my favorite questions

seven questions that drive my writing, attention, thoughts, & actions

Hello friends, it’s been a while (one month, to be precise) since we’ve had a sublime newsletter. Quite honestly, my ability to send this newsletter has been highly dependent on my children going through a full week without catching a virus. We have an exciting announcement that’s been a year in the making coming later this week, and many plans to keep this space alive next year. Stay tuned.

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my favorite questions

the questions that drive my writing, attention, thoughts, & actions

I discovered Ted Gioia’s 12 open-ended questions that guide his life and work via Sam Liebeskind’s Sublime library (thanks Sam!)

What questions guide your life and work? What a powerful question.

As the world has become more and more distracting, the value of focus has increased tenfold. Being alive consists of nothing more than the sum of what we pay attention to. And it’s impossible to care about everything. 

Most productivity advice is BS, and I say this as the founder of a “personal knowledge management tool”. The only productivity advice that matters is getting clarity on what matters to you. You just feel differently about the world when you know what you care about.

Here is an initial (still work in progress) attempt at defining the questions that bring me alive. 

If this resonates, tell me! Because if enough people respond, I’m thinking of doing a workshop type thing sometime early 2024 to help more people turn up the volume of their intuition and identify the questions that make them come alive. 

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(1) How can we go from accumulating insights to embodying and integrating learnings?

When all information is impeccably presented to us, summoned on-demand by a perfectly calibrated chatbot or whatever, and presented to us at the right moment and in the right way, we’ll come to realize learning, reading, and thinking are only the seeds of change. 

The truth is, knowledge does not change behavior – the world is full of crazy therapists, divorced marriage counselors and agitated yoga teachers.

To generate change and action, we need to weave ideas more deeply into the fabric of our lives, we need to embody the knowingness. But how?

[my raw notes and highlights on knowing vs doing and information vs. knowledge]

(2) How can we build interfaces that reliably make us feel the way we want to feel – calm, connected, inspired?

There’s a general sense that the vibes on the web are off. Platform after platform designed to make it easier and more addictive for us to consume endless feeds of content so the corporations behind them can sell more of our attention and data. Content that hardly bothers to disguise the fact that it’s advertising. Uninspiring visions of AI assistants promising to replace reading-for-pleasure with cheap AI-generated summaries. 

How can software help us become clearer thinkers and live more inspired lives? 

What does the design space for software that combines the focus and intentionality of a personal tool with the sense of aliveness and serendipity of a communal space look like?

What does a web designed for self-directed learning, deepening our understanding, and communal meaning-making look like? 

[raw notes and highlights on dreaming of a better internet, building with soul and designing for emotions]

(3) What comes after the algorithm, and how will we discover information?

In a 2017 interview, Ev Williams (the founder of Twitter), said something that has stuck with me since: “the trouble with algorithms, is that it rewards extremes. Say you’re driving down the road and see a car crash. Of course you look. Everyone looks. The internet interprets behavior like this to mean everyone is asking for car crashes, so it tries to supply them.”

The more outrageous the opinion, the more likely it is to be amplified by attention-seeking algorithms, because there’s no engagement as powerful as outrage. 

Every idea that we have is downstream from what we consume. And so it follows that if we are forced to navigate a world where junk media gets amplified and is packaged in bite-sized delicacies that our brain finds irresistible, this has a tremendous impact on our psyche and how we relate to ourselves and the world.

What are the effects of overloading our brains with information? How would a different business model and a collective reverential respect for our attention change things? Once the algorithm knows us, how can we reorient ourselves as a different type of person? How can we stay online, without all of the mindlessness, passivity, and addiction that often entraps us? 

[raw notes and highlights on algorithmic anxiety]

(4) How can I better articulate and educate people on the benefits of having a Sublime library?

I have been transformed by cultivating a habit of knowledge gardening – collecting and connecting all the interesting things I come across – and of doing it in a multi-player environment like Sublime where I can make parts of my garden open for anyone to build upon.

This practice of building a digital garden, a spark file, an idea library, a digital library – whatever we call it – has brought enormous benefits to my life. It’s the closest thing to giving others an API for my mind. It provides a record of my learning journey and helps me explore my values, beliefs, and identity. It helps me plant seeds for dots that will connect later. It’s a gift to my future self – giving me just-in-time inspiration. It helps me pay attention to what I pay attention to.

I think this is what Voltaire meant when he said ‘one must cultivate one’s own garden.’

Sublime feels unexplainable. I’m equal parts humbled and exhilarated by the slow process of getting to the essence of it.

[raw notes and highlights on making sublime and how do you describe sublime at the dinner table]

(5) How can we better align incentives between founders and funders, and enable more people to build enduring companies with patience, care, and preservation at the center?

Something about software is weird. You can listen to a song you liked decades after it was recorded. You can look at a painting from 300 years ago and still appreciate its beauty. Software, by comparison, rarely lasts.

Because I’ve spent so much of my career in tech, where speed and growth is prioritized at all costs, where boom and bust is baked into VC math, I’m also fascinated by the benefits of gradually and slowly building something that lasts.

There are remarkable software products that shut down because they were overfunded, or the valuations they raised capital at set them on the wrong path, or they optimized for an exit rather than a thriving and self-sustaining business.

And so I’m interested in this question, because I think founders are ready for something new, and the world would greatly benefit from it.

[more in perspectives on funding and venture capital]

(6) How can I maintain my creativity, optimism, intellectual vitality, and sense of agency in the face of the stress that comes from building a company and the endless forces luring towards conformity?

We start raw, then our hearts and minds get boiled by constraints, pressure, feedback, and challenges. How do we keep our head up and maintain our creativity and good spirit in the face of obstacles? How do we resist the pressure to follow established playbooks? How do we embrace the periods of relentless action before results? How can we navigate periods of uncertainty, mystery, and doubt without being irritable?

[more in don’t be discouraged and agency, and builder mentality]

(7) How do we reconcile ambition and the desire to do great work with motherhood? 

Great work needs solitude. It needs concentration. It needs time. And it is time that often feels incompatible with child rearing. The expectation to be ever present and the realities of care labor do compete with creative selfhood. 

Ambition and motherhood, this is something I am deeply interested in. What is the shape of an ambitious woman’s life? I’ve seen the two tales before – women that are smart and ambitious but don't give their creative calling time become bitter. Women that put their ambition above all else, only to find a big pit at the other side of being well-known or rich and successful.

When she is with them she is not herself; when she is without them she is not herself; and so it is as difficult to leave your children as it is to stay with them. To discover this is to feel that your life has become irretrievably mired in conflict, or caught in some mythic snare in which you will perpetually, vainly struggle.\

[raw notes and highlights in women and ambition and greatness]

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