The most creative way I’ve built a new habit

It is only one fruit among hundreds of my “creativity” with which I persisted to create my habit of talking to strangers.

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Creativity is rarely a desirable thing when you build a new habit. When you create a habit, you should aim for consistency first and foremost. Creativity connotes with something one-time, fresh and fun.

Habits and creativity just don’t match well.


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I was the most creative when I was learning how to build habits. I had no experience and no knowledge about the process, so I used the trial and error approach. Creativity is very handy in such a situation.

An Impossible Quest

When I decided to transform my life, I came up with a habit that would help me with my relationships: talking to strangers. I was sure that striking a conversation with a stranger at least once a day would improve my people skills.

The problem was, I was a shrinking violet. When I tried to approach a stranger, and God forbid an attractive woman at that, I was terrified. Mad butterflies went crazy in my stomach. My legs felt weak. A lump formed in my throat.

I tried to force myself to strike a conversation with a stranger. I succeeded maybe one time in ten. And the experience was absolutely nerve-wracking and exhausting. I needed a different way.

Forced Creativity

I analyzed what came into initializing a conversation. I decided to make eye contact with strangers and smile at them. That was more doable.

Another creative thing I was doing with building this habit was tracking. I used Darren Hardy’s weekly rhythm register sheet to track my new habits every single day. After several weeks, I noticed that I had more minutes in my “talk with a stranger” habit than I had in all other dozen habits together. And that was even with the discipline ‘downsized’ to smiling.

If not tracking, I would have never discovered that. My subconscious tried to hide that I shy away from this discipline because the experience was excruciating. Without tracking, it would have lulled me into thinking that everything was OK.

At that time, I realized that talking to strangers was definitely not possible for me. I doubled down at making eye contact and smiling. Over the next several weeks, it was about all I did in that regard.

But I also thought hard about how to make the next step. I wanted to talk to people, not smile at them! So, I observed people around me and ruminated: how could I start a conversation? What could I say? What could I praise this person for? How could they impress me?

Once I discovered such a conversation cue, I imagined that I’m starting the conversation with it. For weeks, I was busy with watching people, making eye contact, smiling, thinking hard about them and imaginary conversations.

Spot On!

It appeared that I tapped into two most powerful ways to overcome shyness. I practiced; yes, only in my head, but the human mind doesn’t see much difference between imagination and reality.

And I started to think about others, not me. The shyness curse is that you are involved all too much with your own thoughts. Instead of just taking action, you overthink everything, ruminate about how people would react, analyze your past interactions with an overly critical way, and come up with future doom and gloom scenarios.

It wasn’t that I was ugly, rude or stupid that held me back from interacting with people. It mostly was my own silly thoughts.

When I stopped thinking about myself all the time and focused on others, coming out of my comfort zone was much easier.

The Results

After several weeks of my tiny practices, I finally started to open my mouth and utter words to strangers. Quite often, I used the opening lines from my imaginary exercises.

At first, my attempts were not very often, and I still felt very self-aware in the negative meaning of this expression. However, every new interaction boosted my confidence. And, of course, no one bit my head off, which was a huge relief to my tormented subconscious.
Today, I’m about five years into my small practices. They are my habits now. I automatically notice good things about people around me. I cannot help but smile when I see any person in front of me. I look people straight into their eyes. And I wrote a book about it.

I have some awesome stories. I befriended a street beggar and a consecrated widow. I spoke with strangers about life-death matters. I complimented many attractive women.

No one ever was angry at me for striking a conversation. Only a few times were people annoyed or felt awkward because they clearly had no wish to converse at that time.

This Very Morning

On a train to work I observed how a mom interacted with her 4-year-old son. The boy clearly had ADHD. He was constantly chaffering. His mom was very patient with him, answered all his questions, persuaded him to be a bit quieter, and engaged in his childish imagination games.

Stepping off the train, I stopped by them and said to the boy:

“Hey, young man, you are very eloquent. You don’t suffer for a lack of words, do you?”

I could tell his mom was a bit abashed that I noticed his “energetic” behavior. The boy gave some signs of shyness too. I continued:

“And your mom has a lot of patience for you. You must love her very much, right?”

The small guy said nothing but gave me a sun-hot warm smile, like only kids, can give. His mother smiled as well.

I felt I made their day a little better. I stepped off the train feeling a warm sensation in my stomach.

It is only one fruit among hundreds of my “creativity” with which I persisted to create my habit of talking to strangers.

This article first appeared on Medium


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