01/02/2014 01:55 pm ET Updated Dec 06, 2017

What Being Homeless at Christmas Taught Me About Leadership


The ego serves a very critical role in our survival as human beings. Its main purpose is to keep us safe, physically and emotionally. It keeps us from going to work naked or playing in traffic. The ego likes acceptance, but this often works against personal evolution -- major growth happens when we step outside our comfort zone.

So what if you forced yourself to spend a day being uncomfortable?

In the past five years, my content marketing software company has grown from two people without an office to 45 employees serving customers like P&G, Coca-Cola, and Microsoft. To expand into new areas of leadership and growth, I've enlisted the help of an executive coach.

Our last meeting focused on self-worth and how often we look to the outside world for feedback about our "OK-ness." We scan the emotional horizon for what's "normal" and adjust ourselves to be liked and accepted. This unconscious censoring of our true selves can undermine our ability to lead because we end up modeling it for our teams. The lesson was about finding our authenticity and letting other people be responsible for their own emotions, reactions, and opinions.

My coach gave me some homework: to spend a day as a homeless person and observe how I reacted to others and how they reacted to me. I was to completely transform myself and go to an upscale mall to interact with the staff and customers as they did their Christmas shopping.

I found clothes that would make me look impoverished and bought shoes that were uncomfortably small. I made myself up to look unclean and greasy and carried my belongings in a bag. It had snowed the night before, so I intentionally underdressed.

It's an odd feeling trying to put together an outfit that looks "homeless." The truly destitute don't create ensembles. They wear what they have for survival, not because they're going for a look. Of course, poverty and homelessness take many forms and are not always obvious. Not all homeless people look the way I dressed, but I purposely chose the homeless stereotype to stand out.

As someone who's spent my marketing career focused on branding, looking good, and creating an impressive first impression, putting myself out there as someone to be pitied went against every cell in my body.

When I got to the mall, I sat in my car for 10 minutes, too afraid to get out. I wanted a button that read, "This isn't really me. I'm just doing an experiment." I thought up excuses to justify why I didn't need to do this, but I'd agreed to it. This was an opportunity for growth.

Then, my ego came up with a strategy to ease me into the deep end of awkwardness: For the first hour, I didn't feel worthy enough to go into stores. I just walked around outside with a nauseous stomachache, wishing desperately to be invisible. I began to mentally rank the stores where I would stand out the least. I'd work my way up to the department store.

I watched people scan me up and down, dying to know what they were thinking. I was convinced people thought I was nothing -- worthless. I projected "Please don't look at me" with all the telepathy I could muster, and I was rewarded with people who looked away or stared from the safety of their cars. People on the sidewalk moved out of my way without looking at me. While my outside appearance was fake, the shame and humility I felt were very real.

I watched women with their shiny hair, stylish outfits, warm coats, and kids waiting in line to see Santa Claus and felt shame. I felt guilty that my presence was making people uncomfortable, and I felt wrong for looking poor. I had silent conversations with people each time I made eye contact. I projected shame; they agreed to pity me. I projected that I didn't belong, and they ignored me.

Once I finally went inside, I told myself, "I'm just shopping. I'm just shopping." I figured as long as I was spending the afternoon at the mall, I would try to let go of what I looked like and get some shopping done.

A few times, I forgot how I looked and genuinely enjoyed feeling like another shopper. At the jewelry counter in the department store, I reached out to touch a silver necklace, caught a reflection of myself in the mirror, and was horrified at the person staring back. I thought, "Who is that sad person?"

This happened a few times, so I decided to stop looking at my reflection or I'd never make it through the afternoon. Something interesting happened during the moments I forgot to feel shame: People would talk to me, store employees became helpful, and one man even opened a door for me. At one point, I had the undivided attention of a department store manager who happily helped me pick out silverware.

In these moments, I realized people didn't care. They didn't care what I looked like. They only cared when I cared. If I brought shame, they responded with pity. If I showed up with innocence, they responded with sincerity. It had nothing to do with what I looked like and everything to do with the energy I projected. I learned a lot about myself and other people that day:

Shame and Guilt Serve No One
I learned that whether self-generated or projected onto us by others, shame is one of the most destructive human emotions. As leaders and parents, we must inspire our employees and children to grow without shaming them for making mistakes or being different. We have to let go of the need to be liked. Leadership based on being liked doesn't serve anyone and sets an example of codependency for employees.

Being Comfortable Is Overrated
If you listen to people's stories of growth and transformation, they usually involve some unexpected circumstance: the death of a loved one, a health crisis, or the loss of fortune. If we are capable of transformation in response to unexpected circumstances, then we should be capable of transformation from engineered circumstances.

Why not push our own limits and create our own opportunities for growth, rather than waiting for life to throw us a curveball? Being homeless for a day blew my comfort zone into another hemisphere. I realize I was not truly homeless, but the emotions I felt and the lessons I learned were very real.

What have you done to go out of your comfort zone? What did you learn?