How to Care Deeply Without Attachment

A founder asked me recently: "Should I wait until fear and lack have gotten me to my number, to my exit, and then do the deep work?"

He was considering my next retreat in Sun Valley. He'd been in a group with post-exit founders doing inner work, and he wanted to know if he should wait.

Because fear worked. It brought him this far, so why mess with it now?

This is the ultimatum many founders find themselves stuck in. Founders know they're running on dirty fuel (fear, lack, proving something) and they see it's exhausting them.

So they want to let go of the attachment, but they are scared of not being scared and having nothing to motivate them.

They are afraid they’ll stop caring as much about everything.

That the vision that used to excite them feels distant. The mission will feel like just words on a wall.

That they’ll slide from attachment into apathy. And that apathy will kill their company.

So the question becomes, how do you care deeply without being attached and falling into apathy?

Apathy Isn't Non-Attachment

Here's the distinction most founders miss…

Apathy = not caring.

Non-attachment = not believing your well-being depends on the outcome.

You learned to care through attachment. When you got the A, you got praise. When you shipped the feature, investors leaned in. When revenue spiked, you felt worthy.

So you built your entire identity around outcomes. And yeah, dirty fuel works. It's fuel. It got you here.

But it's toxic. It leaves residue that builds up over time. I've had clients in the ER for heart issues and panic attacks. This isn't uncommon in our ecosystem.

So what does non-attachment actually look like if it's not apathy?

The Two Ways to Be Non-Attached

There are only two ways to be non-attached to an outcome:

Option 1: Don't care at all.

No heartbreak when it doesn't work out. But also no aliveness. No joy in building something that matters. You protect yourself from pain by staying numb.

Option 2: Care deeply AND be willing to have your heart broken.

If you care deeply about building category-defining technology, and you give it everything, and it still fails? That's heartbreak.

If you pour your soul into your team, and your CTO leaves for Google? Heartbreak.

If you bet your reputation on a vision, and the market says no? Heartbreak.

Most people, when they think of non-attachment, choose option one to protect themselves from heartbreak.

But that protection costs you everything. The aliveness you want, the meaning, the joy of building something that authentically matters to you, lives on the other side of your willingness to be heartbroken.

Why This Actually Matters

Here's what most founders don't realize about non-attachment. It's not just healthier for you. It fundamentally changes how much energy you have available to create.

When you're attached to outcomes, you waste enormous amounts of energy:

You focus on the gap between where you are and where you wish you already were. You spend energy being frustrated that you haven't already doubled revenue instead of channeling that energy toward actually doubling it.

You imagine outcomes you don't want. Your mind drifts into visualizing failure scenarios, scaring yourself, then spending energy trying to manage that manufactured fear.

You resist reality as it is. Fighting against what's actually happening instead of accepting it and moving forward from there.

All of that is burned energy. Energy that could be building your company.

When you're non-attached, that energy gets redirected. You're present to reality without resistance. You're focused on the future you want to create, not frustrated by the gap. You're not manufacturing fear about outcomes you don't want.

All that energy that was being wasted? It's now available for actual creation.

And this shows up in practical ways:

Think about your last desperate fundraise. When you needed it to work. How did that meeting go?

The investor felt your desperation. You felt it. The clinging to the outcome was palpable. Nobody signed.

You were wasting energy managing anxiety about the outcome instead of channeling it into being fully present for the conversation.

Now think about the meeting where you were genuinely unattached. Clear on your vision. Totally fine walking away if it wasn't the right fit.

All your energy was available for the actual interaction. You were fully present. You could listen deeply, respond authentically, and let the right outcome emerge.

Same with every high-stakes interaction (hiring your CTO, closing enterprise deals, leading your team through uncertainty).

Non-attachment isn't just a nice spiritual concept. It's how you harness your full energy and your team's full energy toward creating what you actually want to create.

But knowing this and actually getting there are two very different things.

Crossing the Bridge

Between the way you've been motivating yourself and this new way of operating, there's a scary neutral period.

You've let go of the fear-based drive. But you haven't yet connected deeply enough with what you authentically care about to feel that pull.

No push from behind. No pull from ahead. Just disorienting space.

Most founders sprint back to familiar territory at this point. Back to the anxiety they know.

But if you stay, if you sit with the discomfort, something shifts.

When that energy stops being wasted on fear and resistance, authentic creative impulses arise.

We are creative beings. Creation is who we are at our essence. And these impulses tend to be pro-social. They tend toward service.

Ask most founders when they felt most alive. It wasn't hitting the revenue milestone. It was making a real difference in someone's life. In many people's lives.

The heart wants what the heart wants.

So crossing the bridge requires having the courage to follow your heart. To discover what you actually want to create. What genuinely excites you and who you're here to serve.

And then to feel the consequence of NOT following it.

What's the weight of not caring deeply about what you're here to do? Not building what you're actually here to build. Not serving the people you're here to serve. Dying with your best work still inside you.

When you let yourself really feel that consequence, authentic desire arises.

And that desire pulls you forward from genuine care because now it's an expression of wholeness, not a strategy to solve your lack.

Back to the Original Question

Should you wait until fear gets you to your number, and then do this work?

You could. Many do. They wait for the exit, then discover the emptiness is still there. Then they start the real work.

Or you could cross now. Find what you authentically care about while you're still building and let that authentic desire fuel the journey instead of fear.

You'll build from a completely different place. With more energy available. With your full heart in it. And paradoxically, you'll probably build something bigger because you're not wasting half your energy on resistance.

That pull is so much more powerful than any push ever was.

So the question is: do you have the courage to cross the bridge now?

With love,

- Dave Kashen

P.S. Want to cross the bridge with other founders making the same journey? The 2nd Annual Sun Valley Founders Retreat is designed exactly for this. Learn more here >>>​