Welcome to the first issue of The Corporate Dropout!

Every weekend, I’m writing a personal, private newsletter* filled with raw, honest perspectives on what’s shifting, what’s calling, and what’s emerging next in the Corporate Dropouts space.

Real. Raw. No AI. No Grammarly. 100% written by hand. I’ll explain this in a moment…

Every week, I’ll share lessons learned. Mistakes made. Wisdom gained.

Real perspective from real lived experience.

And you are officially subscribed.

*This newsletter is replacing the weekly WaterCoolerCall Recap (as our live calls will no longer be recorded).

Important: To ensure you don’t miss any future issues, please add [email protected] to your email safe senders list and subscribe to “The Corporate Dropout” on Apple Podcast or Spotify.

1 | The Quest for Perfect Content

I spent the first six months of last year trying to figure out the perfect content to put out, to attract people to start a community.

My project was called "Thoughtful Gents".

I had recruited my five friends into this community platform and I just wanted to find the perfect content for them every day.

What I ended up doing is, driving them all away from it cause I was driving them nuts.

I wanted them to read everything I was putting out.

I spent probably two to three hours a day…if not more with ChatGPT… over those six months.

Everyday… having conversations about content, how to position it — and then I would find the perfect nucleus for the content, the brand, all that.

Then I would put a business model around it and I would start simulating it through with ChatGPT.

I would try to simulate it as far down the road, as many years down as I could — to make sure it would work before I even launched it.

I did this over and over and over.

2 | Realization #1: The Power of Conversations

It wasn't until I just got frustrated with it — let it go — and then started posting on Substack, that I landed on the two words, Corporate Dropouts.

And then, I just started showing up to meetings like you see on my Zoom right now, it says “Brad - Corporate Dropout.”

Then people started saying, “Hey, I'm a Corporate Dropout!”

That taught me an important lesson, that connection over content or conversation over content, always, is my priority.

But you know…

…you get into Substack land,

…and then you start getting subscribers,

….and then you feel like you gotta be on the hamster wheel of putting content out.

And so content started winning out again, but I had my Wednesday WaterCooler chats to go have conversations and my podcasts.

So I was still doing conversations, but still doing a lot of content.

And they were just kind of at odds.

I think what I realized again and again in December was that it was the conversations that were driving Corporate Dropouts forward.

It was the conversations that people were enjoying, not the content, per se, like the recaps and the podcast write ups and all that stuff I was struggling to write.

And people that were showing up to my meeting, I kept trying to do breakout rooms and provide quizzes and all this content, like to try to help them make this transition as a Corporate Dropout.

They kept telling me, we don't want to be in breakout rooms, we want to be in a conversation with you.

We want you to facilitate, we want you there.

They wanted me to be there and be part of the conversation.

Where… I was trying to let them go have all the conversations and I was trying to use my time to provide all the content.

Long story short, that was my takeaway from 2024.

→ Always prioritize conversation over content.

3 | Realization #2: Moving Beyond Automation

Now going into this next year, I thought, “okay, what do I need to learn to prioritize in 2025?”

As you start to get into content creation, running a Substack, and my list of things I've committed to, I start feeling spread too thin.

I automatically start going to, okay, “what can I automate?”

What can I automate to do some heavy lifting so that I'm not so bogged down and I can get back to having more conversations?

I got twisted off on a bunch of automation stuff.

There were two podcast episodes where I used Descript to do some automation and heavy lifting with the AI.

The sound came out horrible… horrible!

It lost a lot of the humanity, the conversational stuff that we as humans do, the AI just took it all out.

When I went back to do the podcast this week, I said, "okay, no automation and I'm going to focus on the conversation again.

I listened to the podcast episode in its entirety.

Then I went through myself and found the pertinent moments, the clips that were resonating with me on a deep level and surfaced those, where I was trying to use ChatGPT and Descript to do all that for me.

I kept all the ums and ahs in it and all the laughter and all the awkward moments, all the silent pauses.

And I'm really, really happy with the podcast episode today.

It feels good to me. I'm very proud of it and I feel like I preserved the conversation over the content in that sense.

What emerged from doing less automation was more authenticity.

My focus in 2025, and it may take me the whole year, it may take me 10 years, I don't know...

... is to… figure out a way to continually prioritize authenticity over automation.

Putting together my content strategy for 2025 and keeping that in mind...

…When I first started looking at my content strategy, I started looking at “what can I automate here!?!"

What can I have ChatGPT do for me or Descript or some other AI tool do for me in the whole content ecosystem I've got going on with podcasts, notes, weekly recaps, newsletters, I'm posting to LinkedIn, commenting on people's posts...

Okay! What can I automate here!?!

I started down that road and it just took all the authenticity out of it.

So I just threw that away and started again.

The last couple of days, it's just been kind of churning in the background and I've been having some ideas about how to do this.

The linchpin in this whole thing is...

“I'm addicted to ChatGPT “

…and I'm addicted to all these tools that we have.

It's just too easy to sit down on my computer and go, "write that for me".

There's a nice glowing screen with the words. "How may I help you?"

“You may not help me anymore!”

My pledge to myself is going to be...

My newsletter this year will not be written with ChatGPT, I will not load anything into ChatGPT.

The only thing I will use ChatGPT for this year is brainstorming, because it is a great brainstorming tool and partner, and if I need it to interview me to pull something out that I'm having a hard time articulating.

I had to start thinking, "okay, what is my source of truth here in what I'm doing?"

→ My community is my source of truth... not ChatGPT

If I want to go get a truth, the pattern interrupt there is, "go to your community, ask them what they think, or start a conversation with somebody in your community."

As opposed to go start a conversation with ChatGPT or any other AI tool or even Google.

That will maintain my focus on conversations... that's my source of truth.

And then I thought, "okay, I feel this urgency to get things out sometimes."

I'll have something come from deep inside and it just bubbles up and it's like, okay, it needs to come out.

I thought, "well, what is the quickest way to get something from my heart through my brain into somebody else's brain and to their heart?”

The quickest way I can do that, that's not sanitized, right?

So it's just like me and you having a conversation right now….

I'm not sanitizing anything…

I'm just saying it as it's coming along…

→ And this right here, this conversation is what I want to try to produce as a form of content.

4 | Realization #3: Embracing Voice Memos

The quickest way for me to do that — and I had forgotten this — is to just go on a walk and start a voice memo and talk about a topic.

I went out and experimented with this yesterday and I riffed for like 40 minutes on a topic and it just recorded wind because it was really windy.

I couldn't use it… but that's okay.

It was a good confidence builder.

For my Substack newsletter, I'm going to change the name from "Corporate Dropouts" to "The Corporate Dropout."

It's going to simply be a weekly newsletter of me reflecting on what's going on in the community that week… from the WaterCoolerCalls, from conversations I've had with people in the community.

I'm going to let my inner compass and radar surface, the themes from those conversations instead of ChatGPT.

I'll just go out on a walk and riff on it for however long.

I need to shorten it to probably something more like 10 to 15 minutes.

It's so easy now, on an Apple iPhone, I'm sure it's the same on a Google or an Android, you do a voice memo and it transcribes it right there for you.

It doesn't have to touch an AI tool.

I can go post the audio immediately and the transcription and I'm done.

That's my newsletter every week.

When I'm feeling that urgency, like, "Oh, the community is talking about this, I'm vibing with the community on this, it's coming up on multiple fronts, I'm seeing this theme."

When I feel that urgency, I can just get it out and I can just put it out and it's there.

(If you know someone I should be looking at or studying to improve my ability to freely express myself online as a community host - please point me in their direction. I would be VERY grateful)

5| Lastly, An Invitation To Hear More Corporate Dropout Stories from Cubicle Captives, Escape Schemers, Brave Leapsters, and Self-Made Sages

While you’re waiting for the next issue, here are three recent Corporate Dropout Stories podcast episodes I think you might enjoy:

* S1E7 | Can I Redesign My Career to Fit My Life? | Kate Thompson

* S1E8 | How Do I Stop Doubting My Intuition? | Mila Popovic Geoui

* S1E9 | Can Creativity Save You From Burnout? | Tyson Kartchner

Pick one to start with and dive right in.

I’m honored to have you as a subscriber, and part of a small but mighty community of purpose-driven professionals dropping the corporate.

Lastly, *HIT REPLY* to let me know what brought you here - even just a few words would be great. I read every response personally - and I’d love to hear from you and say hello. (And this is the fastest way to whitelist this email to ensure the next issue lands straight in your inbox…)

Until next week,

Onward!

Brad 8-)

[email protected]

TIMESTAMPS:

01:15 The Quest for Perfect Content

02:26 Realization #1: The Power of Conversations

04:25 Realization #2: Moving Beyond Automation

09:47 Realization #3: Embracing Voice Memos

11:51 Lastly, An Invitation To Hear More Corporate Dropout Stories from Cubicle Captives, Escape Schemers, Brave Leapsters, and Self-Made Sages

13:27 Encouragement from Dr Donna Blevins to Be Authentic