#22. Optimism reversal

I met up with Fi Roberto last week for a drink in Highbury. We worked together for six months at GDS and had a wonderful product/delivery partnership.

As an aside, this was the first time we’d met in person. It felt so natural! I’ve found that working closely together on screens builds the same kind of rapport you get from face to face contact. Although it was definitely nice to have a drink and a chat.

We talked about the balance of our partnership while we worked together. Fi pointed out that I was always trying to push the team to do more ideas, bigger things, take more risks - and that she balanced this by helping me understand that we only had so much capacity, should do fewer things, and should work with the reality of the constraints we had. This was the core of our partnership. It worked because we trusted each other, talked LOADS, and found a shared path. I learned so much from working with Fi. And with Elisse before her.

But what made me stop and think was that it’s the exact opposite at CastRooms.

At CastRooms the core partnership is with my co-founder Mitali. In this partnership it’s Mitali that is pushing us to do more ideas, bigger things, take more risks - and me that’s constantly urging her to do fewer things and operate within our constraints! This partnership also works beautifully - again because we trust each other, talk every day, and make a shared path.

At GDS I was seen as optimistic but at CastRooms I’m seen as pessimistic. Yet inside I’m the same person, making the same judgements, with the same attitude to risk. What’s unsettling is that it feels like my identity has changed. My self-image was always that I’m super-optimistic until I started working with startup founders :)

Founding a startup needs someone with off-the-scale optimism like Mitali (or Ben at Local Welcome) to take that enormous leap. It might even be that these kinds of founders need to be blind to the true nature of the challenge. Or they’d never do it. I’ve been saying for years that I wouldn’t found a startup because I’m not made like that and I think it’s true. I needed Mitali to make that leap and only then corral me onboard.

Stepping back, it’s made me realise that an organisation’s appetite for risk has a huge impact on not only the kind of work that gets done but also how I feel about my own role in doing the work. I hadn’t understood this until now. In cautious places I’m a naive optimist. In gung-ho places I’m a stick-in-the-mud realist. It’s yet another example of how deeply the context of work changes my experience of it.

Anyway, me and Fi had a good laugh about my optimism reversal. And she pointed out that we’re going to need people like her and Elisse pretty soon if we’re successful.

I’m looking forward to the day when that’s true. For all the reasons.

Originally posted on Substack along with an intro/outro, Dan Hockenmaier, Happy Valley 3, Babel (again) and Jetty Broadstairs. Say hello or ask questions on @myddelton.