How to Reconnect With Your Why?

Last week there was a thing I had to do—a big and exciting thing but also the kind of thing that I’ve put off and put off because it’s so big and exciting.

Does that ever happen to you? That you can’t just get going because where would I even begin? And what if it’s not good enough? And what if it’s really hard? And well I guess I’ll just do this other easier thing instead…

As a coach, I’ve seen so many clients in this situation. And I know that there’s a trick to cut through the worries and procrastination: reconnecting with your “why.”

Your “why” is your FUEL. It’s what drives you on a deep level. It’s the key to you feeling tapped in and engaged with your work. When you’re feeling lost or adrift, you can reconnect with your why to ground yourself, harness your motivation, and cultivate a personal connection to the task in front of you.

The big scary thing

My particular big and exciting task was completing my book proposal.

Yes! I’m writing a book! It’s called The Road Trip Career Path: A Practical Guide to Crafting Purposeful, Resilient, and Adventurous Work That’s Uniquely Yours!

It’s a nonfiction career book that offers a new framework for approaching your career like the road trip of a lifetime rather than an arduous, linear climb to the elusive summit of a mountain. It’s a practical guidebook to help you boldly navigate the modern terrain of an iterative and dynamic career in a rapidly-changing job economy. The Road Trip Career Path helps you confidently get in the driver’s seat to intentionally forge a custom path that is fulfilling, adaptable to change, and most of all, enjoyable.

And it’s super exciting! But also super scary! Because it means a lot of scary things like instead of talking about writing a book, actually doing it and finding an agent and a publisher and talking it up very publicly.

Last week, my task was to write the first sample chapter to include in the book proposal.

So to get going, I asked myself the same coaching question I would ask a client in this situation: What makes this project important to you?

I sat down at my laptop and tapped out my response. Here is the real, raw response that I wrote in my journal:

Today I will write a sample chapter of my book. Because I am a writer. Because I believe in the practice of writing. Because it does something for me, something deep and healing and fundamental to the expression of who I am.

I have been a writer all of my life. From the story I wrote in first grade about planting a Cheerio in my backyard and watching it grow into my substitute teacher, Mrs. Doody. (I printed it out on that old school printer paper with perforated holes on the sides.) To the song lyrics I wrote in late grade school. To poetry slam and the Vermont state writing contest in high school. To my blog in the late aughts. To the personal essays about my mother’s last days. To the newsletters of Penney Leadership. To this journal, pages and pages of my heart translated into letters. Writing is a golden thread of my life.

I am writing a book because I am a writer. Because it is something I feel destined for, that I can’t help but do if I am being me in this world. I am writing a book because I want to help people and give them a way of seeing themselves and their lives more clearly, through a lens of more possibility and agency.

I am writing a book to codify things that I know to be true. To capture my body of work and the wisdom that I have gleaned the hard way. To spin that all together and reflect it back to others in a way that will help them learn about themselves, too.

I am writing a book because I have learned so much about myself from reading others’ words. I am writing a book like Parker Palmer—where I offer perspective and stories and gently ask how it might resonate with you. I am writing a book like Tara Mohr—where I gently give words to a thing you’ve been experiencing but haven’t seen clearly expressed, along with practical guidance for approaching it differently. I am writing a book like Michael Bungay Stanier—where I just keep the good stuff, potent and powerful. No fluff. No confusion. Clear as a bell.

I am writing a book to see if I can do it. To prove to myself that I am who I believe myself to be. That I am becoming the truest version of myself, the ultimate expression of Carole-Ann.

I am writing a sample chapter of my book this week. Because I will have it done in time for my book coach to review it when we meet on Thursday. Because I have open time in my schedule that is perfect for this very thing. Because I have arranged to meet Courtney at the Athenaeum and write surrounded by 19th century books and busts of historical figures. Because I can’t believe that this is my job and I GET TO DO THIS and I created this for myself. Because I have an audience of people ready to read this thing if I just stop preparing and talking and thinking and get freaking moving. It is time to be the book, to be these lessons and key ideas.

I know what will get in my way: worrying about getting it right. Feeling daunted by all the things I could include and choosing the right ones. Worrying about making a mess of it and not being able to make something out of what comes out. Of it being jumbled and confusing and not as good as I’ve let it on to be. Feeling overwhelmed by the bigness of it—70,000 words, yikes! Worrying what if no agent or publisher bites. Worrying even more if they do.

But the thing is, none of that actually matters. Because I am doing this no matter what. I am writing this book and that is that. There is no way for me to continue being myself in this world without writing this book. It is happening, no matter the worries inside me or the yesses or no’s I get from outside of me. It is happening. And that is that.​

And that is that.

It turns out that when I actually thought about what makes this project meaningful to me, all of these very salient memories and real convictions came pouring out.

Later that morning, when I set up my laptop at the Athenaeum, I wrote my sample chapter with the momentum and energy of all of that WHY fueling me. And here’s the thing: it wasn’t as hard or scary to write as I thought it would be.

I kept turning to Courtney and library-whispering: I’m doing it!

Of course I was! Of course I am! Because this matters so very much to me. And that is that.

Your turn to reconnect with your "why":

• What is something important that you’ve been putting off?

• What makes it so meaningful to you?

• What’s getting in the way of you doing it?

• What makes it worth breaking through what’s in the way and doing it anyway?