Not gonna lie, I was really nervous agreeing to the challenge issued to the group of entrepreneurs: post some piece of content every business day for two straight months; $50 per missed day collected in a pot to be donated to charity. The hesitations stemming from a few very legitimate restraints and a few very illegitimate self-doubts.


That little voice in my head had a field day: there’s no way you will have that many things to write about, you’ll run out of ideas by the end of week two, nobody cares what you have to say, do you really want to be seen as the kid with their hand up all the time in front of the class, and when I was able to pass through that gauntlet, that little voice knows me well and hit me where it knew it would draw blood…this will be a complete and total waste of your time.


That one hit home, because I was right in the middle of one of the busiest stretches of my professional career, trying to cram the 12-18 month process of buying a historical school building to transform into the Conflux into the next 3 months, December and January = a lot of holidays and family vacations, and I have two young, crazy kids that make both mornings and nights an adventure…every day.


Like I said, plenty of reasons to say no, but two powerful reasons to say yes launched me on the journey: 

  1. My declaration of 2020 being the year when I would stop hoarding information and share my knowledge and wisdom, to illuminate the path I am taking to hopefully makes others’ journey a little less fraughtful
  2. Leadership often means making a tough decision that will put you in the thick of it because you know it’s the best thing for those around you. I knew enthusiastically committing right out of the gate would likely inspire others to do the same, and share their own light, their own journeys, that could then help others in their own worlds.


As today’s post is the last of the challenge, I am blown away by the things I’ve learned about the writing process but more importantly, myself along the way. 


The Creativity Muscle Expands With More Frequent Use

Not only did I not run out of things to write about, my list of ideas continues to grow faster than I could ever write about them; my list is now over 7 pages long. I am honing my ability to parse out the key lessons from my experiences, often creating multiple points of view from the same situation.


Here and Now Works Just Fine

There is no need to wait for the perfect time of day, the perfect amount of time, or the perfect place to write. Although I prefer to write for an uninterrupted block of time first thing in the morning, that’s just not always on the agenda, especially with the kids. What has been very surprising is how effective writing in short bursts throughout the day has been. Instead of opening my ESPN, Kindle, or any social media app when I find a small gap of time, I find myself adding new ideas or knocking out a few sentences…that collectively turn into paragraphs and then a post. Instead of always displacing other things on my to-do list, I am successfully finding ways to fit writing into the cracks and seams of my day, whenever they appear, wherever they appear.


Reporter For My Own Life

One of the most sought after benefits of mindfulness is decreasing stress. This resiliency is achieved by being aware of emotions as they are being experienced. I’ve done multiple meditation retreats, boot camps, and classes over the years, and still practice (semi) regularly. What I did not anticipate was how similar the feeling of being an engaged but detached observer of my life would be in both cases. As adversity smacks me in the face, instead of getting really frustrated or stressed out, I just think of how this will make for a really interesting post. That little pause, that little moment of reflection removes a lot of the emotional sting, keeping me in a very centered, philosophical mindset. 


Strength in Numbers

My first computer in middle school had enough storage to hold exactly 3 songs…2 if they were really long. This was the prehistoric days of the internet, long before streaming or even high speed downloads. So needless to say, my 3 songs were always highly curated. I had to think long and hard if I wanted to download a new song because it would take all night on the ol’ dial up, and I’d have to delete ⅓ of my library. I felt this same pressure in the first week of writing. Since each post was a sizable portion of my catalog, each one felt like it needed to be perfect. Perfection is not a friend to any creative endeavor. Now with a decently robust library, each subsequent post comes much easier and easier, like how Napster and college high speed internet made curating my song selection obsolete. 


Just Hit Publish

I recently heard Seth Godin, who also posts every day, say that he doesn’t publish because it’s ready, he publishes because it’s the next day. I found a lot of freedom in having to post something only because tomorrow has become today. Not everything I’m posting is absolutely amazingly great but that’s not the point. Just as Eisenhower said “plans are useless but planning is indispensable”, each individual post I write is less relevant than who I’m becoming through the process of writing every day.


Easier = Better

Michaelangelo’s quote of “I saw the angel in the marble and carved until I set him free” also rings true for me. At first, I was picking a specific topic to write, and stubbornly beating into submission whether I was feeling it or not. I find that approach takes me a lot longer and produces a meh post. Now, if I am struggling or grinding to express my thoughts, I find it better to put it on the shelf and come back to it later. Then I scan my list of ideas looking for the one that wants to be written, seeing which one tugs at my heart and gets my creative juices flowing, and then I write to set it free. Then the words usually flow out effortlessly in a near stream of consciousnesses. My most impactful/popular posts are typically the ones that actually took me the least amount of time to write. 



Each year I challenge myself to learn one new thing.  A few years ago, I chose to pick up golf for the first time. I successfully became a little less terrible, but when someone asks me if I am a golfer, I cringe and quickly correct them: I’m someone who plays golf; I am not a golfer. I wouldn’t disrespect the sport like that. After 60 days of writing, I still don’t consider myself a writer, but when someone recently called me a writer, I wasn’t repulsed by the term. Who knows, maybe at some point, long past another 60 days, I may just be able to consider myself a writer. That glove may just fit.


Where Do We Go From Here?

The thing I find most fascinating, is how what started as an extrinsic motivation to help others, has turned out to have far greater intrinsic benefits. This I know for sure, I will continue to write. I will continue to report my leadership journey. I like how I am growing and who I am becoming as ‘someone who writes’. I like being able to help inspire and motivate others to become an even better version of themselves, to know it’s ok to struggle, to know it’s ok to hurt, to know that this is the path of an empowergizing leader.

Become a Certified Partner