“Holy shit, I’m doing it again.”

This is an actual thing I wrote in my journal this week. As I sat there reflecting on why my business feels like an unwieldy, overwhelming mess, my uncanny ability to self-sabotage came into full view.

So friends, I have a confession to make.

My name is Rob, and I’m addicted to over-complicating things. For years, it’s been my drug of choice for feeling smart and productive, when all I'm really doing is avoiding the scary, vulnerable work of growth. I use complexity to run from uncertainty and imposter syndrome. And in doing so, those negative emotions only become louder and more persuasive, leading to further complication. It's a vicious cycle.

This pattern rears its ugly head in every context where I'm trying to grow and evolve. Health, relationships, business. I've over-complicated all of them.

But here’s the thing. This isn't some new revelation. In fact, until this week, I was under the impression I’d already done the work to stop this madness.

Round 1: The Initial Reckoning

In January 2021, after a few months of escalating complication, I saw this pattern for what it was—an elaborate way to avoid my most important work. I was insecure, and I hid in complexity.

With that insight, I took some dramatic steps to simplify my business life.

I streamlined the editorial vision of Ungated. I pared down my beastly tech stack into a small handful of simple tools. And I set out to be prolific and imperfect with my writing, instead of focusing on epic, longer pieces.

On top of all that, I started operating from a philosophy of experimentation and iteration, instead of trying to meticulously strategize everything from the top down. Basically, I committed to following my curiosity and learning along the way, instead of expecting myself to have all the answers right now.

And lemme tell you, all of those efforts have done their job. They've helped me get out of my own way, and evolve my business and thinking in ways that wouldn't have been possible even just two years ago.

But yet, here I am. It's clear I've found new ways to over-complicate, and I'm back to feeling overwhelmed and stretched thin.

So this week, I did what I always do when I'm feeling overwhelmed. I started journaling, getting all of my various commitments out of my head and onto the page.

For posterity, here are the various things weighing me down in my business right now.

  • First up, I shifted my business into the Gift Economy. Even though this happened months ago, it’s still causing more uncertainty and self-doubt than I've ever experienced. It's nuts how heavy this decision still feels.
  • Despite telling myself writing would be my sole focus this year, I re-committed to producing micro courses. Most recently, I released Oasis Building 101, and I've also got another one in the pipeline that I am VERY excited about. I keep telling myself these will be simple and quick to make, but they never are. And that's where the problem is.
  • For months, I've been building out an "email oasis" in the background. The goal is to use ConvertKit (Rob's affiliate link) in cool, delightful new ways, and repurpose a lot of the writing I've done over the years into small, self-contained "email adventures."
  • Also in traditional Rob fashion, I'm thinking about podcasting, building a YouTube channel, doing twitter threads, public speaking, and all sorts of new channels and mediums for spreading meaningful ideas. I've come to realize that many of the people I want to serve with Ungated may not engage with a 2,000 word blog post, but they might with a YouTube video. So that's top of mind for me right now.
  • Oh, and I even started a new personal blog for things that don't quite fit on Ungated or Citizen Within. Ironically enough, my first post was about how over-complicated my writing workflow is.

All of this is in addition to trying to publish more, make new internet friends, and the coaching work that now brings in most of my revenue. Point being, there's a lot going on.

What's funny, though, is these projects don't strike me as the same kind of over-complication as before, which was primarily driven by insecurity and fear.

This is something new.

Round 2: Long Games, Played Too Quickly

If I had to boil down my current overwhelm into a single sentence, it'd be this one. I have a lovely long-term vision of what I want Ungated to be, but I'm shooting myself in the foot by trying to build it all at once.

That's what I see when I look at everything I wrote out above. I genuinely want to build an Ungated Universe that includes...

  • A growing library of tiny, delightful micro courses, all available through the Gift Economy.
  • An email automation system that repurposes all of my best writing into small, topical adventures.
  • All of the core ideas of Ungated, expressed across different mediums and formats.
  • A vibrant, nurturing community within the Ungated Collective.
  • And probably a book or two, independently published.

All of these things feel intuitively correct, like essential parts of a greater whole. That's why I've started pursuing all of them. Not out of avoidance or fear, but because they all feel exciting and meaningful.

But it won't come as a surprise that I'm both overwhelmed and frustrated by my lack of progress. By trying to knock over all the dominoes at once, instead of tipping over the first one, I'm sabotaging myself in the same way as before. Sure, I’m in a better place emotionally, but functionally, the sabotage looks identical.

What's most important right now?

This is one of my favorite questions, both for coaching clients and for myself. Not only does it invite you to consider your values and the games you're playing, but it forces you to prioritize the possible steps in front of you.

When I ask myself what's most important right now, the answer is clear. Writing and publishing.

After a year in which my worldview completely changed, none of my old writing about creative entrepreneurship feels true to me anymore. That's not to say any of it is "wrong." Just that it's not representative of who I am going into this next phase of life.

So for me, the most important, urgent work is to document this evolution, and share what creativity, marketing, and online business look like through the Ungated Worldview. I need to go on a publishing frenzy.

Once the ideas have been expressed, not only will it be a weight off my chest, but it'll be easier to execute on the rest of my vision. This is the first domino that will make all others easier to topple. And by focusing on one important thing at a time, I suspect the long-term vision will come to life more quickly.

The lesson for me is simple.

Simplification isn't a one-time thing, but an ongoing process. When you're engaging with the world, there will always be new ideas and opportunities. And some of those opportunities will indeed be worthwhile.

So I need to get better at not immediately saying yes to things that feel exciting. Because when I do, this is where it leads. Right back into the grasp of over-complication and overwhelm.

And with that, I'm putting most of my projects on hold for a bit. It's time to get back to writing and publishing. A lot.