Coaching2025-05-21T09:27:45-07:00

Personalized Private Coaching

Are you standing at the crossroads of “what was” and “what’s next?” Midlife brings unique transitions that deserve thoughtful navigation and support.

While our Funderful group experiences offer community and connection, one-on-one coaching provides the personalized guidance to transform your specific challenges into opportunities for growth and joy.

*Coaching is available to women who reside anywhere within the United States.

You’re Not Alone in Feeling…

  • Unfulfilled – Longing for deeper, more authentic relationships when most interactions feel increasingly superficial.
  • Uncertain – Questioning your purpose and identity as your nest empties and parenting roles shift.
  • Out of Sync – Needing to reconnect with your partner now that you have more time together.
  • Socially Adrift – Watching your social circle shrink as friendships tied to your children’s activities fade away.
  • Disconnect – Looking in the mirror and seeing physical changes that don’t match how young you feel inside.
  • Stretched Thin – Finding yourself sandwiched between caring for aging parents while still supporting adult children.
  • Invisible – Despite your experience and wisdom, feeling overlooked in social and professional settings.

But Midlife Doesn’t Have to Be a Crisis –
It Can Be Funderful!

The Funderful Coaching Experience

As a certified life coach specializing in life transitions, I don’t just listen – I engage, challenge, support, and help you create tangible results:

Putting You at the Center

After decades of prioritizing everyone else, our coaching relationship is refreshingly different – you come first, always. I’m only concerned with your success.

Asking the Unasked Questions

I engage you in powerful, thought-provoking conversations and ask questions in ways no one has likely asked before. Your answers often unlock insights that have been waiting just beneath the surface.

Holding Your Vision

When life’s distractions pull you off course, I’m there to remind you of your bigger picture. I help you prioritize your values, time, and energy in alignment with the future you want to create.

Challenging with Compassion

I’ll compassionately call you on the carpet for patterns that may be limiting your choices or keeping you stuck. I won’t let you settle for anything less than your best, while providing unwavering support.

Building on What Works

We focus on solutions. There are already things in your life that are working well, and together we’ll identify and build upon them in ways you may not have realized were possible.

Expanding Possibilities

I’ll help you stretch yourself, expand, and grow in ways that might seem unimaginable right now. What looks like a challenge today often becomes the foundation for tomorrow’s joy and purpose.

Empowering, Not Advising

In our coaching relationship, you are the expert, and while I have expertise to share with you, the goal is on empowering you to discover your own answers and take full responsibility for creating a life that truly fulfills you.

Through our coaching partnership, we’ll tackle your specific challenges with practical strategies and fresh perspectives. Our work together focuses on creating meaningful forward movement in the areas that matter most to you.

Oh, and by the way, I don’t believe in problems, only opportunities to learn and grow! And after coaching with me, you will, too!

Together, Let’s Transform Your Midlife

Here are some common areas we can work on together over the course of our coaching relationship:

Rediscover Your Purpose Post-Nest

The empty nest doesn’t have to mean empty days. Together, we’ll explore who you are beyond your parenting role and design a life filled with new meaning, fresh routines, and rediscovered passions that reflect your true self.

Reignite Your Relationship

As dynamics shift with your partner, so can your connection. I’ll help you navigate this new terrain, rediscover each other without the buffer of children, and create a relationship that’s even stronger and more fulfilling than before.

Build Your Midlife Tribe

Friendship shouldn’t get harder with age. We’ll develop strategies for creating authentic connections that go beyond small talk, help you find your people, and build the supportive community you’re longing for at this stage of life.

From Self-Doubt to Self-Celebration: Embrace Your Changing Self

The mirror may surprise you, but your worth never diminishes. I’ll guide you to reconnect with your innate value, navigate society’s mixed messages about aging, and develop a relationship with yourself based on love and wisdom, not just appearance.

Balance Without Burnout

Caught between caring for aging parents and supporting adult children? I’ll help you establish healthy boundaries, prioritize self-care without guilt, and find sustainable ways to support your loved ones without sacrificing yourself.

From Overlooked to Influential: Reclaim Your Visibility

Being overlooked in professional and social settings doesn’t have to be your new normal. Together, we’ll develop strategies to ensure your voice is heard, your contributions are valued, and your presence is acknowledged.

Create Meaning Beyond the Mundane

“Is this all there is?” is the question that launches a thousand transformations. I’ll help you explore what truly matters at this stage of your life and craft a future filled with purpose, joy, and authentic self-expression.

Ready to Discover What’s Possible for You?

Let’s Talk! Schedule a free, 30-minute discovery call.

During this no-obligation conversation, we’ll discuss your current challenges and explore if we’re good fit to work together.

Your Funderful Coach

Hi, I’m Cheryl Dillon, founder of Funderful Experiences and your private coach.

With a bachelor’s degree in psychology, professional certification as a life coach, and 15 years of experience coaching individuals through life transitions, I’ve supported hundreds of people in navigating crossroads, aligning with their truest values, and designing lives that energize rather than deplete them.

My coaching approach combines professional expertise with personal insights. As a woman navigating midlife myself, I understand firsthand the challenges and opportunities this stage brings.

In our coaching relationship, I create a supportive environment where you can explore new possibilities, overcome obstacles, and take meaningful action toward your goals. My clients describe my style as refreshingly direct, genuinely encouraging, and infused with just the right amount of humor. They get honest feedback, practical strategies, and a partner who helps normalize their experiences while guiding them toward meaningful growth. If this approach resonates with you, let’s connect and explore how we might work together!

FAQs

How is coaching different from therapy?2025-05-16T07:50:09-07:00

Coaching focuses on moving forward from where you are now rather than processing past trauma. We work on current challenges and future possibilities, using action-oriented strategies to create positive change.

Are conversations confidential?2025-05-16T07:50:44-07:00

Coaching is completely private, safe and confidential. I follow the ethical guidelines and professional standards set forth by the International Coach Federation (ICF).

How quickly will I see results?2025-05-16T07:51:07-07:00

Many clients report feeling more clarity and hope after just one session. Significant life changes typically emerge over the course of 8-10 sessions as new perspectives and habits take root.

Do sessions take place in person or virtually?2025-05-16T07:51:28-07:00

All coaching sessions are conducted via Zoom video calls, allowing you to participate from the comfort of your home or any private space that works for you.

How is coaching different from therapy?2025-05-16T07:52:00-07:00

Coaching focuses on moving forward from where you are now rather than processing past trauma. We work on current challenges and future possibilities, using action-oriented strategies to create positive change.

Can I combine coaching with Funderful Events?2025-05-16T07:53:25-07:00

Absolutely! Many clients find that individual coaching complements our group experiences beautifully. Your coaching insights can deepen your event participation, and connections made at events often support your coaching journey.

Can I coach with you if I don’t live in North County, San Diego?2025-05-16T07:53:49-07:00

Yes! Coaching is available to GenX women who live anywhere in the United States.

Ready to Make Midlife Funderful?

Life doesn’t come with a roadmap for navigating midlife transitions – let’s chart your path together!

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