Learning How to Let Myself Dream Bigger

A lesson on how our capacity to dream depends on our willingness to feel heartbreak.

I woke up on Monday 8am feeling terror in my body, after tossing and turning through the night.

In two hours, I’d be leading nine brave and dedicated humans through the first group call of a 4-week program to re-connect them with the fire of desire and aliveness burning in their souls.

I felt surprised (and slightly annoyed) with the terror. While it’d been nearly two and a half years since I’d led my last group program, this also wasn’t my first rodeo. I’d led many dozens of group experiences before. Why was this showing up?

I sat down on the meditation mat for my 30-minute morning practice — trusting that it’d be my most likely path to peace and groundedness.

I recognized the staticky sensations of terror in my upper back body. They’d only shown up a handful of times in recent memory — right before committing to a year-long rental in Boulder after my wife’s and my chapter of nomadic travel and right after Silicon Valley Bank collapsed when I felt uncertain about my family’s financial security, for instance.

The sensations were definitely some of the harder ones to be with. I put my awareness toward welcoming the terror rather than resisting it. I reminded myself: Beneath every stuck emotion is a hidden desire. If I could tap into that desire, I’d have an easier time welcoming the terror.

What’s the desire beneath the terror? I asked myself.

As I felt beneath the uncomfortable sensations, I found and touched something tender.

Even though I’d led many programs before, this was my first time leading something that I cared about in a really deep way. This wasn’t just about helping people do better at their tech jobs but about changing how they related to some of the most important and vulnerable areas of their lives: their relationships, their sexuality, their life purpose, and more.

I actually really cared about creating the conditions for deep growth and transformation in the program. It wasn’t just work to me, and it wasn’t just about getting the program done. If it was, I wouldn’t have felt terrified.

Once I tapped into the care, I felt the tears flow. The genuine care felt like a warm cocoon wrapping around the terror — and any need to push the terror away dissolved.

For the first time, I let myself truly feel into a beautiful future at the end of the 4-week journey.

One where everyone felt proud and grateful of the major milestones we’d hit and the breakthroughs we’d made.
One where we all felt a more intimate understanding of ourselves and each other, with more compassion for where we were and more aliveness for where we were going.
One where we’d all shared tears and laughter in challenges and celebrations together.

The experience taught me something valuable about what blocks us from dreaming big:

The capacity to dream big requires the willingness to feel how important something is to us — and that often calls forth a higher level of vulnerability.

Dropping the Walls that Block Our Dreams

In the past, I’ve seen myself as a strong executor. I’m great at keeping my focus on the immediate and practical next steps. When I worked in tech, I was a master of iteration — of iteratively experimenting and moving toward something great. It was why I excelled at working on and leading user growth teams, where rapid iteration was the key to success.

What’s historically been more challenging for me is dreaming bigger. In my tech and leadership roles, I was rarely the one holding the multi-year vision of the product.

I’ve always wondered:

What would it take to be able to consistently envision the mountain that I wanted to summit — especially one where where I didn’t know the way — and to direct my energy toward it?

I’m reminded of a quote from Dune (side note: I loved Dune 2, cried at the end at the powerful journey of a hero claiming his destiny, and have already watched it twice).

“Muad‘Dib could indeed see the Future, but you must understand the limits of this power. Think of sight. You have eyes, yet cannot see without light. If you are on the floor of a valley, you cannot see beyond your valley. Just so, Muad’Dib could not always choose to look across the mysterious terrain.”
— from “Arrakis Awakening” by the Princess Irulan

My ability to dream and see the future has felt limited by a mysterious terrain. It’s taken me a while to realize what that terrain was: 

What holds me back from dreaming bigger is the willingness to feel the heartbreak of letting myself truly care — of letting in how important something truly is to me.

If I’m not willing to feel disappointed or heartbroken from an unrealized vision, I’m not going to be very open to dreaming.

My awareness would be contracted, focusing on the practical and immediate future, not seeing past a valley of safety. I’d be limited by an event horizon that I couldn’t see past.

From that perspective, I can see how my focus on execution and the practical and immediate next steps — while certainly a strength that I deeply appreciate — has also been a protective mechanism.

By not dreaming past a certain level of uncertainty, I protect myself from having my heart broken if that dream didn't come to pass.

The Magic of Heartbreak

What I’ve come to realize is a deep relationship between dreaming big and heartbreak:

The deeper I feel my desire and the more I allow for my heart to be broken, the farther I can let myself dream.

My wife and I are embarking on the journey of starting a family. It’s been a journey ripe with episodes and waves of uncertainty — uncertainty of fertility rates, of potential miscarriages, and more.

And it’s been easy for me to not let myself dream about what fatherhood might look like. In fact, it’s been difficult to even make mental pictures of potential scenes from fatherhood even if I wanted to.

Why dream until I’m more certain that we’ll have a child?
Why paint visions of a future until it’s more likely to become a reality?
Why expend energy on something that might not come to fruition?

Now I realize that I’d just been subconsciously protecting myself from being disappointed and heartbroken. And in that protection, I’d also deprived myself of a powerful source of aliveness, an excitement of potential futures.

There’s a deliciousness in dreaming, in letting myself feel the deep desire to be a father that lies underneath the uncertainty of the pregnancy journey.

During a tea ceremony with my wife over the weekend, I let myself feel the fragility of our pregnancy — something that I cherished and that could go away.

And I dreamt of a future where I felt excited to wake up in the middle of the night to soothe our crying child — letting them know that they matter and that their needs are taken care of. It’s a belief that I’ve had to consciously reprogram for myself in my adult life — and what a gift that would be to pass on to my children.

I cried when I felt into that potential future. And on the other side of those tears was a deeper connection with my wife on the parenting journey and more excitement about becoming a father.

I want to let myself feel more excited.
I want to dream of futures that inspire me, that call me forth into being a more expansive version of myself.
I want to summit mountains bigger than ones where I know the way, where I might actually fail.

Now I know that I’m unable to dream past some threshold or event horizon, that’s actually a clue. There might an unfelt emotion in the way. I might be protecting my heart from feeling something.

And the way through is just to let in how much I truly care.