
“I miss you!” I texted my dear friend and old San Francisco roommate Gino this morning.
“I have a confession for you,” he said. “Whenever I get a text from you out of the blue like this, it makes my day. It makes me realize how lucky I am to have you in my life.”
My heart smiled.
Our conversation reminded me of a Simon Sinek talk I watched this morning about generosity, confidence, and fulfillment.
In the talk, Simon explains how we’ll never forget the people who teach us confidence. We’ll carry their names around with us forever. Gino was one of those people.
Since arriving in San Francisco to visit a week ago, I’ve walked around with a deep feeling of nostalgia, gratitude, and warmth. Everywhere I walk, I’m reminded of all the incredible people who touched my life, believed in me, and taught me how to come into my own while I lived here in 2009 and 2010. San Francisco—and the people here—transformed me. They taught me confidence in my ideas, beliefs, and dreams.
As I wander the city, catching up with old friends and stopping by my old favorite places, just to breathe in the profound impact the place had on my life, I’m able to feel how connected everything really is. I’m able to see how the many small conversations, realizations, and acts of kindness in 2009 have manifested into big life choices, cross-country moves, and business decisions up until today. My journey toward deep fulfillment began actualizing here, in San Francisco. It began here because of the incredible people and their profound ability to teach me how to live and realize my truth, and be confident in my pursuit.
Back when I was here in 2009, I was unclear on what fulfilled me and how I wanted to spend my time. This lack of clarity took me to New York, Barcelona, and Boulder. Each place—and the people there—helped me gain clarity on the world I imagine.
Paul Graham said in his essay about cities that unless you’re sure what you want to do and where the leading city for it is, your best bet is to live in several places when you’re young. You can never tell what message a city sends until you live there. You won’t know whether its message will resonate with you until you hear it. And you’ll probably have to find the city where you feel at home to know what sort of ambition you have.
The benefit of moving around, of trying new cities, of meeting new groups of people, is that you expose yourself to seeing, feeling, and experiencing the answers. We cannot think our way to understanding the work we’re meant to do—we must experience it. We cannot analyze ourselves to the point of clarity—we must reflect and share with people who care. We cannot talk our way into feeling confident—we must learn through trial and error.
Through the discovery and realization process, a little time and a little energy goes a long way. Whether you’re texting someone you miss them, talking a challenge out with a friend, committing to 750words.com each day, or helping a stranger collect his loose papers on the street, our little actions lead to bigger impact, collectively and over time. When you touch the heart of one, they touch the heart of another. When you help someone gain clarity on a challenge, they gain insights they’ll use moving forward. It’s all connected. We’re all connected. And we’ll never forget the people and places that help us connect our dots forward.
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Thanks to Gino (and San Francisco) for inspiring this post and Vivek for reading the draft. Thanks to Julian for the image.

The best part about Spring is watching nature come alive again. The flowers awaken in colorful blossoms, the trees sprout leaves and breathe, the grass radiates a scent of so-fresh-and-so-clean. People come alive too. Bikes populate the streets, people stroll the streets smiling, and friends convene in parks to tell stories, play music, and spread love. It’s a beautiful time.
But just a few weeks before this period of glowing life, landscapes are flowerless and trees are leafless. The grass is brown and the wind is chilly. People, too, are reclusive from the bleak outdoors.
Like nature, life is a series of natural changes. The ups and downs, the highs and lows, they’re part of the natural rhythm of life. This is what we all have in common. Without winter, there is no spring. Without rock bottom, there is no ultimate high. Without negative, there is no positive. These ebbs and flows are the key to ever-flowing progress.
Just as the austerity of winter cannot force the life of spring, we cannot force our own evolution. Low points are healthy and natural stepping stones toward our greatest potential. Loss is inevitable in the process of realizing what’s worth having. Pain is a natural part of experiencing deep love.
When you find yourself in a moment of questioning, of anxiety, of wanting to control, remember that this too shall pass. Accept, surrender, and be a witness to what is. The low is needed in order for the high to naturally emerge. Soon enough, the winds will blow their own freshness into you. Your season will change too.
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Thanks to Bear and Vivek for inspiring this post and reading the draft. Thanks to Julian for the image.

“But I’m afraid of rejection,” my client said to me the other day in response to taking action toward a really huge milestone in her career.
“Who are you afraid of being rejected by?” I asked.
“My peers, colleagues, and those I admire who are working on this project,” she said.
“What about yourself?” I asked. “What happens if you reject yourself by not taking action?”
“Good point,” she said.
It’s interesting how we sometimes put the idea of “rejection” into the hands of others, personalizing what other people think.
If I don’t get the job, I’m not good enough.
If this venture capitalist doesn’t invest, the idea sucks.
If he doesn’t love me, something is wrong with me.
Wrong. If you don’t get the job, it’s the wrong mutual fit. If the venture capitalist doesn’t invest, there’s more out there who will love what you’re doing. And if you love you, nothing is wrong with you.
At the end of the day, the only thing we can do is live our truth, speak that truth, and be that truth. When we live from a place of deep honesty, first with ourselves, we can never be rejected. Those who cease to align and accept the truth of who we are aren’t meant to be in our lives anyway.
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Thanks to Julia, Theresa, and Vivek for reading the draft.

Earlier tonight, I was talking with my friend Julia about being in a place of ambiguity. We both expressed how we’re currently experiencing a lot of unknowns. And as two women who love making things happen, sometimes this lack of clarity can be unsettling. That’s when Julia reminded me that in times of discomfort, it’s okay not to always know the answers immediately. It’s healthy to stew in the ambiguity, knowing that action is around the corner, ready to naturally emerge.
The beauty of unknowns is that in them, there always lies a question and an opportunity for growth, which through trust and action creates answers.
In selling all my belongings and taking a leap of faith from San Francisco to New York City two years ago, I had no idea what would happen. I had a chunk of cash, a deep desire to realize my full potential, and an interest in start-ups. I asked myself “How can I live for the question of my most actualized self and let New York show me the answers?” It was through insatiable curiosity and a wild ride that I experienced and realized my gifts.
In deciding to move to Boulder last November, I was uncertain what the mountains would bring me but I knew from a deep and intuitive place that they were calling me. I asked myself, “How can I become the most grounded, self-loving, and healthy version of myself so that I can enable others to fearlessly give their gifts?” It’s been a beautiful journey that’s taken me to new heights.
In launching The Bold Academy in February, I had no idea what would happen. No clue at all. My question was “Is the world ready to unlock their full potential through a 4-week personal accelerator program?” In taking quick action and realizing market interest, I gained answers. This time I have a team of nine people who are invested in our vision.
Every single one of these experiences has brought an array of emotions, a shit ton of ambiguity, moments of panic, reasons to celebrate, and the opportunity to discover answers about myself and the world. I’ve realized that the BOLDER my actions are, the BOLDER my emotions are. It’s all connected. The key lies in accepting the unknowns as natural in the process of finding clarity. Trust that in having questions and taking action, answers will always follow.
What are the questions that you’re living for? How can you take action today?
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Thanks to Julia for inspiring this post and Vivek and Bear for reading the draft.

Over the past few weeks, I’ve felt like I’ve been “trying” to write. Every Monday and Wednesday I find myself asking, “What should I write about tomorrow?” I’m forcing and reaching for content instead of letting it flow and emerge through me. This is not ideal.
Then Tuesday night, I stopped thinking about what to write, let go of the fact that I didn’t post “on time,” and instead became present in the moment. Soon enough, Ryan texted me “no troubles, just adventures” and a story poured out of me. This is very ideal.
That’s when it hit me: Stop trying so hard. Trying is unnatural. It’s forced. The effort emerges from a less authentic place. Instead, pay attention to all the sights, sounds, people, and experiences happening to and around you. Be present. Be you. Inspiration will strike when you stop trying.
Over the weekend I had a friend in town and we were writing songs together. At first we were trying to come up with “hooks” that would make for a good song. It worked fairly well and we created several different song concepts. But then something magical happened. As we were in a state of wonder, enjoying the flow of life, playing guitar as we meandered around the local market, one man yelled out “E flat!” and another said “You’ve got your finger on the pulse.” We both looked at each other and knew that was our key and that was our hook. Not long after, a new song was nearly complete. We stopped trying to write and let creation emerge naturally.
If you find yourself trying really hard to make something happen, stop. Nothing that emerges from a place of forced effort will ever fully represent your depth, truth, and full creative potential. Start being present and let your flow of life create magic.
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Thanks to Bear for inspiring this post and Vivek for reading the draft.

It’s almost midnight on Tuesday and Ryan, a member of The Bold Academy team, just landed in Denver. It turns out the AB bus I recommended he take to Boulder isn’t running this late, we don’t have anyone to pick him up, and a cab to my place would cost more than $80. Theses scenarios are less than ideal. But not for Ryan.
“I’m sorry for the trouble!” I text him.
“No troubles just adventures,” he replies, reminding me exactly why he’s a perfect fit for our team. Minutes later, he texts to let me know that he found some dude to give him a ride.
This has me thinking about perspective, the lens by which we view all of our experiences, and how this impacts the course of our life.
Every day, we’re presented with unexpected circumstances and situations beyond our control. We’re given a choice as to how we respond and these responses determine our future. What might be a major inconvenience to one person might be an adventure to another. It’s all a matter of perspective. It’s all a matter of choice.
Had Ryan let the unexpectedness throw him off, he wouldn’t have worked his way into a free ride. He would have been too wrapped up in what was going “wrong” to see what could possibly go right. He would have looked at the situation as troublesome, instead of as an opportunity for adventure.
In life, most troubles are adventure in disguise. And sometimes changing the course of your life is only a matter of changing your perspective.
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Thanks to Ryan for inspiring this post and Nathaniel for reading the draft.

Fred Wilson wrote a post a few weeks ago about how the internet is making it easier for us to find our voice and use it to make a difference.
Everyone has something to say, something to contribute, everyone can make a difference. And I believe the Internet is making it easier for all of us to find that voice, use it, and make that difference.
I couldn’t agree more. When I started writing and sharing online four or so years ago, I never expected (or even thought about) creating a following or starting businesses through the Internet. I wanted to express and understand all of my ideas, thoughts, and feelings. I wanted clarity and purpose.
So many people approach me and ask about how I created a following. They ask about my “content strategies,” “audience building tactics” and how I “optimize through SEO.” The truth is, these concepts make my head hurt. The only strategy I’ve used is being myself and sharing the ups and downs of my journey. I write to understand and share what moves me, hoping that it might make one person smile or think differently or take action on what matters.
The process of putting yourself out there is an incredible learning experience. Sometimes I overuse ‘fuck’ and make my Grandma cringe. Sometimes people hate on what I write. Sometimes it takes me seven minutes to write a post and other times I over-think like hell and it takes me three hours. But more and more I’m learning that by being simply who I am, and expressing from a place of truth, I attract incredible people and opportunities into my life.
The act of writing consistently from a place of heart has turned my desire to “find my voice” into me finding myself, my purpose, and how I want to impact this world. It’s helped me figure out how to positively impact others which is what matters most.
If you’re trying to find your way, I encourage you to start writing. Right now. It’s the first and most important thing you can do. As Fred says, “You have to walk the walk and talk the talk. Blogging/commenting/social media is the talk part.” And most importantly, be you in the process.
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Thanks to Fred for inspiring this post and Vivek for reading the draft and creating the image.

I want you to pause right now. Let’s take a step back.
Forget everything you need to do today and this week. Ignore the IMs and Facebook notifications popping up on your screen.
Take a deep breath and be still in this moment.
When we take a moment to disconnect from our daily reality… our to-do list, routine, hopes, dreams, worries, desires… what is the bigger picture?
When we press pause on our hyper-connected and always-on world, the world in which the amount of information available to consume is drastically increasing, where the inputs we receive on a daily basis are multiplying… what’s most important to us?
When we take a day to simply be, to enjoy, to feel the warmth of the sun rays against our skin, the soft breeze through our hair, the weight of our foot against the sidewalk, against our world… what matters most?
You already know what matters. It exists within you. It manifests in simple ways and often is staring you in the face, waiting for you to listen. It gives you chills when you hear it, a tingling when you feel it, and a warmth when you know it.
What matters is the bigger picture. It’s being aware of the path you’re on and where it’s taking you. It’s seeing how the little actions you make each day have a profound impact on your week, your month, and your years to come.
It’s realizing that the relationship you have with yourself is fundamental to the future you’re creating. That self-love is the key to giving, and that giving is what leads to your deepest fulfillment.
It’s knowing that now, more than ever, we have the capacity and ability to define our bigger picture, bring it into existence, and shape our world accordingly.
Your bigger picture is within you. It’s your turn to listen.
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Thanks to Bear and this video for inspiring the post, and Phil for reading the draft and helping with edits.
I love this idea! Take a step back this Sunday… what do you believe?
bustr:
I feel like stepping back a little from all of the responding and spending a little time thinking about what I believe these days. From religion to politics to technology to predictions about the future… there’s got to be something there below all of the opinions, reactions, and instincts, right?
My exercise for the day: make a list of things (big, small, obvious and crazy) that I believe in, as of today. I reserve the right to change my beliefs whenever I want.
You should do it too! Let me know if you do.