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Cari Jacobs: “…Write a love letter to yourself — and not just any love letter”

…Write a love letter to yourself — and not just any love letter. One of my clients was feeling quite depressed because she did not feel she could meet someone to date. She was in a downward spiral about all that this meant about who she was. Too this and not enough of that. We sent her […]

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…Write a love letter to yourself — and not just any love letter. One of my clients was feeling quite depressed because she did not feel she could meet someone to date. She was in a downward spiral about all that this meant about who she was. Too this and not enough of that. We sent her on a three-week solo road trip. Her assignment was to reject notions of dating for just three weeks and instead focus on falling in love with herself. Towards the end of the journey, she wrote a two-page love letter to herself. But this was not just any love letter. It demonstrated real love, which includes room and appreciation for all the imperfection and all of the exquisite beauty she had to offer herself and the world around her. As I read this letter, tears dropped from my eyes because she expressed what so many should feel but have not given themselves permission to feel: the wellful of adoration we can have for ourselves. And the authentic love for all we are.


As a part of our series about “How To Learn To Finally Love Yourself” I had the pleasure to interview Cari Jacobs.

Cari rose up through the ranks of the ad agency world in the 90s working on brands like Levi’s, Intuit, P&G, Lexus, General Mills, Honda, Coca Cola and more. She was a marketing leader in the entertainment industry with NBC, CBS and FoxSports and spent three years building a customer experience-led Marketing Practice for Slalom Consulting, servicing clients like Gap, Athleta, Sephora, Salesforce and Atlassian.

But Cari is most known for her work building five Bay Area start-ups in executive marketing roles, including two solar companies one of which was Sunrun, now the largest consumer solar company on wall street; one retail women’s fashion brand, ModCloth, which sold to Walmart; a fintech company called Unison that is changing how we buy and own homes; and a software platform called Torch for coaching and mentoring that seeks to create more conscious leaders.

While her professional career soared, Cari found she was less and less content — less fulfilled — she yearned for more happiness. She began to bridge her fast-track career with a more personal endeavor. In her early 30s, Cari became obsessed with personal growth and self-awareness. She began an active study of mindfulness and meditation, and by 2005, Cari was teaching at Spirit Rock in the Family Program and coaching in Meditation. She earned multiple certifications in mindfulness from Google’s Search Inside Yourself and UC Berkeley’s Greater Good & Science. All while maintaining executive roles and continuing her career as a marketing leader.

But in 2020, the covid pandemic hit — a force majeure of another kind — which prompted Cari to re-evaluate how she wanted to use her talents and passions. She left her corporate role and launched a new career as a full-time coach, earning her most recent certificate from the UC Berkeley Executive Coaching Institute, a program created and facilitated by the Haas School of Business.

So, what drove Cari throughout her life? What made her keep finding inspiration, keep building more life experience, keep creating, leading and exploring? And keep finding one more reason to get impassioned, even when it was hard?

An unstoppable drive to carve into the wind and imagine something there was never there before. To invent new ways to connect, teach, feel human and be human. To take in everything life has to offer. Without flinching. A sort of Force Majeure of the Soul. Of the Heart. To leave the world just a little better than she found it. A little more inspired, empathetic, entertained and loved.


Thank you so much for joining us! I’d love to begin by asking you to give us the backstory as to what brought you to this specific career path.

Well, the truth is that for close to 25 years, I thought I was a marketer — a chief marketing officer for the last 5. I did all the right things to become stellar at my job. I started out in the Ad Agency world and spent close to 18 years working on all kinds of clients from consumer to B2B. I played different roles form media planner to account director to strategic planner. I then crossed over to in-house marketing roles and helped to build 6 startups! But what I have now realized is those first 25 years were only the training ground to my current role as an Executive Coach and Author. It seems crazy to think of it that way now, but the truth is that to be a stellar Executive Coach, you need years and years of on-the-ground training. Like a professional dancer or ice skater, you can “learn” and practice the craft for 20 plus years before you hit the big time. And that is what my first career was in many ways — it was the deep training ground for this, my true calling.

When I was just 32 years old, I was named Vice President of the hottest Ad Agency in the world at the time, Deutsch. I had never dreamed I would make that title — or the salary — at such a young age. I had a killer flat in the Upper West Side of Manhattan and from the outside, it should have been perfect. But I found it desperately unfulfilling. It wasn’t that I was “unhappy” as much as I began to wonder what I was doing it all for? And I began to question what true happiness really was. And I began to bridge to my second passion — the study of meditation. This was in 1999, so meditation was definitely not as accepted as it is today. But this bridge began to give me the keys and clues to the questions I was having around happiness, fulfillment and self-awareness. I lived in both worlds for nearly 20 years before deciding to take the leap into doing the work of helping others find the keys to fulfillment and happiness through and at work.

Are you working on any exciting new projects now? How do you hope that they might help people along their path to self-understanding or a better sense of wellbeing in their relationships?

My most exciting project is my new book, Complete. It is created in a new genre called “prescriptive memoir” coined by my dear friend and publisher, Kim Corbin at New World Library. Through my personal story, the book seeks to normalize a new path for women — “the complete path.” Rather than finding value in the traditional ways we have been taught and condition to find value in — marriage, children, image — we choose a life of being alone. This is a path where we find deep self-love and exuberant joy in the face of what convention has told us is the most lonely, isolating path to walk. It is not advice steeped in preachy stories of “how to.” It is down-to-earth, often painful and hard stories of digging into a deep relationship with ourselves to find complete bliss, satisfaction, joy and bigger purpose for our lives. It’s about finding the pure joy of living life as a solo artist — and loving every minute of it.

Do you have a personal story that you can share with our readers about your struggles or successes along your journey of self-understanding and self-love? Was there ever a tipping point that triggered a change regarding your feelings of self-acceptance?

I got engaged to myself — and then I married myself! When I was in my early 40s, I finally felt like maybe I ‘should” find someone. And I tried all of the typical routes of dating. But nothing was working. I was on a rejection rollercoaster that was tearing down my confidence and making me doubt myself. After years of trying, I hit 50. And I had this hypothesis, an epiphany really: what if I truly stopped looking for someone else to make me feel whole? To prove I was loveable. Or valuable? What if I “dropped” the whole damn thing? And I pondered what else might drop away with the idea of taking a different path. Perhaps my constant body acceptance issues and yo-yo dieting? My self-deprecating ideas that I talk too much (I do!), I am too controlling, too professional, too successful? Would that perhaps fall away when I just dropped the rope on finding validation through finding Mr. Right? And this was a big deal for me! I had been on a quest for years to find the right partner.

But I took my own challenge. And for a year, I worked to fall in deep relationship — in love — with myself. I challenged myself to fall in love with my own company. And at the end of that year, I was the absolute happiest I had been in my whole life. I was grounded and calm and authentic. And so, I decided to make it permanent, and I married myself! Women have been sold a narrative that is in many ways — just that — a narrative! It says we must prove we are valuable by finding the right person, having children, staying youthful, having the perfect career. And then we kill ourselves doing it! For what in the end? I am in no way suggesting that marriage and children is not a great path. But it is only one path! And it’s really the only one we’ve been sold is a curative to finding self-fulfillment. I am walking proof that when you truly fall in love with yourself, it is pure gold.

According to a recent study cited in Cosmopolitan, in the US, only about 28 percent of men and 26 percent of women are “very satisfied with their appearance.” Could you talk about what some of the causes might be, as well as the consequences?

I love looking great! I am all about “all the things!” I color my hair, love great make up, and have a penchant for fashion. But years ago, I had a deep and profound shift around my appearance. At 39, I quit my job to travel around the world. For a year, I traveled through the US, Europe, the Middle East, Africa, Thailand, Burma, Cambodia and India. When in India, I met a spiritual teacher — ironically from the US. I began to sit in deep meditation, staying silent from 9 or 10 am until 7 pm each day for months. The more I dropped into myself, the more I understood my true nature. I began to see the story of who I was and how I showed up was nothing more than a database. A programmable database. And when I came in super close contact with that idea, it was as if my ego exploded, and I could see clearly that we are here alive for an instant! We are here and gone like beautiful flowers. We live these lives that we “make up” in many ways from all of the stories we live, and then our lives come to an end. This could be scary for many. But for me, it was great freedom. To know that I was nothing more than a programmed database of ideas was freeing! Now, of course, we have studied neuroplasticity and we have more and more proof that we can absolutely program ourselves. But back then, I came to this knowledge firsthand. It was at that time that I really began to re-evaluate my relationship with my looks. I had been relying on my looks as a means of self-confidence, attention, validation and more for years. And when I dropped the whole story, I was left with nothing but the beauty of my being. I could have made the choice to stop wearing make-up and to cut my har short. And I can remember staring into my own eyes in front of the mirror at that time and seeing the great depth of my true beauty, and I understood why Buddhist nuns shave their heads! It is a true demonstration of the story of “me” falling away. In that moment, I could have gone that route. But I made a different choice, I decided it was “play,” fun and whimsy! And I unhinged my attachment to my looks as a way to find self-meaning or a way “to be seen” and worked to focus more on my being. My passion for fashion and hair color is still here, but I no longer need the story of it all: that it makes me love-able or helps me to be seen in the world. Now, it is just plain old fun with no story attached.

To some, the concept of learning to truly understand and “love yourself,” may seem like a cheesy or trite concept. But it is not. Can you share with our readers a few reasons why learning to love yourself it’s truly so important?

I once met a 95-year-old woman and a friend asked her what the secret to happiness was. She said, “you have to learn to love your own company.” That really stuck with me. Because at the time, I don’t think I did. Either that or I don’t think I had ever paused long enough to even know myself or what it was like to be in my own company! If we don’t know ourselves to know what it is like to be in our own company, then we have not cultivated a true and sustained relationship with ourselves. To live “the complete path” means that you vigilantly fall in love with yourself — that you learn to find the joy in who you are and relish in your own being. When we make a commitment — a real commitment — to walk this path, we can feel the extasy of being alive! There is nothing more needed! “loving yourself” can feel trite, and that’s because we have not really practiced it all the way through. We do “pieces and parts.” And then we abandon ship for a shiny new toy that feels more interesting than being with ourselves. But the real challenge is to take it head on and falling completely and wonderfully in love with your own company.

Why do you think people stay in mediocre relationships? What advice would you give to our readers regarding this?

We have been taught that being in relationship is directly tied to our worth. That being “alone” means there is something wrong with us. We have an entire system that conditions us to believe this! This of most songs, movies, books — more often than not, there is a subtext that if the boy gets the girl, or the woman gets her man, she is done. Happily, ever after. She is finally seen. She finally has value. She has worth. She is finally, finally loved. People would rather stay in something mediocre than risk not feeling seen. But this feeling — this desperate need to be seen and feel worthy — cannot come from the outside. That is like a junkie taking pills. It’s an inside job. To truly understand ourselves and find value, we have to dig deep into understanding our own narratives, our stories about our own worth. It’s a practice and not an end point. But in the end, you find an abiding feeling of peace and bliss that no one can take away. And no one can call mediocre.

When I talk about self-love and understanding I don’t necessarily mean blindly loving and accepting ourselves the way we are. Many times self-understanding requires us to reflect and ask ourselves the tough questions, to realize perhaps where we need to make changes in ourselves to be better not only for ourselves but our relationships. What are some of those tough questions that will cut through the safe space of comfort we like to maintain, that our readers might want to ask themselves? Can you share an example of a time that you had to reflect and realize how you needed to make changes?

The toughest question I have ever asked myself was around my values. Like most people, I had a pat set of answers around my personal values. Health, family, spirituality. But when I did a deep dive, I actually observed the choices I made over several months against what I said I valued. And that was a surprise! I often ask my clients to do this exercise. Write down your personal values — and dig deep to unearth them from the decision and path your life has taken. Then, spent a few weeks observing how often you actually live to your own values. You may find you live in accordance to those values. Or, like me, you may find you prioritize certain aspects that you would never have muttered out loud when asked what you truly value. The truth is so freeing — and when you have real, unedited information about who you truly are, then you are starting with something real. Something authentic. Then, you are in the “truth zone.”

So many don’t really know how to be alone, or are afraid of it. How important is it for us to have, and practice, that capacity to truly be with ourselves and be alone (literally or metaphorically)?

I think we are afraid to be alone with ourselves in the same way a child who is not quite telling the truth is uncomfortable when she is lying. We don’t want to be in the same room with our shame, our doubt, our feeling of deep low self-worth. Instead, we scramble to numb the truth away. So, the practice is a commitment to knowing yourself — to constantly revealing the truth of who you really are, to yourself. When we can sit in the discomfort of our own being, we can begin to heal the wounds that we so often want to run out of the room to avoid. We can “hug” the parts of ourselves that are lurking — the shadow, the self-doubt, the feeling of never quite being enough — and begin to rebuild a new narrative. It is absolutely in our power to reform our being. But it starts with just getting and staying in the room with ourselves long enough to greet and meet all the untethered parts.

How does achieving a certain level of self-understanding and self-love then affect your ability to connect with and deepen your relationships with others?

Most importantly, it allows us to serve. I can recall that exact day I dropped into the somatic feeling of service. I was working as a consultant on assignment at ModCloth, the women’s clothing brand. And I made the conscious decision in an instant to “serve with all I’ve got.” It came so quickly. And it was born out a moment where I no longer needed self-involvement! I had cut through all of my own pain and found self-love. And then I could let go of the need for all things to flow through how they affected me or my life, and just be present to serve.

In your experience, what should a) individuals and b) society, do to help people better understand themselves and accept themselves?

Know that this whole shebang has been built on nothing more than narratives. These are stories and points of view that have been “given” to us in one way or another. Parents, society, school, work, relationships, the media — it’s all been highly crafted into safe and conditioned stories so we can comfortably settle into nice and neat little boxes. The boxes are safe havens so we can all function with norms and rules of how “to be” in the world. In the same way we have been disrupting businesses and industries for the last 20 years, now we are seeing our ways of being disrupted. When we can challenge our narratives, break the norms that bind us and free ourselves to chart new paths, then we can really live in present time. And no longer stuck on stories and narratives.

Here is the main question of our discussion. What are 5 strategies that you implement to maintain your connection with and love for yourself, that our readers might learn from? Could you please give a story or example for each?

I would call this section “How to go from Loneliness to Onliness. I like that you are referring to them as strategies — because that is different from steps. To move into “onliness” is a nonlinear practice. Here are 5 strategies.

  1. Relish in the joy of your own company
    A meditation teacher I sometimes go to listen to brought in his 90-year-old Mother. Someone in the audience asked what the secret to longevity is. She said, “you have to learn to love your own company.” She went on to describe that she loved playing cards by herself and reading books — that she loved to hear her own laughter as she read. She said most of her friends had died and she had to find a way to be joyful and happy. Being with herself — and truly savoring her own laugh, her mind, her personal way of being — that kept her joyful. And that kept her alive. So, really take action around what it is like to experience the joy of who you are! You will find a switch flips, and what used to feel like loneliness suddenly feels like an opportunity to truly adore yourself, experience the richness of you.
  2. Listen to and dissect your self talk 
    Our habitual thoughts can so easily be mistaken for the truth of who we are. These habitual thoughts come from our past experiences that tell us we are “good” or “not good” in all kinds of ways. To move from loneliness to onliness, diving into the fabric of the mind is essential. You begin by watching the repeating patterns of self talk, particularly those that are negative or tell you that you are unworthy. These can be as simple as “I hate my butt,” or as complex as “I am unlovable because no man is choosing me.” Often, we mistake these habitual thoughts as more than just simple thought patterns. We think they are the truth of who we are. We “become” the thought versus seeing it as the fabric of the mind. Most people don’t even realize they are doing it! Most of us would use mind patterns to describe who they are versus coming to an understanding that thoughts are nothing more than patterns. And we can see them for what they are and choose to separate ourselves from them, maybe even supplant them with new thoughts that tell us all the reasons we should love ourselves. Part two of this strategy is to rid yourself of those in your life who reinforce your own negative habitual thought patterns. I had a lifelong best friend who served a great role in mirroring my own mind back to me. It made me feel understood. But it also held me in position, not allowing me to grow and move form a place of self-loathing and into a place of self-love. I made the decision to let her go, and with her went the reinforcement of my own habitual negative self talk.
  3. Write a love letter to yourself — and not just any love letter
    One of my clients was feeling quite depressed because she did not feel she could meet someone to date. She was in a downward spiral about all that this meant about who she was. Too this and not enough of that. We sent her on a three-week solo road trip. Her assignment was to reject notions of dating for just three weeks and instead focus on falling in love with herself. Towards the end of the journey, she wrote a two-page love letter to herself. But this was not just any love letter. It demonstrated real love, which includes room and appreciation for all the imperfection and all of the exquisite beauty she had to offer herself and the world around her. As I read this letter, tears dropped from my eyes because she expressed what so many should feel but have not given themselves permission to feel: the wellful of adoration we can have for ourselves. And the authentic love for all we are.
  4. Notice what might fall away if you stop seeking validation and value
    I did a ritual for one year where I got engaged to myself. For one year, I made the promise to truly fall in love with myself, to drop all ideas that I would meet a man. Drop all ideas that my life was going to be any different than it was in that moment. I dropped all of the “too muches” and the “less thans,” in exchange for one year of experimenting with what dropped away when I let go of focusing on “the lack.” I dropped fully into the idea that I would be single for the rest of my life. And so much more dropped away along with it! I dropped the obsession with my body and what I ate. I dropped the pervasive ideas that I talked too much, was too successful, didn’t fit the norm. And I dropped what men thought of me! Suddenly, I found the absolute perfection of the life I already had. I began to truly notice the abundance in my life just as it was. I noticed my great butt, my plethora of amazing friends, my fantastic hair, my fun-filled and diverse weekends. I gained much along with it, but what stuck the most was this idea that perhaps my life was meant for a different kind of greatness: one where my soul purpose was not to “mate” or “breed,” but to learn to love and mother at scale. And that may be an even greater gift to the world than I had imagined from the position of lack.
  5. Find ecstasy in the everyday stuff.
    Every day and every moment in the day offers an opportunity to be present. And every day has moments of sheer bliss built right in. We are often so busy in our habitual thoughts or our lives that we miss the ecstasy of what we are actually experiencing! This is part of moving into “onliness.” When we can slow down, notice textures, and feel into our senses — one sense at a time — we can begin to open up the reality of what is really all around us every day. My commutes to work used to be laden with anxiety and rushing. In my trip from the subway to the office, I would walk hurried with thoughts of all my stressors, failures and anxieties rushing through my mind. After beginning to practice being in bliss with everyday moments, I had a morning commute that changed my perspective on life. I was rushing up the same span of blocks on the route I walked every day when I felt the glitter of the sun off a building that hit my face. I looked up and the way the light was cast on the silver skyscrapers was magical! It was not just the “sun” or the “building,” it was the magic of the relationship between the two. The way the building took in the warm bright glow of the sun. And the way the sun interplayed with the billings. I felt a rush, a sensation of bliss move through my body. And my walks were never the same.

What are your favorite books, podcasts, or resources for self-psychology, intimacy, or relationships? What do you love about each one and how does it resonate with you?

I’m obsessed with Esther Perel! Her direct, empathetic and pointed questions and observations are a great inspiration to me. She recently did a series called “How’s Work” in which she delved into relationship therapy with work colleagues. It was remarkable and highly indicative of where the world is going that we are understanding that work is not magically removed from the emotional journey we take in our life! Our work relationships are real and impactful. If our relationships with key partners at work are not aligned, then we can be miserable. And so, she takes on the emotional landscape of work.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? Maybe we’ll inspire our readers to start it…

My forthcoming book, Complete, seeks to normalize a new path for women: the path from loneliness to onliness. The concept that we can lead deeply fulfilling and rich lives of joy, wonder and discovery by committing to ourselves versus going the traditional route. Then, perhaps, we will find a different life purpose. Then perhaps, more and more women will serve with the power of the feminine at higher levels — not only stuck at home with the kids — and we will reshape the patriarchy. When you really tune in, the whole darn narrative has been designed to keep us stuck. And when we can shed this old conditioning and free ourselves from the old story that we must earn our value by finding the prince who will help to take us out of the game by sending us home with the kids, then perhaps we can be a mother to our collective future as a world.

Can you please give us your favorite “Life Lesson Quote” that you use to guide yourself by?

Can you share how that was relevant to you in your life and how our readers might learn to live by it in theirs?

“Life shrinks or expands in proportion to one’s courage.” Anais Nin

Thank you so much for your time and for your inspiring insights!

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