Coach Interview Series: Sasha Cagen

by Brandon

Sasha Cagen

Author, Life Coach, & Entrepreneur

Our main objective here at the National Coach Academy is to enable aspiring coaches to reach their full professional potential. One of the most effective ways to educate students about the world of coaching is by offering them a window into the world of real, practicing coaches and showing them all the different ways coaches make a difference in the lives of their clients.

We hope today’s interview adds another insightful glimpse into the dynamic world of coaching.

Today we are interviewing Sasha Cagen. Sasha is a Life Coach and the founder of the quirkyalone movement. (And yes, quirkyalone is in the dictionary! Sasha coined the word.) She is the author of Quirkyalone: A Manifesto for Uncompromising Romantics and To-Do List: From Buying Milk to Finding a Soulmate, What Our Lists Reveal About Us.

NCA: Can you describe your coaching practice and the kinds of clients you typically work with?

Sasha: In a way, my coaching practice stems from my books. I’ve been a writer and publishing books since 2004. I attracted an audience back then primarily with my book called Quirkyalone: A Manifesto for Uncompromising Romantics which is all about people who don’t want to settle in their romantic lives and also don’t want to settle in life.

When I became a life coach and started working with clients in 2013, my idea (which turned out to be true) was that I attracted people who resonated with this philosophy. Even if they were married, they identified as being quirkyalone or quirkytogether.

In practice, most of my clients are women. I do work with sensitive, self-aware men, too. Those are the adjectives I use to describe the men.

Most of my clients are creative in some way. Many of them are also writers, aspiring writers, or they work in branding. Some of them work in more traditional careers, even on Wall Street. My coaching is really for people who want a different approach to life than what the mainstream approach to life is in the United States. It’s about helping people stay true to themselves and feel alive.

There are many ways that we’re expected to follow certain rhythms or to-do lists as adults and my coaching creates a space for people to question those assumptions. I help people dig deep to find out what they really want and also to uncover what’s been blocking them about whatever it is that they want — whether it’s a romantic relationship, finding work that’s more in alignment with their true self, their joys, their values, etc.

NCA: What initially got you interested in becoming a coach?

Sasha: First, I want to say that I’m a writer and I have been a writer since I was 8 years old. I won a writing contest. [laughing] Writing is something that I’ve always done. I think that writing, in a funny way, is very connected to coaching because words are important. I hear from my clients that the way that I speak to them and articulate things is very helpful to them. It’s also about helping people create a different story about their lives. Over time, I realized that my skills as a writer really combine well with coaching.

The turning point in my career was when I was working in Silicon Valley as a Product Manager, which is a pretty high-level title even though I didn’t realize it was a high-level title then because it sounded boring. Basically, I got lost myself in my 30s because I felt that I had to earn more money and achieve along those expectations of American society. That’s what led me to get involved in Silicon Valley which was really not in alignment with my values. The tech industry and I are very, very different in our values.

I left Silicon Valley. I went to Brazil and wound up spending a year in South America. When I came back to California, I wanted to find work that I believed in. When I looked at the job ads in Silicon Valley, I found it very difficult to get on board with almost anything. It just didn’t excite me or feel like it had integrity.

For years, people had told me I would be a good therapist. At around that time in 2011, coaching was an occupation that was still pretty mysterious and I didn’t really know what it was. However, I had worked with a coach who helped me to get untangled from Silicon Valley and go traveling, so I knew there was value in it. I just went step by step with exploring programs and I wound up doing a program that year that was 10 months to explore whether I would be good at this.

It turns out that I am because I bring my creativity and sense of fun to coaching. I have a lot of sensitivity when talking to people about shameful things or things that are difficult to talk about. Those are the things that are often blocking us because they haven’t had space to be talked about. At the same time, I bring my creativity and entrepreneurial spirit to helping people figure out what to do next and breaking down the steps of making a change into what I call “playwork” so that it’s a sort of actionable baby step in between each session.

During that program, people responded well to me and said that I was a good coach. But I still found it terrifying to become a coach because I felt it was a lot of responsibility to take on for a person’s life. I did a 10-month program and completed a lot of practice hours, but I still was scared to take on that responsibility. I basically walked through my own valley of fear of working with my first clients. Over the years, though, people have had good results with me and I’ve been building my practice ever since.

It’s about holding that space with integrity, which is a responsibility. There’s a reason to feel fear about it. When I had my first official client that paid me a normal, non-training rate, I spent the whole weekend in fear. [laughing] I was in therapy myself and talked about it. It’s very scary in the beginning. I’m a sensitive person and I feel things intensely, so I don’t know if everyone would feel that level of fear, but I certainly did.

I tell everyone that confidence is built through moving through fear, taking risks, practice, and experience. A lot of online coaching seminars try to teach you principles or tips, as if those are the secrets, but there is no substitute for actually feeling really uncomfortable and getting experience, and then becoming more comfortable through that experience.

You cannot tell anyone what to do with their lives. It doesn’t work. It won’t resonate. That’s why coaching is a slow process of asking questions and grounding the person’s answer in their own authority because those are the changes that people remember — in their own language, in the way they think, in the way they feel things. It has to come from a felt experience.

NCA: In working with your clients, what would you say is the most rewarding part of that process and on the flip side of that, what is the most challenging aspect of the work that you do?

Sasha: I tell clients at the get-go that it will take a minimum of three months to see a process of change. But often, my clients wind up staying with me for a long time — almost like therapy. I become a person in their lives where they unpack what’s going on and learn how to move forward. What’s really rewarding is seeing the great transformation that happens over time.

This is the difference between me and what you see in the marketing about coaching. I have never really believed in instant transformation. I have seen, however, incredible change over two or three years from leaving an abusive relationship and being very hampered in many, many ways by all the insecurities that come with living through a relationship like that. Or helping someone negotiate a divorce where they get a great settlement that I can honestly say is much better for that woman and her children because we worked together. Helping someone like that establish her own business, and date, and have sex — all of these things. I like being in the long haul with someone and helping them change their habits of thinking and their behavior.

My clients tell me, “It’s nice to have you in my life because you know me and you know my history.” That’s why it’s a little like therapy because like a therapist, you invest that time. I also love working with sexual issues. I was helping a couple that had never had sex and they were going to get married. They had been together 7 years and they actually have never had sex. I helped them transform that. Something like that is so beautiful.

I also have this Tango Adventure program in Buenos Aires, which is where I live most of the time right now. I’ve helped many women get over their fears of traveling alone to Buenos Aires and learning tango. So many things come through the experience of learning tango about confidence, embodiment, boundaries, and trust. The degree of transformation that happens through talking and through dancing is really beautiful to see.

The hardest part is that it’s intense. You are paying very close attention to someone for an hour and taking in their story. A coach gets really burned out when she takes on too much responsibility. I need to let the clients take responsibility for their own life. This is a hard lesson that I think any coach has to keep re-learning and establishing boundaries between your responsibility and the client’s responsibility.

It’s hard work. I’m very attentive listening to people and I’m also scanning my brain for my intuitions and my creative suggestions. It is true that a lot of times after a session I’m like, “Oof, I’m tired.” [laughing] Because I feel like I give a lot.

NCA: What is one piece of advice that you would give to somebody who is just starting their coaching career?

Sasha: I think the top thing is just beginning. I think there’s absolutely no shame in starting off with low-cost coaching sessions. I think charging some money in the beginning is important because you need to learn the skill of how to charge and ask for money. That’s uncomfortable and people have to learn how to do that with grace and comfort. I would say charging a small amount versus nothing in the beginning is good.

I definitely tell people to do a coaching program. I think it would be irresponsible to get out there and coach people without having completed a training program because the main thing you will learn is that coaching is not about advice-giving.

The sense that people have from reading online or interacting with coaches is that coaches are going to give you principles to follow or they’re going to make some adjustments for you that are going to make your life flow. But everyone who goes through a coaching program learns that it’s about creating space for that individual to find his/her own answers that are most true for him/her. Sometimes it can be good to give a magic little touch of advice or share something from your own experience, but in general, I can feel in myself a lack of resonance when I’ve been talking too much. What the clients most appreciate is a question that opens up a new doorway for them.

The most powerful piece of advice I would give is something a Jungian therapist gave told me, which is basically that you cannot tell anyone what to do with their lives. It doesn’t work. It won’t resonate. That’s why coaching is a slow process of asking questions and grounding the person’s answer in their own authority because those are the changes that people remember — in their own language, in the way they think, in the way they feel things. It has to come from a felt experience, even if it’s in the session.

Coaches need to get out of that advice-giving mentality. It happens all the time on Facebook, with friends, and it just doesn’t resonate. For the most part, people do not want to be told what to do and it doesn’t work.

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