Don’t Let Doubt Lead You Down the Road of Regret

A WRITER CALLED ME LAST WEEK EXCITED about her book and about the Your Captivating Book Mentorship Program, but she had doubts. Was she ready, she wondered. And there was the money factor. And time.

Yet her book idea had been cooking for a few years, she yearned to learn how to make a book that would endure in her readers’ hearts, and her own heart beat wild with enthusiasm.
“Not ready?” I asked.“Well, my mother said, ‘The program is expensive. Be sure it’s worth it.’” And she has four kids.I said, “Oh, your external mother is just trying to look out for you. Just like the internal one.”
And she got it. “Right! I guess it’s really my internal mother that’s raising doubts.” She knew she was doubting if she, not the program, was worth the time and expense.


I’ve been there. In 2000, two months married, I doubted if I deserved to leave a well-paying job and secure position to figure out how to make it on my own as a writer, consultant, and teacher.

“Do I finally take the risk that has been burning inside me for five years or longer, or do I ‘stay home’ and play it safe and wait and wait and wait? Isn’t it selfish to take this risk?” I leapt and never looked back with regret. Since making that leap, this work has benefited literally thousands of people whom I never would have served had I “stayed home and played it safe.”

And I don’t want Doubt to lead you down the Road of Regret.

May 1st – Oct. 30th, 2013

View Schedule Here.

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The Crossroads Nature of Doubt

In Sanskrit, the word for doubt is samshaya. It translates loosely to weighing two paths as equal and being uncertain which one take.Do I leap into an uncertain venture – starting my own business or committing time and energy to my book – or do I do the “safe thing,” listen to my inner parents, and go on with life as usual?Do I fulfill my deepest responsibility to my best self or do I continue fulfilling other people’s obligations?This doubt has wracked the best of us. You know that pursuing a project that matters changes the way you feel each day, the way you allocate your mind and time and energy to something that has meaning and that exhilarates you. It launches and lifts you in flow.Your days have purpose, a more-than-you yearning.And yet Doubt raises its myriad voices.

Not Taking the Road of Regret

When you stand at the Crossroads of Doubt, here are four tools to discern which path to take – the safe road or the “road less traveled”:

1. Look ahead a year from now.
Feel, write, and sketch your way into these questions:

  • How do you want to feel differently about yourself as a creative or writer a year from now?
  • What do you need and want to have learned as a captivating creative?
  • Whom do you want your creative work to engage and enchant a year from now?
  • How would having your book or eBook primed for release into the world change your life?
  • How will you feel in March 2014 if you stay where you are right now and take the safe road?
2. Weigh Your Obligations Against Your Ultimate Responsibility.
When your Inner Mother or someone else who claims to have your best interest at heart says, “You’re not being responsible,” consider this:
If you are meant to write this book, you know it.
And if you know it, you also know that developing, shaping, and releasing it to your future fans is your ultimately responsibility. It’s what you are here for.That’s different from fulfilling your daily safety obligations to others.
When will you say, “Writing this book is my best self’s ultimate responsibility, and I live my days accordingly.”?

3. Weigh your Best Self investments.
Weigh what it will cost you one year from now if you still haven’t written the book or if it’s less than what you’re truly capable of, and if the people who need your book never get it.

That cost could take a toll.


That’s the cost of the least expensive iMac, which is a machine, not a mentor or a pack. That’s what you would pay for about 3 hours of 1:1 with me.For that investment, you gain guidance from someone who serves as a mentor at Western Connecticut State University’s MFA in Professional and Creative Writing Program, who’s taught at other universities, The Kripalu Centre, and at national writer’s conferences among other places. In other words, someone who knows how to craft and deliver a structured learning experience for a select number of authors.You gain guidance from someone who has helped shape proposals, books, and careers that have landed first-time authors 6-figure deals, spots on Oprah, positions on New York Times best-seller lists, and a path of reward not regret.You gain guidance from someone who has published with Penguin and independent presses, and who has designed and published his own series of e-Handbooks and e-Guides. Someone who keeps abreast of the precarious publishing world and your publishing options.Someone who thrives on helping creatives play three seminal roles – Idea Distiller – Experience Architect – Creative Collaborator.http://www.youtube.com/watch?v=44q6DmNOY5k
Consider how gaining the support and guidance your best self deserves this year will get you rolling on a creative career, sharpen your game within your existing field, pay dividends, and serve the people who hunger for your book and services.4. Forget Perfection & the Lone(ly) Wolf Syndrome.
The voice of Doubt says, “But you don’t know what you’re doing!”That’s why you reach out for dedicated help from a trusted mentor and the support and perspective of a dedicated peer pack. We need each other. Not a single thriving author has ever written an Acknowledgements Page that says, “I acknowledge myself for having done everything on my own, thank you very much.” The Hemingways and Fitzgeralds and the Kingsolvers and Gilberts each had or have their mentors and their peer packs.

In the Bhagavad-Gita, a reluctant warrior named Arjuna at first refuses the call for him to be in the world and to rise as a warrior of truth.

“I want to go home. I’m not fit for this. I’ll fail!”

His chariot driver, none other than Krishna, offers this sage advice, the same advice I repeated to myself back in 2000 and that I repeat almost every day:

It is better to perform your own duty imperfectly
than someone else’s perfectly.

Stepping out of the amateur bubble and into your author-artist potential means taking risks. But there’s no reason you should take those risks alone. I would be honored to journey with you. Your peer pack awaits.And that writer who called me with excitement and doubt? She conferred with her best self, her Inner Mother, her finances, and her partner, and she found the resources, confidence, and affirmation.I don’t pressure people. But I do goad them to listen to what matters. The facts: Only a few spots remain for this year’s program.

May 1st – Oct. 30th, 2013

View Schedule Here.

Sign up to receive wait-list notification.


And you very possibly have a wisdom-duty to pursue.

The 6 Mastermind Authors participate in a Virtual Full-Day Author’s Platform Retreat and each receive a 1:1 VIP Daywith me in the Hudson Valley at the Mohonk Mountain House.Still not sure?  Email info@trackingwonder.com or call 845.679.9441, and let’s have a 20-minute, no-obligation pro bono call. We’ll talk out your options. I’ll listen neutrally to your questions. And you’ll hear what makes sense for your best self at this moment.As always, thanks for running with me,Jeffrey
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