Prefer to read (or listen to) this newsletter in your browser? Click here.

💡 The Big Idea: How I Learned to Name and Face the Fear That’s Been Running My Business.

Last week, I attended The Growth Intensive by Darrell Vesterfelt & Corey Wilks. Darrell is a growth strategist who helped scale ConvertKit (now Kit) from $1m to $7m in 15 months, and Corey is a clinical psychologist who helps founders break patterns of self-sabotage.

I got to spend time with both of them when I was at Sponsor Games earlier this year, and they’re both good people. When I heard they were hosting an event together, I was immediately interested.

TL;DR - the event was amazing. But honestly, I knew Darrell & Cory would deliver the goods.

I expected to get clarity on what might be keeping me stuck in my business.

But I didn’t expect to be thrown into an existential crisis.

(Note: This newsletter will be a little bit different because I’m going to share some very personal things that came up while I was there. My hope is that you’ll be encouraged to confront your own Horseman of Fear and realize that you’re not alone in doing so. If it resonates with you, let me know!)

My Horseman is The Fear of Ridicule

On day one, Corey walked us through a framework he calls the Four Horsemen of Fear:

1. Fear of Failure (keeps us from ever starting)
2. Fear of Ridicule (keeps us from taking chances)
3. Fear of Uncertainty (keeps us analyzing)
4. Fear of Success (causes us to abandon our course to protect our identity)

He explained that these four fears tend to manifest when we’re emotionally invested in something. Pretty much every self-sabotaging behavior for a founder, from perfectionism to procrastination to shiny object syndrome, can be traced back to one of these four fears.

Right at the beginning, we had to complete a pretty intense exercise: figure out which one is yours, and trace the lies it’s been telling you back through the decisions you’ve been making.

At the beginning, I was sure mine was Fear of Failure. I’m still relatively new to running my own business, and that felt like the obvious answer.

Turns out it wasn’t.

As we progressed through the exercise, I became increasingly uncomfortable.

Because my Horseman is actually Fear of Ridicule.

Here’s what gave it away: I create content in the PKM/productivity space alongside people with MUCH bigger followings. When I think of Second Brain, I think of Tiago Forte. When I think of Obsidian, I think of Nick Milo. People whose work I respect, whose audiences are massive (at least compared to mine), and whose presence is impossible to ignore.

And somewhere in the back of my head, I’ve been secretly afraid that they — or someone like them — are going to look at what I’m doing and just tear it apart.

The whispers go something like this:

• You don’t really know what you’re doing.
• You don’t belong here.
• You have nothing of value to contribute.
• You’re not qualified to talk about this.

Honestly, I’ve been hearing those whispers for a long time. But after attending The Growth Intensive, I finally had a name for them.

The Lies Show Up in My Work

Once you identify your Horseman, you can start to see its fingerprints everywhere.

Here’s how Fear of Ridicule has been shaping my work without my realizing it:

I struggle with publishing anything that’s not “amazingly unique” or completely original. I know I need to publish YouTube videos regularly, but I tell myself I shouldn’t publish until the idea is so original that no one could possibly dismiss it. The result is that I battle imposter syndrome on almost every video I make, and I tend to drag my feet on my best ideas until someone else does it first (which just amplifies the imposter syndrome).

When something I make doesn’t go viral, I take it as evidence. I’ve never really had something pop off the way others have. As a result, the voice in my head is happy to report: See? I told you you don’t have anything new to add. That leads to me feeling like I can’t actually help the people I’m trying to serve. Of course, I do also have actual emails and testimonials that say the opposite, but my brain never brings those up and chooses to highlight the negative instead.

I feel compelled to cram in more. I see what other creators are doing, and decide I should be doing all of it too. This causes me to end up going down research rabbit holes that look like work but really aren’t. Meta work like this is one of the favorite hiding places of the Fear of Ridicule, and I fall into it often. It feels productive while keeping me safe from being seen.

I temper my real opinions. I soften my framing because somewhere in my head, my Internet heroes are reviewing (and criticizing) everything I make. I don't want to make them mad and get kicked out of the room.

Once I named all of this, I couldn’t unsee it. And I needed to figure out what to do about it.

The Product-Market Fit Mirror

After lunch, Darrell walked us through a different kind of diagnostic: a product-market fit gut check.

The questions were simple:

• Who are your best customers?
• Who are the ones who left?
• When someone interested in your work decides not to buy, who do they go to instead?

But the one that really messed me up was:

If your business disappeared tomorrow, who would be devastated? Who would be fine and just find an alternative?

A lot of people find me because they’re looking for help with Obsidian. They download my free Starter Vault. They watch my workflow videos. They want a better system for the notes piling up in their vault — and to be clear, that’s a real, valuable problem to solve.

But it doesn't mean I should be solving it. And it’s an easy problem for me to focus on when the Fear of Ridicule shows up.

If I'm honest, I've always wanted to do something bigger.

What really lights me up is helping people tap into their innate creativity. I know that work intimately, because at one point I said “I guess I’m just not creative” — and I was wrong. 18-year-old Mike may have come looking for help with a tool. But what he actually needed was someone to believe in him and help him make something of value from his notes and ideas. He needed permission to create, and a system to help him do it.

I can’t go back and give that to him. But I am uniquely qualified to do it for someone like him.

For me, the work I’m able to do that can actually change someone’s life — going from “I’m not creative” to publishing regularly, building a body of work that compounds — is what the tool was always supposed to be in service of. It’s what happens after the system is humming.

And it’s not what I’ve been leading with.

I’ve been showing people the entrance and forgetting to point at the house. The people who walked in and stopped at the entrance have been getting a smaller version of what I could give them.

No wonder I've been struggling to find product-market fit.

That should have been the most clarifying thing I’d heard in a year. Instead, it stung. Because the people I most want to help most have been hiding inside the audience I already have. But I’ve been too scared to lean in and help them to the best of my ability.

And that kind of threw me into an existential crisis.

Obsidian Was the Vehicle, Not the Destination

For years, I’ve been positioning myself as “Obsidian Guy.”

It started when I was going through Ali Abdaal’s Part-Time YouTuber Academy. I was making videos on productivity and creativity, and realized that whenever I mentioned Obsidian, my videos got about 10x the views and comments.

So I made more Obsidian videos. And I’ve been making Obsidian videos ever since.

But Obsidian was never the destination. It was always the vehicle.

At The Growth Intensive, I realized that I’ve slowly shifted my focus from the transformation to the app.

And I’m not OK with that.

From the very beginning of my YouTube journey, I had a coach who told me I’d eventually have to transcend the tool. Not abandon it, but step outside it.

I believe that time has come.

What Obsidian has always been for, in my work, is helping deep thinkers publish their ideas. Helping people who once said, like me, “I’m just not creative,” discover that they are. Helping overwhelmed overcollectors go from consuming endless productivity content to making something new out of the things that they've captured. Helping aspiring writers to ship a body of work that’s uniquely theirs.

That’s what my LifeTheme (personal mission statement) is all about:

That’s what lights me up. That’s the thing I can do better than just about anyone in the world.

And that’s what I’m going to focus on.

The Line Under the Line

There’s one more thing I want to be honest about, because it’s the part that quietly ties everything together.

When Corey walked us through Fear of Ridicule, my mind went immediately to Tiago and Nick. The big names in my space. The ones I imagine watching from the wings, ready to show the world I’m not the real thing.

But Tiago and Nick are abstractions. I’ve met both of them. Nick has become a good friend of mine. And I’m pretty sure that in any plausible version of reality, neither of them would ever tear apart my work.

The real fear is actually even older than that.

You see, my dad started his own business and was very successful. I worked in it for a while, and I chose to walk away from it. For the last few years, I’ve been trying to build something of my own.

And some part of me has been quietly afraid ever since that walking away was a colossal mistake.

That choosing my own path was an act of arrogance I hadn’t earned. That I might fail and have to come back and admit I’m not good enough.

So in truth, Tiago and Nick aren’t the ones whose approval I’ve been quietly chasing. They’re convenient stand-ins for the Horseman of Ridicule. The real audience in my head is one person, and he’s not in the PKM space at all.

I don’t know that I can fully think my way out of that one. But naming it helps. So I’m naming it.

And taking it seriously means I can’t keep letting that fear pick the category I show up in.

The funny thing is that by inadvertently trying to avoid this, I’ve ended up playing it safe. As I do that, my work becomes more commoditized. I make less of an impact in the lives of the people I can actually help, and I become more likely to fail in the end because of it.

Ouch.

It's a self-fulfilling prophecy, and I can’t afford to do that anymore. If I really want to live out my LifeTheme, it’s time to get clear and go all in.

Here’s What I Actually Do

I’ve been reflecting on what happened for the last couple of days, trying to nail down who exactly I’m best suited to help. And I think I’ve finally got it figured out:

Deep thinkers is who I’m for. People who read a lot, think a lot, and sit on more good ideas than they ever ship. People who aspire to be creative but don't think they are. If you’ve ever closed a book feeling lit up and then a year later couldn’t remember what made it matter to you, maybe that’s you! This is my audience because this was me.

Publish their ideas online is the transformation. Not “master Obsidian.” Not “manage your notes better.” The thing that’s actually missing for the people I can serve best isn’t more input. It’s the output. It's the system and the courage to put their thinking out into the world consistently.

Creativity Flywheels is the mechanism. The five-stage process (Capture → Curate → Connect → Cultivate → Create) that helped me unlock my own creativity is the same thing that can help anyone.

This isn’t a brand new direction. I’ve been talking about The Creativity Flywheel framework for years, but I didn’t have clarity on why it seemed so important to me. It’s an evolution of the work I’ve actually been doing all along, just with a name I can finally point at.

That’s who I am. That’s what I can own.

The Bottom Line: What Would You Do if You Weren’t Afraid?

The Growth Intensive didn’t hand me a new business model. It handed me an honest mirror, revealed the fear that’s been keeping me small, and gave me the courage to start saying out loud what I actually do.

For years, I’ve been talking about Obsidian because the tool felt safer to talk about than the transformation underneath it. Fear of Ridicule wouldn’t let me name what I actually want to do. The intensive gave me language and permission to claim it anyway.

If you’ve been carrying around your own version of this — the sense that you’re showing up as a smaller, safer version of yourself because of what someone bigger might say, or used to say — I’d encourage you to ask the same question I had to: What would I be doing if I weren’t worried about being ridiculed for it?

That answer is probably your actual work.

I’m going to go do mine.

— Mike