Category: Reflection

Theirstory

Do my motives matter?

“I saw the Emperor – this soul of the world – go out from the city to survey his reign; it is a truly wonderful sensation to see such an individual, who, concentrating on one point while seated on a horse, stretches over the world and dominates it.”

—Georg Wilhelm Friedrich Hegel

“Faith in the creative process, in the dynamics of emergence, in the values and purposes that transcend past achievements and past forms, is the precondition of all further growth.”

—Lewis Mumford

Is one of these statements more true?

  • To be successful I require a force of will and to be a strong leader.
  • If I trust myself and continue to take action in alignment with purpose, the right things will happen.

Are “great leaders” who do important things examples of success by force of will or are some people just in the right place at the right time? Is force of will a kind of strategy that the system of dominance rewards? Or am I caught in a tautology? We make histories in hindsight.

I have a desire for something to exist in the world, in this case a technology, or really merely an app, but something that supports the purpose of cultivating containers of belonging.

In my current snarl, as much as I want to develop this tech, and do possess the non-technical skills to drive the project forward, I don’t want to invest many years building on a foundation that will ultimately be antithetical to the purpose. And so I keep looking for a container that will allow for people-oriented, thoughtful, and emergent software to be built by people who care more about impact than a now or future payday.

Does this mean I am waiting for permission or searching for the cracks to slip through?

Game B+

Over many years in the startup world, I learned how “the game” is typically played and while it’s not a game “people like me” win at often, it does have a playbook of sorts, and it does involve a set of skills I spent many years developing. There’s a culture around tech startups that is very winner-take-all, that depends on the idea that you need to make moats, guard your IP, and other adversarial concepts. There are countless conversations in this world where compromises to growth in service of community, employee, or climate health are seen as painfully naive. Anything short of hyperscale would be, ultimately, a failure. You matter when you’re the king of the world and other people challenge you to cage fights.

“Successful” tech startups founders are, for the most part, a very specific band of people who are funded and enabled to orient around experimentation and learning. The people in question are pedigreed in various ways, and also deeply committed to the ‘force of will’ hypothesis. It’s hard not to look around at popular tech companies and see patterns that look much like evidence of the success of that strategy, even though of course the entire pool of VC-backed tech looks much the same on paper and there are far more failures among them than successes. (Not to mention the large percentage of such tech companies that are still unprofitable and have engaged in growth tactics that have had negative consequences in various ways for many other people).

But you know what? That’s all irrelevant.

I am not choosing emergence and slow progress because my body falls into a category that venture investors don’t associate with tech founder-ness. My discomfort around taking action doesn’t actually come from anyone else’s judgement. There’s an uncertainty making new things generally produces, no matter whether I think I am making it happen or not.

Driving vs. shepherding

There is something about “I need to make things happen” that feels like it comes from fear not love, that feels like forcing a solution. It indicates I have something to prove instead of something that I’m called to serve.

I am naturally good at getting things to happen. I don’t need to fear that I’ll be lying in bed eating bonbons all day, but what I seem to fear most is a lack of consequence. Somehow, if I figure out a strategy, I think, I can make an impact that matters. It’s a seductive idea that is completely orthogonal to everything I have a felt sense about.

There’s a little bit of this, “yeah, but can’t I just get what I want?” It’s hard to accept that I might not matter in some grand way, it’s hard to believe that just doing things as opportunities arise is enough, let alone believing that just being is enough.

I have to feel my fear and welcome it. Not a fear of doing things, the fear of not mattering. Being Napoleonic is not in my nature (despite accusations to the contrary when I direct someone to help with dinner cleanup). I get so much more joy from leading through listening, coordinating, and having a clear and uncompromising sense of purpose.

The Great

I might not be a person of greatness. That such people even exist and have the right to dominate is a narrative underlying our ideas about leaders.

“What we now regard as states turn out not to be a constant of history at all; not the result of a long evolutionary process that began in the Bronze Age, but rather a confluence of three political forms – sovereignty, administration and charismatic competition – that have different origins. Modern states are simply one way in which the three principles of domination happened to come together, but this time with a notion that the power of kings is held by an entity called ‘the people’ (or ‘the nation’), that bureaucracies exist for the benefit of said ‘people’, and in which a variation on old, aristocratic contests and prizes has come to be relabelled as ‘democracy’, most often in the form of national elections. There was nothing inevitable about it. If proof of that were required, we need only observe how much this particular arrangement is currently coming apart.”

—David Graeber and David Wengrow, The Dawn of Everything

We may at a time in history when it is becoming clear that we have to toss out the hero mythos and figure out how to be ordinary. To feel the small power of each of ourselves as integral parts of our collective humanity.

Maybe I am misinterpreting the options. There’s room for me to make space in myself for whatever I may be called to, without attachment to recognition. Perhaps the answer is: lead, but only in ways that serve, that allow more lights to shine, that emerge from what is necessary. I can honour my vision at the same time as I recognise I am seeing from a particular vista. I can’t actually design the future but I can choose a path through the brush.

Beyond ambition

I want to do something big, but why? It seems I don’t just want to be known, I want to be known in some very specific way: written into history. It makes me wonder what the hole is I am trying to fill. The little me who was told I was smart and special but also that there was something indefinite but wrong about me?

If I am a vessel for purpose, I may become impactful but I’ll be doing so in service, perhaps even despite my intentions. It’s easy to get hooked by the want to be acknowledged, to be acceptable, to be as good as, which somehow equates to being a figure in history.

At the same time, I don’t want my whole self, including exactly these kind of boring and embarrassing thoughts about my own insecurities, to be exposed.

Imagine we all could create a history of the world where we’re important and do meaningful things. Perhaps this, at its core, is the appeal of social media. Many billions of histories, protagonists all. It’s no wonder that influencer (or, ‘creator’) has become the most aspirational career for the youth. You can skip actually doing anything impactful and just get the attention, the sense of being important. Skip having to deal with the messiness of relationship and collaboration and go right to a follower count.

And look, no judgement. We’re talking about the fundamental aspects of human nature and a system where taking a cut of our extracted attention yields actual power and influence. (There’s an interesting sidebar here about how creators want to own the means of distribution, which might collapse into a whirlpool of recursion).

Fear itself

I don’t know how many times I will need to talk myself down from the idol-worship of achievement addiction. How many times I will have to grieve the hope that I can be saved by being called important. Maybe everyone has a Maypole they will spin around forever and this is mine. To matter, I have to put down what gets in the way of service, and in my case, it’s the fear of not mattering.

These tangles are useful. They give me a chance to revisit my motives. I am not stuck, I am not in an inertia. I’m on a path to building technology that supports our freedom, belonging, and responsibility. I believe there are amazing people who will come together and do work differently. I have a wealth of skills, experience, and intention to contribute. I’m not just thinking about things. I am acting, making, and progressing, if progress itself can be anything more than more capacity to feel my choices. And more and more, I can feel into how possible it is to create without it being about glory or redemption. I act and make because to do otherwise would leave me in dissonance or betrayal.

I am expanding my circles of collaboration, which fills me with delicious anticipation. It’s not only in my head even though sometimes I feel alone. Everyone matters. History offers no solace for us now.

Good grief

Death is useless as a concept. It needs to felt in the body.

Death is always living here in me, an initiate walking up stone stairs and snuffing out the candles one by one, a flickering ahead.

Or a slasher film. Massacres of mitochondria. My body devoured by bacteria daily.

It is other death, the death of others, that need special rooms, funeral processions. Death happens continually and abundantly and is only important when we love.

Grief is unstoppable, rolling through, a tsunami.

Grief is the body feeling of love without desire, though maybe there’s still a sensuousness in the breaking open. The raw and pulpy underside of my own flesh and sinew somehow palpable then.

Grief is hot and consuming. It’s not the grey and drizzle of sorrow.

Space to feel may be necessary, a church, a forest clearing, light that catches motes. Room for the mess and the roaring silence. The never returning of someone sounds like the earth caving in.

Even imagining this irrevocable absence feels like too much wasabi. Feeling your goneness has been, always, a fire drill for a cascading catastrophe.

My own death is mere anxiety. Alive, I am always in some way terribly alone.

Even as you live, an idea called your death has always been that reminder. Even made from you, between us are the echoing straits. Love is never fully knowing another. Love is the salt, the sand, and the drowning.

Yesterday’s media:

A platform from which to leap

At the beginning of 2023, I decided to write every day, and to put whatever came of it onto a blog that I would not promote in any way. This arrangement seemed to me to meet some kind of integrity with the idea that I was indeed ‘shipping’ as the startup lingo has it, without participating in a collective performance that would only get in the way of being open with my (probably half-formed and unpolished) words. This plan was effective in its way. I wrote a number of things that were exploratory, though also strange in their lack of recipient- perhaps language can be useful just for one’s own understanding, but only an understanding that escapes the body.

Over time, I started to drift, and post less frequently. The unfinishedness seemed odd or even risky to publish, with the trope of the internet’s indiscriminate memory in mind. And also, I feel myself, when writing to noone, becoming more likely to express myself in the form of college essay or with a touch of what you might call “archness.” I’m more interested in a constant breaking apart or disintegration that sometimes a post can’t contain.

Then I decided, for no good reason that I can think of, to begin putting the posts on Substack. It has been an experiment that brings in a kind of cognitive dissonance- can I continue writing in an undefended way when I am also presumably sending the words, or giving a VC-driven company the task of sending my words, to other people? And is it then my job to manage the ways that such a platform would like me to work for them, showing me analytics and sending me various prompts to continue my investment in their ecosystem (one that I then, for consistency’s sake, invested in to the tune of a one-year’s subscription in another newsletter (consistency’s sake being my least favourite cause in general))?

Well, I don’t know. I certainly felt uncomfortable sending out these little posts, which I’m sure a coach would cite as a growth edge of some kind- bumping into my pattern of feeling like a burden if I am not feeling unimportant. But am I really attached to those kinds of narratives anymore? They seem like this weird way of conditioning myself to be productive in service of something invisible but smelly, to think “of course, if I were seen / had a platform / gained legitimacy” then I would be more likely to get what I want or avoid harsh judgement. While that’s obviously the opposite of true, maybe I could think, “‘my authentic self’ can emerge when I don’t censor myself.” There is a stage that I am meant to be on, and that stage’s performance somehow proves my realness, or at least, my worth and power.

There are so many layers here, because even in that inquiry there are judgements that I think limit my understanding. What could it be like to write or not write, to post or not post, with both the intent to connect and communicate (why else make things public or even epistolary?) and the indifference to being read or understood? Is this even logical in the first place? Part of what is so odd about the social media metaphor is simply that there are few historical examples of social contexts that combine communication and attention-seeking with such intensity and ubiquity, along with trying to negotiate the general lack of communication or attention most of the attention-seeking efforts inspire. In a way, posts on social media are advertisements of our loneliness. What makes an unread newsletter any different?

I have a kind of guilty nostalgia for the semi-private experience of LiveJournal, back before we understood the implications of putting one’s most embarrassing experiences on a platform soon to be purchased by unknown Russians. While I have generally begun to have less interest in text-based media as mediators of communication, LiveJournal was a place for the kind of reflection that journaling offers, while being also hilarious and at least for me, an impetus to take my own problems way less seriously, because it was more entertaining to note my own stupidity. There’s probably some layers of avoidance baked in to that as well- more of a spiritual bypass than an actual loving of my own feckless humanity, but these things are not binary.

I come back to a kind of presence and present when I remember that a sense of purpose has been revealed to me, that I don’t really matter so much– or rather, that the construction of me doesn’t matter, though I matter fully and equally to any other thing, being, or human.

Does writing support this purpose? I think so. Does a newsletter support the purpose? I really don’t know. My sense is that I’m much better at asking good questions than having answers. If going down inquiry road with me leads other people to connect more with the underlying idea that freedom, responsibility, and belonging are the same thing, maybe? I’m unsure that reaching this conclusion can come from anything other than practice. But perhaps for some reason there’s value in sharing my practice with you (because there must be a you, as the tree falling would agree). There’s no more that that, is there? Just the intention of love that can somehow be alchemically infused into the electrons moving and also not moving, the virtual that is also what is.

Our Work and Our Worth

“Money is like water. It can be a conduit for commitment, a currency of love. Money moving in the direction of our highest commitments nourishes our world and ourselves. What you appreciate appreciates. When you make a difference with what you have, it expands. Collaboration creates prosperity. True abundance flows from enough; never from more. Money carries our intention. If we use it with integrity, then it carries integrity forward. Know the flow—take responsibility for the way your money moves in the world. Let your soul inform your money and your money express your soul. Access your assets—not only money but also your own character and capabilities, your relationships and other nonmoney resources.”

― Lynne Twist

“We have come to believe that men and women who do not work harder than they wish at jobs they do not particularly enjoy are bad people unworthy of love, care, or assistance from their communities. It is as if we have collectively acquiesced to our own enslavement.”

― David Graeber

It’s hard to reason about money when it has a kind of theological position in our culture. My old stories about money fall into a few categories. Maybe you have entertained some of these ideas yourself.

Being liked or accepted

  • If I seem to have money, I will be subtly ostracized or mistrusted by others
  • If I appear to have a low income (or even an ‘average’ income) I will not seem credible as a consultant/job candidate/human
  • If I speak of struggling with money, people may believe (or find out) shameful things about me, like I am dealing with emotional struggles or I was fired from a job
  • If I charge for my time at a rate that reflects my worth, I will be rejected or seen as greedy

Fairness

  • If I receive less money than other people with similar levels of education/experience/power/hierarchical role, it’s not fair
  • If I speak about struggling with money, I am being insensitive to people with more systemic disadvantages than mine
  • I have had many advantages so I should make a lot of money
  • I have had many challenges so I’ve been kept from making money
  • Fair pay is the same thing as getting what other people get for the work
  • Non-male founders get ridiculously little investment

Worth

  • If I receive more money than other people with similar levels of education/experience/power/hierarchical role, it’s a sign of my worth or negotiating prowess
  • My personal work is not valuable enough, not good enough
  • How much money I can raise is a reflection of the potential of my startup’s success

Safety

  • I should always be in an upward earning trajectory
  • If I don’t make enough money, my life will fall apart
  • You need at least a million dollars to be able to retire
  • Having a job, a house, a retirement account makes you safe
  • I can’t afford to take time off
  • I can’t have a vacation if I’m not working

Identity

  • I should be doing things for money that reflect ‘who I am.’
  • What’s holding me back from doing what I love is that it’s not a good way to make money
  • Finding a way to make money and do what I love is difficult or impossible
  • If people see all my sides then I will be too something to be hired
  • The person who I’m in relationship with should make enough money
  • Good people don’t care about money
  • Good people don’t neglect their responsibilities by being financially unstable
  • If I were a ‘real’ founder I would be making a product that investors were lining up to fund
  • I can’t do creative work without having enough money to take the time to do it full-time

Competence

  • If I worked harder I would make more money
  • If I made more money, my life would be better
  • I need to find a benefactor
  • I don’t have the credentials to make money
  • All I need to do is get over my fear of being visible and I will make money
  • I can’t find a job even when I lower my standards
  • I shouldn’t pay someone to do something for me if I could do it myself
  • It’s naive to think you could make money without sacrificing your principles
  • Great founders fundraise and bring in large capital investments as a result of their storytelling skills and clear business acumen

It took many years to wrangle with all of these stories and to realize I was operating with faulty priors in the first place.

When it comes to money, there are many ways to get out of right relation with myself and with others. As with any wisdom I have discovered, there are lots of ways to refute what might feel true to me, lots of ways to prove that the wisdom is wrong because there are people for whom the wisdom doesn’t apply.

Wisdom that speaks to me continues speaking, often in layers, often with my own objections layered on.

Wisdom related to money tends to activate me and other people and leads to many objections. Money often proxies for value among us, even in situations that such a metaphor doesn’t hold up well.

In conversation with Peter Limberg from the Stoa / Less Foolish we’ve explored the idea of Alivelihood, framed as “How to make money while doing what makes you come alive?“

Right now I believe that at some point a choice is required to commit to aliveness. For me, any kind of strategising doesn’t support this, it only gets in the way. In other words, aliveness as I experience it starts in the body, in the choice to listen to what is there for me in the interplay of breath, blood, being. The truth rests and abides. It doesn’t need to lead to making money. It does need the conditions to be able to be nourished, literally and spiritually. At times I hear people say having this nourishment is a privilege or a right. To me, it is a choice.

There are a lot of ways this can feel unskillful to express. Do I think it’s easy for people who are financially struggling to make this choice? No. But it’s also, at least from what I’ve observed, quite hard, at least as hard, for people who do have resources.

Making this choice doesn’t mean, “now I am alive all the time in everything I do.” Very few people I have met get to even 50% aliveness without making many choices, without being constantly in the practice of choice, without bumping up against all the deadening we are culturally conditioned to.

What I’m experiencing is that being alive, listening to the body, being willing to be slow leads to more discernment about opportunities. There are certainly people who have found material success by grinding and hustling, and sometimes it feels very alive for me to work hard, to work a lot, to press up against exhaustion. But it does not feel alive to be in fear about the repercussions of not making enough money. It seems more like a situation where, when I keep returning, keep doing the things that feel like they have a positive impact on the world, ways of supporting that show up.

In the conversation with Peter, I came up with a list of heuristics or ways of approaching money that emerged from a time when I went through the (unintentional) experience of having no money, no housing, and no income. I had an amazing transformation when I saw that I remained loved and cared for and that my main job was surrender.

How to be alive while making money

Taking action

  • Know my worth isn’t about money
  • Act from love, not fear
  • Know that I’m OK, loved, where I need to be
  • Believe that it’s possible to have what I need without having to be something that isn’t aligned
  • Welcome fear as an opportunity to see where faith is leaky
  • Ship things – get things out into the world not just in my head
  • Know that I am going to die no matter how much money I have
  • Welcome the possibilities in uncertainty
  • Be willing to live without convenience or comfort if doing so makes aliveness possible
  • Put connection first, be in right relation

Letting go

  • If opportunities to make money arise that align with my values, don’t turn them down
  • Don’t under-charge for my work or discount myself
  • Don’t prioritize free work over paid work
  • Put my full self into the paid work I do, even if it’s small or not ‘important’
  • Don’t let ego get in the way of being honest about my needs and my availability
  • Don’t spend my free time sucked into things that don’t create value for me, i.e. scrolling, shopping, or participating in social media except as very necessary (but still have fun and read and take in information that feels valuable or thought-provoking)
  • Notice when I want to blame, make excuses, or get into grievance
  • Address any dishonesty, mistakes, or dis-compassion
  • Amend situations where my actions impede others’ opportunities to live in their fullness

Any prescription that says, ‘this is how you make money’ feels like it takes me in a direction away from my source of aliveness.

Instead, the more I can feel into the interconnectedness of everything, the more it feels like my best bet is to be in trust, neither trying nor resisting earning money. There’s an underlying abundance that only gets distorted by trying to claim some of it as “mine.” As a tech person, I love the metaphor of open source, of cascading open-ness. The world is not headed in a direction that has any security other than what I can find in my own body and my connection to the world and the people with whom I’m in relationship.

Only Two Values

I had an aha! moment a few months ago when listening to a book on startups that described how many companies create lists of values so long and generic that they become essentially meaningless. Your core values should not be “stuff we think is good” but instead should be the specific qualities your company embodies more than 95% of other organizations. These values should reflect the founders, the team, the product, and the customers. They should be one of your litmus tests for making collective decisions.

The companies I’ve worked for have been led by people who cared about values, but those values were not honed down in this way, and there was some cognitive dissonance as a result.

For GetWith, I created a Three Core Values matrix, which reflects what I’m about and what I want to build with others.

This week I’ve been tasked by my coach to tackle the Brené Brown exercise from Dare to Lead to narrow your personal values down to two and then write about what they mean to you and how you put them into practice. Challenge accepted!

Brown gives these instructions:

I know this is tough, because almost everyone we’ve done this work with (including me) wants to pick somewhere between ten and fifteen. I can soften the blow by suggesting that you start by circling those fifteen. But you can’t stop until you’re down to two core values.

Brené Brown

Here’s the whole list– I will be curious about which ones resonate with you:

The first one was easy. Curiosity is my core motivation, and the practice that feels most rewarding. Curiosity leads me to learn, to examine my own motives, to be able to wonder about the world and other people. It leads me to look for unusual solutions when the common ones feel ineffective.

Curiosity feels amazing, too. When I am curious, I am not in fear, not in judgement, not in suffering. It’s got a natural level of detachment to it and simultaneously leads to listening and compassion.

Curiosity has a downside, I guess, in that there’s a certain insatiability to it. It can lead me to go deep and also to go on meandering paths.

The upside to this downside is that it’s only a problem when around people who aren’t also curious, for the most part. At one point, I thought curiosity was a problem because it led to a lack of focus, but now I see that everything is connected somehow, and productivity can be a result of curiosity as much as a casualty.

I had to ponder my second choice carefully. There are many values that feel wrapped together for me. Where I land, perhaps unsurprisingly in retrospect, is on “belonging.”

Belonging ties into nearly everything I think about and care about. For one thing, I can easily look back on many of the paths I’ve chosen or interests I’ve pursued and see how belonging was a factor. I’ve sought belonging, rejected it, and offered it. I found ways to not belong and created and contributed to communities where I got to experience how distinct and perhaps even opposite meanings of belonging and fitting in.

Belonging feels like my core value, but it doesn’t mean I always feel like I belong in every context. It does mean that I locate belonging in myself and question systems or contexts that exclude people based on factors that don’t have anything to do with connection or mutual resonance among individuals. It means I deeply appreciate systems that promote mattering, interconnection, and caring, which are the bedrocks upon which belonging rests.

In more recent times, I’ve been learning about what facilitates belonging and choosing to belong more actively. I’ve been on a quest to find ways for technology to support the process and practice of belonging and seeking to support the stewards of the spaces where I notice it emerging.

Belonging does have a dark side, but it’s a result of it being half-practiced or using only the instinctive aspects of belonging that rest on us-them dynamics. People feel like they belong because they are not “othered,” and our limbic systems actually run on implicit biases all the time.

As soon as you start going deep into belonging using other parts of your intelligence, it’s clear that the way to have the deepest sense of belonging is by welcoming. There are interesting subtleties to explore, especially because trust and belonging are so intertwined, and for the most part the collective technology we have now doesn’t respect the constraints of systemic trust, which has natural numerical boundaries.

What does it look like to fully live these values? I don’t know, but my guess is that there are a lot of self-defeating behaviours that can’t co-exist with these particular two, and that is fun to think about. Oops, self-judgement isn’t going to work in that system! But honestly seeing where things aren’t working and growth and change? You betcha.

Now I’m super curious where all my closest compatriots land on this exercise. Do tell.