#19. Startup guilt
plus Facing Heaven, The Bear, Obviously Awesome, Babel
Hello!
My whole body is aching today because I spent yesterday moving two decades of clutter out of our loft. I am not used to grafting like that. We’d also stored a ton of house stuff up there to avoid moving it during the renovation. Fat chance! Our loft joists had bowed beyond safe limits due to some dodgy work by the previous owner and so had to be replaced. (Nothing to do with too much clutter, honest).
Two decades of clutter comes courtesy of the dubious luxury of having had non-functional storage spaces in the places we’ve lived. A damp basement, a cavernous space under a raised ground floor, and now this dodgy-loft conversion. I say dubious luxury because it’s allowed us to avoid making decisions about throwing things out. So. Many. Books. For someone that rarely looks back I have a remarkable hoard of keepsakes too.
Anyway. I’m breaking with my own self-imposed structure of two main topics today because the first thing I wrote turned out to be quite long. Also if I’m going to write more regularly this year maybe it’ll be easier if I don’t have quite such an over-engineered formula to live up to each week?
Startup guilt
We’re about to start raising money for CastRooms. 2023 is going to be a wild year for us. Make or break. But before that starts I want to spend a little time looking back.
One theme that stands out from 2022 for me is feelings of guilt. Before we started CastRooms I imagined our journey would be exciting and scary. But one of the dominant feelings that I ended up experiencing was various flavours of guilt.
So this is my weird story of last year in terms of rolling waves of guilt :)
From April to June we were figuring out our initial positioning in the market and planning the foundations of our product. I did lots of competitor research at the same time as firing up a user research pipeline and speaking to tons of DJs. My instinct was that I didn’t know the landscape well enough to build the right product or create a useful strategy. So I spent time exploring and asking lots of questions.
This was when the first round of guilt kicked in. From my second week at work. It was weirdly hard for me and Mitali to get up and running even though we’d been looking forward to this for six months. Our excitement at the open-road freedom of starting our own company didn’t magically translate into a sense of momentum. Spending time asking questions and exploring, rather than cracking on with ‘making things’, felt complicated in an unusual way. I think because the days and weeks were intimately connected to spending the actual limited money we had from our investors.
Looking back, it seems I forgot how difficult it is to form a new team, to build trust, to understand the competitor/user landscape, and to generate the shared understanding needed for progress and momentum. Of course it takes a while to find your feet. So despite feeling guilty for three months by July we were starting to run nicely…
From July to September we focused on building the prototypes necessary for our first tests with real users. We were making a multi-person experience where a bunch of people - some of them friends, some not - would gather online to watch and listen to a live performance from a DJ that they loved. A small online party! We wanted to make this experience from scratch to start running and observing test parties.
My guilt here was a user researcher guilt. Why was it taking us six months to test things with users when it’s possible to prototype and test in days? I had made a conscious decision not to test static mockups and a single-person experience because our riskiest assumptions were about behaviours in a group context. I felt that our biggest learning would come from prototyping a more realistic context-of-use and I accepted a ton of usability risk to get to this situation. But even though I’d made a conscious decision to do this I still spent six months feeling like I was ‘doing it wrong’.
Looking back, I’m OK with this decision despite six months of researcher guilt. We started test parties in September and the group behaviours we observed taught us all sorts of unexpected things core to our proposition. It’s true that we found usability issues that we could have caught earlier with static mockups. But in our extreme early stage startup I don’t think usability risk was the right focus. We were mostly interested in value risk and a little bit of feasibility risk. (Also I realised later that my user researcher guilt was ignoring the multiple customer interviews we were doing every week. It wasn’t like we’d done six months with no user research.)
From October to December we ran test parties every week and added in the final technical element of our product. Our test parties gathered a small crowd to watch a DJ they loved playing a live set - which turned us into small-scale promoters and meant spending a LOT of time on logistics. At the same time me and Tommy were building the final element we needed to complete our intended context-of-use. This would let us observe important behaviours before pitching in January.
The guilt during this period came from all angles. With limited time we chose to sacrifice important things - automated testing, multi-browser support, smooth join flow, mobile support, data collection, accessibility - to get the element done before Christmas. My user researcher guilt now expanded to add designer guilt, developer guilt, analyst guilt and inclusion guilt. Not to mention strategist guilt that came from being so head-down I had no time to look up and see the bigger picture. I don’t think I’ve ever felt like such a fraud and a sham at work as I did during this period.
Looking back, getting that element in place was transformational even with all the sacrifices. The tests we’ve done with it advanced our understanding of our product possibilities tenfold. All the pitch-preparation we are doing now references that element as the central plank. We sacrificed things to get there, and bits of our product are held together by string, but we tested our riskiest assumption in time to pitch.
And that’s where we are now. 2023 and time to pitch.
It’s strange to realise how much of my feelings about the startup have been guilt. Before I wrap this up I want to reflect on how I feel about these guilty feelings.
Some guilt was to do with my personality. I am an agoniser, a re-thinker, a sceptic, a questioner. I hold things too close and worry too much. There are things that I could and should do to work on this. To be honest writing this piece is one of them. It helps to contrast my feelings of in-the-moment guilt with the knowledge from hindsight :)
Some guilt was about not knowing what to do and feeling like a fraud. There’s a knowledge gap around the early stages of a startup when you are pre-customer and getting to product/market fit is a distant dream. Lots of product wisdom is about optimising existing products, with known customers, in defined markets - as this is where most products and their teams find themselves. I found myself hungry for the moments in Lenny’s podcast when a speaker would go off-script and talk about how things are different early on and collecting these gems. They call it the zero-to-one journey and I’m hoping that now it’s got a name it might be easier to talk about?
But most of my guilt comes from feeling out of step within a culture of conformity. People on Twitter/blogs/conferences/podcasts speak so loudly about their ‘one true way’ to do things - develop a product, do user research, be data-driven, avoid exclusion by design, set up your development environments - that it makes me feel lesser-than when I’m not doing things their way. Early in my career I accepted these loud opinions as truth. As I’ve got deeper and worked in all sorts of contexts - agency and in-house, large organisations and startups, public / private / voluntary sectors, designer / researcher / product manager roles - I’ve turned sceptical about orthodoxy and doctrine. These things are only useful inputs if you are thinking for yourself. And yet, despite this being so central to me that I did a talk about research heresies in 2018, I still somehow feel guilty when I see loud doctrine and compare myself to it.
This tweet from Edo van Royen sums it up nicely:
Anyway, that’s my story of CastRooms in 2022 through the lens of my unexpected feelings of guilt. It’s a weird frame but it crept up on me as an intriguing way to reflect on a year of big decisions and associated responsibilities.
Perhaps my goal isn’t to eliminate guilt but instead recognise and understand it better? Perhaps guilt is a built-in balance against becoming blasé and overconfident? Perhaps guilt is one of the mechanisms that keeps me focused on whether or not we’ve made the right big decisions? And perhaps guilt is the cost of having the freedom and the privilege to reach my own decisions in the first place?
Either way I think the guilt is here to stay. And I’m OK with that. Mostly.
Eating
Living temporarily in London Fields, despite weird feelings about the difference today versus growing up here, does have undeniable pleasures. Facing Heaven is a neon-lit plate-glass backstreet tiny corner spot thirty seconds from our flat that serves Sichaunese inspired dishes (‘facing heaven’ is the Sichaun chilli that points upwards!). Easily the best vegan place I’ve ever been to. By miles. And miles. And miles. Go.
Watching
Jeff has been telling me to watch The Bear for months but I heard someone else compare it to Uncut Gems and ignored it because I hated that film. This was a terrible move. The Bear is beautiful, moving and compelling. TV at its best.
Reading
April Dunford is my favourite find of the last six months. She talks, tweets and writes so clearly that I’ve been saving her book - a practical guide on positioning - for when we needed to put it into use at CastRooms. Which is now. It is not disappointing.
Listening
Justin recommended Babel by R F Kuang and I’ve been listening to it on audiobook and slipping off into its world. It reminds me of His Dark Materials and also Jonathan Strange and Mr Norrell which are strong recommends for me. I don’t think I realised how much I’m into bookish speculative / fantasy fiction set in a slightly-altered past?
Right. Off to finalise bathroom designs and agnoise about kitchen colours. If you have an eye for interior design and want to suggest bold looks for a splashback that would go with our Soho Forest Green matt handleless kitchen I am all ears. Srsly.
Enjoy your week. May your days be as sunny as the one unfolding outside right now :)
Will
What about some yellow tiles https://pin.it/1BuaytP
This guilt angle is fascinating, Will - I think a bunch of the PM discourse has sort of been about this feeling but without putting a finger on it.
As a fellow skeptic and questioner, I agree it’s vital to have some way to balance those tendencies out. And you seem to be managing it amazingly.
I’m looking forward to trying Castrooms one day. If you’re taking requests, I’d be all in for a set with Photay :)