Taking the Leap: Stephanie of Oaks and Sails On How To Learn To Believe In Yourself
An Interview With Savio P. Clemente
The last strategy to establish strong beliefs in oneself is Resilience. Believing that you can means that you have to persist despite every obstacle thrown at you. It’s the willingness to continue the game even if you’re on the losing end of the scoreboard. Resilience is built from taking everything you are made of, the encouragement you receive, the risks you have taken, and trusting the outcomes to the point that you would do it all over again when things don’t turn out the way you wanted. My resilience was built from growing up in hard circumstances and seeing that despite everything I have gone through I am still here alive and well.
Starting something new is scary. Learning to believe in yourself can be a critical precursor to starting a new initiative. Why is it so important to learn to believe in yourself? How can someone work on gaining these skills? In this interview series, we are talking to business leaders, authors, writers, coaches, medical professionals, teachers, to share empowering insights about “How To Learn To Believe In Yourself.” As a part of this series we had the pleasure of interviewing Stephanie D.B.
Stephanie is an experienced educator who turned to life coaching to expand her impact. Her work consulting teachers and educating children of all ages helped her realize that in order to change the world, she needed to change lives, and changing lives meant working closely with people’s dreams, fears, and sense of self. She is highly knowledgeable around human development, a master of creating order out of chaos, and considers herself a Jill of All Trades, with knowledge and experiences across a broad spectrum. Stephanie lives in Los Angeles and her favorite part of the day is watching her two young boys live life fully, experiencing every moment with confidence, vibrancy, and compassion. To get in touch with Stephanie, you can schedule a meeting at oaksandsails.com
Thank you so much for joining us in this interview series! Before we dive into the main focus of our interview, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?
I was born and raised in Los Angeles. As a child, I was in love with the world. My family wasn’t well off financially, but the most valuable thing my home offered was a huge wooden piece of furniture full of books, sketchbooks, and random knick knacks.That bookshelf was my only access to the world. As a ten year old, I was reading about indigenous cultures, Freudian psychology, trigonometry, poetry from the late 1800s, and trying to teach myself french. If I wasn’t reading, I was writing plays, illustrating comics, choreographing a dance, painting on canvas, eating bugs, or playing tackle football. I was hungry for knowledge, to expand my horizons, to deeply understand everything and everyone that came my way. I was also determined to be the best at everything I did, and looking back, I’m amazed at how everything she touched was successful. That little girl’s inner fire and courage to express herself inspires me everyday.
What or who inspired you to pursue your career? We’d love to hear the story.
After transitioning from teaching, I felt inspired to return to my love of writing and signed up for a writing workshop at a public library. This workshop was led by a life coach who introduced me to Martha Beck’s work. Down the rabbit hole I went, learning more and more about life coaching, and the effect it had on me was quite eye opening. It affirmed my philosophy as an educator that the greatest impact is created by developing the whole person, not just the brain. All of my successes as a teacher and as a consultant always reverberated back to connecting to each person emotionally, developing their strengths, igniting the grit to face their fears, and giving them the space to be themselves. Through Martha Beck’s work, I was able to experience for myself, all of the instinctive gifts I had given to my students, colleagues, and families I came into contact with for the past 15 years. I decided to enroll in her ICF coaching certification program, and here I am now, guiding people towards whatever goal they aim for and the hurdles they want to overcome. Now I get to learn about people much more closely and make space for them to blossom. It’s a dream come true!
It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
The funniest mistake I made, both in teaching and coaching, was to assume that I had to have all the answers. In reality, no one has all of the answers. Facts change as we gain more information and they depend on the perspectives we take; what we have at best, are very well tested hypotheses. I remember in my classroom one day a child asked if tornadoes were possible in California. I replied that they aren’t possible due to its mountain ranges and mostly dry weather. But lo and behold, there was a tornado in Los Angeles this year! I chuckled when I saw it on the news, thinking of my students, and it taught me that my work is not to give answers, it’s to create space for questions, discoveries, connections, and to nurture each person’s sense of self to the maximum. As a guide, I need to be a wise facilitator, not an assuming lecturer.
What are some of the most interesting or exciting projects you are working on now? How do you think that might help people?
I’ve just started the process of converting an abandoned garden at a school where I work into a literacy garden. The experience reminds me of my favorite book, the Secret Garden, where the main character discovers an old abandoned garden and in the process of beautifying it, love and kindness heals wounds. This project combines my love of people, gardening, learning, and reviving things to their former glory. Since I studied architecture in high school, I’ve been able to dust off some of my old drafting and design skills to create something beautiful for people to enjoy. I’m planning to host a community event where volunteers can come together and pull weeds, plant trees, paint planters, repair benches, etc. and beautify this garden. Once it’s complete, I would love for it to be a place where children can come to read, learn about the natural environment, and find tranquility in their day.
OK, thank you for all of that. Let’s now shift to the core focus of our interview. This will be intuitive to you but it will be helpful to spell this out directly. Can you help explain a few reasons why it is so important to believe in yourself? Can you share a story or give some examples?
Nothing can be done, no progress can be made, if you do not believe in yourself. You may be able to skim along to an arbitrary success, but it will be built on a house of cards. Without a solid sense of self, even the slightest whisper, will make everything that your accomplishment rests on fall apart. I remember I worked with a teacher who was an excellent speaker and led student discussions quite successfully. But she did not believe she was successful and thus, avoided leadership opportunities. When we would reflect on the work together, she would apologize profusely. The slightest critique would shatter her confidence. Without confidence, she was unable to take the risks and feedback needed to strengthen her abundant teaching talents, a talent that could have positively impacted her colleagues. Progress requires courage and courage requires every ounce of you, including beliefs about yourself. Think about every action hero you’ve ever seen. Is Batman going to save Gotham city if he’s full of self-pity? Or is he going to save lives by taking a risk and jumping off of buildings, picking himself up after every battle?
What exactly does it mean to believe in yourself? Can I believe that I can be a great artist even though I’m not very talented? Can I believe I can be a gold medal Olympic even if I’m not athletic? Can you please explain what you mean?
To believe in yourself means that you know your strengths, your weaknesses, and that you accept them as they are. You trust yourself. To believe in yourself means you have the confidence to take risks and leaps of faith in reaching your goals. It also means that if you fail, you trust that you can figure it out. Believing in yourself means you are willing to work hard and put yourself out there for something you really love. Are there artists out there who are not talented, but believe in themselves? Absolutely. But who said you needed to have a talent to pursue joy? Who measures talent? There have been countless creatives and innovators in history whose work was undervalued during their time, but that we admire to this day. These progressive minds, such as Vincent Van Gogh and Thomas Edison, pursued their joy regardless of being labeled as not very talented.
Was there a time when you did not believe in yourself? How did this impact your choices?
I remember I was a freshman in college and getting advised to add an art minor to my major. I was excited to learn new art techniques to enhance my raw talent, but most importantly to spend time with my art. At that point in time I was a self-conscious 18 year old, shy, and still not bold enough to advocate for myself. I asked a question (still don’t remember what the question was) and she reprimanded me. I sat there with tears in my eyes and thought that I should have known better. I thought I deserved the scolding and slinked away, never completing the paperwork to add the art minor to my major. All of the hours I dedicated to drawings and paintings, the joy and passion I felt when I made art, all of it went down the drain because I did not believe in myself. Looking back now, I did not deserve that reaction, I did have talent to explore, and if only I had believed in myself, I could have stood up for myself because I deserved better. My life did not progress in art because I did not believe in myself at that moment in time. I did this more than once. I stalled my own love for drama, singing, and writing in my young adulthood because I thought I couldn’t do it.
At what point did you realize that in order to get to the next level, it would be necessary to build up your belief in yourself? Can you share the story with us?
The day I decided to write a novel was the moment I realized how important it was to believe in yourself. I hadn’t written a single creative piece since high school and here I was about to take a leap into fiction writing in my late 30s. I had to work myself up to get the courage to sign up for a writing workshop class. I had to believe in myself when I shared my work to receive feedback, which in turn advanced my writing. I had to convince myself that I had enough talent to join a writing conference and mingle among other writers. Every time I sat in front of the computer to write, even if it was a blank screen, I had to believe that I had everything I needed inside of me to get it done. And I did get it done. Every part of the writing process is a confidence battle, even when it gets published and it’s at the mercy of other people’s opinions. But my worth and value is not tied to other people, it’s tied to how I see myself and what I believe about myself.
What are your top 5 strategies that will help someone learn to believe in themselves? Please share a story or example for each.
1 . The first step in believing in yourself is having a Strong Sense of Self. Know your strengths and weaknesses, and accept them. My work with my students, teachers, clients, and even in raising my two boys always starts with a self- reflection of what they are good at and what they want to work on. I had a student who was good at number calculations, but had a hard time reading. Knowing this gave him the confidence to ask for support when reading through a mathematical word problem. He was able to demonstrate his knowledge by knowing his strengths and weaknesses, owning them, and getting the support he needed.
2 . The second strategy to build up belief in oneself is to create A Supportive Environment. Sometimes the environments we work or live in are not conducive to your personal growth. Sometimes that means we have to let go of people, places, relationships, desires, or environments that hinder us. Find people who believe in you and who can offer support during the times you crumple and have a hard time picking yourself up. Think about the people in your past who believed in you when you were starting to give up. It could have been a teacher, a coach, a child, a family member, or a friend who encouraged you. They fill in the gaps when you are too tired to do it yourself and can offer an alternative perspective when the negative self-talk creeps in.
3 . Taking Risks is a journey towards strengthening the muscle of believing in yourself. Every time you take a risk and you succeed, your competence and self-confidence gets an extra boost. The first time you get on a bike, you are doubting your ability to ride. But every time you take a chance and go a bit farther without falling, your ability grows and your confidence grows. Eventually the belief that you can do it is more prominent because you’ve increased the frequency of your successes. After enough practice, you don’t question yourself one bit as you hop on your bike for a ride around the block. But none of it would have been possible without taking that initial risk.
4 . Everytime we have the confidence to take a risk, we have to be open to Trusting the Outcomes. Taking risks is tied to trust. With this strategy, you believe in yourself regardless of the outcome. This is most evident when watching a small child dance. They dance freely and enjoy the process regardless if they are able to dance to the beat or if they fall as they attempt their version of a shuffle. By the end of the song, the child beams proudly and wants to do it all over again. Young children haven’t lost the ability to believe in themselves, so they attempt everything knowing that if they fail, fall, or get messy, it really doesn’t matter. They aren’t afraid to try things again, get help, or move onto something new because they trust that whatever happens, there’s always a way out. All of which, translates into trusting that you have the power to change an outcome if you choose to.
5 . The last strategy to establish strong beliefs in oneself is Resilience. Believing that you can means that you have to persist despite every obstacle thrown at you. It’s the willingness to continue the game even if you’re on the losing end of the scoreboard. Resilience is built from taking everything you are made of, the encouragement you receive, the risks you have taken, and trusting the outcomes to the point that you would do it all over again when things don’t turn out the way you wanted. My resilience was built from growing up in hard circumstances and seeing that despite everything I have gone through I am still here alive and well.
Conversely, how can one stop the negative stream of self-criticism that often accompanies us as we try to grow?
We all have experienced bouts of self-criticism. I have found that the best way to dismantle them is to first of all, identify them, and then face them directly and question them, which is a technique I learned from my work with Martha Beck. If you are thinking, “I’m a horrible cook and I should never cook again!” Stare right at that thought and ask yourself, “Is that 100% true?” After some thought, you might recall a time you made a dish that your friends devoured. Once you realize that, your perspective changes a bit and you might be open to thinking, “Well, actually, maybe I could make that dish again.” This then reverses the negative-talk cycle into a more positive one.
Are there any misconceptions about self-confidence and believing in oneself that you would like to dispel?
The one misconception I see parents, sometimes even teachers and employers use all the time is asking someone else to just believe in themselves so they can be better at baseball, reading, deadlines, communication, whatever else they are expecting of the person. Believing in yourself is an experience outside of someone else’s expectations. It’s an internal process independent of what anyone else wants or thinks. Your child will not get better at baseball by believing in themselves if they aren’t interested in becoming more successful at it. And even if they are interested, their definition of success may be hanging out with friends on the bench and not being the best one on the team. Your student will not improve in reading by just believing in themselves if they aren’t motivated to read words because their definition of success is just being able to get a good night’s sleep. An employer can’t expect someone to just build confidence for a presentation when the employee has a social anxiety disorder. A person’s success isn’t tied to believing in yourself because not only is the definition of success a personal one, but also believing in yourself is a state of being that persists despite the failures and successes.
What advice would you give to someone who is struggling with imposter syndrome?
It’s impossible for you to be an imposter because there’s only one you. Ten different people will look at the same problem and utilize ten different approaches, ten different tools, to come up with ten different solutions. Your unique strengths, perspectives, and experience are why you are valuable. They hired you, not the person you think they should be. I would also suggest making a detailed inventory of your strengths and successes. If the negative self-talk creeps in, face them and question them. Some people prefer to do this type of work with the support of a therapist or coach.
Ok, we are nearly done. You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
Oh, boy. I get such grand ideas on a daily basis, it’s hard to choose just one. The one thought that percolates most often for me is completely revamping early childhood centers so that it is free for all children, hires highly educated certified teachers that are well paid, and offers free in-house parenting/therapeutic support. I’ve noticed over and over again how families have the greatest impact on the values and opportunities children have, which in turn affects their contributions to society. By giving children the most enriching environment, regardless of their family’s circumstances, they have better opportunities for success. By finding ways to support parents who are stressed and overwhelmed and new to child development, they would have more information at their disposal to handle parenting in a positive way. These enriching experiences already exist, but they tend to be more available for children with means. It would be a dream if it was an experience that all children and their families had access to, rather than a select few. The social, emotional, cognitive, physical, and societal impact would be huge.
We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US, whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we both tag them :-)
I would love to have lunch with Hazen Audel. My family loves to watch his show and my boys like to pretend they are him, finding imaginary snakes in the “jungle,” which is our backyard. I think he completely embodies the idea of believing in yourself by having the courage and strong sense of self to take risks as he explores difficult places around the world, trying to survive. I would love to learn more about the different tribes he has interacted with and their customs! In another life, I would love to be an explorer and live closely among nature.
How can our readers further follow your work online?
I’m brand new to social media, so be patient with me folks! You can follow me on instagram @oaksnsails or visit my website at oaksandsails.com
Thank you for these really excellent insights, and we greatly appreciate the time you spent with this. We wish you continued success.
About The Interviewer: Savio P. Clemente coaches cancer survivors to overcome the confusion and gain the clarity needed to get busy living in mind, body, and spirit. He inspires health and wellness seekers to find meaning in the “why” and cultivate resilience in their mindset. Savio is a Board Certified Wellness Coach (NBC-HWC, ACC), #1 best-selling author, syndicated columnist, podcaster, stage 3 cancer survivor, and founder of The Human Resolve LLC. He has interviewed notable celebrities and TV personalities and has been featured on Fox News, The Wrap, and has worked with Authority Magazine, Thrive Global, BuzzFeed, Food Network, WW and Bloomberg. Savio has been invited to cover numerous industry events throughout the U.S. and abroad. His mission is to provide clients, listeners, and viewers alike with tangible takeaways on how to lead a truly healthy, wealthy, and wise lifestyle. Savio pens a weekly newsletter in which he delves into secrets to living smarter by feeding your “three brains” — head
, and gut
— in the hope of connecting the dots to those sticky parts of our nature that matter to living our best life.