I wrote last week about modern dating being broken because we’re all so dopamine depleted from our smartphone addiction that we literally don’t have the chemical building blocks to create the feelings of lust and desire.
The other major culprit, amongst many contributing factors, is that we don’t teach people how to cultivate and strengthen their own intuition. We’re looking for answers everywhere externally, instead of inside ourselves.
Which is why I’m so excited to bring you this conversation with Gregg Levoy. Gregg is the author of an incredible book called Callings: Finding and Following an Authentic Life. This book should be required reading for any seekers on this planet; anyone who has felt a seemingly irrational inner voice pulling them towards a certain creative endeavor, a job, a relationship, leaving a relationship, towards telling their truth or showing up in the world as their full, authentic selves.
In 2021, I had what was my dream job. I was head of marketing at a massive company; I had just been promoted to Senior Vice President; I oversaw a team of seventeen people. I had done the thing. I had climbed the corporate ladder. After almost fifteen years ascending towards what I thought I wanted, I immediately started to get the inkling (or a Calling) that it was time to go; that there was more out there in the world for me.
It was incredibly destabilizing to come to terms with what my intuition was telling me. After a year, the whisper to leave had gotten incessantly louder and I resigned in the spring of 2022, with no plan for what was going to come next. The first thing I did upon arriving for a four month stint in LA, was read Callings and I could not believe that it felt like someone had written a book to me, for me, about me and exactly what I was experiencing. In that moment, I felt like the universe had delivered me a trail map into the unknown.
I asked Gregg if he would be willing to have a conversation about his work through the lens of dating and relationships, and he so kindly indulged me.
Some time stamps from our conversation above:
1:15 What is a calling?
7:55 Women who dream about the sex of their baby are correct 100% of the time!
19:20 Daily practice to cultivate intuition
22:14 Is it a dealbreaker if one partner isn’t “doing the work”?
25:50 Quaker clearness committees: “listening each others souls into discovery”
39:45 If callings don’t scare you, there’s something fishy
45:14 Dialog with scarcity
47:30 What happens when we ignore callings?
54:14 Why is modern dating so challenging?
1:06:00 You will have your bliss when you answer your calling
[side note: this conversation was recorded in July of 2024 and was originally intended to be a podcast. When I came back to revisit the recording for this substack, I was delighted to re-listen to the conversation and I hope you are too. The relationship I mention at the end of the interview is the one I wrote about on the Plus One subtack]
These are the books Gregg recommends at the end:
Belonging by Toko-Pa Turner - he describes it as “the most beautifully written book about what belonging to someone else really means”
The Course of Love by Alain de Botton - he describes it as 2 story lines - one is a couple falling in love, and one is a therapist explaining what’s going on at every point in the relationship
And now coming back to my own thoughts on intuition and our relationships:
In the absence of a connection to our own bodies, our own wisdom, we look for rules we can follow from external sources, to bring predictable logic to our inner life and foster a sense of safety in our actions. Rules can be important guideposts on the road to developing intuition, but we treat them like the final destination. It’s analogous to how we teach children about the world in black and white absolutes through statements like “when a man and a woman love each other, they have a baby” but then the child grows up and (hopefully) realizes that in fact most of the world exists in the grey, with nuance and subtlety. That “rule” gives us training wheels; a starting point to experience the world through, but we’re meant to take the training wheels off at some point and bike on our own. As a society, we’ve gotten stuck on the rules; never making the developmental leap into our wise adult selves.
Social media is flooded with rules-based content that has much more virality to it than teaching someone to listen to their inner wisdom. Like the “diet and exercise” solution to weight loss, a calm inner dialogue takes consistency and work, is kind of boring, and much less likely to go viral.
If you search “dating” on instagram - these are some of the immediate results:
5 types of men to avoid in midlife dating
8 signs it’s not going to work out in early dating
How to behave like a high value woman
One of the “rules” I see most often for young women is how long to wait to have sex with a new partner. It’s often some combination of the following formula:
Don’t message the man first + Don’t initiate plans + No sex until the [fill in the blank] date = a path to commitment
If we taught women to tap into their own knowing, instead of overriding it, they would always, always know when they felt fully safe and comfortable to sleep with someone. They wouldn’t need to follow an Instagram rule.
One of the best descriptions that I’ve ever heard of our intuition and the knowing that all of us carry in our bodies, is from Elizabeth Gilbert (author of Eat, Pray, Love), talking to Tim Ferris on his podcast. I keep this as a note on my phone and I’ve referred back to it many times.
“The body knows first. The body knows first but only always. One of the things that Martha [Beck] says … because culture and civilization have overwritten the software system of the body so much and told you don’t trust that, what you trust are the rules and the mores and the fear-based, scarcity-based, grasping, this is how you have to act, this is who you have to be in order to be safe.
The wisdom of the body is so incredible. It’s such an amazing machine. It’s such a fantastic machine and it’s ancient. It’s been honed by literally millions and millions and millions of years of evolution into this phenomenal machine of reception, of conscious reception, of being able to respond and being able to know. The mind, thinking mind, is brand new. It’s the newest update. It’s only a hundred thousand, maybe 200,000 years old. It’s got a lot of bugs in it.
So what Martha says is that if you are given this amazing body that’s this incredible antenna of operating in the world and always knowing what’s right for it and what’s wrong for it, and you override it with the mind, essentially, it’s as if you’ve been given the brand new, fanciest, like highest speed operating thinnest MacBook Air and you’re using it as a placemat. And it’s like, no, open it up and start using it because it’s never wrong. It’s never ever, ever wrong.”
And lastly, this is what I know to be true about cultivating intuition: it requires prolonged solitude. No devices. No content consumption. No music. No podcasts. And spaciousness. The knowing doesn’t come in the five minutes you put your phone down between work calls. Walking helps. Journaling helps.
If you want to submit a topic you want me to cover or a specific dating and relationship question, anonymously, you can do that here.
You can read my 2026 dating and relationship predictions here.
