A Letter For Process & Progress #8

Weekly Update (2/4/25) of Radical Transparency

Some of you may have noticed that I haven’t made a post in 4 days, maybe you didn’t, either way I noticed. It ate at me over the last 96 hours as I felt disappointment and shame in myself for not delivering. I made it 60 days consecutively of writing before I faltered on Friday on my way to my goal of 100 straight days.

I’ve struggled with the idea of failure my whole life, at least since I can remember. One of my earliest memories is of playing in a rec basketball game in 2nd grade, I was 7 years old and it was one of my first organized games ever. My team lost the game. I felt like a loser and a failure and my actions followed. My memory of that moment isn’t a positive one - it’s a horrible one. I broke out in uncontrolled rage.

I remember stomping around Eisenhower Elementary’s gym yelling and crying and throwing an absolute tantrum. I’m pretty sure I physically assaulted my parents as they tried to calm me down. Every parent and kid in the gym saw me, shook their head in disgust and I’m sure got in their car and had a conversation about how it’s not okay to act that way. It was embarrassing… it’s still embarrassing.

I don’t know where I get that from - the hatred for losing and failure. It’s almost always been a stronger driver in my psyche than any sort of joy for doing well or making positive progress. Even more perversely I used to take deep pride in this trait as well. I’d brag to people that I was a deeply competitive person who hated losing more than I liked winning. I heralded it in job interviews and when I’d meet new people playing pick-up hoops or other sports. I find myself asking in this very moment:

Where does it come from? Why do I feel and act that way?

There has to be some anthropomorphic reason - is it just survival? Is it passed down from generations and generations of my ancestors who ingrained that trait into my dna so that I felt it and then used it? I only know my families’ history so far back - my grandparents grew up very poor and with near-zero privilege. One side was farmers in small rural Minnesota and the other on the streets in Milwaukee fighting to survive a deeply abusive alcoholic household.

Maybe their generation needed this trait and I’m just left to deal with it in a different world and environment. I know deep down that I don’t need it anymore. That I’m slowed by it or held back by it. That I should observe when I’m feeling it, explore why I’m feeling it, and then find a way to act on it that helps me rather than hurts me, like it always has.

I’m trying to balance the emotions now and give myself the grace to just accept it in the moment. When I woke up this morning and sat at my coffee bar with my giant notebook and markers I didn’t know this was the direction my morning reflection would take me. I’m glad that it did. It’s something I’ve been needing to reflect on and so maybe this moment was meant to be for that.

Here is where my exploration of those emotions and feelings of failure, in regards to this project, have led me:

• Maybe I needed a break and reset on the project and the universe provided me that, it just happened 60 days in

• I both overcommitted last week and gave other things priority.

• Neither of those things were bad - I had a great week.

• I went to 10 social events, hosted and spoke at an event, had friends/colleagues travel in and stay with our family, and continued my push with my business to make it great and better for our clients. ALL GOOD THINGS

• It made me realize I don’t have good enough systems for the project. The only system I had was to block 45 minutes every afternoon to write, but I often neglected actually focusing in during that time or scheduled things during that time

  

  Not good enough…

• I need to plan how to write better and create better systems. I’m going to try:

  • Writing in 2 big blocks per week

  • Writing all 7 posts in those 2 blocks and scheduling them to send

  • Creating a planning block of time and being more organized and thoughtful about my topics/subjects

  • Having a system and flow to the writing, keeping it natural but more focused

• Incorporating my typewriter into the project more. I’m reinvigorated after the curated typewriter sale last Wednesday to use mine more and make it a bigger piece - I moved to far away from it and too digital

  

• There needs to be an IRL (In Real Life) piece to this that builds more human to human connection. It’s just too human of a project to not do that

  

• Gratitude shared amongst humans is best - I want to get back the feeling I had when Debbie Millman responded to my letter to her with such love.

• I want to try to reframe what I’m doing from “How I” or “How to” to “How You”. I’m going to do my best to practice this over the next 44 posts

  

• My new goal is to get to 104 total posts. Maybe I’ll do that in exactly 44 days, maybe not. I still think the 100+ goal is important, I’m making it 104 because that’s the equivalent of 2 years worth of posts if I were writing weekly. Writing 104 posts, I surmise, would put me in the top 1% of all substackers in terms of total volume of posts.

Highest Level of Resonance This Week:

The event that I helped organize and spoke at had 80+ people show up and it was awesome. Met some great people, had some great conversations, and it’s inspired me to get out from behind my screen and in person with more people more often

Big Ask of the Week

I want this to be more of a 2-way street between my readers and myself. So I’m going to start asking something of you all every week to try to get that engagement going. Here is my ask this week:

Tell me your story or thoughts about your struggles with the emotions and feeling of failure

It can be in the comments (public) or in email/DM (private). I will not share the emails/DMs ever unless you say it’s okay to. We can only grow if our perspective widens, so your input would be extremely valuable.

With love and deep appreciation,

-Andrew