A Guide to Moving Courageously Into a New Uncertain Space

“We become brave by doing brave acts.” ~Aristotle

I remember walking into my boss’ office at my day job to turn in my resignation, almost exactly 10 years ago today. I was quitting the life of a regular paycheck, to become a full-time blogger and writer.

I was filled with an overwhelming sensation of fear, and an overwhelming sensation of joy.

I’ve now come to associate this feeling of ‘joyfear’ with the important moments of my life:

  • The first moment I held each of my newborn kids in my shaky hands
  • Starting Zen Habits, not knowing what I was doing, jumping into the unknown
  • Creating live workshops & retreats last year
  • Publishing my first book (and every book thereafter)
  • Moving my whole family to San Francisco from Guam
  • Unschooling our kids

Each of these has been incredible for me, filled with uncertainty and joy. The fear of uncertainty can lead a lot of people to put off moving into a new space in their lives, but I’ve learned to embrace this fear, to dive into it, to see it as a place of growth and transformation and learning.

This year I’m moving into new uncertain spaces (more on that next month), and I’m practicing some more with the discomfort and uncertainty of these new wide open unknown areas. I’m practicing with leaping into the abyss with joy.

Here’s what I’ve learned so far — I’m sharing in hopes that it will help others who are moving into uncertain spaces in their lives.

Find Your Devotion

We don’t put ourselves in the middle of fear for no good reason. We do it because there’s something we care deeply enough about to push into that fearful area.

Remind yourself of why you’re going into this uncertain space. What do you care deeply about? Who or what are you devoted to? This might be a cause, it might be people who are in need or struggling somehow, it might be your loved ones, it might be the team or customers you serve. Find the love and passion in your heart for this cause or these people.

Then remind yourself, each day, of this devotion. Remind yourself of it as you do each step, each task … this is what you care deeply about.

Your devotion, the thing or people you love so deeply … is greater than your fear and discomfort.

In fact, the devotion turns this uncertain space into a space of shaky and heartfelt love.

Get in Touch with the Fear & Uncertainty

Most people either run from the fear, or try to find ways to turn it off, to not feel it, to eliminate it.

Not us. We’re going to get in touch with it, and allow ourselves to fully feel it.

Why would we want to fully feel fear and uncertainty? Because it’s nothing to hate, it’s part of our experience, it’s actually the place we want to be.

Feeling the fear and uncertainty fully, allowing it to be, even welcoming it … this shows us that it’s not so bad. It’s nothing to panic about. We can grow up from our childish need to run, and instead just stay with it patiently, with gentleness and compassion.

We can touch the uncertainty and stay with it, welcome it and even find love for it.

Practice. Get good at fully feeling it. And learn that you can take it in and transform it into openness and joy.

Move Through It with Small Actions

The fear isn’t something to run away from or otherwise avoid. It’s actually the path we want to walk, because through this fear is creation. Through this fear is learning, growth, transformation, impact on the world, beauty. Through this fear is something meaningful.

So we’re going to move through it, but in small steps. We’ll use the ideas of exposure therapy to move through the fear — the idea that we can get used to the feeling by giving ourselves small, manageable doses, gradually increasing the doses in steps we can handle.

You do this through taking small actions daily.

Want to be a writer? Write a little every day, clearing space and allowing yourself to be present with your fears of writing (and failing). Want to start a company? Take the small actions required to research it, create a website, find team members, start making revenue, experimenting and learning.

Take small actions daily, exposing yourself to the uncertainty, and building trust that you can handle it.

Find Play & Gratitude

Moving into an uncertain space doesn’t have to be an exercise in rigorous discipline or self-punishment. It can be joyous and fun!

When you move into this space, see if you can find a way to play. Can you get messy and creative? Can you turn it into a game? Can you play upbeat music that gets you moving? Can you do it with others and feel the excitement of collaboration? Can you play your music for the world and see them dance to it?

As you turn it into play, allow yourself to feel the joy of that. And yes, there’s some fear mixed into the joy, but you could also call that ‘excitement.’

And in the middle of everything, pause and see if you can find gratitude for being in this uncertain space. Gratitude for being able to be here, for being alive, for being able to serve those to whom you’re devoted, with love.

Gratitude transforms the activity from one you are forced to do, to one you get to do.

Seek Support

We are not alone in this uncertain space, even if we feel like it. There are others who are forging this path as well, and we can form (or join) a group of people pushing into it as well. We can call on mentors, teachers, coaches. We can ask for support from loved ones, team members, online forums, social media friends.

When we ask for support, we are acknowledging that we are not an island, but interconnected with everyone around us. We serve others, but in turn we are supported by thousands and thousands of others who make our food, build our houses and cars and roads, create the Internet and the devices we use, and support us in an infinite number of other ways. We humble ourselves by thinking that we can’t do everything alone, but can do so much more with connection to others.

Seek support, find gratitude for that support, and feel yourself moving into this unknown space with the help of many others. May you have a joyfear-filled journey.

“Go to the edge of the cliff and jump off. Build your wings on the way down.” ~Ray Bradbury

Retreat: Go Deep Into Mindfulness (in Tulum, Mexico!)

I’m excited to share with you a mindfulness retreat that I’m holding in early May …

In this 5-day, 4-night retreat, we will:

  • meditate every morning
  • do yoga (if you like)
  • dive deep into mindfulness with daily workshop sessions
  • have time to reflect & contemplate our lives on the beautiful beaches of Tulum
  • visit Chichen Itza, see the Coba Ruins, swim in the hidden Cenotes
  • eat some amazing food
  • and connect with other like minded adventurers

The retreat will be led by me (May 2 – May 6, 2018) and is limited to 12 participants.

Get more info and book a spot here.

I hope you’ll join me — I’m looking forward to playing and going deep together!