Going for a big, daunting, thrilling dream

I regularly beam out resources from Harvard Business Review, but never before have I had the opportunity to share an HBR article written by....ME!

In April, I became a contributor to a knowledge base that I respect and consult daily.

I'm so proud and excited to share this article on a topic that's at the heart of Penney Leadership: how to build an intentional career path that is unique, enjoyable, and adaptive to change.

Please read it and share it with someone who needs a reminder that you can always take a detour.

Here’s a behind the scenes of the process (read: dreams and doubts) that can go into a career achievement like this…

A big, daunting, thrilling dream

Last week was a big one: I became a contributor to Harvard Business Review (HBR).

On the day the article went live, I refreshed and refreshed the page all morning long. I did my best to keep cool, but I definitely had so much frenetic energy that "cool" meant making it 15 minutes before checking again.

At about 1:15pm, I hit refresh for the millionth time and squeaked, “It’s up! It’s up!”

It was such a thrill to see the headline and my name on the real page! And the photo they chose of a happy, yellow car set against a sky blue background! My bio at the bottom! With my photo in the green HBR overlay! It was so freaking exciting and I felt so proud!

Though the article going live happened in a flash, the process of getting there was anything but quick.

This has been a big, daunting, and thrilling dream of mine for some time. And for most of that time, I was far too scared to take action. (Can you relate?)

Discovering & rediscovering learning edges

When I started writing Penney Leadership’s newsletter seven years ago, I curated other people's ideas. I pulled together podcasts, articles, and videos, and wrote a sentence or two about how they might help you in your career development.

You might have had a similar feeling in your career: Like you're not an expert or an authority, just a learner hoping to some day be good enough to be considered competent.

Then I read Playing Big by Tara Mohr, which gently called me out for hiding behind other people’s ideas instead of sharing my own. I took the challenge and started sharing my own original thoughts as newsletter articles.

It felt so scary and raw at first. I wondered: Did I have something to say? Who would believe me? And when there is so much to know in this world, how could I confidently say anything for sure?

What I’ve found is that my writing strikes a chord for some people. Sometimes they say, “You put into words something that I’ve felt but didn’t know how to say,” or “I feel like you wrote this just for me.” It is the best feeling for me when my writing brings others comfort and clarity. That is my deepest wish.

So I built the muscle and my voice over time. You gotta put in the reps! To date, I’ve written 151 issues of the Strategic Leader’s Toolbox. Now, sharing my original ideas doesn’t feel like a learning edge for me anymore (an area where I'm stretching myself to grow)—it flows quite naturally. That’s because I’ve had enough practice to trust myself.

What does feel like a learning edge for me is publishing on another platform—pitching an idea and working with an editor to bring it together in a strong way.

It took 18 months to hit "Send"

HBR is the ultimate platform in my field—it's the publication that I go to most often for guidance to share with clients, and it's arguably the pinnacle of thought leadership on leadership development. I wanted to be a part of it. I wanted to swim in those waters, share ideas that could help others on a grand level, and yes, get the validation that my ideas are good enough.

So, instead of actually pitching HBR, I embarked on a journey of information-gathering. I took a course with an HBR published author on writing for high profile publications. I poured over HBR's submission guidelines. I strategized on who I could reach out to for a warm introduction to an editor.

This went on for about 18 months—it went way beyond the healthy amount of information gathering and into what Tara Mohr would call hiding again. This time, I was hiding in research and waiting to be sure that I knew I'd be 100% successful before I put myself out there.

I got stuck here for a long time because going for a dream is vulnerable and scary. What if they said no? Or even worse, what if they said yes and then I actually had to write a thing that was good enough for HBR?

(Have you ever held back from going for a new job, a promotion, a conference proposal, or sharing an idea at work because you were afraid you'd fail...but also that you'd succeed and have to follow through?)

After a year and a half, I had heard myself talk about it enough without taking forward action that I was annoying myself. It was one of those situations I would have been able to coach a client through, but I couldn’t seem to nudge or encourage or challenge myself to take real action.

This January, I joined a free training with Amber Petty on writing a "half-assed" writing pitch. I needed the nudge to make it good enough, not perfect. That's a hard thing to comprehend as a former straight A student, but I'm starting to get it. I finally hit send on an email I had been drafting for a year and a half. Here's a video of me actually clicking "Send!"

The writing process

The editor responded, and we met virtually. I shared some story ideas, and we zeroed in on one that she liked.

I wrote an outline that she shared at the weekly editors' meeting and we got the green light to move forward with a draft.

I wrote the first draft in the notes app of my phone while I sat in my car during my daughter's dance class. That's surprisingly where I do my best writing—I think because the stakes are low on my phone. I’ll tap something out there, without the pressure of a blank word document waiting for genius to emerge. It’s just quick thoughts from my fingertips.

I gave myself a time limit for writing (I could see myself taking another 18 months to make it perfect) and reminded myself again and again that it didn’t need to be bulletproof at this point, it just needed to be a solid first draft. I wrote it, had three people I trust give me feedback, and turned it around in a few days.

Then I waited three weeks to hear back.

I did the dance that so many of my clients do during the job application process: Should I follow up? I don’t want to be annoying or come across as rude. But what if she’s lost track of the piece and would appreciate the reminder? I sent a short, polite check in.

She responded with some overall feedback: “Right now this is focused on ‘why’ when the focus should be on ‘how.’” She was right, and I took that and ran with it to almost fully rewrite the article. I turned it around in three days again. And this time I waited a month for a response.

The "I Hate It" Point

When my editor wrote back this time, the tracked changes made me go cross-eyed. This edit was more detailed—some changes were easy to accept and others I needed to noodle on.

Somewhere in the middle of this draft, I started to question everything. Am I actually a shitty writer? This idea is totally stupid and doesn’t work. Why did I even put myself out there for this when it’s so much easier to write for my own newsletter with no editor and critical feedback?

She asked for a new draft by the end of the week. I pushed through and sent her a new version, riddled with tracked changes, comments, and responses. I didn’t feel at all confident. Surely, she’d write back and say, “Forget it, you’re not ready.”

She told me she’d take a look and the next step was to send it to a top editor. I googled what a top editor was and waited.

In the meantime, I attended my weekly writing group meeting. The leader was talking about how, with almost every piece she writes, she hits a point where she questions everything—why she had the stupid idea to begin with, whether what she wrote was actually terrible, and if she should go back and get a day job. She reflected that this is a normal part of the writing process. She calls it the "I Hate It" Point. And that came as a huge relief, because that's exactly where I was.

Two days later, my editor sent me a clean, unmarked up document. The top editor had made some line edits to make the piece flow, but the meaning of all my sentences were intact. And it looked great!

She asked for my okay, along with my headshot and bio, and said it was queued to publish on Monday.

WOW! I had felt like giving up, but we were suddenly there. My dream was coming true—but I didn't believe it until I hit that final "refresh" and saw it appear on the screen the following Monday.

From pitch meeting to publication, it took about four months. But the process of building up the courage in the first place—well, that was the biggest hurdle.

Your Turn:

• What is a big, thrilling, and daunting dream that you have?

• How might you be hiding instead of taking action?

• How would taking on your dream enable you to honor younger versions of yourself?