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The Art of Letting Go: How Founders Must Come to Terms with the Reality of Separation

Letting go is one of the hardest lessons a founder has to learn. We put our heart and soul into our business. We live for our business.

Chase Damiano
4 min read
The Art of Letting Go: How Founders Must Come to Terms with the Reality of Separation

Letting go is one of the hardest lessons a founder has to learn. We put our heart and soul into our business. We live for our business. Early mornings and late nights, missed calls and cancelled plans. When we go home to our loved ones, we often struggle to turn off the business switch because it takes up such a large portion of our headspace. Our relationships strain, and our business forces us to prioritize things in ways that would have previously seemed extreme to us—forces us to make sacrifices we would never have imagined ourselves making.

We do all of this individual work to improve our business, yet what our business needs the most is to separate from us.

Like parent, like founder

In many ways, being a founder is like being a parent. And as with parenting, there’s a time when we must let go of our deep attachment to our child.

To some parents (and, ahem, founders), this might seem counterintuitive. Before our child’s birth, we belabored about their potential. We toiled in the throes of pain—pushing, pushing, pushing. We gave birth to this helpless, fresh, beautiful creation with a boundless future. From that point on, we’ve nurtured, provided, and taught. We’ve bonded by showing them the way. We’ve made mistakes. At our worst, we’ve been toxic and too commanding. We’ve exploded and acted resentfully, caustically, controllingly, and selfishly. In moments of turmoil, everything has gone wrong.

Nothing gets more time and attention than our child. We sacrifice everything for them, and through our emotional ebbs and flows, we bask in our relationship with them.

And slowly, they outgrow the need for our exclusive guidance. They form a new identity. What once was an extension of us has become their own individual.

As you might have guessed, the child in this analogy is the founder’s business. And just like the child, their business takes on its own identity, too. It develops into something beyond the founder themself.

But those growing pains are truly that: painful. Parents and founders alike often wonder, Why?

Why does our creation want to move on? Why can’t we hold on?

Why can’t their destiny align with ours?

Grappling with growth and separation

Founders have a hard time wrestling with and accepting this shift in dynamics. Although we often link feelings of insecurity and abandonment to a child’s experience, parents equally process these feelings, especially when their kids seek independence.

Letting go is hard, plain and simple—especially with a founder’s first business. When we have a vision, we hyperfocus on executing it, and even though we know this won’t last forever, it can feel impossible to understand the inevitable momentum of growth. We go full throttle, and it’s hard to switch out of Go, go, go! mode.

But we’re in the business of creating and letting go. Workloads, trajectories, products, teams, individuals—they all change.

From the perspective of the newborn business, what starts as a few caretakers eventually turns into a village; crawls turn into sprints; and ideas turn into fully formed thoughts and realities. Now, the business has a purpose, a vision, and a path to get there. It doesn’t necessarily need or want to lean solely on its creator. You may find yourself no longer at the center of it all. New management teams, new products, new markets, new expansions—these are how our business will flourish.

It needs to experience change. It needs to build new support systems. We shouldn’t expect to, and frankly can’t, do it alone.

But when do we make the switch? When do we decide to accept our child’s transformation?

Time to separate

Timing isn’t something that’s spelled out for us. We can read all of the books and articles on the planet, listen to all of the podcasts and watch all of the tutorials, but timing is something that we just have to feel out. When our senses tell us to let go, we face the music…and just let go.

However, the processes of birth and growth are different for different founders and different businesses. Sometimes we merely give birth and give way to someone else. Sometimes we’re better caretakers in the beginning when they are young but we really struggle when they get older. Sometimes we need the most help with the birthing but really shine as they become teenagers.

We’re all different. The art is in knowing that we are not our companies. We are separated, by default, as a mother separates from a child upon its birth.

Our job is to bring it to life—not to be its life.

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