The Mindful Workspace: 

Proximity, Compassion, and Generosity at Medium

Jonathan Rosenfeld
15 min readFeb 16, 2014


On February 15th 2014 I gave a talk at the Wisdom 2.0 conference in San Francisco. Below is a transcript of that talk, including some of the slides I used.


Mindfulness and its place in tech companies is a complicated subject. As my wife likes to say, there is no end to talking about mindfulness at Medium. My children would agree. Fortunately, there will be an end to this particular talk.

One of the reasons we’re never done talking about mindfulness is that it’s an evolving practice. When thinking about helping a company to change, to evolve, I’m struck by the relationship between Darwinian evolution and mindfulness.

What does The Origin Of Species have to tell us about crafting a more mindful workspace? I don’t know. I’m neither an expert on Darwin nor mindfulness. But I can say that I’m inspired by Darwin’s words:

“It is not the strongest of the species that survives, nor the most intelligent that survives. It is the one that is the most adaptable to change.

Startups are notorious for rapid change. Startups are also notorious for failing or, in Darwin’s words, not surviving. To quote one of our engineers,

“We talk about the company as if it was an organism. I’ve been with companies and teams that have failed, not because people weren’t smart enough, or hard working enough, or good people, but because they didn’t know how to change. We examine things, and shift in a mindful way.”

If Darwinian evolution favors adaptability, mindfulness optimizes for adaptability. Jon Kabat-Zinn defines mindfulness as

“Paying attention in a particular way, on purpose, in the present moment, non-judgmentally.”

Those words serve as a simple guide as we work on the ever-evolving project of building a mindful company. Darwin makes it clear that evolution—change—is non-negotiable, so we best proceed deliberately.

Change happens. Change needs a strategy. That’s why at Medium, I hold the role of Change Strategist. This talk is about change, and how at Medium we are using mindfulness to guide both our strategy and our day-to-day actions to build a healthy and dynamic company where generosity and compassion rule.

Mindfulness is all about responding to the moment skillfully. In the same way that evolution is a perpetual practice with no end—and thank goodness for that—one doesn’t finish practicing mindfulness or becoming more mindful. And it’s no coincidence that I’m giving this talk in the context of an industry that is never finished with the products it creates. Technology is an industry that thrives on iteration, and iteration is central to Medium’s practice of building what I call the Mindful Workspace.

In a sense, at Medium we are following the wisdom of Darwin by following the wisdom of Jon Kabat-Zinn. Part of what’s wonderful about a practice that is both complex and unending is that one is always learning and getting stronger and better. Mindfulness enhances our capacity to see what’s in front of us without judgment or bias. This clarity allows us to make aspirational rather than fear-based decisions about the work we do and how we relate to one another.

Change without strategy and the power of physical proximity

I’d like to explain my current work by sharing a bit of my journey into change strategy. It’s a subject I’ve been thinking about rather obsessively since I was a kid.

It was in 7th grade when I first saw the need for change strategy come into stark relief. I attended a recently desegregated school. Officially, the desegregation of my school represented profound positive change: black and white children brought together to become friends and learning partners. In practice, the opposite was true: children seen having friendly conversations with children of the other race were subject to violence.

As fate would have it, the most integrated experience of the day was the cafeteria. Even though the cafeteria was probably 50 yards long and fairly wide, it had only two tables, each running continuously from one end of the room to the other.

The long tables were constructed of shorter tables placed end to end. The races couldn’t segregate, so there were various cusps where black and white children sat next to each other.

One day I came to the cafeteria and the tables had been turned.

The long rows had been broken, and the whole cafeteria had segregated tables. “Oh shit,” I thought. Not only could I no longer visit with my friends, but the school, I knew, was in trouble. Within weeks we had riots and the police had to come in to keep things under control.

Could it be that something as simple as allowing a small group of open and receptive black and white children to sit in proximity to one another provided a stabilizing force, which allowed integration to go forward without severe violence? I don’t know. But when those tables were turned, it seemed to me that those in charge of the integration process, while having great ideals, had massively disrupted the status quo without a strategy for the change that inevitably followed.

Change Elements: Proximity allows for generosity and compassion

This next story ends with people talking early and often, but it doesn’t start that way.

In my early 30s, I trained family therapists in short-term therapy. The team and I used a one-way mirror to observe a colleague working with a family.

These were tough cases. A typical case might involve an adolescent sex offender and parents with substance abuse problems.

When it came time for the staff to debrief, the room would often be silent. No one wanted to say anything for fear of injuring their colleagues. I got it. But how were these folks going to get better if they wouldn’t give one another feedback?

My solution was to introduce two change elements. What is a change element? It’s a new structure that’s inserted into an existing organization to help it evolve to a higher level of complexity. Change elements are about productive disruption. They are a response to the question, If change is inevitable, how do we move forward in a constructive evolutionary way?

In this case, the change elements were identifications and appreciations. If you thought your colleague did something awesome, you could give an appreciation. If you thought they’d not handled a situation well, you could give an identification—on the condition that you yourself had struggled through a similar tough spot. In essence giving an appreciation was an act of generosity and giving an identification was an act of compassion.

With these change elements, there was no shortage of constructive feedback. Given a framework for mindful dialogue, these professionals were eager to share generosity and compassion with one another. People started talking early and often, and they got better clinical results.


Now the Medium story.

At Medium we think of the company as a product. About two and a half years ago, Ev Williams, our CEO and founder, asked me, “How do we build a company where people are productive, creative, and engaged but not working crazy hours?” I said, “We remove as much pointless, non-productive anxiety from the workplace as possible.”

Anxiety eats up cognitive bandwidth. It encourages concrete rather than abstract thinking, which compromises people’s creative problem-solving capacity. If you reduce anxiety, you get the productivity and creativity without the crazy hours. Mindfulness also reduces interpersonal anxiety. This frees people up to be better colleagues and collaborators.

Recently one of our designer’s articulated the effect of mindfulness on anxiety:

“There is so much anxiety at startups, but instead of being anxious with each other, we’re focused on this idea that we can all be better. Normally at a small company like ours with so much talent and experience, there would be lots of power struggles with individuals trying to take over. Mindfulness tames that.”

So if Medium thinks of the company as a product, we might call this product the Mindful Workspace. What are the features of the Mindful Workspace? Let me share our work in progress with you.

Feature 1. Change Strategy and Leadership

It starts at the top. In the early days of the company, we had an agreement among our most senior individuals to be constructively open with one another regarding needs and aspirations. Our leaders committed to using the development and growth of the company as an opportunity to be their best selves. Essential to this agreement was the decision to meet regularly to check in and hold one another accountable for commitments made and actions taken. I’d like to think this level of self-reflection and accountability is central to who we are. It’s certainly central to whom we look to hire.

Everyone at Medium is encouraged to see themselves as a leader. To be clear, “leader” does not mean “manager.” Part of leadership involves being generous with feedback, particularly mindful positive feedback. What that means in practice is that feedback needs to be given in paragraphs and not adjectives. This requires one to pause and reflect on the “why” and “how” behind how you perceive someone.

Since the early days of the company I’ve worked with our leaders to think about change strategy. I don’t code, design, or contribute to the primary product in any direct way. Thus I’m dedicated purely to company culture. Companies should consider hiring a dedicated individual if they want to sustain a commitment to building a Mindful Workspace over time.

Feature 2. Organizational Structure: Holacracy

At Medium we use an organizational management tool called Holacracy. Holacracy describes itself as

“A new “operating system” that instills rapid evolution in the core processes of an organization. Holacracy provides channels so anyone who senses a tension can process it into organizational evolution. People become the sensors of a conscious organization, driving its continual evolution.”

For Holacracy to work, one needs to be mindful. At the same time, the practice of Holacracy supports mindfulness. And so we have an elegant positive reciprocal feedback loop.

Ev Williams describes some of the mindful benefits of Holacracy:

“One of the principles is to make the implicit explicit — tons of it is about creating clarity. People are actually encouraged to bring stuff up. It’s called processing tension; it’s very efficient and you really take advantage of everybody’s perspective and ideas.”

A lot of the friction associated with organizational change is mitigated by the fact that when people have tensions, those tensions can be processed and integrated into the evolution of the company.

One of our engineers describes her experience with processing tensions:

“Rather than being satisfied with the status quo, I feel empowered to bring things to the table that could be improved upon.”

Feature 3. Language

Over time we are working to develop a shared vocabulary to support our Mindful Workspace practice. Every day we use specific Holacracy terms like “tension,” “energize,” and “objection.” We integrate language from our meditation practice and from mindfulness teachings—including “pause,” “being present,” “clinging,” and “aware,” — into our day-to-day conversations. Communication about best practices within the company frequently speak to our attempts to use language in a mindful way.

Feature 4. Skillful Communication

In an environment that favors curiosity, compassion, generosity, identification, and appreciation, it’s relatively safe to have tough conversations. I don’t want to misrepresent our success. We are working on this, and I think we are doing better and better every day.

Like all companies, we have frequent misunderstandings, people get disappointed, and people get frustrated with one another. The hope is that this frustration will turn into curiosity rather than judgment.

When things go wrong at work, I think we’ve all asked the question, “What were they thinking?” Hopefully, some of the time we also ask, “What was I thinking?” Sometimes the answer is simple: one or both people were not thinking, they were reacting. When people are working to be mindful and not judgmental in a conflict, I encourage them to follow my particular maxim:

“To find the mindful voice, consider what a curious person would say.”

One of our operations people expressed how he puts this principle into practice:

“At my old company I just accepted that I had to be thick-skinned, and I just expected everyone else to be that way too. Now if something happens and I’m feeling bad, I find myself reflecting about it and taking constructive action.”

The end goal of skillful communication is for all of us to bring a generous and compassionate disposition to conflict with colleagues. Sometimes we succeed and sometimes we don’t.

Feature 5. Meditation

We believe that practicing meditation is one of the best ways to energize mindfulness. We also believe that you can be mindful without practicing meditation. Our meditation sessions and retreats are very explicitly opt-in.

Our meditation teacher is with us three days a week for two sessions. Each session includes a brief teaching and a 20-minute meditation. We have an annual Medium Mindfulness and Meditation Retreat. I’m going to give you some numbers about participation but bear in mind, we were 15 people when our first mindfulness and meditation teacher began working with us. We are now more than 50.

40-70% of the company participate in weekly meditation. Approximately 70% of the company attended our last meditation retreat. We also have a meditation retreat benefit: the company will cover the cost of you and a +1 to attend a weekend meditation retreat once annually. Recently our senior leadership used the benefit to attend a retreat together.

It’s hard to measure our people’s participation in meditation and mindfulness, let alone quantify the results. I certainly believe, and the research supports, that people who meditate frequently become more resilient and less reactive to their work frustrations as well as to the people they work with.

As one of our editors describes the benefits of meditation:

“Since I started meditating, I find myself at work reacting differently when people ask things of me. I don’t rush. I seek others’ advice more. I feel more open to others’ feedback. At home dealing with my wife and kids, I’m more patient and mindful of everything around me.

Certainly these effects contribute to an environment where people have the confidence and calm to be open and forthright in giving and receiving feedback. That is, an environment where people talk early and often.

It’s tricky to promote something while suggesting that it’s truly optional. We try to give clear mixed messages. This past June, we held our first annual Medium Mindfulness and Meditation Retreat. We encouraged people to come and to bring their partner if they liked. We ended up holding the retreat at a center that was not large enough to hold the whole company. This was our way of saying, “we absolutely hope you all come, and we absolutely hope and expect that not all of you will come.”

Just to name it, it is not our goal to have everyone in the company actively meditate. Imagine having never meditated and showing up at a company for your first day of work to find that everyone meditates every day. This would not work well for some people.

A member of our support team talks about how mindfulness and meditation change the way she interacts with colleagues:

“Practicing mindfulness changes your relationship to yourself and your co-workers. When you meditate together, it humanizes work. It changes your relationships. People are more respectful and open.”

The Mindful Workspace in Practice

Among my half dozen books that have not yet been published or written, I’m particularly proud of Tolerance Creates the Space, Generosity Fills It.

It’s actually my first book not published or written. I believe that didn’t happen sometime in the late ‘90s. This story belongs in that book.

For two and half years, Ev Williams and I have been talking about how to build and scale a mindful company. Until recently there was a specific tension between us. It went something like this:

I’d want to roll out a bunch of complex Mindful Workspace features all at once, and Ev would say, “Do we really need to do all of this at once?” “Absolutely,” I’d reply. “All these features complement one another.” We’d go back and forth. I might say, “You need to think about it more systemically.” “I am,” he’d say. Finally, about six months ago, Ev commented, “I wish you would think more like a product manager.”

These words blew my mind. They continue to blow my mind. I suddenly realized how much I’d been lost in my old ways of thinking. I have some compassion for myself. I spent twenty years in academia and the non-profit world, designing programs and writing grants. I realized at the moment of Ev’s comment that even with ten years in tech, I’d never stopped thinking like a grant writer. In the public sector, you design whole, fully featured programs or you don’t get funding. Iteration is not an option.

Obviously Ev and I work in physical proximity. We also work in aspirational proximity, particularly around building a mindful company. We also work, as all people do, in psychological proximity, so thank goodness for mindfulness.

It’s easy when working with others to get frustrated and anxious—anxious about being misunderstood, under-appreciated. It’s easy to be unaware and project negative things onto those with whom you work. Easy to exist out of the moment by taking a present conflict and turning it into inevitable catastrophe down the road.

Judgment gets in the way of people speaking early and often. In a Mindful Workspace, people are curious about one another’s thoughts and actions without judgment. They identify with their colleagues and their company. They appreciate the various contributions that everyone makes to the greater effort.

One can take a frustrating conversation and, with a generous spirit, tolerate the frustration; with compassion, stay present; by listening, eventually get the clarity that you and your colleagues need to go forward and do your best work.

Being mindful let’s you talk early and often.

At Medium I am more constructively challenged than I have ever been in my professional life. I’m used to coming into an organization, making an assessment, hopefully articulating some compelling recommendations, and then subsequently getting good feedback on the outcomes. Sounds good, and it’s been the foundation for a rewarding career. Having said that, I know I can do better work, and I know I can’t do it alone.

I am deeply humbled and grateful to my colleagues at Medium for their willingness to talk early and often. While I get a lot of support, I’m frequently asked to do better. I’m challenged to take my thinking to a higher level, to make my actions more impactful. It’s only fair, given that I ask the same of those around me.

I don’t know for sure, but I’d like to think that my experiences are representative of everyone’s at the company. Our people at Medium deserve a lot of credit, but I don’t think we would be where we are—and I wouldn’t be standing here on this stage—without a commitment by many people over time to bring mindfulness to the world.

Here are two quotes that I feel really capture what we’re working on when we’re working on the company as a product. The first is from an engineer and the second is from a product scientist:

“We all know that hindsight is incredibly valuable. What if you could get hindsight ahead of time? Mindfulness lets you get other people’s perspectives, ahead of time.”

“People here are generous. We trust each other, so that makes it easy to form and reform work teams.”

Going Forward

At Medium we claim no special knowledge or accomplishments regarding work and mindfulness. Everything I shared today represents a work in progress—and of course things often don’t go as well as we would like, or perhaps as well as I’ve represented them.

Right now we face the challenge of scaling our mindfulness and meditation practices as the company continues to grow and change. I’d like to think that what we are doing runs in parallel with the rise of mindfulness in the public consciousness and discourse.

We are all about to witness remarkable things happening in the world of work. I know this room and this community are filled with individuals who practice mindfulness and who can lead as agents of change. I trust that here we have open-minded leaders who will create the space for mindfulness to become central to our work lives. I believe that we are all on a remarkable journey, and I look forward to hearing and sharing more.



Jonathan Rosenfeld

VP Coaching & Executive Development @ StockX: Mindfulness, Change Strategy: