The Scariest Thing I’ve Ever Done
Can One Business Change the World?
This Small Business Saturday, I have no promotional discount, only the three convictions that have guided my journey as an entrepreneur.
1. The practice of making the impossible feasible starts with the unwavering determination to do something that scares the shit out of you.
I started doing things that scare me at a fairly young age. At age five, I successfully kidnapped my best friend, Stephanie, unleashing a literal manhunt in the dead of night. At eight, I learned how to jump from a 10-meter platform on the count of three. I grew accustomed to pushing the envelope, seeking the limit of possibility.
As I grew in my career I developed a motto:
“It’s only fun if you’re not sure it’s going to work.”
A series of unlikely events led me in the summer of 2016 to an unexpected choice. I had thought for a long time about how I would support Hillary Clinton’s campaign for president, failing to do anything more than consider the prospect. Then in July of 2016 I received an offer to join the campaign as a field organizer in southern Florida.
The stakes of this choice seemed high. Like most older Millennials born to managerial-professional parents, I grew up in the culture of pre-Recession extreme capitalism, the idea that the value of a life’s work is measured in how much money you earn. I had always subverted this construct slightly by spending the first ten years of my career working for nonprofit organizations in fundraising, communications, and marketing. But the salary growth paradigm still loomed large. Field Organizers were expected to be available every day from date of hire until November 8, with no days off. This job would be a lot more work for a lot less pay, with no prospects of a job on the other end.
If you are lucky, life will open doors for you that offer the chance to do something terrifying, something so crazy, you may question your sanity in your willingness to risk everything to do it. Lurking at the bottom of this pit of questions and uncertainty is fear: fear that you are not enough, fear that you will fail. Fear is the force of nature that gives you permission to put your head down, keep quiet, and make yourself small, and ignore the big-crazy-scary opportunity life offers you.
In the months prior, my life had been transformed by The Artist’s Way. Billed as a spiritual path to higher creativity, the self-guided course had led me to appreciate synchronicity, or what I had come to lovingly call “right-time-right-place magic.” These moments are often a strange combination of exhilarating and terrifying, and the job offer to join the campaign was no different. I had no idea what lay on the other side. “Stay put!” the voice of fear screamed. Yet, the circumstances that had led to the job offer were too unlikely to be a mistake. I took the job.
Changing the status quo doesn’t start with fear or smallness. It begins with a big, ambitious idea, and a recognition that, though it may seem impossible, you are willing to stake your most precious gift — your time here on planet earth — to see it realized.
Hillary Clinton’s defeat in the 2016 election was yet another unexpected twist of fate. I had never intended to join the new administration as many campaign staffers did. Instead the moment of extraordinary failure put my life’s work into perspective. Suddenly, the somewhat uneven experience of my early career came into focus as a constellation of possible future impact. I saw the deep need for a more strategic framework from which to help big, ambitious ideas take root, and my capacity to help move such ideas forward.
In that moment of extraordinary failure, I decided to take yet another terrifying leap. I started a company.
2. Miserable failure is usually a sound indication you are doing it wrong.
When you work for someone else, you take certain things for granted. You have a job description, work responsibilities, a set salary or wage, and a schedule. Whether you’re building houses, waiting tables, or crafting spreadsheets, there is a way that things are typically done, and you are expected to comply with the prevailing standard. You show up at an appointed time, perform your tasks, and are generally courteous to both your colleagues and customers, or else you risk losing your job.
Starting a business and working for myself, none of the things I had previously taken for granted held true. Where and when I worked, who I worked for, and what I did day to day were all up for discussion and adjustment. Not only that, but how much I was paid depended entirely on my ability to persuade people to hire me to on a case by case basis.
My high-level vision was clear:
I wanted to create a brand strategy and activation agency to help mission-driven leaders take their ideas from ideology—their foundations — to action and impact. An experience-based seven-step framework I called the Heptagon Method informed the services I offered. Slowly, over a period of weeks and months, I learned how to position my services and how to identify my target customer, but I always felt the overbearing should of a culture that said I should be doing something differently.
American culture places a high premium on entrepreneurship, perhaps because of its close association with the American Dream. But starting my own company, I’ve realized how fundamentally toxic the culture of business truly is, and yet how much confirmation bias ensures our compliance with current standards of behavior.
Here’s a summary of the current “standard” of entrepreneurship:
You are overworked. You are stressed. You are tired. Are you working right now? Because you should be working. If you are not working right now, you are lazy. Are you hustling? Are you caffeinated? Good entrepreneurs are tired, caffeinated, and always hustling. Are you post-revenue? Have you been accepted to an accelerator yet? Have you raised your seed round? Where is your business plan? Are you talking to investors about your business plan? What about your balance sheet? How will you scale? What is your exit strategy? Are you tired yet? Because you should definitely be tired. BUT STILL WORKING. ALWAYS BE HUSTLING, Okay?
The bottom line? How will your big idea make you a bunch of money so you can sell it to someone else and get onto the next thing. As an “entrepreneur,” I felt lionized for my conviction to go out on my own, but most of the time was completely alone in my work, and lonely in the idea that I wasn’t working on a unicorn billion dollar tech idea. I was interested in creating a business that could become an engine for culture change, which was of course much more easily said than done. In the meantime, I spent a lot of time feeling afraid of the impending failure associated with rejecting the prevailing paradigm.
I faced successes and failures, both in my efforts to advance the work of my own organization and that of my clients. Yet, the right-time-right-place magic of synchronicity persisted. I found my work converging with both politics and civic engagement. Gradually, I realized I wasn’t just building a model for the social sector overall, but seeking to leverage the impact of that model within the intersecting domains of democracy reform, civic engagement, and social justice. I wanted to inspire movements currently separated along geographic, racial, ideological, and socio-economic lines to see themselves as connected.
I realized the greatest failure of 2016 was the inability to see the negative space. The political class, namely those in Washington DC, New York, and the San Francisco Bay Area, had spent so much time arguing about the qualities of both candidates, they had failed to see that the very grounds of the argument were biased. Our standard of leadership had been so diminished, we failed to realize our complicity in perpetuating an expectation of failure, and an insistence on change. The past half-century had wreaked havoc on the American economy and the average person’s lifestyle. The disruption of consumer technology paired with automation had eliminated many jobs while creating others. Neither Hillary Clinton nor Donald Trump were willing to point ambitiously towards the future. Instead, they looked either hopefully or disparagingly in the rear view mirror.
We never undertook a process to define the shared values and vision a majority of Americans support. We never took the time to consider why a plurality of Americans are politically disengaged. We refused to acknowledge how the current standard of corporate behavior and the present dimensions of capitalist profit-seeking might be directly connected to the political dysfunction fraying the fabric of civic engagement. We failed to recognize the ways in which America’s history of racism and a long-lived culture of domination — of winners and losers, of us versus them — could perhaps finally be undermining America’s democracy.
In the weeks after the election, campaign leaders pointed to segments of the population responsible for the loss — young people, white women — and shook their heads in disappointment. They pointed to Russia and James Comey and sighed. A few briefly pointed to themselves and “took responsibility” for a failed strategy. But no one said, “I’m sorry.” No one said, “America deserves something different, and we are going to do everything we can to not just put a band-aid on this thing, but really fix it from the ground up.”
Like a good girl, I waited for someone else to show up and lead the way. I watched new organizations form virtually overnight. I saw somewhat suspect individuals get huge investments from tech billionaires. I celebrated grassroots organizations making exceptional headway getting more people to run for office, getting more volunteers mobilized to canvass and text message, all in the name of electing more women, more ethnic minorities, and more progressive candidates.
In a number of close races, a few dozen districts flipped from red to blue while still others went further into their respective extremes. For every candidate who flipped a district, there was another great candidate who lost. The 2018 midterm elections came and went, and the focus quickly shifted to those seeking the Democratic nomination for President in 2020.
Just because you’re A/B testing your message doesn’t mean either is good.
At no point did anyone say:
“Guys, I think we need to reconsider the premise of the question. Is it possible we are doing this wrong?”
I realized that once again a hole had opened up in the universe.
It was time to change the game.
3. The conviction of a higher purpose shines the brightest light.
In the summer of 2017, I started writing a book. Part memoir, part how-to guide, it was meant to provide in-depth examples and research to clarify the impact of the Heptagon Method. At first, I had thought of the book as a chance to give the milk away for free, to help leaders, regardless of whether they chose to work with my agency, to use a more strategic approach to brand activation.
As the months — and politics — wore on, it became clear the book was connected to something bigger. (You can listen to the first chapter here).
I see now that “fighting” for anything depends on a shared understanding that someone will win and someone will lose .Being inside of the machine advancing Hillary Clinton’s candidacy, I gained a deeper understanding of the “losers” who the past two decades of political leadership — including that of Bill Clinton and Barack Obama — have left out in the cold.
Fed up with being overlooked and under-served, most Americans have reliably seized every opportunity to vote for change. By getting outside of the elite echo-chamber of Washington DC and New York, I had the chance to witness the lived experience of those who are desperate for us to stop doing what we’ve always done.
In so doing, I have come to see that it is not just electoral politics that are broken by a winners-take-all paradigm, but the core guarantee of dignity at the heart of the American dream. Becoming “an entrepreneur” has shown me that this dysfunction is as present in how we do business as it is in how we do politics. Changing America’s future from one of despair to one of hope will require more than incremental changes in strategy or investment. To make tomorrow look different from today, we must stop doing what we’ve always done to stop getting what we’ve always gotten. We must embrace the chance to deeply and fundamentally change how our systems of governance, economics, and justice work together to promise dignity and equity for all. We can’t count on government or business or nonprofits to solve this alone. We are going to need to architect and execute systemic change, together.
I’ve also learned that all of us are smarter than any of us, and the solution to “the problem” is unlikely to come from a group of analysts squirreled away crunching numbers in a back room. To build the future we all want, we have to commit to a culture of engagement and mutual understanding. We have to move beyond the negativity of resistance to embrace the possibility that the future can be both different and better than today, and commit to working towards that future together.
Few things in life are certain, but one thing I know for sure is that the current culture of politics in America is broken beyond repair. The greatest voice and power lies with those in the extremes while those in America’s exhausted majority are unheard and overlooked. Continuing to do the same thing and expect a different result is the definition of insanity.
The Purpose Power Town Hall Tour across America is my attempt to to defy the status quo, to begin aconversation outside the echo-chamber at the grassroots. I want to bring people together in real life to find the connection and conviction among us that can transcend our current culture of fear.
I’m grateful to have the support of iFundWomen, a program designed to help female entrepreneurs raise the funds they need to achieve their business goals. In a culture where women receive less than 3% of venture capital investments, crowdfunding is often the most accessible alternative.
Asking for my community to support me in underwriting this vision is in some ways even scarier than starting my business to begin with. It’s not a typical feel-good cause. But my hope is that you share my vision enough to help make it a reality.
On Small Business Saturday, I’m asking you to stand with me and invest in this vision of possibility. When we work together, all things become possible.
Learn more about the Purpose Power Town Hall Tour here.
