Meeting an entirely new version of yourself on the other side of discomfort

If you want to feel fulfilled, you need to make progress.

And if you want to make progress, you need to take risks.

One of the simplest ways to do that is to practice intentional moments of discomfort.

Big ones, too. Stepping so far outside of your comfort zone that you meet an entirely new version of yourself on the other side of it.

When I spent six months building and launching a software product, it was quite possibly the most uncomfortable I have ever felt in my career.

But it was also the most fulfilled I have ever felt. Funny how that works.

When we finally went live, I reflected on my journey and noted all of my intentional moments of discomfort during that period. Here’s an inventory of them. Think about how you might be able to make this kind of progress in your own work.

First, stepping out of my financial comfort zone meant creating a sustainable business with recurring revenue that doesn’t involve selling my time. And building a product that not only created value for others, but captured some of that value for myself.

That was a first for me, as someone who isn’t particularly financially centric by nature.

Second, stepping out of my artistic comfort zone meant launching a technology project that was more complicated, robust and code based than my previous projects. And surrendering control to multiple collaborators whose brains worked very differently than mine.

Never tried that before, since my modus operandi has always been to sit in a room alone and make things.

The next moment was stepping out of my intellectual comfort zone by architecting a professional, repeatable, standardized, documented discipline that others could apply to their own lives. And writing a methodology that could trail blaze and entirely new field of study.

Talk about a stretch. As an artist who works nonlinearly and stream of consciously, the structure of a curriculum was a welcome challenge.

Fourth, stepping out of my entrepreneurial comfort zone required viewing myself as a startup founder. Doing things like analyzing the competitive landscape, defining a pervasive, expensive cultural problem, identifying the total addressable target market and inventing and new category in the marketplace.

Wow, that was that a challenge. Felt like going to business school, but without the tuition and hangovers.

Fifth, stepping out of my interpersonal comfort zone meant involving a small cohort of trusted people in the creative process from day one. And, actually requesting, accepting and implementing their feedback on the product. Essentially treating them as an accountability board to whom regular company updates were required.

Very scary for an individualist rebel like me who fundamentally loathes feedback and doesn’t need external accountability.

Next there was stepping out of my creative comfort zone by thinking more visually. The software required me to attach abstract images to my writing, adding a stronger sense of weight to my work. And elevating the usefulness and impact of my product by appealing to multiple users senses and personalities.

It was like doing chin ups for my brain. Painstaking but ultimately healthy for the body.

Seventh, stepping out of my business comfort zone meant grownup things like setting up automated business processes, writing a pitch deck and positioning the company for growth through enterprise solutions that could increase annual recurring revenue and customer lifetime value.

This was another healthy exercise in left brain thinking, perfect for a right brainer like me.

Lastly, stepping out of my existential comfort zone meant choosing to have the transformative experience of launching a project that would scale my talent, multiple my contribution to the world and challenge me to evolve spiritual in more mature ways. Actively taking time each day trying to transform the way the human race thinks about the creative process made me feel alive in a completely new way.

Considering this whole journey happened to me during the global pandemic when helplessness was running rampant, it sure felt good to feel useful to the world.

Whew, that’s a whole lot of getting out of my comfort zone. It may be time for a hot stone massage.

I’m reminded of something my mentor once told me:

First you write the book, then the book writes you.

That seems to apply for just about everything we do in this life.

Fulfillment is a function of progress, and progress is a function of risks. Take more of them.

How many intentional moments of discomfort have you practiced this week?