Last month, I bought a house.

Buying a house is more complicated than nearly anything else I’ve done – besides, perhaps, running a business.

Over the last few weeks, I’ve highlighted some of my most popular articles from the last two years. In doing so, I realized that many of my personal favorites are those I reference repeatedly; they’re evergreen.

But over the course of the eight months leading up to the purchase, I learned a lot. So today I’m sharing the article I wish I’d been able to read when I started.

This is not an argument for or against buying a house. If you want to be talked out of buying a house, read Ramit Sethi. If you want to hear reasons to buy a house, ask a Boomer.

Instead, this is what I wish I’d known about house buying when we got started back in February.

I’ve seen a lot of backward industries:

• I’ve worked in large non-profit arts organizations.
• I’ve worked within family-owned SMBs.
• I had a chef throw a plate at my head in a restaurant.
• I’ve worked in fast-paced, drama-filled tech companies.
• I’ve obtained a myriad of impossible-to-get permits at Robin’s Cafe. San Francisco doesn’t make brick-and-mortar permits easy.

So believe me when I say that I’ve never met as backward, corrupt, and intentionally complicated an industry as real estate. First, let’s define some terms.

The people you’ll meet:

• Buyer – That’s you!
• Seller – The current owner of a property.
• Agent – Agents work for either the seller or the buyer – but actually they work for themselves. Their goal is to get you to buy or sell a house, and serve as a liaison between you (the buyer), the seller’s agent, and the seller. Agents aren’t financially motivated to help you get the best deal because their commission is a percentage of the price of your house. A small price reduction barely affects their fee, even though it matters a lot to you. You are not legally required to have an agent in most states.
• Mortgage broker – These folks help find your mortgage – assuming you aren’t paying all cash. They’re very salesy and eventually sell your mortgage to someone else. The benefit is that they’re available all hours and can get you information very quickly.

The companies you’ll work with:

• Real estate brokerage – Agents work within brokerages, and split income, usually 50/50, with an agent. Brokerages also list houses for sale. There are small, boutique brokerages and also national chains like Compass and Coldwell Banker.
• Mortgage company – The company that ultimately holds your mortgage. If you get a mortgage with a specific bank or credit union, they’re not likely to sell your mortgage to a third party.
• Title company – The company that ensures successful transfer of ownership between the buyer and seller.

The terms you’ll hear:

• Buyer’s agent vs. listing agent – Typically, the Buyer and Seller each have an agent, and agents discourage you from communicating directly with the other party because it keeps them as the middleman.
• Pre-approval vs. pre-qualification – These are terms you’ll hear from your mortgage broker, and represent whether you are qualified for a mortgage. Pre-qual is a soft estimate of how much you’ll be able to borrow. Pre-approval is documented and stronger.
• Foreclosure – When a bank is selling the property, instead of a person. Not for the faint of heart.
• In contract – An agreement between buyer and seller that the buyer will purchase the real estate, assuming specific conditions are met
• Earnest money – Money you put down (usually 3%) to show proof that you are serious about buying a specific property
• Contingencies – The requirements that need to be met before you buy.

Our adventure started in February of 2025. My then-girlfriend and I were planning on renting, when – seemingly out of the blue – she texted me a house for sale. A house we saw that weekend – a dilapidated mansion with spectacular views – became the focus for my learning for the next five months.

The mansion had a lot going for it – great views, extremely quiet, an abundance of indoor and outdoor space, pool, garden, easy rental opportunities, and more.

It was also a completely ridiculous project. It had been a party house, built in the 1970s and then illegally rebuilt, which, we later learned, triggered county requirements like seismic retrofitting and a sprinkler system. There were three levels of decks with incredible views, but they had been poorly built and were on the verge of collapsing. We discovered two nests of bees in the walls – so active in the spring that the buzzing could be heard inside the house!

After five months of research and seven offers on the property, we walked away. More than the repair and reconstruction required, we walked away because of the county requirements. The onus on a new owner to make up for the previous decades of illegal construction was too high.

We bought another house in the same city, which also has views, a pool, and rental opportunities. Our new house isn’t a mansion, and needs only modest repairs – and we’re very happy here. But I learned more about real estate during this months-long sprint than I ever thought possible.

These are some of my biggest takeaways.

Mindset

1. Don’t fall in love until after you buy

It’s really helpful if you don’t fall in love with a single property until after you own it. This is the single biggest purchase most people will ever make, and the decision is usually made emotionally. Instead, try not to get too excited until after you’ve purchased. Obviously, you don’t want regret. Make sure you like the house you’re about to buy! But too often people fall in love and then get into a bidding war out of the desire to win a deal.

2. An entrepreneur’s mindset

The thing that helped me the most through my real estate learning journey was what I’ll call an entrepreneur’s mindset.

We wanted a home, yes. But I also didn’t want to lose money on a project – if anything, I wanted to make money.

Know how to protect your downside and plan for contingencies in case things go wrong.

If your circumstances change and you can no longer afford your mortgage, what are you going to do? What are the ways this property could cash flow, even if you weren’t living in it? Are there cosmetic repairs you could make that would improve the value of your home?

3. They treat you like the product, but actually you have all the power

I’m fascinated by how different industries talk about their customers. At Robin’s Cafe, we had diners. At Zander Media, we have clients. At Responsive Conference, we have attendees. Facebook, OpenAI and most software companies have “users” – which is the same term that drug dealers use to describe their customers.

In real estate, agents call real estate “inventory” and us, the clients, are called “buyers.”

There’s a sense as you begin to get serious about a property that you are a cog in the machine. Agents will push you to bid on a specific property. Mortgage brokers request that you sign before you’re ready.

The most important thing to remember is that you hold all the power. As the buyer, you can walk away at any time. (Though if you wait too long and contingencies are past, you stand the risk of losing your earnest money.)

You always have the power to walk away.

Research

4. Know what you want

We had lots of criteria starting out:

• We wanted a house that was not too far from San Francisco
• That was safe
• And that we could afford
• We wanted within walking distance from an interesting town
• Ideally we wanted open space nearby
• The house should have rental opportunities
• And best case scenario for it to have a pool
• Weirdly, we both had a thing for double front doors just because that felt fancy

However big or small, list out the criteria you want in a house. You’ll have to settle on some of them, but the clearer you can be on what you want, the more likely you are to get it.

5. See lots of houses

The best way to learn about houses is to see lots of houses. Agents are great for this – but don’t commit to working with one agent for a long time, or maybe ever. You can call the listing agent – the person who is showing the house – and ask to see it. I prefer not going to Open Houses because there are other people and a (false) sense of urgency. Even driving by houses for sale is useful to get a sense of regions and neighborhoods

6. Do your research

In this industry more than anything else I’ve ever experienced, it’s essential to do the research. The more thoroughly you get to know a specific region, neighborhood, and even a specific street, before you decide which house to buy, the better off you’ll be. Use ChatGPT to do Deep Research on a variety of topics related to things you see in each house you visit. Ask real estate agents a lot of questions. Talk to people on the street.

7. Get lots of (free) quotes

I’m surprised that home buyers don’t visit homes they are seriously considering with an entourage of contractors, plumbers and electricians.

There are two different types of quotes – those you pay for and those you don’t. If you call a local HVAC company and request a pre-sale quote, they’ll charge you. But, instead, if you say that you are planning to buy this house and just want to plan for your future, they’ll likely come to the house, look around, and send you an estimate of costs.

A lot of the difference depends on whether they write up a multi-page summary of their findings or just a single page with a price. Either one works fine when it comes to negotiating down the price of the house.

But even if you did have to pay for every technician at every house you’re considering, those few hundred dollars would save you tens of thousands in having avoided bad decisions.

8. Talk to the city or county

One of the most under-leveraged aspects of real estate is talking to your local jurisdiction – the city or county within which your property falls. Even just the question “What’s this city/county like to work with?” which any agent or contractor should be able to answer, will help inform your decision about the amount of work you’re willing to tackle and the amount of bureaucracy you are willing to wade through.

The county where the mansion sits is quite a bit easier to work with than the city within which we now reside. But since our new house requires so much less renovation, we decided that trade-off was worth it.

Moreover, the city or county will have some amount of records about the property in their files and some people within the city/county may even be familiar with the property itself.

Talk to your local jurisdiction before you buy!

9. Read the fine print

I’m continually shocked that most people don’t read every bit of fine print in every document. The very first real estate agent who showed us a house requested that I sign an exclusive agreement with him even in order for him to show us the property. Had I not read the contract in advance, we would have been stuck with him without recourse.

The title company who transferred ownership of our new house from the previous owner to us was surprised that I requested the 250 pages of legal documentation in advance of the day of signing. And that we protested that they had only given us one hour to review the documents in person.

Is reading fine print and intentionally obscure legal language a difficult question? Yes, of course it is. And as you go into a hundred thousand dollar project, it is also a necessity.

Never, ever sign without reading the fine print.

Cautions

10. Everyone has something to teach you

Real estate, especially when you’re just starting out, is a matter of talking to a thousand people. And everybody has something to teach you.

In the last seven months, I’ve been on the roof of ten properties with at least a dozen different roofers. Every time I go up, I learn something new about roofs from a casual comment the roofer makes.

Talking to an abundance of people, even if you only learn one new thing from each, will enable you to make better decisions going forward.

11. A false sense of urgency

As with most forms of unethical selling, everyone will try to create for you a false sense of urgency. Agents will tell you to bid now. Mortgage bankers will tell you you have to sign today, or else deadlines won’t be met.

And it is true, especially in a competitive real estate market where time matters. But it rarely matters as much as the people you’re working with will have you believe.

Don’t get swept up in the adrenaline of the rush and lose sight that you are considering among the biggest purchases of your life.

12. Agents are out to get you

There are a lot of good people in the trades. But it has been my experience (and is widely agreed) that people who make their living in real estate – agents, brokers, mortgage brokers, etc. – are out to get you.

But of all of these, real estate agents are my least favorite.

I’m reminded of the Charlie Munger quote, “Show me the incentive and I’ll show you the outcome.” The money circulating around real estate is large. Most of us don’t otherwise handle transactions in the 100s of thousands of dollars. And when someone is compensated purely on a percentage basis of the cost of the home, their incentives are – at best – only loosely aligned with yours.

It’s hard, but not impossible, to buy houses in the United States without an agent. And how to choose an agent – or avoid getting one – is a longer topic than this article will allow. But know, going in, that “your agent” is not on your team.

13. Read How to Buy a Used Car (and then do that for houses)

Last week, I revisited my article, “How to Buy a Used Car.” There are a lot of similarities between buying a used car and buying a house.

14. Read Abundance (and know that’s not the world we live in)

Ezra Klein’s Abundance is a hopeful picture of what the world might look like if we were to build in the United States. And it isn’t the world we live in.

Instead we live in a world where the accelerated rate of change exists in stark contrast to the slow tedium of hundreds of years of bureaucratic process. Even as technology enables us to move and think faster than ever before in human history, the lethargy of governmental bureaucracy stagnates growth.

That’s how it is right now – unfortunately. Plan accordingly.

Conclusion

I’m thrilled with our new home, and the sensation of being a first-time home buyer. But perhaps even more importantly, I’m no longer overwhelmed by an industry that previously felt impenetrable, overwhelming, and ridiculously complex. Hopefully this article is a first step for you to achieve the same.

Last week’s Responsive Conference was the best event I’ve produced. Attendees have been raving about the experience, my team bonded in new ways, and I walked away without the post-conference crash that too often accompanies producing a big event.

One of the things we did especially well this year was to incorporate alternative event formats into the conference format. Specifically, there are three atypical formats that I think every event organizer should incorporate.

Fishbowl

A fishbowl is a panel with 1-3 additional seats on stage. Your audience is encouraged to sit in that seat and join the speakers in conversation.

Why this works:

Fishbowls challenge the audience to stay engaged. Every time there’s a new participant in the hot seat, the audience – even if they weren’t fully engaged before – has the opportunity to reengage with the conversation.

This format also adds variety for the speakers. Most panels fail because panelists talk to each other about pre-planned topics or things they know too well. Regularly adding new people to the conversation changes the dynamic with each new attendee.

Best-case scenarios:

A fishbowl can work with four seats on stage, where one seat is empty for participants. At its best, though, there are five or six seats available, of which two are available to participants or the facilitators.

This session can work in a fixed seating format, but it works even better when the audience is literally sitting around the speakers, while the speakers are facing each other in the middle. A literal fishbowl shape added to the intimacy of the experience for everyone involved.

Considerations:

You need a strong facilitator – The first consideration is that a strong facilitator has to set the context for this format and keep people moving in and out of the hot seat (or seats). This facilitator needs to describe how a fishbowl works and encourage attendees to join in. The facilitator can occupy one of the seats on stage throughout or facilitate from the side.

The audience needs to be engaged – a fishbowl only works if attendees participate. This requires the facilitator to encourage attendees to jump in. Some gentle facilitation may be required to make this happen.

The people on stage need to be engaged – this isn’t an issue for most speakers, but participant speakers should know that this won’t be a typical panel. Most speakers don’t want to phone in the experience – they want to enjoy the experience! But a fishbowl is not a panel, and some speakers may be hesitant.

Interview-in-the-Round

An interview-in-the-round is a session where each speaker interviews the next speaker. It works like this:

• Speaker 1 interviews Speaker 2
• Speaker 2 interviews Speaker 3
• Speaker 3 interviews Speaker 4
• Speaker 4 interviews Speaker 1

​Here’s an example from Responsive Conference 2019.

Why this works:

Attendees want to hear from the speakers. In this format, they get 15 minutes uninterrupted from each speaker (assuming a 60-minute session), with another 15 minutes where that speaker conducts an interview. Assuming good speakers, it is always a good experience for attendees.

Best case scenario:

Speakers have an intimate experience on stage, which then translates into the attendees’ experience of the session. Through intimate one-on-one interviews, they are able to go places that they wouldn’t in a larger group.

Considerations:

Unpredictable outcome – The “outcome” from an interview-in-the-round is unpredictable. There isn’t someone in charge of summarizing the experience for attendees, so event organizers might feel uncomfortable with the experience.

Speaker egos – The problem with this format comes down to speakers’ egos. It isn’t a common format compared to panels, and as a result, speakers feel like they won’t be able to get on stage as much as they expect to. This isn’t factual – in an interview-in-the-round, speakers generally get more stage time than in a typical 4-person panel. But from an appearance perspective, they often feel like they’ll get less limelight.

I’ve never seen attendees dislike this format, but speakers may have to be persuaded.

Unconferences

I define an unconference as any event where the attendees set the agenda. I’ve written a full article on how to run an unconference, so start there.

Why this works:

Unconferences work because there is always more collective intelligence in a group of attendees than in a single person on stage. An unconference makes use of that collective knowledge by allowing the attendees to determine the agenda.

Best case scenario:

The best-case scenario for an unconference is that it channels the focus of an entire group, and everyone walks away reenergized and with several new ideas.

Considerations:

The problem with an unconference by definition is that speakers and facilitators aren’t the highlight. This makes selling tickets against name-brand speakers and brands nearly impossible. An unconference can be a great experience for attendees, but it is much harder to monetize.

Gatherings and events are a competitive advantage in business, especially in an age of AI. Our loneliness epidemic and the enduring popularity of books like The Art of Gathering both demonstrate that humans want to gather in new, interesting, and immersive ways.

Any kind of gathering is better than not, but panels and happy hours need not be the only way we do so, and these three alternative formats provide some welcome variation.

The future is unpredictable

In 2015, the authors of Responsive.org wrote that “the future is becoming increasingly difficult to predict.” Today, with global instability, political partisanship, and a more rapid rate of change than ever before in human history, those words feel prescient.

The tension between organizations optimized for predictability and the unpredictable world we live in has reached a breaking point. Only organizations that adapt to this ever-changing world will survive.

We structure organizations the same way we did in decades and centuries past – built for a time when predictability mattered more than speed of execution.

I’ve had anything but a conventional career path. Across more than two dozen different industries – from circus acrobat to self-taught restaurateur – I’ve witnessed the same bureaucratic practices; the same good people stuck in outdated systems.

And nowhere is that unpredictability more obvious than in live events.

A few small fires

​Responsive Conference 2025 is next week. There have been a few small fires: a team member is in the hospital, a keynote speaker asking to change their call time, and nametags scheduled to arrive a week late.

A friend asked me recently if I was going to propose to my girlfriend on stage at the conference. My answer was – quite obviously – no. And not just because she wouldn’t want that kind of public attention.

Events are an act of service. Great events exist for their attendees, speakers – and only then for the organizing team. To take the spotlight with an engagement proposal defeats the purpose of producing an event. It takes the focus off of them and their experience. When the organizer takes up too much space, they undermine the service the event provides to the community.

The utility of community

On September 16th, the day before Responsive, my friend Jenny is producing the Conference for Conferences, a 1-day event about how to run more immersive and experiential events.

Then, Responsive Conference, which I often describe as a three-ring circus that we always design as an experiment in the very principles we gather to discuss.

Within the curation of Responsive Conference, too, there are sessions that address the intersection of community, change, and AI.

Suzy Welch, PhD is the creator of Becoming You, a popular NYU Stern course and book that helps individuals reinvent their careers. I’ll be interviewing her, alongside startup operator-turned-consultant Shelby Wolpa, about career reinvention.

Jesse Freese is the founder of a 2000-person community called StartupExperts which brings together HR, Operations, and Finance startup leaders. He will be sitting down with Marcus Sawyerr, who runs EQ, a network of executives, to discuss the role of community and how successful leaders leverage collective intelligence to keep pace with change.

Events are a competitive advantage

Running events is a logistical nightmare. From a team member in the hospital to last-minute schedule changes, there is always another fire! The work of producing events – selling tickets, organizing people, managing ambiguity – is largely thankless work. As with any good performance, you only notice when things go poorly.

But the community, trust, and a shared understanding that events create are priceless. In 2016, my producer and a speaker met and got married. I’ve been told “That moment at Responsive Conference changed my life…” dozens of times. Events aren’t just about gathering people — they’re about creating containers where community, trust, and possibility emerge. They create reference points people carry forward.

And running events creates leverage for the organizer. You become the community builder – the person people look to. They build trust much more quickly than singular conversations can.

The thankless work isn’t, in fact, thankless after all. In an age where AI makes everything faster, it’s messy, unpredictable human experiences that give us an edge.

With Responsive Conference only 25 days away, I’ve been thinking back to February 2016, when I ran my very first unconference. That experiment paved the way for the first annual Responsive Conference later that year, and the format has been woven into every Responsive event since.

An unconference flips the traditional model of a conference on its head: instead of a pre-set agenda, the participants themselves decide what gets discussed. It is deceptively simple, but it’s also one of the most powerful ways I know to spark connection and create unexpected breakthroughs.

I’ll be teaching a workshop on “How to Run an Unconference” at the ​Conference for Conferences​ the day before Responsive, and of course, we’ll be running unconferences throughout both days of Responsive Conference 2025.

Don’t have a ticket yet?
​There’s still time!​

What is an unconference

An unconference is any event where the agenda is set by those who attend. The rules of an unconference are simple:

1. Whoever shows up are the right people
2. Whatever happens is fine
3. Whenever it starts is the right time
4. It is over when it’s over

In less flowery language this just means ditch expectation and don’t try to control the experience.

Flow of the Day

After attendees arrive, an empty conference agenda is posted on the wall with time slots and a variety of meeting spaces. Leaders share a theme or question they would like to discuss and post it in a time slot. If you post a topic, it is your responsibility to turn up to that session and introduce your topic or question. If you are not hosting a session, you are free to attend whichever of the sessions you are interested in.

Attendees are encouraged to adopt any of a number of roles:

Leader — who is facilitating each breakout
​Scribe — is someone responsible for taking notes for each group
​Nomads — give attendees permission to move between break-outs

The Law of Two Feet

Everyone at an unconference is encouraged to practice the law of two feet. The law of two feet says that if you become uninterested at any point, you are encouraged to leave and join another session. In an unconference you are also invited to take breaks at any time, with the idea that it is sometimes in the breaks that the ‘A-ha’ moments arrive.

Roles & Responsibilities

There are three main components necessary to a successful event — recruiting, production, and a strong facilitator.

A Word on Recruiting

In my experience, it is helpful to have an extended network to help with recruiting, not just a single person. All other logistics can be handled by a single person.

Production

Among the organizers, someone has to be in charge of logistics, including:

• Venue sourcing and ongoing communication
• Setting the date
• Attendee arrival emails
• Day-of logistics
• Recruiting

Facilitation

A strong facilitator can make or break any event, but especially one with as fluid an agenda as an unconference. On the day of the event, the facilitator plays a crucial role. It is essential to have one strong facilitator overseeing each unconference, to welcome attendees and provide context for the event.

How to Facilitate an Unconference

Here are some tips, most learned the hard way over hundreds of hours of practice in the last two years.

Stay Centered

Despite having spent a fair amount of time on stage, I found myself getting nervous and feeling rushed in the hours leading up to a day-long unconference. My single biggest piece of advice for a facilitator is to arrive with plenty of time to spare so you won’t feel rushed. You are responsible for the framework within which the attendee experience takes place. As such, staying grounded and centered is the single most important thing you can provide, even though in the moment it may feel like it is more important to make sure the space is set up or the coffee is ready.

Don’t Participate

This one might seem odd. It can seem like the entire point of organizing an event is to participate. In my experience, doing so decreases the ease with which I was able to coordinate new sessions, lead an end-of-day wrap-up, and refocus attendees when necessary.

In my view, the facilitator of the unconference is there in service to the attendees. I have found it gets in the way of the attendee experience to actively participate in sessions and workshops that occur throughout the day.

Practice

The facilitator should practice before the beginning of the unconference. Review these guidelines for a successful unconference and be able to describe unconference rules from memory. Practice your welcome speech.

Incorporate movement

I have always found it very useful to incorporate movement into events. When we have short periods of movement interspersed with other kinds of learning, we shortcut the passive sit-and-absorb tendencies we all learned through the education system, and which have carried over into most events. Read this article on the importance of movement within events.

Conclusion

Events are a lot of work, and something I’ve learned to produce of necessity. However, in this hyperactive digital age, I’m convinced of the value of what Tony Hsieh calls “spontaneous collisions” — the value of people spontaneously crossing paths. If you’re considering putting on an event of your own, I encourage you to do so. When we create a container — an event or gathering — we create the opportunity for emergent possibilities to fill the open space.

I’ve been delinquent in writing Snafu this last week, because…

• I bought a house and moved in
• ​Responsive Conference is coming up in 32 days
• There have been some minor family emergencies
• I’ve had several Zander Media film shoots
• The state of the world? ‍♂️

Anyway, I thought I’d take this excuse to look back at some of my favorite essays of the last few years…

​How to run an unconference – I wrote this a decade ago, but still send people to it when they ask how to get started running events. In fact, I’m going to be leading a workshop on this topic at my friend Jenny Sauer-Klein’s the Conference for Conference on September 16th, which is the preamble to Responsive Conference 2025!

​The free pass system – I’ll be sharing this essay with new friends for the next decade. It’s such a simple reframing of boundaries and expectations in friendship, and has already improved mine.

​Some reflections on turning 39 – I got more positive feedback on this article than most. I think the mix of practical reminders and authentic reflection worked.

​Tilting at windmills – Choosing your battles is an essential skill, as is not arguing with reality. But the idea of going to battle against unrealistic odds when you choose to? It’s a little bit crazy, and I kind of love it.

​AI inflection point – One of the unexpected benefits of my foray into housing was this AI inflection point. This technology is transformational, and anyone who isn’t addressing it in their daily lives is going to be left behind.

​How to buy a used car – My girlfriend is buying a used car and I referenced this article to remind myself of what we should look out for. (I think that’s a goal for all great writing: write what you want to read and will reference in the future.)

​How to run a self-experiment – I’ve been running self-experiments since discovering the term from my old professor Allen Neuringer. The idea is to test hypotheses in small ways and on yourself, but to do so as rigorously as possible.

​How to fast – Another reference article and on the habit in my life that is the hardest thing I do. And also, likely, one of the healthiest.

​Discipline isn’t hard – In a world that is convenient and comfortable, we need manageable discomfort in our lives. But it doesn’t have to come through force. Instead, I want a re-definition of “discipline” back to the original meaning of the word.

​Habits for hiring – Hiring and managing people is hard work. And when you find great people, it makes a world of difference. These are some lessons about hiring and management I wish I’d learned a decade sooner.

​How to change someone – This article got me started. It is about my father, published with his grudging permission, and I think about it regularly. You can’t change people, and anyway it is none of your business.

I’ve never thought of myself as a great salesman. But a few months ago, two friends asked me for help with their sales and self-promotion.​

That resulted in teaching a cohort of ten people about sales. And when the 10-week cohort wrapped recently – just two months out from Responsive Conference – I didn’t have the time to run the cohort again.

Instead, I recruited some of my students and a handful of other volunteers to practice sales by selling tickets to Responsive.

I started the workshop by telling my own Responsive story, which goes something like this:

The future of work

In 2015, I was introduced to Responsive.org, a movement started by 6 organizational design nerds to describe the tensions facing organizations in the twenty-first century. As someone who’s worked in dozens of different industries – and seen a lot of the same dysfunctions across silos – I related to the challenges described. Moreover, the manifesto isn’t prescriptive. It doesn’t propose to solve everyone’s challenges.

I asked the authors of Responsive.org what I could do to help, and someone suggested I run an un-conference. I expected 30 people to show up, and instead we had 300 travel from across California for our free 1-day event. Attendees ranged from global CHROs to baristas from an employee-owned, self-managed community kitchen.

I realized there was an appetite for these topics and – never having been to an HR or organizational design conference, but as a longtime circus performer – decided to try my hand at building an event of my own.

7 months later, the first Responsive Conference was a resounding success. Chris Fussell came and gave a talk about “team of teams.” Joel Gascoigne argued that teams should be either fully distributed or entirely in one location, but nothing in between. Tony Hsieh (RIP) sat in the back with his entourage and took copious notes. I got lucky and the ideas espoused in the Responsive.org manifesto had struck a chord.

And those arguments – including “the rate of change continues to accelerate” and “the future is increasingly hard to predict” – have borne out a decade later. Once fringe, those ideas are now commonly accepted. And Responsive Conference continues to serve as an intimate, immersive gathering for founders, executives, and people leaders from around the world to build more resilient work.

What a story does

Having both lived that experience, and told that story a thousand times, I can reiterate with ease. But then comes the essential step of helping other people tell their own stories. Which means, first, we have to reverse engineer my story.

My story does several things:

• It’s entertaining – it shows how a circus performer can end up curating a business conference.
• It’s self-revealing – It helps people know a bit about me with some self-deprecating humor and humility.
• It’s intriguing – it invites the audience to consider learning more about the event or inspires someone to take a risk and start something of their own.

My story isn’t a hard sell. (I despise hard selling.) I don’t conclude with a “please buy a ticket to the conference!”

The goal is to connect, entertain, and leave the audience wanting more.

After sharing my story, I asked the members of our newly christened Sales Squad to draft their own stories about Responsive Conference for review.

If they’ve attended Responsive Conference previously, what impact did it have? If they haven’t, what’s their connection with the future of work that inspires them to participate?

Homework

Everyone has a story. Write a short version of your founding story – whether for a project, business, or personal mission – in less than 300 words.

What led you to start?
What problem were you trying to solve?

In a low-stakes conversation, tell this story to someone new. What questions do they ask? What do they laugh at? What lands?

A few weeks ago, a salesman from an AI lead generation company cold-called me.

I told him I was busy, but invited him to follow up with a short Loom video showing how his product could help Responsive Conference. I promised to watch the Loom and respond if I was interested.

He followed up – without the Loom, and with a generic pitch.
He lost the sale.

I posted about my experience on LinkedIn, with the takeaway that there are two types of selling:

❌ Coercive selling: fast-talking, pushy, ignoring requests to “follow up later.”
✅ Authentic selling: clear, respectful, tailored, and actually helpful.

Coercive selling might get short-term results, but it destroys trust. Authentic persuasion builds relationships. As BJ Fogg, PhD, says, it’s “helping people do things they already want to do.”

What’s surprising about this story is what happened next. My LinkedIn post blew up. A lot of people commiserated with the experience of being pitched but not listened to.

And other people – these are strangers on the Internet! – started lecturing me on the difference between a lead and a qualified customer, and told me that I owed it to the salesman to listen to his pitch.

I don’t think I was sharing a controversial take. I believe that coercive selling ruins trust. If a salesperson doesn’t listen to a simple request during the initial sale, they’re very unlikely to take care of the customer after the sale is closed. Great sales is about taking care of people.

These beliefs aren’t universally held. Apparently, there are angry salesmen on the Internet who are willing to fight about these ideas.

For the first time in my life, my response is: bring it on! I’m delighted to fight with these strangers; to tilt at these windmills.

Because the world needs more people who actually give a damn.

Homework

Find a moment (online or off) where you genuinely disagree with something. Don’t stay silent. Speak up. State your case clearly and calmly. The goal isn’t to win, but to practice not avoiding conflict when you really care.

A few years ago, a friend and I kept trying to make plans. I canceled several times – once due to a car crash – and after the third or fourth reschedule, she told me it wasn’t working for her and that she was going to deprioritize our friendship. I apologized, we talked it through, and agreed I’d take responsibility for reaching out.

I followed up for six months with no response. Eventually, she let me know she was no longer interested in being friends.

I was hurt. We’d had a clear agreement, and she’d gone back on it. That experience stuck with me – and led me to adopt my best friend’s “Free Pass System.”

When you notice someone does something that doesn’t work for you, you are responsible for telling them so. The key is to tell the other person before the issue has become insurmountable.

Tell the person that their behavior won’t work for you going forward, and why. Detail the specifics of what you want to change going forward.

They get a Free Pass up until this point – assuming you still want a relationship with this person. Grant them grace up until this point. That’s only reasonable because you haven’t told them that their behavior doesn’t work for you!

But you have to set clear consequences. Setting consequences is hard because most of us don’t have practice. First, articulate the boundaries for yourself. Then, describe them to the other person.

Consequences aren’t punishment – they’re about clarity. They tell the other person what you will do if the behavior continues, so that you’re not reacting or building resentment, but fostering the relationship that you want.

Here are a few examples:

• If someone is flaky after you’ve communicated that it doesn’t work for you, don’t schedule with them again.
• If someone shares a secret that you shared in confidence, don’t share private information with them in the future.
• If a client doesn’t pay on time, add delinquency fees to the bill.
• Boundaries can be small and nuanced – like the fact I don’t talk to my parents if they sound crabby at the start of a phone call because that’s when our conversations are most likely to go poorly.

To summarize the Free Pass System:

• When someone crosses a boundary, identify the boundary to yourself, and then to the other person.
• If you don’t want them in your life anymore, cut them out of your life.
• Otherwise, give them grace – a Free Pass – up until now.
• Describe to them the clear consequences if they do the unwanted behavior again.
• Then, if they exhibit the behavior again, enact the consequences you’ve communicated.

I don’t bemoan the loss of friendship with that person who wrote me off. As a result, I learned how to set better boundaries.

Whether in friendships, family, or business, the Free Pass System helps you set and hold boundaries. It won’t fix every relationship, but it will improve the ones worth keeping.

Homework

Sit down somewhere quietly for 10 minutes and write out for yourself one behavior that someone in your life does that bothers you. What is it, specifically, that you don’t like?

Then describe the boundary you will set – anything from a timeout to removing them from your life – if that behavior happens again.

Finally, share your Free Pass and its consequences with the person involved.