100 Conversations with Stephanie Benedetto
What would I learn from 100 conversations with entrepreneurs who inspire me?
That’s what I’m about to find out.
The Challenge
I’ve challenged myself to have 100 conversations with inspiring entrepreneurs to learn about their brilliance and the gift they bring to the world. I’ll make a new video for each conversation documenting the process and sharing my insights about purpose, business and transformation. This challenge was inspired by Kyle Cease’s 100 Day Self-Connection Experiment (thanks, Kyle!) and I can’t wait to see how this adventure unfolds.
The inspiring entrepreneurs I’m looking for meet the following criteria:
- They have a purpose or calling to share with the world.
- They are experts, givers, teachers or healers.
- They’re passionate about helping others.
- They’re open and playful enough to enjoy my curious questions.
What I Learned From 100 Conversations
I’ve officially completed my 100 Conversations Experiment! So many adventures have happened along the way, and it’s been life changing.
Here’s an article sharing my 10 Lessons Learned From 100 Coaching Conversations.
Check out the latest awesome feedback!
Watch Videos of My 100 Conversations Insights
Video #88 – What Lies Beyond Your Greatest Fear?
Flat and colorless, like a cardboard box. That was me. "Where did Stephanie go?" he asked. I'm noticing the power I've been hiding. Watch this: I always thought my Shadow was the thing I’ve been hiding from. It turns out the Shadow is just the monster at the door...
Video #87 – My Deepest Fears About Being All of Me
While I was at the Brisbane Airport leaving Australia, it seemed like a good time to leave behind some of my biggest fears while I was leaving the country. These were my biggest fears about expressing my true self. Watch this: There’s something truly powerful about...
Video #86 – What Are You Pretending Not to Be?
Lately I've met some people who were pretending not to be what they really are…and all of them were magical. A witch masquerading as a therapist masquerading as a coach. A shaman and channeler masquerading as a coach. Watch this: Now, you might not consider yourself...
Video #85 – What It Means When It Hasn’t Manifested Yet
Sometimes what I know, about myself, what's possible and what's coming, doesn't match up with what I see in the outside world. What does it mean when what you feel and know on the inside doesn't match what shows up? Watch this: Just keep going, one action at a time....
Video #84 – Can You Really Do ANYthing?
I love when people ask some variation of this question, "If I work with you, will I make [BIG INSPIRING AMOUNT OF $$$]?" This is my reply. Watch this: It seems to me that anything is possible…and it also seems there are some limitations like this (finite) body and...
Video #83 – What Happens When I Show Up With Nothing
What happens if I show up with nothing to say? Something inevitably comes out of my mouth. Maybe it's even something pretty darn useful. Watch this: I think that wasn’t so bad. What if you lived your life that way? I wonder what might happen?
Video #82 – Four Minute Meditation For Self-Acceptance
What is your body asking for today? So many times our nervous system is bracing for attack, feeling panic, worry, stress. And when we try to "make" ourselves relax, guess what? It can make it worse! Here's a meditation to create space and self-acceptance. Watch this:...
Video #81 – Meet Barney the Tripod Cat, My Hero
When I started pet sitting for Barney, he was a healthy, happy orange cat with four legs. That's only significant because he's now missing a limp and most of his tail. Is he still healthy and happy? You bet. This is why he's my hero…and someone else is, too. Watch...
Video #80 – When In Doubt, Be Silly
Has it been a hard day? A long week? It is so, so, so important (for me, anyway) to take the time to be ridiculous. Watch this: What do you do to relax and get silly?
Video #79 – What Is Impossible, Really?
I made this video almost a year ago, and I’m not sure I’d say the same things today, or come to rest in the same place if I did. I still like asking the questions. What if there are no limitations, only possibilities you have not yet realized? Watch this: Something...
Video #78 – What If You Have a Core Wound That Won’t Heal?
Sometimes our bodies get tricked into thinking an old emotional wound is happening NOW. We're safe in the present, but it doesn't feel that way. This is the message I needed to hear to let go of Abandonment, Annihilation & Despair, and I'm sharing it with you....
Video #77 – Who’s Got Your Back?
So many of our relationships seem to come with conditions. As long as you’re a good girl, a nice guy, a hard worker...you’ll get the attention and approval you seek. If not, they’re gone. That’s an old story. Now I’m asking myself, “What would it take for me to give...
Video #76 – Coping With Loss
How do you deal with loss? Whether it's a relationship or a career or a dream, it's painful. It's asking for your attention. Watch this: There's a way to transform that loss through grieving into something that's truly beautiful. What beauty can you discover in your...
Video #75 The Secret of Choice & the Golden Cleavage
Have you ever “chosen” something in the future, instead of right now? “I’ll choose that trip after I have the money for it.” “I’ll choose to attend that event after I have a date.” How many times have you convinced yourself that you’ve chosen something that you...
Video #74 – Coming Out of the Closet
I haven't been letting the world see what I'm really, really good at. I haven’t been showing people the fullness of my power and greatness. It's like I've been wearing a cloak of invisibility or something. Watch this: So now I'm coming out as the awesome, powerful...
Video #73 – The Joy of Apologizing & Radical Self Love
Have you ever apologized to someone and felt GOOD? Who were you really apologizing to? There’s a practice called Ho’oponopono of radical self love and forgiveness. This is a new twist. Watch this: What if you say these words to yourself right now?
Video #72 – Does Change Have to Be Hard and Painful?
There’s a lot of evidence in life that change is painful. Most people live in fear of change because it seems unsafe. But what else is possible? Watch this: Sure, change can be hard. Life is full of suffering. But what if it were simple and easy to change? What would...
Video #71 – What Are You Taking For Granted?
We lost our power for over 30 hours due to downed power lines. Yikes! There’s nothing like freezing in the darkness to remind me how lovely it is to have heat and power. It got me thinking… What else have I been taking for granted? Watch this: What appreciation can...
Video #70 Ask a Question to Receive What You Desire
Are you asking for what you desire in a way that makes it easy to receive? I've been experimenting with asking questions over the last few weeks with some very interesting results. Watch this: In the past I've been "praying" for what I desire, instead of asking....
Video #69 What If You Were a Blank Slate?
When I was fifteen years old, I asked my boyfriend what he liked about me. “You’re like a blank slate,” he said. A blank slate? As in EMPTY with nothing to offer? Watch this: Now I have a different awareness of what he meant, a new appreciation of the blank page and...
Video #68 What Choice Can You Make Today to Change Everything?
They like to say the path to change is long and hard. It's going to take a long time and you're going to have to "go deep" and "do a lot of work" to deal with your issues. What if it could be simpler than that? Faster? Watch this: A completely profound change can...
Video #67 Are You Waiting For the Acknowledgement That Can Never Be Given?
I had a very serious face when I was a little girl. People used to say, "Why are you so serious?" So I started smiling. People seemed more comfortable with that. It was a habit I've cultivated all my life; looking for what people wanted and giving it to them, so that...
Video #66 – Playing the Yes Game
How to Attract and Receive Your Secret Desires What would you like to create? Sometimes it's easier to say what we DON'T desire, rather than what we do. That's where the Yes Game comes in. Watch this video: This lets you understand what YES feels like in your body,...
Video #65 – 3 Reasons They Don’t Buy Your Stuff (and Other Tragic Tales)
Are you making offers and not getting sales? I've been experimenting with all kinds of outrageous offers over the past couple weeks, and I've learned a lot about when it works and when it doesn't. I'm also NOT a fan of high pressure sales, especially in coaching...
Video #64 – What Are You Making Up That’s Messing With Your Life?
It recently occurred to me -- recently as in this morning -- that 99% of the stuff in my head is made up. Judgments, projections, fantasies, nightmares. Stuff that hasn't happened and probably never will. Watch this: The good news? I don't have to take ANY of it...
Video #63 – How to Slay the Monster Who’s Ruining Your Life
I try so hard to be good. Spiritual. Mature. And that just isn't me. Watch this: I want to scream and throw a temper tantrum. I want to shake my fist at the sky and demand an answer. Some days, anyway. It doesn't always look like that. But when I try to make it look...
Video #62 – Life Is a Game: How Will You Play It?
A thought experiment from Michael Neill (I just love him!) Watch this: Pretend I'm a casino owner who is going to pay you to play in my club, with my money. All you have to do is show up, play, and look pretty. How would it change your game? How does it change the way...
Video #61 – The Honeybee’s Secret to Unleashing Your Genius
Have you ever felt like there's more you have to share, but you don't know how to access it? I'd like to tell you a story about a flower and a bee… Watch this: The blossom of your heart is ready to open. It’s waiting for just the right tone to be struck by what fills...
Video #60 – Do You Deserve to Get What You Want?
For most of my life I've had this belief that I'm not supposed to get what I want. It's no wonder I never thought to ask myself, "What do I want to create here?" Instead, I spent my time filling the roles and needs of people around me. Watch this: I'm happy to say...
Video #59 – Are You Missing Out On Powerful Unexpected Connections?
I recently spent two months minding my brother’s Airbnb in Colorado. This gave me a chance to meet some extremely interesting people and have some unexpectedly powerful conversations. Watch this: The connections, abundance and love you’ve been looking for are right...
Video #58 – Stepping Into the Shadow: Going Where You’re Afraid to Go
I enjoy a good challenge. But… When I’m called to explore the dark corners of me, it gets pretty scary. Watch this: You don’t have to go to those uncomfortable places. It’s a choice. But learning the gift of your darkness and regaining access to all of yourself is an...
Video #57 – The Price of Having “Too Much Fun” In Business
I got good and pissed off the other day with some (constructive?) criticism that I received. Apparently, including a two minute, goofy bit in our course was “not an efficient use of time,” and “unprofessional.” Well. Here’s what I have to say about that. Watch this: I...
Video #56 – Lies About Mind Control That Keep You Trapped and Miserable
Is it possible to control your thoughts? Some experts say so. I find that trying NOT to think something is about as effective as trying not to think of a pink penguin. (Yep. Just did it.) Watch this: I love a good navel gazing ramble on the nature of thought. But when...
Video #55 – 3 Reasons to Have Scary Adventures
I went on some exciting and somewhat uncomfortable adventures over the past few months. One of them involved a Big Bad Wolf! Watch this: Here’s the thing: If you want adventures and change in your life, it’s going to be scary. Embrace it. Live it with everything...
Video #54 – The Power Sacred Conversations & the Unconscious
In the most powerful conversations with people, I'm aware that there's nothing I need to do. Something happens just being present with what is. That painful feeling, resistance or belief knows what it needs in that sacred space and the shift begins to happen on its...
Video #53 – Are Your Fantasies Holding You Back?
I was addicted to longing for the fantasy of some unattainable guy for most of my life. It seems like fantasies are harmless, all fun and no reality to weigh it down. But the fantasies we feed often keep us from creating what we really want. Watch this: It might be...
Video #52 – The Secret Power of Learning By Being
Do you have a mentor? Watch this: Learning from someone who's mastered what you want to do is incredibly powerful. But it's not what they teach you with words that has the biggest impact. There's a way of learning by BEING, by showing up, rather than doing and...
Video #51 – Do You Trust Yourself?
I was raised to trust my intellect instead of my intuition. But there were a few instances when an inner knowing kicked in, maybe because it seemed like there was no choice. Watch this: When I was faced with a tough decision at age 16, that knowing suggested another...
Video #50 – What Do You Want That You’re Afraid to Ask For?
I was afraid to ask for what I want for a long time. It still scares the crap out of me sometimes and I find myself thinking… "You mean, I'm allowed to ask for what I want?" Watch this: Yep. You're allowed to ask for what you want, sweetheart. What are you ready to...
Video #49 – How Can You Turn Your Weakness Into Your Biggest Strength?
It's high time we stopped beating ourselves up for our perceived shortcomings. You have a superpower or two. Or three. Its dark side often presents as a weakness. Watch this: What if that "weakness" became your biggest strength? How can you use it to your advantage?...
Video #48 – Warning: This Video May Change Your Life
If this video was going to change your life, what would be in it? Watch this: There's this LIE going around that it's going to take a long time to change your life. It took years to get you into the situation you're in, to build up the walls, to manufacture the...
Video #47 – What Would It Be Like to Bring Your Best Self?
My old way of doing things just isn't working for me anymore. I used to set a goal, tuck my head and charge like a pitbull to make it happen. I thought I could “make” things happen with my actions. it just doesn't seem to work that way for me anymore. Watch this: I'm...
Video #46 – The Cure For Business Burnout Is Monkey Business
Life is too short (or too long, depending on your perspective) NOT to have fun with it. The same is true for your business. Are you having a hard time getting yourself to do what needs to be done? Watch this: It's really easy to get caught up in what we "should" and...
Video #45 – The Secret to Moving From Decision to Commitment
There's a difference between "deciding" to do something, between recognizing you should do something, and making a commitment. We get tripped up in thinking we need to “feel” like it. Watch this: Feeling is NOT necessary for commitment. The only thing necessary is...
Video #44 – When Your Relationship Is Doomed
My husband knows me better than anyone. He knows the way I stand with my toe pointed when I brush my teeth and that I loathe sharing my favorite snacks with other people. When something goes wrong, he’s the closest one to me, and it’s so, so tempting to blame him....
Video #43 – Is It Possible to Change Everything In 5 Seconds?
I admit: I was a skeptic. Any book with its own hashtag plastered across every page has to be self-help pablum, especially with a promise like, “Get everything you want in just five seconds.” Except… Watch this: I experienced the shift for myself in stepping out of...
Video #42 – How to Create a One-of-Kind Business That Changes the World Without the Cheesy Sales Gimmicks
Don’t listen to what the experts tell you about how to build your business. They’re not going to tell you the most important thing you need to know. Watch this: It’s YOU that breathes life into your business. It’s YOU that need to awaken for this to happen. If you...
Video #41 – How to Find Exactly What You’re Looking For
Are you haunted by a big vision you want to share with the world? There’s only one place to find what you’re seeking. Watch this: When something is missing in your life, it’s natural to want to look for it out there in the world. That’s a necessary part of this...
Video #40 How to Change Your Life In An Instant
What if you could transform your entire life in an instant? I think you can… Watch this: It’s not magic and it doesn’t take years of therapy or massive willpower. When you change, the world changes. It only takes one shift. Who are you becoming?
Video #39 – What If You Said Yes to the Secret Desires of Your Heart?
“And, when you want something, all the universe conspires in helping you to achieve it.” ― Paulo Coelho, The Alchemist I've believed this for a long time, but now I'm actually beginning to think it may be true. Watch this: This doesn't mean everything we want happens....
Video #38 – Do You Ever Hate Yourself?
I’m not supposed to talk about it. SELF-HATE. It’s a scary thing, especially when I find it living inside me. But it’s not mine and it’s okay to talk about it. Like this… Watch this: Whatever it is that’s eating you, it’s okay. That doesn’t mean you shouldn’t get help...
Video #37 – How to Make Today Feel Like Your Birthday…Even If It’s Not
I celebrate my birthday this month! (Yes, all month.) I’ve issued myself a Birthday Challenge to see what happens. Watch this: It’s lovely to get Facebook comments, emails, cards and phone calls wishing me a happy birthday. I’m lucky to have so much love in my life. I...
Video #36 – Transformation: BS Hype or Salvation?
It all started with an argument passionate discussion with my husband about the nature of transformation. He claimed it was “BS.” That was kind of hard for me to hear, given that I’ve devoted my life to personal transformation. Fortunately, we were able to find common...
Video #35 – Can You Really Have It All? The Power of Choice
I got an email just the other day from a women’s leadership coach: Be the wife, mother and entrepreneur you’ve always wanted to be. Live the good life. You CAN have it all! This claim concerns me deeply. Here’s why: Watch this: I’m pretty sure I don’t have this...
Video #34 – Stop Denying Yourself
Have you ever made yourself stop wanting something for so long that you forgot you ever wanted it in the first place? It’s like letting a limb go to sleep for a long, long time. Long enough to almost forget that limb ever existed. Until it wakes up. Watch this: I’ve...
Video #33 – 3 Things You Must Do to Get What You Want
I used to be that girl. The one who sat on the sidelines. The shy one in the corner. The one who said, “No, thank you,” when she really meant YES. THAT girl. Not anymore. Watch this: It’s time to show up and be seen. It’s time to give of yourself and be noticed. It’s...
Video #32 – What’s Really Keeping You From What You Want?
I have a lot of excuses for why I don’t have what I want. Some of them are pretty convincing. Maybe you can relate? Well, here’s the #1 thing that’s holding me back from really getting what I want. Watch this: Why am I so afraid of change? It’s what I yearn for and...
Video #31 – The Dark Side of Your Superpowers
I’m obsessed with superpowers. These are the things you do so easily and naturally that you probably don’t even think of them as superpowers at all. They’re just too easy. But your family and friends say, “How do you DO that?” I love superpowers because they can be...
Video #30 – The #1 Way to Have a Unique Business No One Can Ever Copy
So many entrepreneurs are struggling to "get the word out" about their businesses and differentiate themselves from the competition. There's an easy answer to this problem. Watch this: It's not "easy" in the sense that it's without challenges. In fact, it's often the...
Video #29 – The #1 Gift You’re Missing Out On
Right now I’m struggling with something. I’m not quite sure what to make of it. Watch this: What I know about what’s possible is just the tiniest sliver of what’s available to us. How can I create a goal without clinging so tightly that I miss something even better...
Video #28 – Is Hiring a Coach Worth the Money?
Lots of “successful” people say you need to have a coach if you want to play bigger and make a real impact on the world. (I put “successful” in quotes to indicate the dubious definition and often careless use of the term.) So you’re “supposed” to hire a business coach...
Video #26 – How to Help Someone You Love When There’s Nothing You Can Do
Have you ever seen someone you love in pain? It’s awful, especially when there’s nothing you can do to help. But maybe there is… Watch this: I believe that when we help ourselves, when we give ourselves exactly what we need, when we are happy, it helps everyone. Does...
Video #25 – What I Learned About Life From a Wicked Splinter
God, I hate splinters! I had one stuck under my nail the other day that was impossible to remove. Then it woke me up one night with a powerful message. Watch this: Those irritations, the pain, the aggravations in life are necessary. We need them to call our attention...
Video #24 – How Death Taught Me About Inspiration
Man, this video was hard to make. Watch this: I recently lost my cats, Java and Loki. They had a long, happy life, but it still wasn't easy to let them go. The weeks surrounding their deaths (they died within 2 days of each other) weren't easy. It was a roller coaster...
Video #23 – 4 Simple Steps For a Profitable Business
I’ve been talking to entrepreneurs starting a new business lately, and all of them are making the same fatal mistake. Avoid this mistake and your business is 80% more likely to succeed. Make it at your own peril. Watch this: There’s one thing that’s absolutely...
Video #22 – The Inspiring Power of Saying NO
Saying no hasn't come easy for me. Watch this: I've gotten really good at stepping into the roles life has presented for me without considering what I actually wanted. So I've set myself a 60 Day Inspiration Experiment, during which I'll say NO to any new opportunity...
Video #21 – How to Piss People Off and Make Money Doing It
I love an audacious, outrageous, irreverent marketing campaign. Watch this: Cards Against Humanity's latest Black Friday stunt offers proof that what we're selling is NOT our stuff, or even the benefits of our stuff. It's a feeling, an experience, a worldview. You can...
Video #20 – Why You Have Facebook Jealousy
Ever have a case of Facebook jealousy? There she is in your Facebook feed, looking all happy about something, bragging about her life, the money, the whatever and...ERGH! The green eyed monster rears its head. Watch this video: I took a deeper look to discover what’s...
Video #19 – 3 Tricks to Defeat the Perfection Monster
Are you a perfectionist? Consider how many things you haven’t done because you were afraid you wouldn’t be “good enough.” I didn’t play sports in school, even though I’m a born athlete. I didn’t apply for college and ended up defaulting into a community college. I...
Video #17 – What Gift Are You Most Grateful For?
I am overflowing with gratitude for THIS moment. I can make a choice to do what I love in every moment. Just like this one, sitting down to make this video for you. Watch this: I’m intrigued with this question: What if what you want also wants you? It’s the like...
Video #18 – Why You Can’t Hide From Yourself
I spent time with a dear friend the other day and asked how things were going with his daughter. He stiffened. “Well, she’s getting to be that age, you know.” I didn’t know, so I asked. His answers were chopped, strained. “Ah,” I thought to myself. “He’s not...
Video #16 – Why I Hope This Offends You
Why are we so afraid to be offended? Watch this mini rant: Recently a member of our Facebook group dropped the f-bomb several times in a post. Another of our members was offended. Unhappy emails ensued. It's actually good to be offended because it’s a challenge. It...
Video #15 – How to Use This “Dirty Word” to Get What You Want
Did you know there are tools to make getting what you want INEVITABLE? Yep, it’s true. Learn the Power of This Dirty Word Here: Don’t be afraid to use this word. You’ll be recruiting a powerful psychological principle of influence as an ally who makes sure you do what...
Video #14 – 40 Days to Transformation, Habits & Body Oil
In the Bible, it rained for 40 days and nights during the Flood. Venus forms a pentagram in the night sky every eight years, returning to its original point every 40 years with a 40-day regression. Some traditions believe the ghosts of loved ones linger for 40 days...
Video #13 – What’s In It For You?” 100 Conversations Manifesto
The unexpected almost always arises in my 100 Conversations experience. That’s what makes it so much FUN. Watch My 100 Conversations Manifesto: Usually, I’m the one asking, “What are your takeaways?” at the end of a conversation. One brilliant budding entrepreneur...
Video #12 – Confessions of a Transformational Junkie, Coming Out & the Demonic Imp Returns
This is my official “coming out” of the Awakened Business, and my multiple confessions of insecurity, transformation addiction and giving dependence. If that doesn’t float your boat, whet your whistle or otherwise arouse your curiosities, then… Don’t Watch This Video:...
Video #11 – Hallucinations & the Demonic Imp Within
What is the message you most need to hear right now? Watch this to find out: For me, it’s usually the message I’m avoiding. Lately, I’ve been seeing a demonic imp, a horrific infant pulling itself across the ground, mouth full of sharp teeth, reaching for me. It’s a...
Video #10 – I Am a Powerful Mofo and So Are You
I’m tired of pretending that I’m weak and helpless. Aren’t you? Isn’t it time we owned the power of our true identities? WARNING: This video contains obscene language. Consider this your “trigger warning.” Watch the Mofo in Action: Rich Litvin helped me learn about...
Video #9 – The Lies Marketers Tell
Betrayal is an awful experience. Especially when it happens to someone you love. Watch the whole story here: I am a marketer. Sometimes I hesitate to call myself that because I know how maligned marketers are by many people. Do I really want to lump myself in with...
Video #8 – Quit Hiding Your Best Stuff!
I'm guilty, too. Watch my confession here: For years I've been working as a business coach and internet marketer. I'm damn good at breaking things down into actionable steps, hatching results-oriented strategies and wordsmithing a killer headline. I'm the Queen of the...
Video #7 – Don’t Wait For the Answer: Live the Question
When it comes to the Meaning of Life and Other Mysteries, I don't have a clue. (Okay, I have a clue and I'm following some others, but I certainly don't have the Answer with a capital A.) Watch me live the questions here: For some reason, I'm not supposed to admit...
Video #6 – Ask the Most Powerful Question to Get a Powerful Answer
I love asking powerful questions! Even the ones that can never be answered. (I call them "imponderables.") Powerful questions = powerful answers. Watch me get on my soapbox about the power of questions: With the right question, you can control someone's mind. Think...
Video #5 – The Irresistible Power of Owning Your Awesome
Inspiration is contagious. Watch this and catch the inspiration here: I "caught" the idea for my 100 Conversations Challenge from Kyle Cease. He challenged himself to meditate for two hours every morning for 100 days in his Self-Connection Experiment, and every day he...
Video #4 – What If There Is Nothing Wrong With You?
When I was in high school, I went through a phase of memorizing things that moved me: Edgar Allen Poe, C.S. Lewis, Shakespeare. Yes, I was a geek with a dark side. Still am. 🙂 This quote from Rumi was one of my favorites. This was before I knew who he was or anything...
Video #3 – Insecurity: Am I Making A Difference?
Some days I know that what I'm doing matters. On these days, I can clearly see the impact of my actions and life is good. Other days, I doubt myself. I wonder, "Am I really helping these people? Am I making a difference?" Watch this for more: Then I remember a deeper...
Video #2 – What Life Do You REALLY Want?
Why do you do what you do? Really? Most of the time we're really not being honest with ourselves. I want to make a difference in the world. That's my top priority. It's not making money or having freedom. It's not spending time with my loved ones. It still...
Video #1- Quit Hiding and Just Do It!
I'm noticing that sometimes entrepreneurs who have the most to offer (myself included) are holding back. We love learning, reading and studying to become world-class experts. And that's a super power. But... https://www.youtube.com/watch?v=q1AVQwEubIs Sometimes it's...