Leading from Behind: What I’ve Learned From Launching a Freelancers Association

I arrived in Denver in the spring of 2018 with nothing more than a car full of belongings and the residual odor caused by a month-long road trip from New York City. My landing was as soft as the twin mattress behind my friend and business partner's couch where I slept for those first weeks. Like many transplants, I moved here for work. The sun and proximity to nature were a welcome bonus (and probably why my business partner was unwilling to move to New York City).

The following months were a struggle for stability: Navigating the (comparatively easy) bureaucracies of vehicle registration and all the minor complications that stream from that, integrating into a new community, making friends as an adult, and trying to take care of myself. The slower pace and active lifestyle in Denver made self-care quite easy. In NYC, the fast pace and busy people streaming past seem to whisper "why aren't you working harder?" while here in Colorado, the public seems to cheer "take time for yourself, be in nature, be well.” The change in time zone magically turned me into a 6 a.m. morning person. Soon I was going to the gym and eating fresh produce from a farm just two miles away. My three roommates and I created a wonderful cozy home where we shared food and time together. The hipster millennial dream, I realized.

The Power of Yes

"I'm writing to see if you'd be interested in collaborating in [a] way for Denver Startup Week.” wrote Paul Bindle.

I had never heard of Denver Startup Week, I was still getting settled, and work was stressful. There were many reasons to turn this down. I, however, had just finished a four-year-long criss-cross country journey that taught me the power of saying yes. I could listen to all the reasons I had for saying no, most of which found their root in my own insecurities. I chose not to listen.

Soon the Denver Startup Week session "Better Together: How Freelancers Can Win" was born. Paul Bindel, my partner Katie Falkenberg, and I were on our way. Our session was selected and the RSVP count started to grow.

While excitedly sweating over the hundreds of RSVPs, I had no idea the impact this little project would make. What doors this simple "yes" would open. I didn't know (though perhaps I suspected) that Katie and I would be dissolving our business by year’s end. That I would be tending to a community of freelancers, creating meetup events, finding sponsors, and building a week-long conference of my own.

I could have never guessed that Denver Startup Week would be the launchpad for my own startup: Better Together.

Coming with Questions, Not Answers

One hundred twenty-five people came to our event, and we came with questions. You see, I am an expert in only one freelance experience: my own. This experience has taught me many valuable lessons that are worthy of sharing, but it is still limited to my context and perspective.

We didn't approach this session as experts who were going to download our wisdom to an audience. Instead, our strategy was to use our experience in group facilitation to support the emergent expertise of the crowd. I believe that a group is often the best teacher in the room and that defaulting to experts acting as teachers with their audience as students is often less effective for learning (but that's a topic for another post).

We came asking the question, "How can freelancers win?" This session was a test of our assumption that freelancers could answer this question better... together 🤓.

Answer they did. To summarize, we found that being one's own boss is amazing, but it can be overwhelming, lonely, and hard to find steady work. Most importantly, though, we found that there was energy for something...freelancers wanted to be connected and they didn't feel like they were in any meaningful way.

The Denver Startup Week session ended but there was clearly a hunger for more. So we created more.

Driven by Purpose

Initially, we hosted a follow-up happy hour. Then, based on feedback, we hosted a networking event in a less distracting environment (Galvanize Golden Triangle [RIP]). It was clear that there was energy here. Freelancers wanted to be meeting each other; they wanted to be learning, growing, and doing so together. By the new year, I had taken on building Better Together on my own. Paul and Katie put their energy into other things, and I found new collaborators through the budding freelancers network that was growing from the DSW session just a few months prior.

I wrote a vision of a world I want to live in as a freelancer, and I created a purpose statement for the group.

Our purpose is to improve the quality of life for independent workers and their communities.

All decisions are weighed against their service to this purpose. It is our North Star.

Something magical happened as we forged our own path towards this purpose: We found others’ paths who had been here before.

The Power of Asking

Through the new year, Better Together hosted an event each month. We started the year off with a design thinking event that asked: "What do freelancers want?" Then we used the feedback we got from the group to create events that reflected their answers.

Through this process, I've learned the skill of asking. Asking for feedback, asking someone out for coffee, asking for venue space, asking for food sponsorships, asking for help. Asking is a form of vulnerability. When I ask for help with something I am exposing that I can't do it alone in a culture that fetishizes the lone individual. Even as I write this article I know that I will ask one of the copywriters in my network to edit it, exposing my spelling errors, poor grammar, and abuse of commas to someone who is an expert, someone I can't afford to pay for their time. It’s painful, in a way, to expose the soft underbelly of my weaknesses.

It is also freeing and creates the most amazing opportunities.

Enter Emily Leach, founder of the Texas Freelancer Association, #FREECON (the Freelance Conference), and Freelance Business Week. Through the Better Together community, I was connected. I asked to connect so I could learn from Emily’s experience. By the end of our conversation, I had agreed to host Freelance Business Week in Denver.

Different forms of Capital

I knew nothing about running a week-long event, so I was foolish enough to try. I had support from Emily and I had become proficient at asking for support from the Better Together community. In short order there was a group of five amazing women sitting around my dining room table sorting out how we were going to pull this off.

So far I've done much of this work without money or financial capital. Instead, I've learned to recognize and leverage the many other forms of capital. Money is not the only thing that makes the world go round. There is a popular idea that puts forward 8 forms of capital. Through the months of work on Better Together, I hadn't been accumulating much money, but I had been building Social Capital through working hard for others in exchange for their trust and admiration. I had been learning from those I was collaborating with in the form of Intellectual Capital and Experiential Capital. Further, I was seeing the growth of Cultural Capital within the Better Together community.

These hundreds of hours of valuable time I and many others were committing to this project might not have been making us wealthy in a direct manner, but they enriched us in many other ways (some yet to be uncovered).

Watching this community come together to host monthly meetups and put on Freelance Business Week Denver has been an awesome experience. Through asking for help I've gotten to encourage people to take on work they didn't know they were capable of. Stories of collaborators found through the community and seeing first-hand how willing everyone is to help each other out has been a joy to witness and to lead.

Leading from Behind

"A leader is best when people barely know she exists, when her work is done, her aim fulfilled, they will say: we did it ourselves." - Lao Tzu

Through this process, I have been learning how to lead from behind. By elevating others, I elevate us all. There are simple ways that I've achieved this, such as putting other people on stage instead of myself. Giving volunteers creative control over events. In the spring I straight-up left for two months and trusted that the people who offered to help would do a good job. (They did an amazing job, it turns out.)

Leading with trust and compassion is perhaps one of my best superpowers. When you trust people to come through and deliver, they seem to do so. The less I micromanage, the less I stress that things aren't being done my way, and the more that others step into leadership.

Being compassionate when people don't come through is also an amazing way to keep myself healthy. When someone backs out of a commitment, I applaud them for taking care of themselves and setting boundaries. I honor the challenges that others face, and in so doing, I honor my own challenges.

This compassion opens me to the community. I am able to be vulnerable with my people. In June during a stressful move to a new apartment, I began answering "How are you doing?" honestly within the Better Together community. "I'm stressed and depressed," I would share, and people were there to hold me, to help me, to encourage me. Through the lens of all our outdated leadership tropes, I was showing weakness! Leaders, as the myths and legends go, should never be weak.

Well, that's bullshit. You are going to stumble and fall and hurt yourself, and your health (mental and/or physical) will be tested. If that's not happening, then you're not taking risks, you're not reaching out of your comfort zone, you aren't growing. Growth is often painful.

So now it is September. Soon Better Together will officially launch. There are business plans to finalize, membership models to explain, and work to be done. It is in this space that I have come across an obstacle. I see myself shying away from making decisions, I continue to fact-find, muse on all the different ideas, do more research. I find myself hiding from decisions that only I, as the leader, can make.

The lesson I'm learning is that even a leader who leads from behind must, ultimately, lead.

Conclusions

Denver Startup Week 2019 is upon us. Better Together will be hosting a session for freelancers and clients nearly one year to the day after its inception. I could try and quantify our success, tell you about the number of emails and meetup group members, the stats on our events, the number of sessions coming up at Freelance Business Week, but that's for a different post. I think numbers are often a problem when thinking about success. Sure, our SMART goals require them, but they don't paint the whole picture. The success is in the pursuit of a vision. I feel enriched by this work and the people around me are excited.

Besides, this is only the very beginning of the story of Better Together and the independent "soloist" community in Colorado. Denver Startup Week was a most amazing and welcoming community that launched something beautiful into the world, something I couldn't have imagined. Something that I am honored to be the steward of.

I hope this story has given you some nuggets of wisdom that you can take forward into your own project. I hope it will help you overcome the fear of saying yes, even when you don't know what good could come of it. That it will help you appreciate the different forms of capital you can invest in by asking for help and being vulnerable. That it will show you how having a purpose can lead you toward your goals more swiftly and securely, while also helping you to find allies along the way.

Opportunity is always calling. Stay curious and listen to what it has to say.