How finding the right mentor is the secret to life

the most valuable things I've learned so far with Sasha Chapin as my mentor

I notice a tendency in you that also exists in myself: discrediting what you’re good at as incidental. Like regarding your people skills as a fake ability (they are not). It might be generative to ask: what would it look like to really double down, to believe that I could be among the very best in the world at my particular thing?

My mentor said this to me recently. Not to long ago he was a stranger whose work I followed and essays I read. Now we meet every other week and know each other very well. This relationship has empowered me to raise the bar way higher than I could have ever raised it myself, in pretty much every area of my life.

It feels like an incredible amount of luck that I stumbled across this particular person at the right moment in time, but this relationship was not random. It started, as so many do, with one scary email.

I gave birth to my son very traumatically at 3:03am on New Years Eve, and spent those first few months of 2025 in a strange and distant haze.

This timed up well with my 30th birthday so I had lots of hours to spiral, rewatch GIRLS, and relive all of the decisions that led me to staring catatonic out the window at strange hours with a baby on my chest.

During those 4am feeds, I thought a lot more about work than I assumed I would. I worried about how I had spent the weird, mad dash of my twenties. What if I pointed my ambition in a bunch of wrong directions? Should I have waited out the pandemic and continued acting? I regretted not moving to London. What if I started working at startups right out of college? I regretted not moving to San Francisco. Suddenly my strange string of experiences stopped feeling charming and started feeling clunky. Looking back made me feel a tightness in my chest. Looking forward made me salivate like how you do before you get nauseous.

With no line of sight to where I was going, I knew I needed help. I needed a mentor. Someone I could lean on as I navigated this stereophonic life transition.

Mentor. /ˈmenˌtôr/

I’ve always liked the idea of mentorship, but in real life, it had always fallen a bit short.

When I reflect on relationships with people who have guided or shaped me in important ways, there has always been something slightly off. Either too casual, where I consider them a mentor, but never explicitly say it, or too structured, where we’ve been matched in some program and I can never fully relax into it because I feel the need to be put together.

This is what I knew to be true about mentorship. Fantastic in theory, but stale in practice. A really good… idea.

So I made a short list of what I was looking for:

• Someone curious and considerate. A person who, just by their nature, would be both open and skeptical to this idea.

• Someone I could provide value to. I wanted to take being a mentee seriously too, allowing the seesaw to tilt in both ways.

• Someone with taste. I’m talking about real style. Someone with discernment about what good is. Someone that might intimidate me slightly by their level of excellence.

• Someone who lives and works creatively. Who does not have a “normal” path.

• Someone who would know me without knowing me. I wanted to find someone who would get it, and get me, but who did not have any real context on my life.

• Someone further ahead by 5-7 years (ideally in all the meanings). I wanted to learn from someone who was significantly wiser than me, but not so much so that things would seem impossibly out of reach.

• Someone genuinely interested in my growth as a person.

Enter Sasha Chapin.

I don’t know how I first started reading Sasha’s writing, but I remember having a very strong first impression of him. I’d perceived him to be living this beautifully creative, entrepreneurial life. He wrote incredible essays about whatever he found interesting: enneagram, meditation, wise lists of stuff he knows. At the time, he had just spun up a successful perfume company with a friend. I was so fascinated by the conviction he had and the ease with which he seemed to bet on himself.

After a few exchanges, and a few months, we were supposed to get on a call. But he cancelled last minute so I composed a moonshot email pitching him on being my mentor.

I remember asking Matt if he thought this was crazy. He was like, I’ve never heard of anyone doing that before so it could be crazy but it also could be genius.

I took a big deep breath, hit send, and waited.

In order to keep the actual email short, I included a notion page on why I thought we’d be a good match for this kind of relationship. (I’d never done this before.)

I used a dumb stock photo as if to say, I’m a person who gets it. I thought if he found that weird or funny, we might be a good match.

What I have learned about putting yourself out there is that the outcome in your head is almost always much more frightening than the reality is and, whether you get what you were hoping for or not, you wondered why you were ever that afraid in the first place.

And so we began to meet every other week.

When I met Sasha, I had just decided to start my business, which really meant beginning to think about what I wanted it to be, while doing some part time consulting work. I was usually making just enough money, sometimes less, to cover our part time childcare. I was extremely afraid to put myself out there, full of fear that if I finally did, people would see me for who I actually was and no one would care.

Now, I’m running that business, consistently in awe at the kind of work I get to spend my time on, the collaborators I get to make things with, and the flexibility that it allows so that I can enjoy this amazing stage of motherhood.

The next cohort of my mastermind, Reach Out Party, filled up six months before the start and has a 400 person waitlist for the March 2027 cohort. I am producing 100 person events in different cities sponsored by global brands. I am working with dream clients and last week, I booked a speaking opportunity for a year in advance. I am making more money than I was at my fancy startup, and I don’t feel out of alignment making it.

Most importantly, If I were to measure success by the number of good omens or waves of possibility I feel in a given week, I am rich beyond my wildest dreams.

There are many components that have made this possible, but one of the undeniable levers to the positive momentum in my life has been the mentorship from someone who is challenging and nudging me toward a life I actually want.

The consistency of our calls has planted a tiny chip in my brain that makes me think Sasha shaped thoughts, and make Sasha shaped decisions. Here are some of the most important lessons I’ve learned from this first year together.

Learn to meditate

I took a transcendental meditation course in college, and I enjoyed it in the beginning, but found it difficult to stick with. I was too busy, too tired, and too immature to know that being 20 years old pursuing a musical theatre degree was the least busy and tired I’d ever be.

Whenever I asked Sasha about meditating, he shared his experience, but never pushed it on me because he knows that, like ending a toxic relationship, meditation is a thing you have to come to on your own. But I noticed a magnetic internal calmness about him in our conversations. I wanted to develop that quiet confidence myself so I started meditating again, only this time I took it very seriously, like it was somehow the key to my ultimate success.

I sit silently in the morning for 20 minutes after I’ve washed up but before my coffee. Sometimes I’m really antsy. Sometimes I fall back asleep. Most days I am uncomfortable. But the compounding effects have been enormous.

I have not reached enlightenment, but my capacity to hold bigger things, in life and in work, has expanded enormously.

Go toward what pulls you

I was raised in a pretty traditional Jewish family, believing for a long time that the most respectable career you can have is a Doctor or a Lawyer. To keep up with my brothers (older - doctor, younger - lawyer), I realized I’d been pushing myself to do things that I thought “should” make me happy.

In this scarcity-based desire, I made lots of career decisions that I would feel great about for a while because it seemed impressive, and then I would severely crash out, and quit, totally embarrassed by the outcome.

When I first met Sasha, he had spun up a perfume company, just because he was interested in it. A few months later he decided to remove himself from the company, because it wasn’t working for him. I remember hearing him talk about it with such grace and nonchalance. Shrugging, “you can only know for sure how something is going to go if you actually do it. And then you learn.” Seeing the way Sasha makes decisions about his own life inspired me to experiment with doing what I love more.

My main fear around doing work that felt “risky” or that wasn’t the norm was that it wasn’t going to work… But the more I’ve said yes to work I’m pulled to, the more energy I seem to get. Now, I am less concerned with the outcome and more concerned by doing things that encapsulate the kind of desire I fall into. My arm being pulled by the paintbrush. And then, whether it works or not, I learn.

Finding resonance is about finding congruence

Congruence is an idea base in psychology that Sasha introduced me to a few months ago. This essay of his might just be my favorite. Basically, you want the smallest possible gap between how you’re presenting yourself to the world and how you actually are. People usually aren’t evaluating your credentials or even your confidence level. They’re evaluating whether or not you feel real. And we are all really, really good at sensing when someone does not.

What you pay attention to opens up, and paying attention to congruence has deeply impacted my day to day. It impacts the way I share my ideas online, the way I reach out to people, and the way I show up in my relationships, personal and professional.

With more practice, and attention, I’ve started to notice my ideas are much more resonant, my emails are much more unignorable, and my connections are much more meaningful.

How to learn the difference between a shiny object and a great idea

As an enneagram 7 (The Enthusiast), this has been, and is, very tricky for me. I want to do everything, and live every life. I am almost always thinking about what is next. One of the struggles of starting my own business has been making sure I’m prioritizing the right things… I’m constantly asking myself, is this a distraction or an actually good idea?

Having a through-line has been a strangely helpful guide. Find your people. It has become a lot easier to measure what is actually worth pursuing by connecting it back to those three words.

One time I had the idea to host an event called Anti-Networking. It was going to cost me ~$5,000 to put it on. I was terrified no one would come and it would be a huge waste of time and money. I remember asking Sasha if he thought this was a distraction or a great idea and he asked me this question back:

Does doing this event connect to the ultimate core of your work? If not it’s probably a distraction, if yes, it’s probably a great idea.

But still the money felt like such a risk. He said, if you think you’re going to regret spending $5,000 at the end of your life then probably don’t do it.

I paid the deposit for the venue that night… Three weeks later I found a presenting sponsor for the event, covering the cost. 100 people came and I had a waitlist of over 250. It’s now an event series that pops up in different cities. Denver and London are next.

Stop discrediting what you’re good at as incidental

I notice a tendency in you that also exists in myself: discrediting what you’re good at as incidental. Like regarding your people skills as a fake ability (they are not). It might be generative to ask: what would it look like to really double down, to believe that I could be among the very best in the world at my particular thing?

*Deep breath* This again.

For the past seven years I have been studying the tangible and non-tangible ways we can get ourselves to develop meaningful connections. I’m fascinated by the idea that one good email or dm could change the course of your life. And even more fascinated by the fact that even though most of us know this is true, it is still so difficult to prioritize.

For a long time, this had been my sig-gig. My little passion. Something that I enjoy helping people do a lot. I have spent years mastering this skill of how we connect with the people who open doors that change our lives.

Through my work with Sasha, I continue realizing how easy it is to undersell this skill, instead of seeing it for what it is: the rare and lethal combination of what I love, what I am good at, what the world needs, and what I can be paid for... my ikigai, or reason for being.

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Sasha has been one of the most powerful door openers yet. Our first year together has been equal parts uncomfortable as it has been fun. Working with Sasha is like having someone slowly and painfully unravel your limiting beliefs, assumptions, and self sabotaging habits one by one onto a long parsons table, watching as you pace in front of it nervously.

Finding the right mentor is not a silver bullet to happiness or success. But seeking out a relationship with someone who believes in you, without trying to protect you might illuminate the path you’re on in unexpected ways.

More than anything, having a good mentor is like knowing there is a buoy out there in the deep water, making you braver as you swim into the unknown.

If I had to describe our relationship now, I’d tell you Sasha feels like my half brother. For better or worse, we share some DNA that makes us unequivocally related, and yet, we are so different. If we were at a party in a group conversation together, we’d lock eyes and be thinking the same thing. And yet we find each other’s interests completely perplexing. He scoffs at my theatre references and I cock my head at his various ideas about how to get himself in peak physical condition.

One time, we were on the phone, I was walking in a public park with my baby. I told him I was fine, but he sensed my incongruence. A bubbling frustration in my voice that made me feel like screaming. So he told me to do that.

“I’m in a public park.”

“So? Cover your mouth with your hands.”

I walked a few steps from my baby covered my mouth with my hands and I screamed. A true mentor is someone who gives you permission to surrender to yourself.