The surprising power of impossible dreams

And why I think we should be dreaming more

Lately, I’ve been thinking a lot about the concept of dreaming.

When most of us hear the word "dreaming," we think of something that isn't real—a fantasy. Even Merriam-Webster defines it as “a series of thoughts, images, or emotions occurring during sleep”. It’s literally a figment of our imagination.

And yet, I think dreaming can have a powerful effect on the reality we create in our lives — if only we were to let ourselves do it.

If we were to get coffee in one year, what would you love to say?

I was at the early stages of my coaching journey when I found myself sitting across the screen from this coach with big glasses and the most piercing eyes. I had already told her all about how I was stuck and all the things that I wished were different. That day, she asked me one question that really stuck:

If we were to meet up for coffee in one year, what would you love to be able to tell me?

At the time, I sort of brushed it off with some easy answers. I wanted to make coaching financially viable, host some events, maybe find a way to make writing my newsletter feel easier.

Great. What else?

I felt myself stiffen. What else? That was it!

Except... it wasn't. Deep down I knew there were things I had thought about but avoided saying out loud…things that felt too scary to admit.

And here was a space to say it.

This isn’t anything serious, I told myself. We were just dreaming together, that’s all. So I took a breath and let it all out.

I want to say that I’ve written a book.

I want to say that I’ve hosted a retreat.

I want to say that I’ve given a few talks about things I’m really passionate about.

I want to say that I’ve brought together friends from my different friend groups and that they genuinely bonded.

I want to say that I’ve coached execs and leaders who have been working much longer than I have.

I want to say that I now know how to take up space and boldly present myself to the world!

the broad colorful strokes of a dream

With each statement I made, I could feel myself letting go of hesitation, and letting in feelings of freedom and wonder, along with a dash of nervous giddiness. I mean, was it okay to say these things? To want them? To believe it could be possible?

I left that call feeling drunk on life. I truly felt like I had all of the opportunity in the world. At the end of the call, she asked me: Do you want to work on this together?

My whole being screamed YES YES YES!

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But within a few days, I found myself dismissing the whole conversation. It was one thing to play pretend, it was another to seriously work on these topics. And I was losing conviction. What if I was wrong? I was so scared of being too idealistic, getting judged, and failing, that it felt safer to not dream at all.

But is it too idealistic?

But my reality check was not actually needed. On the flip side, this past year I witnessed possibilities that I couldn’t even imagine. Stepping away from tech brought me into a world where I was surrounded by dreamers, and what’s crazy is that I saw so many of them succeed.

I saw coaches start up brand new businesses and make sustainable money doing it.

I saw The Commons become a staple of the Hayes Valley neighborhood and so many people step up to love and care for it.

I saw a coffee pop up started by a fellow ex-techie open its second storefront and support other fledgling businesses through exciting collabs.

I saw fellow MIT alums own their softer sides and create beautiful art, musical performances, and dance, while absolutely glowing in self-assuredness.

I saw people go after so many different dreams and ways to live, ways I didn’t even know were possible.

And what was so cool was that being surrounded by these dreamers helped me dream a little bigger too. And I gotta say, in one year, I made some cool shit happen (from launching a paid online community, to working with clients I adore, to hosting events that successfully brought strangers together).

In this world of creators and whimsical experimenters, one thing was clear: a lot can be possible, so long as you dare to dream it — and then dare to go after it.

A simple but powerful brainstorm

So let’s give it a shot! If you’re game, I’ll walk you through an exercise that I like to use to get clear on what you want.

First, I ask myself: what is my current dream for this upcoming year?

This part is the warmup. Almost everyone can come up with some baseline dream that is one step-function better than what they have today.

Second, I ask: what would I love to see in one year if I had zero constraints? In other words, imagine I have left reality and jumped into my very own fan fiction. What would I like to see?

I’ve seen people have all sorts of feelings towards this question. Some find it laughable — what’s the point in imagining a world that cannot exist? Others fear what will happen when they say something they’ve never admitted before. Still others fear that it will shake their ability to be content with what they currently have. I feared that I’d get so caught up in my fantasies that I’d abandon all semblance of logic.

But the truth is, you will still be you. You will still have your rationality and decision-making logic. You can have wild dreams and still calmly choose whether to pursue them or not. Speaking your dreams doesn't mean you have to pursue them all—but exploring them will teach you a lot about yourself.

So let’s try it. Go say all of the crazy things.

None of it has to actually stick or be true.

Say to yourself: Okay that’s great. And what else?

Keep going until you run out.

If you’re really brave — do it with a buddy. Let someone help you crank up the dial of what you allow yourself to dream.

It’s this very practice of casting aside your judgment and saying it all that can help us start to get a sense of what actually feels most meaningful to our core.

I promise by doing this you’ll discover something new and important. You’ll uncover the threads of what you actually want.

But what about the how?

Maybe you’re thinking — “Okay this all sounds nice, but what about actually making it happen?"

What’s cool is that almost every time I see someone reach their “what”, they stop hyper fixating on the “how”. Meaning: when the “what” resonates enough, the “how” just sort of follows.

One client of mine thought her dream was to figure out how to build a business around the social needs of new parents (like via social media). But after dreaming, she realized that what she wanted most was to work on advocating for and solving her own needs as a parent. The how was easy — for both her life and her business, she now wants to focus on developing in-person experiences, collaborating with local businesses, and having real conversations with her friends.

Another client originally thought she should spend her sabbatical figuring out how to make a lucrative side business. But when we dreamed, she realized that what she wanted above all else was to figure out what she was even passionate about in the first place. The how for her now is exploring her passions, which is where she’d want her side business to come from anyways.

I originally thought I wanted to finally make coaching a sustainable business. But when I dreamed bigger, I saw that what I wanted most was do things that were bold, playful, and from the heart. So how do I get there? This year I’ll be hosting heart-first in-person things, proposing wild collaborations with people who inspire me, and coaching people who also want to show up more boldly in their lives.

Maybe dreams aren't just fantasies after all. They might actually be the first step toward creating a reality we truly want. And there is actually no shortage of “hows” to get us there.

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If you’re game to do some big dreaming, I’d love to invite you to join my Dream Party on Feb 8 in Redwood City. It’s gonna be in-person, squishy, and heart-based — all the things I’ve been wanting in my own dreams 🙃. It’s going to be a bit of an experiment, but if you’re open to that, I think it’ll be a great time :) RSVP here.

Can’t make it? I always love helping people uncover their dreams via a 1-1 coaching call! Just reach out — I’d love to chat with you <3