Times have been hard for me recently, but I finally have an open road ahead. No external commitments. Nothing on my calendar except birthday parties and weddings. So I’ve been able to do some deep reflecting about my character and past conflicts.
A friend introduced me to this old, psychological concept called Integrating Your Shadow. It’s Jungian, so esoteric and likely to be clinically out-dated, but it helped make sense of situations where I’ve ended up blaming myself or others.
I understand it like this: When we find ourselves criticising others, it relates to some weakness in ourself that we’re unable to see. That’s our Shadow. It’s part of us, even if we don’t accept it. Figuring those weaknesses out, and accepting them, is a step towards accepting ourself for who we really are.
Sometimes, it’s a simple as seeing my criticism of someone else is also appropriate for me. Other times, I’ve asked myself, what other weaknesses have they seen in me when I was critical of them?
Here’s an example, just one part of my shadow that I’m starting to see.
A recent pattern of mine was that I entrust people with important responsibilities as my organisations grow. But of they drop their promises and wreck something I’ve worked hard to build, I get angry and distrustful.
I’ve supported people through expensive mistakes. Sometimes, we’re talking tens of thousands of Euros out of my pocket, and I’m not bothered. It’s okay as along as we learn and fix our way of working so it won’t happen again. I feel good about my team moving forward stronger, having learned and evolved. I get consistent feedback that I’m a patient teacher and leader.
But my patience gets thin when someone breaks their word. There’s the shadow - there’s something going on about myself that I’m not able to see.
When that big mistake was because someone just decided to drop their promise to do something, it felt like a betrayal. I’d try to be more patient when my trust was betrayed, but that just seemed to make bad situations worse.
Why do I try to calmly give them another chance? Why do I hoist responsibility on people who aren’t sure in themselves? If I’m honest, part of it is altruism but part of it is ego. I want to be a person who helps others grow. I want to be a patient person. But I use these things to block myself from seeing a weakness, that I’m a naive, over-trusting person who takes betrayal to heart. Bad combo. To others it’s obvious though - I effectively let other people take advantage of me.
I’d try to take responsibility for these situations, and blame myself. I’d say, I could have been a better leader, been more careful, or provided more guidance. Or I should have made different decisions and avoided this situation altogether.
Other times, I’d try to understand the other person, and separate their blame from their character. They’re not so bad, it was shitty thing they did, but they’re working on themselves. Or, I see they’re going through a lot right now, so I should give them another chance.
Neither was very constructive in the long run.
Suppressing my criticism with “positivity” was counter-productive. It created a loop of blaming myself for the wrong things, and building frustration trying to solve the wrong problems.
It created dishonesty between us because they couldn’t see the disappointment in them that I was swallowing. So they felt they could rely on more patience from me, rather than making changes to honour their commitments.
My company employed startup founders as freelance teachers, and it quickly turned into a family of entrepreneurs who really helped each other out. That was wonderful, and soon, everyone was using their work with me to fund “their main business.” It was a big enabler. But as some people started to see they could be more flakey, they’d push their responsibilities to others by guilting them to “be more supportive.” It became a cross-subsidy where the reliable people were always bailing out the disorganised ones.
Then I started to blame myself for how the company culture was becoming toxic.
In these situations, I was critical of others, even if I didn’t say it out loud. But I wanted to be supportive, not critical, so would squash it in my mind. Instead I’d stay positive and look for a constructive way forward.
Those criticisms in my mind were an early clue to seeing my own weaknesses. That patience had a dark side.
A freeing idea is that your shadow is already obvious to everyone around you - it’s only you that doesn’t see it. Seeing my weaknesses as no secret, it was easier to own up to them rather than let myself be defensive. In a way, to save face, I actually had to confront my rationalisations.
This concept also worked for me because The Shadow emphasises character weakness as something separate from blame or duty in a given situation.
Blame is about who made the mistake. Weakness is about character. Duty is about ownership of the outcome.
Being clear on these differences has been helpful.
Someone can take on the duty of handling a problem, even if someone else was to blame for causing it. They can take the duty of getting a team to a goal, even if people on that team have weaknesses.
When I was blaming myself for other people’s failures, I was trying to be a good, patient, virtuous leader. But I was confusing blame and duty.
When I justified other people’s mistakes by trying to understand and accept their weaknesses, I wasn’t doing the same for myself. I was blaming myself to avoid accepting my own weaknesses.
I’ve started become aware that my different values and virtues have shadow sides. Each pursuit of a virtue comes with an inherent weakness.
When I try to help other people grow, I can create situations where I have more to lose than them, and they’re not ready. More honest acceptance means seeing I do it for egotistical reasons too, and stopping myself if it’s too risky.
I’m good at predicting trends, but can stick to bad bets just because I want to be right. Consequence: I’m stepping away from full focus on peer learning. It’s a shame I couldn’t spread it as a more mature educational discipline. Accepting that doesn’t mean giving up on the concept, just on the bets I placed on it.
I love being an educator. It lets me connect with people on a deep, personal, uplifting level. But educational service businesses depend on sales. I’m good at sales proposals and presentations, but not at the day-in, day-out aspects that make a consistent salesperson. So I have to accept I don’t have what it takes to see a sales-based business through. It’s cool, there are plenty of other options.
When I feel a criticism, exploring it reveals the fuzzy outline of a weakness in myself I haven’t seen. Accepting those is helping me make more enlightened choices, and life is starting to feel more smooth.
I still have a lot more of my shadow to discover, though. It’s a process.
I’m on the Kernel Stewards team, where we help ~2,000 fellows understand the what the development of blockchains mean to humanity on anthropological scales. I’m particularly interested in enabling fellows to build things with blockchains that are altruistic and prudent.
I’m also building a communication tool for community groups and unconferences. It focuses on autonomising teams rather than “coordinating”.
In the past, I've designed peer-learning programs for Oxford, UCL, Techstars, Microsoft Ventures and The Royal Academy Of Engineering, 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)
Making sense of DAOs (2022)
Choose happiness (2021)
Emotional Vocabulary (2020)
Project portfolios (2020)
The history Of Lean Startup (2016)
Entrepreneurship is craft (2014)