How to Know Whether to Stay or Go – Cindy Stibbard’s Guide to Healing After Heartbreak

How to Know Whether to Stay or Go – Cindy Stibbard’s Guide to Healing After Heartbreak

In a powerful and deeply honest episode of Evalina Beauty’s Life is Beauty Full podcast, host Samantha Legge, Founder and CEO of Evalina Beauty, sat down with Cindy Stibbard — certified divorce and relationship coach, educator, and transformation expert — for an insightful conversation about love, relationships, heartbreak, and how to navigate one of life’s hardest questions: Should I stay, or is it time to go?

Whether you’re questioning your marriage, trying to find your way back to yourself after heartbreak, or simply seeking to build a stronger connection with your partner, Cindy’s wisdom offers clarity, compassion, and courage for anyone navigating the messy complexities of love.

From Heartbreak to Healing: Cindy’s Journey

Cindy’s work is deeply personal — born from the ashes of her own 22-year relationship. After more than a decade as a stay-at-home mom, she found herself disconnected, voiceless, and financially dependent, struggling to reconcile the life she had built with the person she had become. Over time, unresolved issues, infidelity, and growing resentment eroded the foundation of her marriage.

“I brushed things under the rug, ignored indiscretions, and lost myself in the process,” Cindy shared. “And when you start abandoning yourself like that, resentment builds — and love starts to fade.”

Feeling unseen and unheard, she eventually stepped outside the marriage — a choice she doesn’t excuse but understands as a symptom of deeper disconnection. That painful experience ignited her mission: to help others navigate relationships with clarity and courage and move from heartbreak to healing.

One of Cindy’s most transformative tools is what she calls the Relationship Audit — a guided assessment that helps individuals and couples gain a clearer picture of the health of their relationship. Think of it as a personality test for your partnership.

The audit examines 11 core metrics — including communication, shared values, parenting, intimacy, conflict resolution, and emotional safety — and provides a data-driven snapshot of where things stand. Most clients, Cindy says, already sense the answers. But seeing the results laid out can be both validating and empowering.

“They’ll say, ‘I knew this, but I needed to see it,’” Cindy explains. “Once you know where the holes are, you can make informed choices — whether that’s focusing on repairing the relationship or preparing to leave.”

The audit is often the first step for those stuck in indecision — especially people who’ve spent months or even years in therapy without gaining clarity. And it’s not just about deciding whether to leave; it can also guide couples toward rebuilding stronger, healthier relationships.

A central question Cindy asks clients is simple but profound: Are you staying out of fear or out of love?

If fear is the only thing keeping you in your relationship — fear of the unknown, fear of being alone, fear of finances — Cindy guides clients to envision what life could look like beyond the marriage. This includes exploring housing options, financial realities, co-parenting arrangements, and more. Often, breaking the unknown into tangible steps helps people feel more grounded and confident.

“Fear isn’t real,” Cindy reminds us. “It’s just false evidence appearing real. The more you plan and prepare, the more manageable the unknown becomes.”

And sometimes, planning reveals that more groundwork needs to be done — such as returning to work, understanding family finances, or waiting until children are older — before making a final decision.

If the decision is to part ways, Cindy urges clients not to rush straight to a lawyer. The first call, she says, should be to a Certified Divorce Financial Analyst (CDFA) — a specialist who can help you understand your financial picture, from assets and debts to long-term support needs.

“Most people go straight to a lawyer, and that’s when the fear sets in,” Cindy notes. “A CDFA helps you see the numbers clearly — what you’ll need, what’s realistic, and how to negotiate wisely.”

This clarity can prevent costly legal battles and empower you to make informed decisions, whether you’re splitting assets, planning for child support, or envisioning your financial future post-divorce.

If someone decides to leave the marriage, Cindy emphasizes that leaving a marriage is never the end of the story — it’s the beginning of a new one. Cindy counsels that healing isn’t about “getting over” a relationship but about rebuilding a life around the loss.

“You’re going to grieve, even if you’re the one who chose to leave,” she says. “But grief doesn’t define your future happiness. It’s part of your story — and part of your courage.”

To support people through this stage, Cindy created a program called Rise, designed to help clients rediscover who they are, rebuild their lives, and embrace new possibilities. From redefining identity to creating new routines and goals, this phase is about transformation — and self-compassion.

One of the most damaging myths about divorce, Cindy argues, is that it represents failure. Society often equates success with longevity — but that’s a flawed metric.

“Your marriage was not a failure if it lasted five, ten, or twenty-five years,” Cindy says. “It was a success for that chapter of your life. You built a family, raised children, shared experiences. That’s success — even if the marriage ends.”

She challenges clients to reframe their perspective: Would you want your marriage for your child? If the answer is no, it’s worth questioning why you’re choosing it for yourself. Children, after all, model the relationships they see.

Cindy also shared valuable insights for those before marriage — or those considering whether theirs has run its course:

  • Have the hard conversations early. Discuss money, family values, parenting, and future goals before you commit. Misalignment in these areas often leads to conflict later.
  • Consider legal agreements. A prenuptial, cohabitation, or postnuptial agreement may feel unromantic, but it’s a practical step that protects both partners if things change.
  • Revisit your shared vision. Over time, values and priorities evolve. Regularly reassess whether you’re still aligned in your goals for the future.
  • Ask yourself: What’s our purpose now? Once the kids are grown or life circumstances shift, evaluate what keeps you connected and excited about your shared future.

Ultimately, Cindy reminds us that leaving a marriage isn’t the “easy way out.” In fact, it’s often the harder path — one that demands courage, resilience, and radical honesty with yourself and your partner.

 

“It’s not about what you’re no longer getting,” she says. “It’s about what you can no longer give. If your heart isn’t in it, it’s kinder to set both of you free.”

That courage also extends to making space for your own healing, even in the face of societal judgment, religious beliefs, or external expectations. As Samantha reflected during the episode, “It takes bravery to choose a new path, especially when it’s challenged by the people closest to you.”

Life is messy — but it’s also beautiful. As Cindy’s story shows, even in the most painful transitions, there’s an opportunity to rediscover who you are, reclaim your voice, and create a future that feels aligned, joyful, and deeply your own.

If you or someone you know is looking for help making a relationship decision, you can connect with Cindy at cindystibbard.com or follow her on Instagram @cindystibbard.

Cindy Stibbard is a certified divorce and relationship coach, educator, and personal transformation expert. After navigating the end of her own 22-year marriage, Cindy dedicated her career to helping others move from heartbreak to healing. Through her coaching programs, including the transformative Relationship Audit and Rise post-divorce program, she empowers people to gain clarity, rebuild confidence, and chart a path forward with compassion and strategy.

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