• Ariana Friedlander

The Beauty in "Oh No!" moments

A few years ago, I was bustling about my kitchen, putting clean dishes away while deep in thought. We have a sneaky cabinet that's tucked under an overhang of the countertop. As I finished putting away the slow cooker there, I stood up quickly and smacked my head on the counter.

The force and shock of the collision snapped me back into the present moment as though I was rudely awakened from a dream. I saw stars and felt completely disoriented. I had a lump on my head for a week. In short, it hurt!

Yet, I also found a valuable lesson in that experience. I let myself be distracted by distant thoughts instead of being present in the moment. Because of that, I sustained a completely avoidable injury.

It was a valuable reminder of the importance of being aware of my surroundings.

I call such experiences the beauty of "oh no!" moments (that's the PG version, in my head I call them "Oh sh*t moments").

We've all experienced such times in our lives where we are proverbially smacked in the head and forced to reckon with our present circumstances.

I had a similar experience after A Misfit Entrepreneur's Guide to Building a Business Your Way was published. Reading the completed manuscript made me painfully aware of my shortcomings. It illuminated for me the ways I still had room to grow and improve as a Misfit Entrepreneur.

The premise of A Misfit Entrepreneur's Guide is that the journey of entrepreneurship is one of mastery. One doesn't arrive at being an all-knowing entrepreneur but must commit to three practices. We used a biking analogy to describe the three practices. There's the rider, which is understanding yourself. There's the bike, which is understanding business. And there's the bike ride, which is being on a meaningful journey.

Instead of forging ahead as the "expert" Misfit Entrepreneur building out new programs, I felt called to do my own inner work. I had spent my first five years in business with a heavy focus on the bike and felt a great need to give some more attention to the rider. Because of that, I told myself I wasn't ready to be a teacher of Misfit Entrepreneurs.

Lao Tzu said, "Knowing others is intelligence, knowing yourself is true wisdom. Mastering others is strength, mastering yourself is true power."

I had gotten to know myself much better through my entrepreneurial endeavors but was a far cry from self-mastery when A Misfit Entrepreneur's Guide came out.

This was a profound "Oh No!" moment because it changed everything I had planned. And I felt like such a fraud because my emotional and mental health needs were not being met at the time. After the book came out, I didn't have the bandwidth to rebound from rejection or setbacks like I used to.

I was depleted and tender and mad because I knew better.

My therapist told me this is the second arrow. When we are hurt and we add to our suffering by judging ourselves for experiencing pain. As though we are somehow less worthy because we are suffering. When in fact, such struggles are a part of our shared humanity. It is possible to both hurt, and have worth and value as a person.


Leaning into my pain was rather uncomfortable, like an itchy wound scabbed over. But doing so was an essential part of my journey. Putting myself out there by sharing portions of my journal in A Misfit Entrepreneur's Guide invited me to reckon with the still wounded parts of myself.

More specifically, I had to learn how to be kind and compassionate to myself. "If you have a cruel inner critic like me, there’s a good chance that every little mistake you make could be twisted into the worst thing ever." This sentiment first expressed in A Misfit Entrepreneur's Guide continued to tear me apart inside after the book came out.

I felt haunted by feelings of inadequacy!

I retreated into safe spaces where my pain was welcome and I was shown love regardless of how I felt. I invested in my spiritual well-being. I went deeper with my journaling practice. I sought counsel. In short, I asked for help and committed to helping myself.

During that time, my journaling practice changed. One day when I was particularly bothered, I wrote words of encouragement to myself in the third person. This was a new tactic and a completely different way of speaking to myself. I called it the voice of compassion.

I realized that in order to change the dynamics with my cruel inner critic, I had to intentionally shift my journaling practice. Acknowledging that my writing was reinforcing negative self-talk felt scary. I needed a place to be real with myself - there was no positive thinking my way through the pain I was enduring. I had tried that before and found it only suppressed my "negative" feelings more.

I needed to allow my feelings to surface without shooting the second arrow.

Eventually, I decided to invoke the voice of compassion in my journaling practice regularly. The voice of compassion is the anthesis of my inner critic. It shows me kindness and concern, like a mother speaking tenderly to her injured child.

By routinely invoking the voice of compassion in my journaling practice, I created new thought patterns in my mind. Instead of reacting with judgment after experiencing a setback, I began automatically showing myself compassion. Instead of accentuating the hurt and pain with shame and ridicule, the voice of compassion soothed my nerves.

Awareness isn't learning. It is a step in the process. True learning occurs when we change our behavior. There's often a huge chasm between awareness and change. "Oh no!" moments are invitations to see the intended growth through.

I had written A Misfit Entrepreneur's Guide for two reasons: 1) as an exercise in synthesizing what I had learned on my entrepreneurial journey in one place for others like me. And 2) to shed light on the seldom talked about emotional trials of the entrepreneurial journey. Little did I know it would catalyze even more profound growth after its release. Writing the book isn't what changed me, striving to live up to the ideals expressed in it after the fact did.


Are you ready to experience a personal or professional transformation? One of the benefits of Journal Jams is the generous sharing from others - their experiences, ideas and practices are a valuable source of inspiration for your own journey. Check out our next Journal Jam this Wednesday, and experience a profound shift with just 20 minutes of journaling.

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