Every job I’ve had has been a kind of dojo. At every position, I’ve had the privilege of meeting and working with a bunch of smart, interesting people; I’ve got to work on disparate products with real-world applications; and I’ve learned a lot about new markets and industries.

But they’ve also stretched me personally in important ways. Here’s one way of breaking it down, from the very beginning.

As a SysOp at Daily Information, I ran a BBS and later one of the first classified websites - but ended up doing lots of very different things that crossed development, computer repair, visual design, sales, and more. It was an idiosyncratic small business that was run out of a Victorian house in North Oxford and I loved every second. I learned to flexibly wear different hats and move from role to role to role as needed, as needed. For an introverted kid who was scared to talk on the phone, let alone make a cold call, that was a pretty big deal. (I learned how to make a pretty decent G&T, too.)

As a learning technologies developer at the University of Edinburgh, I learned how to explain complicated technical ideas to a non-technical audience. I was immersed in the web, and I quickly realized that my colleagues were not. Helping them through the new internet world became pretty important for them, and for me. I gave my first ever presentation here, and saw connections between the emerging web and the potential for facilitating learning that no-one else had seen yet. (I also hacked the cafeteria menu to get the lowest-cost possible meal and was banned.)

As a web administrator at the University of Oxford’s Saïd Business School, I learned about navigating corporate structures and helping advocate for agile ways of working. I became a go-to resource across the School for internet startup knowledge - by the end of my time there, MBA students were stopping by the IT department to chat with me.

As co-founder of Elgg, I learned how to bootstrap a business, build an open platform from scratch, seen an open source community, run events, do marketing, and more than anything else, how to identify assumptions and work from first principles. I had no idea about how investment worked or how to think about valuations; I had no idea about team dynamics or how to build a company culture; I didn’t know what user-centered design was; I wasn’t sure how to run a team remotely. I learned all of these things. I hired and fired my first person, and hated it.

As CTO at Latakoo I learned a lot more about leading a team and interfacing with non-technical management. I also learned about how to build for legacy industries - I’d done that in education, but broadcast television was a new universe for me. I helped build a pitch deck and give an investment pitch to investors for the first time. I also had my first VC experience on Sand Hill Road.

As co-founder of Known, I learned formal design thinking and user research. I built more pitch decks and investment documents than I ever had in my life. I gave design thinking workshops and learned how to be a formal consultant. And I engaged in acquisition talks for the first time - a very different kind of sales.

As a senior engineer at Medium, I learned about software development in a much larger team for a much higher-scale product. My software development skills were pushed much further than they’d been in the past. I worked with formal product management and had a very different class of problems to solve. And honestly, got over my nervousness and some of my imposter syndrome: chatting with Ev, who I held in very high regard, was initially terrifying. The people I worked with had been on very different, much more high profile journeys. I spent the first three months sleeping very little, but eventually decided that I belonged.

As Director of Investments at Matter, I had to become an extrovert. I took over a thousand startup pitches, sometimes over continuous twelve hour days. I taught design thinking bootcamps and held strategy opening hours for dozens of disparate startups. I attended industry dinners and tried to represent the organization well. But most of all, I evaluated the teams and business strategies for many, many startups run by all kinds of different founders; I read their legal docs and understood their structures; I evaluated founder mindsets; I got to know many incredible people. I invested in them, and was there for them as best I could. It was my first (and last) job ever that didn’t involve coding: instead, I was a human standing with other humans, using my experience to be the wind at their backs.

As VP Product Development at Unlock, I re-learned being a software developer, and learned blockchain decentralization for the first time. I coded apps that ran on Ethereum and attended industry events. I learned about DAOs and gas and all the rest of it. It transformed how I think about the internet - and I did it during some of the heaviest personal struggles of my life, so I learned (imperfectly) how to juggle these things, too.

As Head of Engineering at ForUsAll, I’ve learned a lot about the importance of culture and structure. I’ve managed a larger team than I’ve worked with in the past, and have navigated a variety of human issues that have been very challenging. I’ve also played the part of a formal product owner in a very different way, writing formal product specs, Jira stories, and sprint plans, as well as working with engineers to build new architectures and refactor technical debt. I’ve also learned a lot about how to think about cultural change within a larger organization: ForUsAll is on the journey from being a financial services organization to an empathetic, scalable tech startup. And on top of that, I’ve learned a ton about how finance works, and the underlying mindsets required to navigate a whole new set of legacy infrastructure and ideas.

Looking back to the beginning of my career, I wouldn’t have imagined getting to where I am now: the things I’ve learned have pushed and pulled me into a whole new person. I’m grateful for all of it, and I’m excited to keep learning. It would be a sad thing to join a team and not learn or be pulled in these ways.