Go Make Something Embarrassing

“If you’re not embarrassed by the first version of your product, you have launched too late.” (Reid Hoffman). This is one of my all-time favourite mantras to instill in the entrepreneurs I work with. Don’t wait until it’s perfect, even though that feels safer. Don’t wait until you have all the answers and your idea is polished and pretty. Don’t wait until you feel ready. Launch before; way before all that. Run quick, cheap experiments to test your hypotheses and keep iterating. It might feel all kinds of uncomfortable, but it’s the best way to make sure you’re actually building something people want.

Well, this autumn (2020) I’ve been walking my talk. 

I’ve worked with people 1:1 for a long time, but for a while now I’ve been chewing on the idea of expanding to small groups. I spent the summer conducting research interviews with purpose-driven people in transition, learning what their main challenges were, and what they’d find most helpful in terms of support. 

And across the board, they told me: “a group coaching programme”. 

My interviewees were proactive and committed people who cared deeply about contributing to the greater good, but didn’t know how to move forward. They felt overwhelmed by too many options, held back by self-doubt, lost and isolated in the middle of all their questioning. They’d tried to think themselves out of this, but they’d just become more paralysed. 

They knew that continuing to think about their transition wouldn’t work. They wanted a live programme, working alongside others, with professional support. Income was uncertain and money was tight, so a lengthy package of 1:1 work would feel tricky right now. But to work in a small group alongside me? They’d love it! 

Great, I thought. I’d learned what they wanted.

But there was only one snag. I didn’t know how to go about delivering it. 


While I’d run lots of workshops and facilitated many events, I’d never yet worked with this kind of format.

And so my first instinct was to go away and build it in private. Behind the scenes, I’d map out what I thought would be helpful, do lots of research, create modules and exercises, then present it as a ready-made solution.

And the best part? Even if not a single soul bought it or was helped by it, nobody would ever know!

It was low-risk and low-visibility. I loved it. 

Then I remembered Reid’s advice. 

Did I care more about showing up as professional and put-together, or about serving my people?

Paul Graham writes

“One of the biggest things holding people back from doing great work is the fear of making something lame. And this fear is not an irrational one. Many great projects go through a stage early on where they don't seem very impressive, even to their creators. You have to push through this stage to reach the great work that lies beyond. But many people don't. Most people don't even reach the stage of making something they're embarrassed by, let alone continue past it. They're too frightened even to start.”

I didn’t want to miss out on creating something great because I was afraid of making something embarrassing. 


And so, for the sake of the people I want to serve, I’ve completely turned the tables. In September 2020 I launched the beta run of my group coaching programme. I advertised it as a prototype rather than a finished product, and invited beta testers to help me build it as I went: telling me what would be most helpful week by week, and giving me feedback as I went. 

And how’s it been? I hear you ask.

  • Have I fallen flat on my face?

    More times than I can imagine. I now have very scabby knees. It’s felt vulnerable, exposing, and messy. 

  • Has it been risky?

    Yes and no. It’s definitely felt emotionally risky. There are moments that I’ve found very uncomfortable. I’m someone who likes to have my bases covered, so I’m pushing myself to trust the process that I believe in for other people.

    And despite my emotional risk, in reality the stakes are very low. I’m explicit that it’s a prototype. And so I attract people who find that exciting, who know I’m learning and want to help contribute at a budget-friendly price. I get to under-promise and over-deliver. 

  • Have I shown up and served my people?

    Heck yes. Far more than if I’d played it safe and small. I’m being courageous for the sake of others’ growth. This way, I actually help them get where they want to go, rather than assuming I know the way. And by publicly stepping out of my comfort zone, I give others permission to do the same. 

  • Will I look back and be embarrassed at the first version of my launch?

    Honestly, I’m already embarrassed! :) There are so many things that I’ll already do differently in my next prototype, which — at the time of writing — starts in January 2021. I’ve made lots of mistakes. That means I’m doing things right. 

  • Have people got huge value anyway?

    Absolutely! Sure, not everything has landed. Sometimes I try things that don’t work.

    But there are huge benefits to the format, too. People get to design the programme so that it’s tailored to their exact challenges. They get to build relationships with other purpose-driven people around the world (and get access to their network). They get to work with me at a lower price point than our 1:1 work. They’re getting real-life results — even though it’s the first time I’ve done it. 

As Paul Graham continues: “Imagine how much more we’d do if we weren’t afraid of making something lame.” 

I know that fear has held me back from launching all kinds of ideas in the past. 

This time, I’m choosing not to listen.


Something to chew on: What’s something you’ve been sitting on for a while, hesitating to actually put out in the world? What’s one cheap and easy experiment you can take to make it just a bit more real? 

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A Purpose-Driven Case Study: Product-Market Fit