Radical experimentalism — A more fun approach towards living your best life.

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Over the past few years, I’d invested over $10,000 in various different dating-related programs, coaches, and trainings and, yet, I had now found myself feeling lonelier than ever.

The experiment was — what would it be like to have all of the amazing relationships I could ever hope for with a bunch of amazing women all around the world.

In order to help realize that, I hired a dating coach that I’d initially invested about $1500 in; I then took a retreat that I’d invested another $3500 in; then I took a bunch of different courses, each of which ranged from $95 to $295, and sometimes even more.

Some of them I found to be incredibly useful, others were OK, and the worst ones completely distorted my image of myself.

And yet, for better or worse, it all worked — I felt myself, at the end of all of that, feeling far more confident in my relationship-building skills and my ability to meet cool, interesting people who I wanted to date.

So as I sat there on the uncomfortable, dirty metal park benches in the middle of Washington Park in Denver on a warm October day with my head in my hands, I found myself feeling lonelier than I’ve ever felt in a long, long time.

I’d just been dumped by somebody who had, all along, told me she was emotionally unavailable and refused to believe it.

Another long-distance relationship had sputtered out when we both simultaneously realized that we’d never live in the same state. And then the one woman who actually seemed to give a shit about me all but stopped talking to me when I told her I didn’t feel the same.

The one common theme among all of my relationships over those few years was that I’d continued to chase unavailable women, never once asking myself, why am I so drawn to these people?

Even though finding those women had grown exceptionally easy, building the sorta fulfilling relationship that actually brought joy and satisfaction to my life always slipped through my fingers.

So, as I thought long and hard about what I was doing in my life, I decided to start looking into one final relationship-focused experiment: therapy.

Dozens of sessions, and several thousand dollars later, I can honestly say that it’s been one of the smartest investments of my adult life.

It hasn’t been until very recently that I’ve started to map out my life in a more thoughtful way, looking at skills and interests and hobbies that I want to get better at.

Things like building and growing my personal relationships with friends, learning a new language and dating in a totally foreign culture, building a sustainable business around skillsets and software that I’m stoked to teach others, and dozens of other ideas.

I view these as experiments — everything I pursue is, for better or worse, an experiment, because all of those things have a chance to fail.

Moving to a new country? Can go horribly, horribly wrong. (See: covid, etc.)

Starting a new relationship? Often ends in heartbreak.

Building a new business? 90%+ of the time, it’ll end in failure.

The point is that when I view life as a series of Radical Experiments, I often find myself feeling more excited, happier, and energized by my day-to-day.

Beyond that, I think the worst position you can ever put yourself in is that something you’re trying needs to succeed — that’s too much pressure for anyone to handle.

Experiments are scary, in that most of them fail, but they’re exciting in that the end-result is totally unknown.

Maybe learning how to use a Pioneer Mixing board will make you quickly realize that DJ’ing probably isn’t for you, at least not right now.

Or, maybe after several sessions and lessons you quickly start to realize that YOU F**KING LOVE DJ’ING and it becomes a new career that you’d always wished you had.

Who knows. That’s the point.

In the article I’m going to walk you through my process of Radical Experimentalism and how you can put this into play in your own life.

Step 1. Create a mind map for your Ideas.

I don’t care much about helping people grow their revenue — to me, that feels like something that any snake-oil salesman can do from his parent’s basement, and something that I’ve been sold far too often.

What I do care about is working with people in order to enable them to spend as minimal time as possible on the things they don’t enjoy, and as much time as possible living their best life ever.

To me, that’s exciting — and a way in which that goal is often realized is through revenue growth, which is why you’ll find me working directly with sales-teams in order to make that happen.

Typically, dreams often start in the form of a mind-map — I’ll start with a single-sentence that explores the why behind what I want to do, and from there, things get weird.

I like to break my ideas up as such:

  1. The Rocket (Ideas) — This is the core behind what you’re doing, and why it matters. The thing that gets people excited to work with you, or that gets you excited to do the thing you’re about to embark upon.
  2. The Fuel (Revenue, Metrics) — This is how you push your idea-rocket into orbit. If you’re a business-owner, the best fuel is revenue because that keeps your idea afloat and gives you the flexibility to execute on those things.
  3. Astronauts (Partners, People) — In order to realize an idea, you need supporters. People who will either invest in your ideas, help you push them out into the world, or who are exceptional craftsmen at making those ideas come to life.
  4. More Rockets (Hobbies, Leisure Activities) — I also create an area for building More Rockets — finding inspiration for future ideas, and ways in which I will realize that in the form of leisure-activities, exercise, mentorship, etc.

Here’s a detailed video and breakdown of how I go about that:

Step 2. Identify your risk, and pick and experiment (or three).

A few years ago, I realized that in order to create opportunities to build wealth, I must first invest a ton in learning and experimenting.

That entire time, I never really had an criteria for how I’d go about making investments — everything always felt painful.

Even if I was simply buying a microphone to start a podcast for a few hundred dollars it always felt painful.

Now, I have a criteria for how I go about taking risks and investing in things — I will never invest more than 5% of my total net worth in a single experiment.

This forces me to think small, but also allows me to go about experimentation in a way that is freeing and enabling.

The worst-case from any experiment is that it totally fails, and you gain nothing.

But often, I find that even if I don’t earn back the money that I’ve invested into something — whether it be coaching, training, a course, equipment, or something else — I often learn a lot through that process.

Over the years, I’ve grown my expertise in sales, marketing, videography, productivity mastery, and dozens of other areas.

Not to mention the countless tools that I’ve picked up through those trainings — Final Cut Pro X, Notion, Miro, investment programs, etc.

And I’ve developed a much more empowering mindset — even if the experiment doesn’t pay off directly, at least that investment is being used to support an amazing creative.

So, next identify your risk level — that could be 5% of your net worth or, if you simply don’t have the resources to invest in something, maybe that risk is social capital or looking bad.

And then finally, from your Mindmap, pick an experiment or two that you’d like to realize over the course of the next 3-6 months — for me, I picked a ‘Relationship-focused’ experiment that involves a bunch of postcards and one WHACK adventure, and then I hired a team to help film a proof-of-concept for The Michael Kilcoyne Experience in Kyoto.

How I choose these is typically based off of what I’m most excited about — since I’ve been thinking a lot about my friendships, I wanted to pursue something in that realm.

And as for the show, a good friend of mine has been encouraging me to create a travel-related show for months, and since I’d just started getting more and more excited about it, I decided to just go for it!

Both are currently being put into action, and I’m incredibly excited to see what turns out 🙂

Step 3. Track experiments and learnings and double-down on what’s working.

Once I’ve identified those experiments, I start to break them up into specific goals and projects in Notion — I use a template called The Gamification 2.0 Template, which you can access here.

(WARNING: It’s for advanced Notion users, but it includes various entry-level variations.)

And then I basically start dumping high-level Goals, breaking those up into Key Results, and then smaller projects.

Here’s what my Life Roadmap looks like, for the next few months:

Some goals are huge — we’re talking months-long undertakings, that take several projects to realize.

Some are much, much smaller, like building + launching my website and getting my first 500+ visitors.

As I continue to go through and work on and launch experiments, I try to keep an overarching view of what’s worked, what hasn’t, and provide as much feedback as possible on that.

I track that through my ‘Trainings’ template, which keeps track of the specific courses and teachings that I’ve gone through or am going through, and includes a bunch of notes on what’s been effective, what I learned, and things like that.

Here’s a link to that database with a detailed review of each of the programs I’ve taken, and what I got from them.

When something has worked — either, I worked with a company and that resulted in positive revenue growth for them, or a show launched, or a marketing approach worked — I try to double-down on that as much as humanly possible.

If it’s a partner, I try to figure out a way to work with them more closely.

For example, I was recently on the official Notion HQ webinar with one of my favorite Notion-related coaches, Marie Poulin, a few weeks ago.

After that webinar, I told myself, I have to work with this person!

So we’ve been in communications back-and-forth for a while, trying to figure out better ways to collaborate together.

Win — win!

A typical MBA program costs anywhere from $60,000 to $100,000 — which boggles the f**king mind.

Over the last few years, I’ve invested pretty close to that on my own education — I’ve tallied close to $40,000 between different courses, programs, coaches, and other experiments — and through that I’ve been able to come up with a few lucrative experiments that have helped me generate a significant amount of income and many business opportunities.

The same can’t be said of MBA programs — sure, you’ll likely to graduate into a six-figure job working as a consultant or an investment banker, but then you’ve also just spent several years of your life working on theories.

The Radical Experimentalism approach is far, far more interesting to me — instead of spending years of your life in classes that you don’t give a shit about, which spit you out into a world that has completely changed since you entered it, you’re actively living your life and pursuing things you find interesting.

Through those processes, you’ll identify a lot of things you enjoy, many things you hate, but will also be learning on the fly.

To me, that’s a far more compelling way to learn about entrepreneurship, building relationships, or living the life you want to live.

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