“I don’t want to be somebody else.” — Tina Fey
I’ve realised I’ve conjured a tidal wave of expectations that I was stuck surfing, and to regain control of my direction, I have to let it crash over me.
Giving a kid a chance
In high school, people told me I was going places. I was a nerd and sold computers to make money. I wore this silly double-breasted suit because I thought it made people take me seriously.
In university, I needed to pay rent. So I puffed up my CV with impressive words to get a job. But in the end, I got hired by an older student doing a business degree. He needed customer service people.
I made websites for local businesses on the side, and kept learning more challenging stuff. Server stuff, HTML email stuff.
The next step was quitting my day job, but that needed a leap of faith. I needed to believe in myself. Also for some reason I thought it was really important to get nicer business cards.
I quit university after a few years. I was really unhappy there but kept at it because it was what I was supposed to do.
Live cheap, work hard, and prove you can do just that little bit more. Soon I could move from my basement studio in the suburbs into a non-basement studio in the city. It was harder to pay rent there, but I was rubbing shoulders with Vancouver’s big city internet types.
The rise of the freelancer! Get clients. Do good work. Get recommended. Do something better. Increase your rate. Repeat.
The trick was pushing myself to do new things, but making promises I could keep. Sometimes I’d push too far, and have to pull a marathon of all-nighters to make up for my failures. It was interesting but stressful.
Through those ups and downs, by age 22, I was Director Of Digital Media at a big marketing agency. The agency salespeople started playing me up as a kind of tech whiz-kid, and that reputation served us both well. It was a big hit when I showed up to corporate pitch meetings wearing gansta-sized track suits with a brushed-metal Macbook under my arm. I’d write strategy papers and they’d tell the clients, “this kid gets it.” Inside, I wasn’t so sure.
I had a self-image to live up to. I was building a reputation for myself that opened doors, but I also had to maintain it.
The Wave can open up wonders
“The only way of discovering the limits of the possible is to venture a little way past them into the impossible.” — Arthur C. Clarke
Over almost two decades, the wave of expectations kept getting bigger and it gave me a lot.
Living up to my promises to the world helped me grow. The expectations and commitments are a powerful force - benevolent but menacing - like a wave in the ocean. If you can surf this wave - it will push you forward and you can do more than you thought possible.
I started a few tech businesses. Some actually made money. I got to move to London and started a more few businesses which all failed, but kept opening doors to the next one. I hustled together a little startup conference, which I swore I’d never do again. That grew to 30 cities but made no money. As startup accelerators became a thing, they started asking me for workshops. I told them I wasn’t a teacher, but my wave of expectations told them otherwise, and within a few years, my workshops were picked up by the best accelerators and universities in the UK.
I got interested in the demographic changes in Africa, and how technology was helping bring people out of poverty. By writing a blog post questioning this potential and circulating it to my network, I got to speak to the forerunners in African startup support.
It seemed like the clock is always ticking, and the way out was forward. Bigger ambitions, bigger challenges, bigger stakes. Bigger promises to myself and to the world.
That has to catch up with you eventually.
When the UK’s national engineering association wanted to start an African innovation program, someone recommended me.
I had big ambitions for it, and after I started, I had good ideas how to make it better. But just like when I was a kid, I had to prove it.
Turning to face my expectations
“Sooner or later, I hate to break it to you, you’re gonna die, so how do you fill in the space between here and there? It’s yours. Seize your space.” — Margaret Atwood
After three years, that project got wrecked by ugly international politics and I walked away for ethical reasons. This experience showed me that supporting people through foreign aid made me part of the problem, not the solution.
I started asking myself — why are you still trying to prove something?
The question evolved — why am I trying to be what I’m trying to be?
I sold what I could of that business, and gave myself some much-needed time off to think. I’d spent the last 5 years developing peer learning techniques, which were good for the world.
I had a rare chance now. 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 get a cat, maybe even two.
It was time to disengage from my past expectations and commitments to make space to find this new direction.
This meant letting The Wave Of Expectations come crashing over me. Stop caring about sunken costs and lost potential. Stop caring what people think of me. Stop using money as an excuse for compromises. Time to challenge my own self-image, and why I kept setting goals that got me in bad places.
Sounds easy, right? Just pick new goals. Not quite.
Through other people, The Wave kept smashing me, trying to keep me moving in its direction.
People acted like I still owed them, like I should continue. Some friends became manipulative, others felt they should encourage me to keep going. But it became clear who was being encouraging because they just wanted something from me. It was getting toxic. I needed to move on without them.
From years of entrepreneurship, I’d learned how to fire people and let people down easy. You can rip the band-aid off, but that still leaves you with doubts and ripples in your mind. Did I do the right thing?
“You can spend minutes, hours, days, weeks, or even months over-analyzing a situation; trying to put the pieces together, justifying what could’ve, would’ve happened… or you can just leave the pieces on the floor and move the fuck on.” –― Tupac Shakur (when he was 17)
Over a few years, I kept my hand in a few old things, helping out here and there. There was always an opportunity to be flown out to mentor, or someone trying to hire me to consult or teach. I even tried to start an education program again. This time on my own terms, I told myself.
I wasn’t really ready to let go, and keeping the option to go back felt safe.
Before I knew it, I was back in the same pattern, building up a wave of expectations to ride, rallying people around this new program, working with people who kept me locked into the same course, while still breaking their own commitments.
I was responsible for being back here, and didn’t know what to do about it.
Someone introduced me to this old, psychological concept called Integrating Your Shadow. When we find ourselves criticising others, it relates to some weakness in ourself that we’re unable to see. Figuring that weakness out, and accepting it, is a step towards accepting yourself for who you really are.
For example, I’ve always tried to bring on partners once I got something going. At first, I’d tell you I’m way more inspired and excited when I’m bouncing ideas off people, that two heads are better than one. But digging deeper, I saw I feel insecure about certain skills myself. Then I get frustrated with people who procrastinate because of that same insecurity.
I saw that I entrust people with important things but then get angry with them when they drop their promises. Deep down, I want to be someone who enables others and gives them a chance. People say I’m very patient, and I am. That is, except when someone breaks their word. I saw this limit of my patience, and realised I need to navigate to avoid these situations, not rely on even more patience to get out of them.
I made a short checklist of what makes a bad deal for me, and realised - oops - that was every project I was in.
I stepped down from everything, every position where I saw my time and effort wasn’t reciprocated, every project with someone who compromised their trust with me without apology. This meant ending some large-scale projects and partnerships with big European institutions. It meant not finishing stuff. It meant letting myself accept why my new home, Bulgaria, was a corrupt, difficult place to do things, in spite of all its great people and potential.
“All goals apart from their means are illusions. Becoming is a denial of being.” — Bruce Lee
Once I let it, my passion easily 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’ll be able to take an idea to launch in a matter of days or weeks, and I’m happiest when I’m creating useful stuff for people.
I have time before I need to make serious money again, and besides, money follows talent, which grows from passion.
I still work hard, but I truly work for myself. I work on what matters to me, and make sure I can focus without distraction. I don’t make compromises to include others, I make them to stay independent.
Gone are other people’s fires to fight, or planes to catch, or people to impress. I don’t have to take meetings or answer email.
I keep a stable of interesting pursuits, and carve out days and weeks for them. They’re all connected in some meaningful way, and overall, I’m more productive than ever. It’s just not so visible; I’ve been keeping away from a public, professional persona until I’m ready.
My home in Bulgaria is calm, my neighbourhood full of creative friends. My time is under my control. My days start with yoga, and it’s easy to keep healthy habits.
I’m back to living cheap, just not like a poor student. It’s basically the same but with better coffee and nothing weird growing in the fridge. Oh, I live in a top floor studio now, and I have two awesome cats.
When I see The Wave starting, I call myself on it. Something comes up that pulls me back in, or I get caught up in my own internal sense of urgency, and I lose a day or a week of mental energy to it before I can let it go. But I let it go.
I’m happy, learning and getting back into the flow of creating. Let’s not set any expectations this time, and just see where this goes.