Risky Business
By Scott Kalechstein



“Life is a daring adventure or nothing.”             
 — Helen Keller

Negotiating a full and rich life is risky business. It involves a commitment to living on the edge and often walking towards, not away from, what I fear. My joy is not served when I repeatedly retreat from risk taking to drift stagnant in my comfort zone. Moreover, when I am engaged in such a lack of engagement, I often find external causes (excuses) for my discontent. They usually involve pinning the blame on those closest to me.

A few months after moving five hundred miles to Marin, my beautiful connection with Venus was beginning to feel suffocating. The juiciness between us had dried up, and so had my sense of self-responsibility. “If only she wouldn’t be so into the relationship, I would breathe easier,” I secretly and not so secretly fantasized. Oh how seductive, to take the focus off myself and project my shadow onto my wonderful partner!

This train of thinking was derailing my ability to see her for who she was and enjoy the gift of her presence. To get back on track, I inquired of my inner conductor, “Could the source of these feelings have nothing to do with Venus? Have I been cutting off my own air supply by hanging out in my comfort zone and avoiding the oxygen of being fully alive?”

I made a list of what I might be doing if I weren’t afraid — risks I would be taking, adventures I would be having — and realized I was using the security of a relationship to hide from my insecurity, the fears coming up around making new friends, and exploring a vast new playground of possibilities. I was feeling strangled, not because Venus had her hands around my neck, but because I wasn’t sticking my neck out! I needed to break free, not from the relationship, but from my paralysis. As soon as I started taking action to create a juicy life in Northern California, the juice returned to my connection with Venus.

I do have a hate/love relationship with risks. I hate anticipating them, but I love the expanded aliveness and self-esteem that comes from taking them.

My first major experience of both resisting a risk and really going for it was in high school. On my very first day as a freshman I woke up to a mountainous range of pimples . . . my first acne breakout! On that dreary day and for two subsequent years I dragged myself to school, kept my head low, and shied away from almost all forms of social contact. Ashamed of my appearance, I took no risks and reached out to no one, especially anyone of the opposite sex. My main extracurricular activity was popping zits.

In my junior year the pain of hiding became too great to bear, and something inside of me snapped. I moved myself, mountain range and all, out into some self-_expression. I joined some clubs, ran for student office, and auditioned for a school play.

I landed the lead role in a comedy about an awkward adolescent with a bad case of acne. When I had a good look at the script I seriously pondered backing out. One of my lines was, “Damn these zits! I’ll never get a girl interested in me!” The only thing more terrifying than thinking about doing the play was the idea of not doing it. I imagined everyone in school knowing exactly why I quit. I had to follow through.

My performance was a big hit! At times I felt myself lightening up about my pimply predicament and laughing right along with the audience. When it was over it felt like I had fewer secrets, and suddenly was a visible and popular person in the school. I was invited to parties, given compliments, and approached by people, even female people!

Within three weeks I noticed something major and miraculous in the mirror. My pimples had almost all disappeared. I had a new complexion! At the time I attributed it to the new acne cream on the market, but in hindsight I think it had more to do with my willingness to leave my comfort zone, expose myself, and bring lightness and levity to my hidden pain and shame. Breaking out of my shell and facing my fears was just the medicine my face needed to stop breaking out.

It has been my experience that the more I escape from internal prisons, the clearer and smoother my external world becomes. I love testing this out and collecting evidence that life supports those who say yes to life instead of putting off their dreams or their sense of aliveness for some other moment besides NOW!

I don’t mean to imply that when we leap a net suddenly appears in the form of a six-figure income. There is a popular self-help book titled “Do What You Love, The Money Will Follow.” Yes, it follows, but not always right behind us. In my case it took seven years from when I first started going for my dreams until I was able to quit compromising for a living. During that time I constantly doubted my decision to deviate from the road I’d been on. “Why have I risked everything? This is so hard! What was I thinking?”

My mind, exclusively schooled in the language of logic, was screaming “ILLOGICAL!” But it pays to learn a second language, and the day I quit college was the start of my education in listening to, and acting upon, the voice of my intuitive teacher.

I had two years of being an undecided undergraduate under my belt and it was time to declare a major. Instead, I declared I was dropping out. Out of the blue I told family and friends I was leaving the road-much-traveled to follow my inspiration and train as a healer and workshop leader. My parents thought I was lost, and dangerously messing with my future.

The road I was taking was completely off the map. And with no role models, I was going to have to pave it as I traveled. I was as frightened as my family. I didn’t know if I had leaped into a new life or off the deep end. After all, insanity and spiritual growth can both involve listening to voices!

I worked odd jobs, wrote and performed music, and studied matters that deeply mattered to me. I took lots of personal growth seminars, trainings, and voice lessons. I focused on my own healing process, my spiritual and emotional education, as well as developing my musical and improvisational abilities. During that time I gradually, very gradually, developed an audience and clientele for my gifts. Seven years of baby stepping towards my dream led up to a grand and terrifying precipice. I quit the day job and leaped.

For fifteen years now I have been a full-time speaker/singer/workshop leader. My bills have been paid, I’ve never starved, and I’ve always had leftovers in the bank. But those first years of taking the road-not-traveled were bumpy indeed. During that time I could have written a book that said, “Do What You Love, The Chaos Will Follow!”

And doing what I love, I have found, offers no immunity from chaos. It still follows, and occasionally overtakes me, especially when I value accomplishing external things over maintaining internal peace and balance.

Like yesterday. I woke up in the morning and prepared to meditate. But the bathroom could not wait, and while I was sitting I casually checked my voice mail. There was a message I thought would be best to return promptly. While on the phone I started checking my e-mails. A few, I thought, would do no harm to quickly respond to. Then hunger grumbled good morning. While preparing breakfast I turned the phone ringer on and almost instantly it rang. Before I knew it, I was fully immersed in anxious activity. Multi-tasking, I lost sight of my single most important morning task and responsibility: to take quiet time and set a peaceful tone for the day.

We all have days that get away from us. For some people it’s even years. Or decades. How much time can whiz by before we wake up one day, take inventory on what we have been doing, and check to see if it matches our core values and truest sense of purpose. Such soul searching pushes us to the edge where our fears and passions converge, where a comfortable choice is usually not the wisest.
After all, how many of us will look back from our deathbeds and wish we had risked less and pursued fewer dreams?

 It’s been a dream of mine to vacation on the magical island of Bora Bora with someone I adore. In a few months I’m taking Venus there. I did not make this decision with the rational mind, which can only look at my finances and ask things like: “Is this practical?” “Should you be spending this kind of money right now?” And “Why not wait till you have your life more together?”


I’m willing to have a day get away from me once in a while, but I’m not willing to look back on my life and realize that most of it got away from me. I’m not willing to hide and save face because I’m afraid the world will judge my blemishes. Life is a risky business. There’s too much at stake to play it safe.

“If I had my life to live over, I’d dare to make more mistakes next time. I would take fewer things seriously. I would take more chances. I would climb more mountains and swim more rivers. I would perhaps have more actual troubles, but I’d have fewer imaginary ones. You see, I’m one of those people who lived sensibly and sanely, hour after hour, day after day. Oh, I’ve had my moments, and if could do it over again, I’d have more of them. In fact, I’d try to have nothing else... Just moments, one after another, instead of living so many years ahead of each day. If I had my life to live over, I would go to more dances. I would ride more merry-go-rounds. I would pick more daisies.”
—Nadine Stair
(age 85 at the time she wrote it)

Scott Kalechstein is a modern-day troubadour living in Marin County and traveling the world as a speaker, singer and leader of workshops. His music has been called ‘the soundtrack of awakening’ and can be sampled at

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