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Challenge: Follow Your Dreams

What Losing A Child Taught Me About Following My Dreams

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My husband and I recently made our second trip to Faith’s Lodge, a gorgeous retreat in rural Wisconsin for families who’ve lost a child. It was a second annual pilgrimage there to process the stillbirth of our daughter Maeve, and this time, it was very different. We are farther down the road in our grief journey, we had our “rainbow baby,” Fiora, with us, and it was the first since I started my fourth company, Life With Passion.

During this trip, I noticed something startling. Our group facilitator, John, asked the same powerful questions I now ask of my clients, questions that get under the surface and help us get conscious of what’s going on underneath. My favorite from the weekend: “What are you pretending not to know about yourself, and how does that serve you?”

Whoa. As my husband says, “Heavy.”

I LOVE powerful questions. Questions like this one help us process the changes involved in parenthood, whether grief, joy or both, and check in with ourselves on the journey of learning to live in our new worlds.

I absolutely love being an entrepreneur and Life With Passion, inspired by the loss of Maeve, is the pinnacle of the journey of following my dreams to make a big impact and create meaning out of not only my grief, but my gifts.

We’re all grieving something in our life, even if it’s not a loss as obvious as that of a child. My mom recently reminded me that grief is how we process anything we wish was different but are unable to change, whether the loss of a relationship, a person, an idea, anything important to us.

Many of my clients come to me grieving their inability to live their dreams, even though they perceive it as being frustrated and stuck. Asking them similarly powerful questions helps them process what’s holding them back from starting that dream business, or growing it where they want it to be.

The same is possible for you, too.

Answering these questions are akin to cleaning up your computer and emptying its trash when you’re about out of storage space. Giving voice to these truths frees up space in your mind, space that you can then strategically fill with what you choose. You recover space for strategies, space for structures, space for self-belief and confidence. All of this, combined with action, not only feels amazing, but is a recipe for success in business and in life.

I’ll ask it again, “What are you pretending not to know about yourself, and how does that serve you?” I answered that I’m pretending not to know just how much I manage the more emotional part of me, because sometimes “going there” feels really scary. It’s common for grief to feel out of control and I love structure & order, so it’s especially uncomfortable for me. It serves me by giving me an illusion of being in control or safe. Now that I recognize this, I can evaluate whether it’s truly useful and contributes to my overall goal of being healthy and happy, or if it detracts, and it’s time to look at making a different choice.

I have discovered SO many parallels between the grief journey and the entrepreneurial journey. There’s a lot of fear and uncertainty in both, and in both, getting conscious of it is what allows us to address it and to move forward toward what we want rather than staying stuck day after day, year after year, because we’re scared of the uncertainty.

No matter if we’re grieving, starting a business, or both, we all need someone to walk alongside us, ask us the powerful questions, and support us in discovering the answers. That’s why I do what I do.

Ask yourself the question, and see what you learn about yourself, your grief, and your business, then share with us below.

Christine McAlister is a Business + Success Coach at Life With Passion, where she helps high-achieving, motivated women rediscover their unique gifts and create freedom-based businesses. She and her husband founded the non-profit Miles With Maeve in honor of their daughter.

A version of this article originally appeared at

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