Five shifts that enabled my journey to co-owning a vacation property in Big Sur with 15 friends

Reflections on a very unexpected path

I just spent the weekend with 15 friends (plus 4 kids) at a shared vacation home we all own together in Big Sur.

This is a wild statement, it gets wilder when you consider most of us met less than 10 years ago. 

Never in a million years would ten-years-ago-me think this was even a tiny bit possible.

Here’s how it happened and what I’ve learned along the way: 

1. Embrace ‘crucible moments’ to forge strong friendships at any age.

One of the biggest misconceptions is that you can’t form new friendships past your 20s. I beg to differ. Many of my strongest relationships have been formed in my thirties through ‘crucible’ experiences - Burning Man, personal development retreats, start-ups - situations that created vivid shared experiences, forced us to rely on each other and build trust, and where I was encouraged to bring my fullest, most authentic self. 

2. Becoming comfortable with conflict radically changed what’s possible in my life. 

I grew up in a household of two avoidant attachment types, my parents, and eventually a third, me.  (Avoidant attachment types are extremely independent, self-directed, and often uncomfortable with intimacy, typically they suppress their own emotions and are uncomfortable with those of others.) For example, I never saw my parents fight, and I can only recall three times before the age of 30 were I expressed any anger or even displeasure toward them.

The cost of avoiding conflict is avoiding your truth and, in my case, this meant suppressing who I was in situations where my truth who creation friction. Being able to be with other people’s disapproval is a game-changer and utterly necessary for a big project like this house where we each care about different things. I’d recommend waiting to sign a 30-year mortgage with anyone until you know you can disagree vehemently and still love each other deeply.

3. Big visions are very possible to manifest, but only if you consistently move from idea to action. 

The first thing most people say when they hear about our shared vacation home is “I’ve always wanted to do something like that!” And then it turns out they’ve never got past a few conversations at most. If a project like this appeals, seek out some models of how to do it and pitch the one you like best to a few close friends. 

Indeed if shared home ownership in any of its flavors is your jam, check out Phil Levin and his

Supernuclear

newsletter. Co-living and community are his passions and we are SO lucky to have Phil as part of our project, guiding our legal, financial, and decision-making protocols. Phil wrote a blog post about how we made the Big Sur house a reality, which you can read here.

4. If you want to live an atypical life, surround yourself with people who dream outside the box.

It’s probably no accident that two-thirds of the group involved in this house has founded a start-up or some other kind of business. This is a group of people who routinely dream up something out of the ordinary - be it a business idea, a vacation idea, a dinner party, or a company. If you want to start something fresh, it’s way easier when you have people in your life who want to jump on board or cheer you on. 

5. When imagining a new kind of project, start with the upsides first, feel how awesome things could be - and only think through the downsides afterward. 

I used to think about big projects from fear: What if it falls apart? What if we end up hating each other? What if the house burns down?

Most people do this when faced with the unknown - I get asked 99% more about how we manage conflict than what the best parts of this project are. 

The year we bought the property I had started asking myself the question: “Will this expand me?” instead of “Will this make me happy?”. Optimizing for happy / avoiding fear makes it easy to get swept up in all the hard work and things that can go wrong. Optimizing for expansion makes it easier to think, will I learn? Will I grow? Is this likely to bring more magic into my life?

On that note, I’ll wrap this up with a list of my favorite things about our shared vacation home project:

• Most obviously, the house is way nicer than most of us could afford on our own and takes significantly less time to keep up as we share the load.

• We get to spend deep quality time together, days on end in a place we are investing in together. (Note: This is decidedly not a timeshare, we bought this place together so we can be here together, at least some of the time.)

• Everyone gets to lean into what they enjoy. In my case, I’m co-leading interior design/furnishing/house supplies, which means I’m blessed not to have to think about our taxes, broken showers, or managing contractors.

• This property continues to bring fantastic people into my orbit. It’s one of the best places to make new friends, as other people involved in the project bring guests and I get to hang with them for a few days. 

• My daughter has a place she comes back to every few months, and every time she’s older and the place changes alongside her. As a city girl, time in nature like this is priceless.

• I have a place in the world I know I’ll still be visiting well into my old age. I don’t feel like that about anywhere else I’m likely to live in the coming decades. (New Yorkers of my generation, even if we can afford our own place, probably won’t live in the same apartment for more than 10-20 years.)

• I have a canvas to play with and am discovering creative parts of myself (interior design, landscaping). 

• As someone who grew up as an only child, on the road a lot with few friends, I have found a place to call home, friends I’m committed to building something with for the rest of our lives, and a place I love so much that I never wonder where to go when some says “close your eyes and imagine you’re somewhere you love…”

I share this story as I believe opportunities like this are closer than many people are aware of. It requires us to give ourselves permission to dream big dreams, to face and overcome our limitations, and to take bold action with others.

Do you have a big dream you’ve been holding on to? Is there something you could do to move it forward this week?