My Longing to Lead Again: Navigating Career Transitions for Entrepreneurs
Slowly emerging from semi-retirement (after 5 years)
Me leading a cacao ceremony, connecting people to their hearts.
Over winter break, as I sat with my emotions about selling my startup, I realized my sadness stemmed not from shame, but from longing. I’ve written ad nauseam about the shame that’s bubbled up since I sold my startup 5 years ago. I felt like a failure. I hadn’t made the returns I wanted, and to top it off, the product no longer lives on. But as I sat with my fiancé over the break, talking about my fears about deepening with Downshift, a new frame emerged. I miss my company. I miss leadership, I miss the fantastic culture, I miss the energy of operating and building with a wonderful team.
As the tears flowed, it hit me: I’m ready to build again. Longing was my portal to action.
This experience is not unique to me. Many ambitious professionals face similar struggles when navigating career transitions for entrepreneurs. Longing, I've come to realize, is a universal human experience that holds the key to unlocking our most authentic selves.
Touching Disappointment
I’ve always wondered why disappointment is such a scary emotion for people to feel. In the whole scheme of things, I thought fear and anger would top the list.
Last fall, I attended a founder retreat where I had the opportunity to meet my disappointment head-on. It was during a share circle run by my Downshift teammate, Steve Schlafman. No fixing, just listening. The question was simple:
What does your heart deeply long for?
In front of a crowd of people I had just met, I tapped deeply into my longing to be a mother. It’s a desire that I share mostly with girlfriends, and it’s more of a fact than a feeling. But with this space, I felt the heartfelt desire, reverberating truth, and gut-wrenching disappointment of not yet being a mother.
Frankly, I was embarrassed to share a personal desire with a room of founders who I was sure only longed for success and ambition. Yet most of the people in the room shared heartfelt desires for the basics: love, connection, family. I felt my shame around my longing melt away, and I was left with the truth of my desire.
The founder retreat opened my eyes to the power of facing disappointment head-on. By creating space to acknowledge and share our longings, we tap into a deep well of desire, truth, and grief that can guide us toward more fulfilling lives and careers. For those navigating career transitions for entrepreneurs, this process can feel especially poignant.
The Three Components of Longing
When we touch longing, we touch three things at once: desire, truth, and grief. Each of these holds power when we name and claim them.
Longing springs from our innate desires and wants. Don’t fear your desires. Rewrite the story of your selfishness, and turn it instead towards creativity. I used to criticize my desire to be married and to build a family as traditional or even average. That’s how immersed I was in hustle culture. I’ve had to learn to accept and celebrate this desire, not as opposite to my ambition but as a pillar next to it. What is more human than the drive toward desire? It keeps us alive.
Longing reveals the truth of what matters most to us. I’ve spent the last 5 years trying to kill my work ambition. When I realized I missed my startup, and I felt that pain, it unlocked the truth: work and service will always be an important value in my life. I don’t have to fight or resist it anymore. This is a truth that’s deep within me that took me years to wrestle with, but a few key moments of emotion to see plainly.
The grief of longing is wanting something but not having it. Disappointment is the tip of the iceberg, grief lies heavy under the surface. My shame about Chewse “failing” was in fact a way to avoid my grief. Feeling grief without shame is pure. It’s like jumping into ice-cold water that’s clear; not a comfortable experience, but cleansing. The moments when I have felt the grief of losing my company have been my greatest moments of healing.
For anyone navigating career transitions for entrepreneurs, longing can serve as an internal guidance system. It connects you to a sense of purpose and direction, pushing you to pursue what matters most, not just what’s comfortable.
Connecting With Your Longing
The foundational step toward connecting with your longing is to stop vilifying your desires. We all have some kind of programming from our family or society that tells us desire is selfish, hedonistic, and unproductive. It took me a while to own my longing to be a mother because I’m used to the entrepreneurial drive of business at all costs. Wanting a family felt like a weak aspiration because I’m supposed to dream bigger. This is where doing the inner work with parts work (IFS), psychedelics, individual coaching, or group programs like Downshift are invaluable.
The other part of the work is getting comfortable with feeling emotions. The data locked up with longing is accessed by feeling. This is the gift and curse of being alive. For us heady overachievers, feeling emotions is like learning a new language. But this is the terrain that holds treasure in our development journey. I find Somatic Experiencing, journaling, and breathing exercises to be helpful modalities for getting comfortable with emotions.
With those in place, it takes motivation to submerge into these waters. Longing is a pathway to healing, purpose, and authenticity. It requires courage but when you come up for air from the dive, you’ll hold riches in your hands. There’s an alchemy to the process, one that shifts longing from shameful to powerful, from selfish to creative.
For me, I’m enjoying dancing with my longing to build a company again, and I acknowledge the hunger in me to lead. At the same time, being in touch with my desire for motherhood has brought a new depth and meaning to my relationship with my fiancé as we plan our future together.
Longing is more than just a feeling; it is a call to action. It pushes us to confront our fears, take risks, and pursue what matters most to us, even when it’s uncomfortable or challenging.
So, my invitation to you is this: don’t shy away from your longing. Lean into it, listen to it, and let it guide you toward the life and career you truly desire. Share your experiences with others and create authentic spaces to listen to their longing, too. For those navigating career transitions for entrepreneurs, this can be a powerful catalyst for positive change and growth.
Don’t hesitate to reach out to me if you have questions or need support on this path. I coach ambitious professionals and founders looking to reshape their relationships with work. You can DM me or book a consult.
❤️ Tracy