You should have seen teen-aged Sal, always trying to live up to other people’s expectations.
In high school. I sold computers, and wore this green, double-breasted suit because I thought it made people take me seriously. My CV was puffed up with HR buzzwords I read in a book, that I thought would get me a job. I hated university but stuck through because that’s what you’re supposed to do. When I started freelancing, I made sure I had really nice business cards. I remember a turtle-neck sweater phase.
But playing to expectations wasn’t all so silly.
Setting higher expectations for myself helped me grow. Learning to make websites back in the Netscape days was hard, but it set up my career.
The rise of the freelancer! Get clients. Do good work. Get recommended. Prove you can do something even better. Increase your rate. Repeat.
A few years of that and I had a commanding job title at a big marketing agency. I’d wear gangsta-sized track suits to client meetings and the salespeople would explain that I was some kind of tech whiz-kid they should listen to. And for the most part, I lived up to what people made me up to be, ending up with some big results and big budgets.
I’ve seen other people do this too. They’re able to podcast every month because they’ve set that expectation, and now need to live up to it. People who only work well on deadlines have a similar approach. For me it was a bit different. Promising the world I’ll blog every week doesn’t work - it only makes me feel bad about myself when I don’t. But promising the world I’ll be able to double the success rate of a program, or train Roma kids to code, or any big challenge - I tend to rise to those challenges.
Expectations built up like a wave, and propelled me forward. All I had to do was surf! Stay standing, figure it out as I go.
In my thirties, most of my business successes happened when a few people saw potential in me that I didn’t. After the first Leancamp conference almost bankrupted me, I swore I’d never do that again. But people wanted more and that grew to 30 cities. The first few startup accelerators thought I’d be a good educator. I didn’t. The dean of a London university asked me to teach, so I took up the challenge. I ended up designing programs for Europe’s top accelerators and universities.
When I wanted to shift my focus to peer learning, I wrote about it and asked for feedback from a bunch of entrepreneurs I knew. Almost 20 were so interested, they offered to collaborate with me in a new peer learning company! Source Institute was born.
When I got interested in how tech and demographics were getting people out of poverty around Africa, my reputation opened doors. I blogged about it, which got a bunch of African program directors to talk to me and teach me. And within a few months, a major UK association was asking me to run their new African program.
These expectations though, of myself and from others, started to control me.
After three years of putting my heart into that African engineering program, the rug was pulled out under me. A sad aspect of international development is that the funders’ agendas are usually misaligned with who they say they help. You can still do some good within the world of aid, but when you do, whatever you’ve built gets hijacked to serve the funders’ ulterior motives. The most common cases are whitewashing a company or rich person’s reputation, but it’s deeper than that. Any organisation that survives by doing projects for funders doesn’t grow by getting more impact, it grows by getting more funding. Funder relationship management is about ego, not impact. That means making the funder look good, not overshooting their targets or telling them when there’s a better way. So anything that actually works gets co-opted and diluted to serve a political agenda.
I’d been warned that supporting people through foreign aid made me part of the problem, not the solution. The program I built ended up being used to help Prince Andrew look good at the cost of the African engineers we were supposed to help. Now I was part of the problem.
I learned it the hard way.
I’d spent five years developing peer learning with the intention of sharing these innovations - improving the whole world of education. The peer learning stuff was working well,but my strategy for disseminating it wasn’t working. The problem was all these existing expectations of me were not aligned with another strategy.
One option just moving to East Africa and continuing my work for free, without looking for funders. I had savings from my last 2 companies, and a lot of allies and supporters across the contentment, plus my team of peer learning facilitators.
But nobody who said they “supported me” wanted to support me with that. They’d become used to the high day-rates I was paying them, or they’d built their whole financial model around foreign aid.
Even my closest teammates just expected me to find another funder. They weren’t interested in helping if I wasn’t paying them a thousand euros per day. They’d be become dependant on these teaching gigs I hired them for - that money funded their businesses.
So I walked away.
Not just from the program, but I also saw that I’d reached a ceiling with the impact I could create with that client, and with NGO clients in general.
I wanted to continue my African efforts alone, but I was too burnt out. Getting right on a plane and starting from scratch wasn’t realistic for me without a serious break.
I had to let The Wave Of Expectations come crashing over me. Stop caring about sunken costs of what I’d started. Stop chasing potential. Stop caring what people think of me. Stop using money and social norms as an excuse for ethical compromises. Just let the consequences hit me and wash over, then float up to the surface when it was all over.
I wrapped up my contractual responsibilities, and tried to leave a positive legacy. I was already transitioning my team to take over more of these programs, so I just accelerated that and stepped down within a few months.
And I was gone.
I had accepted failure and got out, which gave me time to think.
I struggled with the idea that the program wouldn’t be as good in the hands of a typical NGO supplier (who typically do the minimum). I beat myself up that could have been more outspoken against the injustices I’d seen. I could have fought back harder.
I had underestimated the psychological cost of walking away.
Then I started asking myself — why are you still trying to prove something?
I had this idea of myself and who I should be. Now I’d taken on this persona as the entrepreneur-maker. I saw myself as an empathetic person who could relate to others and adapt to make each relationship work. I saw my purpose as supporting them.
But I also saw how that idea of myself had led me down this path. When Source started, most of my supporters were entrepreneurs who’d gone through break-ups with their partners, and I had become a supportive rock for them to build up their confidence again. So I’d inadvertently surrounded myself with people who were not easy to work with.
That opened another question — why am I trying to be what I’m trying to be?
This was a rare chance. I could afford to step back, and pick any new direction for my life. I could get into solar energy, start a beach cafe or a spa, study philosophy or machine learning. I could stop pin-balling around the world and get a cat, maybe even two.
Just pick new goals. Sounds easy, right? Not quite.
First of all, it was hard to let go sunken costs, and previous work still feels like it’s worth seeing through. Maybe not in the way originally planned, but there’s still these mostly-written books lying around, and people who still want to work work with me.
Some close collaborators wanted to be supportive, and encouraged me to stick it out with the old direction. But it became clear it was because they had something to lose if I changed course. They made deals with me to get what they wanted, knowing they’d break them as soon as I was committed. After getting deceived a few times, I felt surrounded by soap-opera level dramatics.
All I wanted to do was get out.
Any experienced entrepreneur has learned how to fire people, but it’s a bit different when they (were) your friends. I still wanted to give them the benefit of the doubt. I tried to end things with them nicely, so they could save face but I was left with doubts and ripples in my mind. Did I do the right thing?
About a year later, I found myself hustling up a new pan-European program, selling a vision, making complex deals, partnering with science parks and universities. It had settled in Bulgaria. My thinking was, why not apply what I’d learned at world-class places in Bulgaria, my new home? Why not do this without clients, so I could be in full control this time?
My experience (and pride) told me to start off the program, create a bandwagon for the others to jump on. But when it came to launch, the launch partner couldn’t hold up their end of the deal.
How did I get myself back in such a similar situation?
That’s the thing with expectations. I created them in myself without really noticing, until I created them in others.
It was time to challenge my own self-image, and look inward to know why I kept ending up in bad places. I hadn’t really let go of expectations I had of myself. It was time to let the wave crash over me again.
I ended partnerships with big European institutions. I let local people down who wanted that program to work. I accepted again, what I’d already been warned: Bulgaria’s corruption is still entrenched, and a few good, young people will be stifled in this environment. I accepted I wasn’t the person to change any of that.
At least I gave it a shot.
I’m happiest when I’m creating - coding, writing, designing. I’ve found the best defence against the wave is to stay locked into a creative routine. Now, my days start a simple act, drawing a little sunset over calm waters. It’s a meditation to remind me of the calm that exists without expectations.
I got two cats.
I’m living off savings, living cheap, a bit like when I started freelancing, but with a few more treats like good coffee. It’s nice to not have the constant pressure of a service business. No more planes to catch or email to answer. Instead I focus on routines that serve me, like daily yoga, learning new skills, a healthy diet.
When I see The Wave building again, I try to spot it early, but I’m still not great at it. A few past injustices have come up again and pulled me back in. I started to create “shoulds” for myself. I lost days and weeks of mental energy to these things before I could let them go. But I eventually let them go.
Once I let it, my passion found it’s way to other pursuits.
Lots of new ideas are sprouting, and I’m returning to my tech roots, sharpening my axe with the newest breed of software development architectures. With them, I’m working towards a skill level where I’ll be able to take an idea to launch in a matter of days or weeks.
I’ve been keeping away from a public, professional persona until I’m ready. Let’s not set any expectations this time, and just see where this goes.
I’m in a cozy place, preparing for parenthood, dabbling with some art projects, getting my hands dirty with ZK and ML. One of my more “product-y” projects is a communication tool for community groups and unconferences. It focuses on autonomising teams rather than “coordinating”. Another is a set of primitives for “hyperstructuring” Free Software to help contributors get paid fairly.
I’m also part of Discover Mode - where I’m a solver-for-hire helping a Web3 projects with product design and strategy.
In the past, I've designed peer-learning programs for Oxford, UCL, Techstars, Microsoft Ventures, The Royal Academy Of Engineering, and Kernel, careering from startups to humanitech and engineering. I also played a role in the Lean Startup methodology, and the European startup ecosystem. You can read about this here.
Menus and kitchens (2023)
Retreats for remote teams (2023)
What do you need right now? (2023)
Choose happiness (2021)
Emotional Vocabulary (2020)
Project portfolios (2020)
The history Of Lean Startup (2016)
Entrepreneurship is craft (2014)