tools to help you move forward. We might explore frameworks like the Life Wheel or the Ikigai model to map out what matters most to you and how to realign your time accordingly.

The Changing Landscape of Retirement: Gen X Takes the Stage

We’re currently witnessing a significant demographic shift. The last of the Baby Boomers are reaching traditional retirement age, and Generation X is now stepping into the spotlight. This generation, known for its independence and adaptability, may approach retirement differently than their predecessors.

Many Gen Xers may not envision a complete “hard stop” to their working lives. Instead, they might seek ways to remain active, engaged, and impactful through:

• Seasonal or Part-Time Work: Maintaining income and social connections while enjoying more flexibility.
• Contractual or Project-Based Roles: Utilizing their expertise on their own terms.
• Phased Retirement: Gradually reducing work responsibilities.

For this generation, working with a retirement coach can be particularly valuable in navigating these non-traditional pathways. Together, we can explore encore careers, identify meaningful part-time opportunities, and craft a retirement that aligns with your desire for continued engagement and purpose.

Real People. Real Stories.

Here’s what some of my clients have shared:

“Retirement loomed in my mind as a large blank slate. I couldn’t imagine what kinds of things I would be doing or who I would be without my work… Jennifer led me through a journey of discovery. Now, I am looking forward to the many opportunities coming my way.”

“Eight months in, I felt stuck. I was struggling with the uncertainty of what my future might look like. Working with a coach helped me confidently pivot and explore bridge employment.”

These stories are reminders that wherever you are in the journey, you don’t have to navigate it alone.

The Bottom Line: It’s About Being Proactive

Ultimately, the right time to start working with a retirement coach is when you’re ready to be proactive about creating a meaningful retirement. Whether you’re years away, months away, or already living it, coaching offers a guided space to think through your emotional, lifestyle, and identity transitions—not just your finances.

Don’t wait until you’re facing challenges or feeling lost. Reach out to learn how coaching can support you in designing a retirement you love.

Get your free guide or book a free 30-minute consultation here. Let’s achieve that retirement you have planned for.