The moment I hit “Send” on my resignation mail, I looked out my office window to see tiny pieces of ash floating slowly down the orange Pacific sky, like shimmering, fiery snowflakes.
It was early September 2017, and it was the end of a long, sad summer. The tinder-dry forests in the mountains surrounding Seattle had erupted into voracious fires, and they seemed to burn forever. Smoke blotted out the sun in an otherwise cloudless sky. And now, on this fateful day, a rain of ash.
I am a believer that the universe sends subtle dispatches to help us pick our way through life. But this one was beyond blaring. The question was: Is this affirmation…or foreboding? I had no way to know. The temperature was 83 degrees, but a chill ran through me.
“What the hell have I done?” I whispered under my breath.
That email marked the end of my 27-year Microsoft career, and the opening of a new chapter that I was neither familiar with nor confident in. It was a testament to the power of an idea to transform a life, even when you’ve got no clue where you’re headed.
Here’s a look back at how I arrived at that unlikely moment, what’s happened since, and where I’m headed next.
The accidental consultant
First, an admission: None of this was exactly planned.
With more than two decades of Microsoft experience under my belt, I was, by the early summer of 2017, one happy corporate camper. My career as a resident “creative” and communications strategist was a rewarding one. I’d built new programs, produced keynotes and cool videos, hit the road interviewing Bill Gates in various amazing places, and generally soaked up the energy and brilliance of the place.
Nobody would have mistaken me for a budding entrepreneur.
Everything changed in 2015, however, when I became obsessed with an idea: that skill in storytelling could be imparted as a strategic tool, something that could deliver measurable business impact. Then one day, I watched James Whittaker deliver one of his famous, slap-in-the-face motivational presentations, and I figured: Why not make it happen? It was the culmination of everything I’d ever done professionally, including my long and happy pre-Microsoft career as a journalist.
Fortunately for me, Microsoft had recently hired a new CEO, Satya Nadella. A savvy leader with a poet’s sensibility, Satya transformed Microsoft’s Machiavellian corporate culture in ways that no one could have foreseen. Suddenly, ideas like mine, which before would have been laughed out of any conference room, were now welcomed. Invited, even. Without my quite intending it to happen, this one took over my life.
The best promotion I never got
Looking back, I can point to a small set of seminal moments that set me on my current course. The big one came on a hot June day last summer, when my then-manager Al – a most excellent Englishman, full of class – sat me down and reported, with proper British sympathy, that my promotion had been denied.
“Everyone loves your work,” he told me. “But it’s not exactly what we’re paying you for.”
That’s because the “work” I’d been doing was completely off the books. For months, I’d gone from group to group across the company, presenting my vision for storytelling, called “Storytelling for Impact,” and honing a workshop I created that put people through the paces of building original, high-impact business stories. On one hand, it was a viral sensation. On the other, I’d gone completely rogue.
The news that I’d not be promoted brought home the truth that pursuing my passion came with a steep cost. I knew a half-dozen managers who wanted to talk to me about joining their teams. But I understood that doing so would mean prioritizing their organizational goals, not my personal work. Nobody was going to give me free reign to only do that.
Something had to give.
An unfair advantage
At a friend’s urging, I started listening to the Gimlet Media podcast, StartUp. The earliest episodes are first-person accounts from the founder of Gimlet, a guy named Alex Blumberg, whom I remembered from his work on NPR’s “This American Life.”
Alex decides that he’s going to launch his own podcast media company. His stumbling quest to launch the venture is the stuff of addictive storytelling. Alex is the ultimate underdog. “I’m just one guy with a stupid little plan…I don’t know what the f**k I’m doing,” he admits.
Alex’s ineptitude is eclipsed only by his enthusiasm. Blind faith might be a better description. He has no money and no business plan. Just a vision, a faithful wife, and a lot of talent. Early on, he visits a legendary Silicon Valley venture capitalist, whom he knows from his former NPR work. The conversation has the quality of a lamb soliciting hunting advice from a wolf so well fed that he decides to take pity.
“What is your unfair advantage?” the VC asks Alex, explaining that this is a central question that investors ask when deciding whether or not to write a check. After Alex stumbles, the VC all but roars it out: Your unfair advantage is what you did with “This American Life”! You know how to do a podcast better than almost anybody else in the world!
I listened to this while walking across the Microsoft campus on a sweltering Tuesday afternoon, and despite the clear sky I felt struck by a thunderbolt. It’s not that I imagined that I was as talented as Alex. Then again, I also wasn’t asking anyone to spot me a million bucks. Point was, I had something similar to what Alex had.
What I was doing was no pipe dream. It had been proven, in the harshest of laboratories. I had already worked successfully with many thousands of Microsoft employees. Executives called me back. I had my own unfair advantage.
Off the rails
For nearly two years, I’d been visiting the far corners of the company like an apostle on a mission. Except, I didn’t proselytize; I was purely reactive. I’d visit one group, someone would hear about it, they’d reach out and ask me to present to their group, and so I would. Wash, rinse, repeat.
By the time I listened to StartUp on that hot summer walk, I was averaging one workshop a week. I’d worked with engineers, program managers, marketers, sales people, communicators, service groups, and executive leadership teams. I’d keynoted the Microsoft Women’s Summit and a variety of global summit events. I’d done workshops with new hires, diversity and inclusion groups, and disadvantaged college kids.
It was a grand adventure – and a pure learning experience. My ask was not for money, but insights. In every session, I’d insist on a consult with someone in leadership – to learn about their needs, their challenges, what they considered “success.”
At every turn of the wheel, my program got a little sharper, a little more effective. I was a stickler for feedback, and asked every participant to rate his or her session and experience. The numbers felt ridiculously high, especially in the scathingly frank culture of Microsoft, but they rarely wavered, even with the most introverted of engineers.
The stories I witnessed astonished and humbled me.
Nevertheless, as awesome as this all was, I would wake up every now and then and remember that nobody was actually paying me to do any of it. The million-dollar question loomed large: Was this a way to make a living?
I got busy with research and learned that a handful of other storytellers had stepped out as successful consultants. I read Paul Smith’s book, Lead with a Story, and Cole Nussbaumer Knaflic’s Storytelling with Data, and found kindred spirits.
I had lunch with a local woman who split time between writing young adult fiction and consulting with corporate clients to integrate storytelling into their cultures. Clutching her cards closely to her vest, she told me, “I can only say that it is a highly viable thing to do.”
I hired a coach, Libby Wagner, who has made an adventurous life for herself as “the boardroom poet,” helping companies connect their souls to their missions. Libby is funny, generous, and savvy – a grounded woman not given to blowing sunshine up anybody’s pant legs. “You’re holding a handful of golden tickets,” she told me. I wanted to believe her, but it still seemed like fantasy.
As summer faded, feeling my time and options running out, and with zero sense of certainty, I decided to take the plunge.
The final curveball
It was a late August evening when I opened a bottle of wine in my Seattle kitchen, poured a glass for my wife Eve and one for me, and raised a toast. “This is it!” I said. “We’re going to do StoryCo. Remember this moment.”
The very next day, I got a call from my old friend Jonah, who runs UI design for a little service called Microsoft Azure. “I want you to talk to you about coming over and building the story for a new part of our business,” he told me. “Great!” I said, “I just decided to go out on my own!”
“I don’t think you understand what I’m asking,” he replied, explaining that the job was major: building a team and working as a principal in engineering/design, rather than traditional marketing, to architect and deliver a new story framework.
It was, in many ways, the job of my dreams.
I re-corked that bottle of wine and spent a few weeks considering this amazing new option. It could not have looked better. But I sensed a coolness in the back of my thinking as I considered how I might tackle the job. It’s not that the work wasn’t compelling (it was awesome); rather it all felt so familiar. I understood that StoryCo was a pipe dream – that I was unqualified, inexperienced, and quite likely delusional. But, like a bad cliché in a Hallmark movie, I realized that I’d never forgive myself if I didn’t at least give it a shot.
I emailed Jonah and told him I was withdrawing from consideration for his job. “I’m sorry to hear that, but I understand,” he wrote back. “Just make sure everybody knows you were on the short list for this one.”
A stark awakening
My last day at Microsoft, exactly one year ago today, I threw my own farewell party. I wanted to leave on quiet, authentic terms with only the people I cared about in attendance. No treacly speeches, no glad-handing or false affection. Just a fun few hours with my favorite folks, with a minimum of fanfare. Perfect.
I came home with Eve and we shared a late glass of wine. The autumn night grew dark and we fell into a deep, happy sleep. Then, at precisely 2:30 AM, my eyes popped open.
Suddenly, I was fully and coldly awake. I understood, in a way I hadn’t earlier in the day, that I was unemployed. Un. Em. Ployed.
My bank account, which for decades had been blessed with a twice-monthly soaking of direct-deposit cash, was now just a kind of a repository, like a rain barrel filled in anticipation of a long drought. There was no business. I had no web site. I was at square zero. Actual, paying customers were months away. At best. This firepit of worry burned in my gut for an hour or so, and then I faded back to sleep.
I spent the autumn and early winter doing the stuff I felt I needed to do to become an actual, grown-up consultant. I completed a business plan and put together a variety of systems and processes (many of which remain lovely ideas). I hired a small army of accounts and financial specialists to help me get properly incorporated, and to pay myself if and when any money arrived. I enlisted a designer to create a logo and set up a webpage. It all proved to be far more complex and expensive than I expected. The deeper I went, the more impossible exit became.
And for more than two months, without fail, almost always at 2:30 AM, I woke in a cold sweat; that same, middle-of-the-dark fear poking me awake like a haunting in the night.
Finally, in mid-January, I “launched” StoryCo. (OK, all I did was hit “Publish” on my web site and post a message on LinkedIn).
The name was the product of my failed imagination. For months, I’d expected to be visited by inspiration for just the right thing to call this new venture: something clever, cool, and not-yet-taken. I actually delayed doing certain work as I waited for the epiphany. But then one day I had a task that could not be ignored, so I opened a OneNote page and wrote “Story Company” at the top. The tab label abbreviated this to “StoryCo.” Good enough.
My larger worry at this point was finding a customer. I fumbled about looking for business.
At the start, I tackled one of my first and most onerous worries: the question of whether Storytelling for Impact – born and raised within the peculiar walls of the Microsoft Corporation – would have any currency out in the real world. I fretted that this would prove to be my Achilles’ heel.
When I finally voiced this to Libby, she laughed and said, “You’re bringing storytelling to Microsoft. It’s an engineering culture, and you’re making it work. That’s like growing a garden in the desert.”
I was fortunate to get some good early opportunities, all of them through references from friends and acquaintances. I ran a series of workshops and did some organizational development consulting with a team at Delta Dental of Washington. I presented at a meeting of financial services and insurance executives in Portland. I landed a keynote gig for the Public Relations Society of America annual meeting.
The results of those early forays outside of technology suggested that what I offered had universal relevance, resonating well beyond the walls of my old employer. Soon, however, Microsoft would be back in my life.
As early weeks of 2018 passed, that rain-barrel of a bank account began to evince some hollowness. Lots of folks were showing interest, but I was learning how long the cycles of this brand of business really were.
Microsoft was, of course, an enticing customer, but the road to that rich opportunity was blocked by bureaucracy. For months, I’d been running a long, often frustrating gauntlet of paperwork and processes to become set up as a vendor. I was lucky to have the sponsorship of the folks chartered with raising the state of the storytelling art at the company, but the approval process was plagued by one bureaucratic glitch after another.
Finally, in early February, the green light: StoryCo became a preferred Microsoft vendor. And then the floodgates opened.
For the better part of five months, my calendar was filled with an amazing array of excellent Microsoft challenges. It was almost as though I hadn’t left; the word-of-mouth effect generating reference after reference. I flew to Paris, New York, Dallas, and Las Vegas. At the big “Microsoft Ready” sales conference, my session was standing-room-only, and earned the highest marks of its particular “track.”
Returning to the halls of Microsoft was like going back to an old school. So familiar, yet so irretrievably different. I was no longer an amateur chasing a dream. I understood the value of what I offered, in concrete terms. I was willing to say no to clients who didn’t feel right. Now, I could focus exclusively on the work, the pure challenge of empowering people through this odd, subterranean thing called storytelling.
The next chapter
Following a welcome respite in the slack days of August, I am now back in full-time mode.
Once again, I am blessed with a nice slate of interesting client challenges, including not just keynotes and workshops but executive coaching and extended organizational development and creative contracts as well. My proverbial cup is overflowing, and I have never been more grateful. Yet I do feel compelled to reach higher.
For one thing, I need to follow up on a commitment that I made to myself – and implied on my web site – namely, to produce regular blog posts and newsletters. All through the year, I’ve told myself that I’d make this happen as soon as I felt I had my feet on the ground. I’m now realizing that it’s not a B-level priority.
And so, to begin, I intend to simply blog a lot. I want to share the insights and the discoveries I am fortunate to experience through my work, and I’d love to make some new friends and spark some new conversations along the way. I’ll use these posts as a sort of feeder to social media postings, newsletters, and, ongoing engagements with people in all corners of business and the globe.
The end game here is a book. One huge need is to make the benefits of Storytelling for Impact available to anyone, without having to step into a corporate conference room. Many people have asked for this, and so I’m currently working with an editor and putting together a proposal. This is another huge, frightening frontier for me. But also fun, and enlightening. Along the way, I’m discovering all kinds of books, of course, and I’ll report on these as well.
Thank you for reading. I invite you to join me on this unlikely adventure, by signing up for my newsletter, checking in on the blog from time to time, or dropping me a line any time at firstname.lastname@example.org. And if you like what I’m doing, please share, repost, tweet, and tell all your friends and coworkers!