Progressive Experimentation

Reflections on going "all in" with business experiments

When I ran my Gift Economy experiment a few years ago, the biggest mistake I made was going all-in right away. Like, I literally woke up one day and flipped a switch that made all of my products and services available on a "choose your own price" basis. Pretty bold!

I say this was a mistake for a two reasons. First, it felt terrifying and existentially perilous. Emotionally, that decision was like leaping off a tall building while only having 60% certainty that a net would appear. To say that experience fucked with my head and heart would be an understatement.

The more I embrace experimentation as a way of life, the more I want each new experiment to feel simple, enlivening, fun. If an experiment feels like a matter of life and death, I’m more likely to overthink, over-plan, and second guess. Bottom-up businesses work best when we iterate quickly, through the accrual of tiny experiments that feel alive. But when we’re stuck in a mindset of having to go big or go home, the aliveness often disappears, and we end up running fewer experiments and dramatically overthinking the ones we do run.

The second reason is that it was a ton of work to make a full switch to this business model, given that I already had multiple products and offers. The amount of copy I had to write, automations I had to build, checkout forms I had to update, etc was fairly substantial. It took several weeks of tedious work to get to that “flip the switch” moment. This also means that, once I decided to end this experiment, it was a ton of work to undo it and revert back to normal. Truthfully, I knew within two months that I didn’t want to keep running my business this way. But I was uncomfortable with the idea of undoing all my initial work, and backtracking on my bold proclamation. So I ended up running it for five months.

I don't regret my foray into the Gift Economy at all. It taught me some valuable lessons about who I am and what I value. It also gave me ample opportunity to work on my relationships with money, generosity, and surrender. That said, I suspect I could have learned those same lessons faster, with a lot less work and emotional turmoil. If I were starting over, I would keep things simple, and start by rolling it out for one product or service, perhaps “choose your own price” coaching sessions. If that felt good after a month or two, then I would start expanding it into other areas of my business. If it felt bad, I would have scrapped it quickly. No hard feelings.

What’s funny is that I’m still working my way into fairly radical business and marketing models. Non-coercive marketing, when fully implemented, is just as radical as gift-based economics. But frankly, it doesn’t feel wise to make giant leaps into the unknown anymore. Instead, I’m progressively experimenting and iterating. One alive step at a time.

---

Rob's Daily Invitation

This is an excerpt I pulled from my upcoming project, The Forest, which I'm calling a ''choose your own adventure" guide to 1,000 true fans. As I've been working on this project the last few weeks, most of the writing hasn't been like this. Instead, it's been about designing an ecosystem of experiments and inquiries and other hands-on activities to help you weave these concepts into your own life and work. It's easy to fall into the trap of consuming more more more. But the real work of building a joyful business comes from following what's alive for you, progressively experimenting, and iterating your way towards a life that is uniquely your own. Care to come explore The Forest with me?