When Life Feels Crazy: 6 Questions for Cracking Up & Breaking Through

Plant in dried cracked mud

“Every really new idea looks crazy at first.” ~Abraham H. Maslow

Once, when I was in a painting workshop, I hit a wall of resistance, totally stumped by what to paint next.

My painting teacher came over to explore some questions that could help unblock me. But my “wall” was concrete, or industrial metal, or super-duper spy-movie-like with some computer-code contraption locking all security systems down.

“What if a crazy woman came into the room?” she asked me. “What if the crazy woman painted for you? What would she do?”

“She would explode everything up!” I answered.

“What would she do on the painting?”

“She would rip it up!”

“If with respect for what you’ve already painted you allowed her to go crazy on the paper without covering what you already painted or ripping it up, what would she paint?”

I looked at the painting. It was an image of me. “She would crack me into a hundred pieces…”

“Great!” She said. “Paint that!”

I took out a small brush and started drawing black cracks, as many cracks as I could, cracking the body into thousands of pieces. I felt high as I painted. Free. Without interpretation or need to understand what I was doing, I energetically painted cracks all through my body. I finished the painting with glee.

A dear friend, who is a Jungian therapist, told me recently about the “Crazy Woman” archetype. The Mad Woman who likes to step in sometimes to shake our world, wake our reality. I told her I knew this woman. I had met her in my creativity.

But secretly, I was coming to understand her beyond that. In my own life, things felt uncertain, chaotic, ungrounded. I was feeling somewhat like the crazy woman myself.

I was living alone, a year after divorce in the house I lived in with my ex-husband in Venice Beach, CA. I never felt unsafe or in danger in my home or neighborhood. In fact, I felt the opposite; my home post-divorce had become my respite when everything else in my life seemed turned upside down.

One random Saturday morning, I awoke to find a young woman, around 25 years old, coming off of some meth or heroin high in my back studio that I usually kept unlocked because the perimeter of my house was well gated.

She was going through my cupboard filled with old wedding pictures.

She wasn’t an archetype, but a real person. I had to double check twice to make sure I wasn’t hallucinating. I was in shock, yet typically, when in shock I knew I tended to act unusually calm and reasonable.

I approached her. “Why are you here?” I asked.

“I thought I lived here.” She said, seeming vulnerable and confused.

“I have to call the police,” I said.

“But I don’t want to go jail!”

“I’m sorry I have to call…” I said to her.

She picked up her backpack, and while I told 911 that I had an intruder, she lit a cigarette as she casually walked out the side yard gate and continued down the street away from my home.

This wasn’t a dream. It really was happening. There was a stranger in my home when I awoke one random morning.

She left her tennis shoes and socks behind, which I showed the two policemen when they arrived.

“This happens all the time,” one of the cops said. “Just last weekend we had a squatter make dinner and take a shower in someone’s home around the corner from you. Welcome to Venice!”

Well, no. Actually I had been living in Venice for ten years. This wasn’t a welcome but a warning sign to make sure my side gates were better protected. Though the young woman seemed fine when she walked away, I still felt shaken.

After talking to my friends on the phone, telling them about my intruder, I was able to find my ground. 

I saw the intruder as a reflection of what I had been feeling lately and told myself, “Sometimes it’s okay to see the Mad Woman and to accept her.”

I knew I was physically safe. She didn’t steal anything either. That night, I put her shoes out on the street corner so she would have them to wear, and in the morning they were gone. Her intrusion woke me up and made me curious to explore deeper. 

These were the questions upon her departure I contemplated: 

1. What if I allowed myself to feel as “crazy” as I felt and let myself live the life I always wanted to live?

How would I live it? (i.e. what would I paint?) Could I let myself crack?

2. Would I let my controlled, safe little world open up to something new or daring?

Was I ready to uproot the life I knew and create something totally different?

3. What if nothing had to make sense?

If the dots didn’t have to connect? If I didn’t have to know how my decisions would dictate my future? What would I do then?

4. What if I didn’t have to live according to the rules and expectations I had put on myself and the conditionings put on me that I bought into?

The ones that were based on how I was raised, my family’s expectations, or the beliefs I was taught to believe about myself?

5. What if my life was about being fully me, filled up with me, and no one else?

Not by a relationship or for my parents or my roles in society regardless if they thought my choices were “crazy”—what would I do differently?

6. What would happen if I accepted feeling out of balance, in unknown territory, and stopped trying to be something other than me presently?

What life choices might I make then?

After asking these questions of myself, something told me it was time to take off into a new adventure.

I thought about things I’d been afraid to do before or resisted: I feared skiing because of my weak ankles, but what if I tried again?

New York was a place I had thought about living in—what if I went to explore a new city? Or what if I started a new career path? What would I want to create in my life then?

As I asked these questions, I started to become interested, uncovering layers into exciting new territory.

So I ask you, what if metaphorically you met your Inner-Mad Man or Woman? What message would he/she have for you? 

Creating a life change isn’t actually “crazy.” It’s the most fulfilling and exhilarating thing we can do.

What if you were to take a risk, jump into the unknown, shake up your world, leave your cautious mind and all that it says about you or about how you live your life and ask yourself, “If I were totally free, what would I do?”

Even if you don’t plan to actually do it, I’d love to hear. Be crazy and just for the fun of it. You never know what can happen.

Photo by Olearys

About Lynn Newman

Lynn Newman has a Masters in Counseling Psychology, is a writer, painter, and game creator (like The Game of You & The Game of Insight – An Interactive Way To Know Yourself, Create The Life You Want). She’s big into unleashing the truest, free-est parts of you, to experience more joy, purpose, and passion in life. Visit her at

See a typo or inaccuracy? Please contact us so we can fix it!