Published each week in January for our Wiggle Work Winter Wednesdays Writing Workshop.
By Joni Trythall, Wiggle Work Chief Wiggle Officer (CWO)
“I want us to trade lonely and isolated lives that experience brief bursts of connectedness for intimately connected lives that know only brief intervals of feeling alone.”
— Jennie Allen
I’m writing this guide as part of a writing challenge alongside Wiggle Work friends. While the details change a bit each year, the gist is that we get together for planning and then consistent writing during an otherwise dreary winter month. There’s a special channel in Discord where we talk through ideas, seek advice, and share published posts for group reading and celebration. It has become a yearly highlight for me personally and professionally that has opened my eyes to the detriments of writing in isolation.
I launched Wiggle Work as a space for remote tech workers in August 2023. I was going through one of the darkest times in my life, and Wiggle Work was my way of climbing out of this bottomless hole. Instead of continuing to retreat from the world, I mustered the energy and courage to take the steps to reconnect with people. Being homebound from surgery, my only option was to do so online. While I am generally one to prefer in-person connection above all else, I am so grateful this has been an option for me as it has allowed me to overcome several limitations over the past decade. Each day after creating this space got brighter and lighter, allowing me to continually envision and work towards making sure it provides this same outlet to others.
Before Wiggle Work, I founded Ela Conf, a conference and community for marginalized individuals in tech. I also founded my college’s anthropology club and tried and failed to launch a design group in Delaware. What we choose to do with our spare time when anything is possible is incredibly enlightening. I have always chosen to craft communities with this precious time and have never regretted it. Even when challenging situations arise, it would be impossible to regret something that has and continues to teach me so much about myself and bring me closer to such incredible peers—I can’t regret something that brings unmatched fulfillment and satisfaction to my life.
One of the more impactful things I’ve learned is that connection and community do not happen by chance—especially in a remote context—and you specifically are the perfect person to start these spaces you’d like to see in the world. It’s too easy to live a guarded, isolated life because it can feel safer that way. Safer from the vulnerability that comes with expressing the need for others. Safer in the assumption that it’s a protection from rejection or negative experiences. But the true strength exists within breaking down these walls and embracing others and the responsibilities of creating these essential spaces.
My intention for this project is to blend and share lessons I’ve learned the hard way (and some easy, luckily) and the great insight I’ve gotten from others on starting, managing, and growing online communities. And, of course, to get to know all my fellow writing challenge partners even better through their projects and our behind-the-scenes chatter.
I’m so grateful for all the people I’ve met that have directly contributed to my love and whole-hearted belief in the power of connection and community—thank you for enabling me to belong.
“True belonging doesn’t require that we change who we are. It requires that we be who we are.”
— Dr. Brené Brown
Belonging is what community is all about and making sure people feel this is the highest priority of community building. The desire to belong is one of the most natural, intrinsic human traits—it’s a survival mechanism and motivator that we can’t fight. Belonging and “finding our people” is critical to our success and happiness, and yet more of us are as lonely as ever. We live increasingly disconnected lives where there’s a twisted sense of celebration in attempting to do it all alone.
Communities in the form of safe spaces that are structured around a common interest are one of the most powerful ways to design experiences that foster belonging. We can’t all choose our family, but we can choose which groups and people we give a piece of ourselves to in order to connect and grow together. These shared experiences build bonds, reassurance, and familiarity—we feel seen and able to contribute to something larger. We feel most ourselves and purpose-driven through this deep, genuine connection with other humans.
We’re drawn to groups where we feel welcomed, accepted, valued, cared for, and appreciated. These are strong, essential feelings that require more than a transactional approach to relationships. Everything can seem just right on paper, but if a proposed community isn’t instilling these feelings of belonging, then it’s hollow and people will not give their true selves to it. The mission and actions of a community must be sincere and involve openness that inspires others to give the same of themselves. Without this important, visceral feeling, there is no community.
Loneliness harms us, lighting up the same area of our brain as physical pain. It causes disease, mental health issues, and shortens our lives. It’s a profound form of suffering that, as a society, we’ve seemingly accepted. When we are lonely, we disengage, compounding the problem. And this isn’t just a personal issue that gets set aside when we clock in at work. Loneliness at work fosters low commitment, erodes our cognitive and focus abilities, and makes emotional regulation more difficult—our output and interactions with colleagues suffer.
Communities and a deliberate culture of caring and belonging are the most impactful ways to ensure we bring our best self to our work and are the most fulfilled by these connections. Too often, though, this is dismissed as personal fluff or a family problem. This causes us to feel high maintenance for having these needs, and wrongfully assume others must be doing fine in isolation. As a result, we can feel like an exception or broken. We attempt to convince ourselves it’s fine and that we’ll get through it, but we can’t and shouldn’t dismiss this innate, necessary need for connection.
Proximity is one of the first and most important aspects of building a community and fighting loneliness. The most successful relationships will come from people we see often through shared interests and general like mindedness. These interactions are also more likely to happen organically and not require tricky planning and increasingly impossible free time. These in-person run-ins can fast track the getting to know people stage of building something more substantial than small talk. When in an office, it’s much easier to envision and feel the positive potential of these deeper connections.
But our lives are more online now. More of us are working from home, which can be an incredibly isolating and lonely lifestyle. Follow any work-from-home group online and the posts you’ll see most often, by far, are questions around how to not be so lonely. We are working in silos without watercooler chat, without after hours gatherings, without being told happy birthday by colleagues, without people and without a mutual cause to be a part of. Many remote employers do not know how to craft a healthy work culture, so it’s up to us to create and find these outlets.
As physical proximity becomes increasingly challenging, we must turn to online spaces in order to combat this expanding, dark loneliness cloud before it literally swallows us up.
Online communities can rightfully have a poor reputation. We can all reference too many examples of spaces that were not managed well or at all. Besides feeling lawless, lack of structure, guidance, and opportunities makes connecting with what can amount to cartoon avatars on a screen impossible.
It can be too easy to assume that if you provide a general space for gathering, that people show up and the job is done. This is not only not a community, but there is the potential for real harm to be done here as it will be a poor reflection on the person supposedly leading and the lack of guidance can too quickly turn into uncomfortable moments that drive people away at best, or lead to harassment at worst.
Once successfully built or discovered, these online spaces are to be cherished and looked after seriously and attentively—there is a lot of meticulous work that goes into making an online space feel intuitive, welcoming, comfortable, and like a good fit. Crafting a feeling and communicating your personality takes much more effort to achieve online.
Establishing sincere belonging makes anything possible. Members will be eager to give back to the space that’s improved their personal and working lives, that brings them joy, and that allows them to feel seen and understood. People that hate networking will find that it’s the most effective, sincere way to make important connections without all the phony interactions and grandstanding that comes with a more traditional approach to expanding our networks. The folks that thought they were managing OK alone will get a newfound insight into just how bad off they may have been, promising themselves to prioritize these needs from now on.
Communities help fulfill this essential, foundational human need and desire to belong. Being a driving force to facilitate this well is one of the most powerful and rewarding roles we can play in life.
As with anything worth doing, there are challenges and risks here. Aside from the time commitment, there’s a guarantee of some awkward moments, some sad moments, and some potentially angry moments. We’re talking about people here, and people are endlessly complex. You can work tirelessly to cover every base, account for what seems to be every scenario, and yet something will still negatively surprise you.
There is also the need to be vulnerable. Developing relationships is a give and take, and part of that giving is sharing a bit of yourself with others—even the imperfect parts and struggles. Members will appreciate and echo these sentiments. Community leaders that struggle with sharing, vulnerability, or humility will probably find that members are equally standoffish and not able to truly connect.
Not all communities succeed, but this is not to say they failed. There’s so much to be learned from these instances and applied to the next effort. Don’t let joining an unsuitable space or failing to launch one convince you that you’re incapable of this work or destined for isolation. We just have to keep going because that’s the only actual option.
Deciding to start, build, and maintain a community can easily feel overwhelming, scary, and not worth it. Not letting these defeating, unproductive feelings and thoughts take hold is key to success. It takes time, but there is a perfectly matched group out there for everyone. It’s one of the most worthwhile endeavorers there is.
“Belief is a shared crusade—and a sense that the tools and opportunities are available to achieve that goal—is an intensely liberating feeling. People get a sense that they have control over their own destiny.”
— Jono Bacon
Establishing and truly believing in a unifying community mission is the first step to bringing people together—so finding the driving reason and purpose. Like with everything I get into, I would have never started any space if I over thought this aspect when an idea takes hold. I brought each community to life by recognizing significant issues I was facing and reaching out to a few folks about their experiences and any similarities. Points of friction and shared interests or life experiences are great places to start when forming an intentional, purposeful space to gather.
As a brand strategist, I know there are much more formal and thorough ways to go about this initial step and, like with so many things, the approach you take will depend on your goals. For me with Wiggle Work, the risks associated with “failure” were low, since any number of people hanging out in this little bubble I created would be a win and something to celebrate and invest time and energy into. There is also minimal (but not non-existent) joining effort required of new members.
A formal process would involve significant research and consultation with prospective members. Prioritizing includes a market analysis to identify gaps, financial planning for costs and time, and a comprehensive onboarding strategy for founding members. A tool like a SWOT analysis (Strengths, Weaknesses, Opportunities, Threats) can go a long way into breaking what can seem like a larger-than-life task like this into actionable, effective first steps. But with all that said, sometimes having the heart, an impassioned reason to gather, and a few friends to come along can be enough validation for getting a space off the ground.
Defining a purpose statement is critical when starting community design and development. Basically, what is your community about and why? Skipping this step can so often lead to aimless, awkward spaces, with no clear, sustaining direction forward. Formally defining a purpose sets the format that people need to feel motivated and that they understand what’s expected. Without this overarching guide, a community can struggle to reach audiences and make a real impact. You may have brave introverts who had taken a chance on joining, only to swear off joining similar groups entirely going forward.
A mission statement will even further help with clarity and outreach—so, what are you here to do and for whom? How do you create the future you are envisioning? Wherever your community is mentioned, this single sentence statement will be used, and it should be attention-grabbing and focused. People want their problems solved—how does your community do that? People don’t want to be alone—how does your community address this? Having these foundational elements in place will help guide decision making, help communicate the right message to the right people, and foster a greater sense of trust and loyalty.
A community’s brand should also have a consistent (but context flexible) personality and voice and tone, which is often reflective of the founder, what appeals most to the audience, and what fits best with the established goals. A good place to start here is listing out top desired adjectives along with completing a personality scale to help visualize where you’d like to end up between things like traditional vs progressive, serious vs fun, corporate vs friendly, cool vs warm, subtle vs bright, elite vs approachable, and so on.
As you establish the values, personality, and tone, writing copy and visual design will become much easier since there are now restrictions placed on what’s possible. Controlling how people feel when interacting with your brand is especially important for communities since people are specifically seeking emotional experiences along with functional benefits. The goal is to build a brand that people fall in love with, that brings value to their lives, that speaks to their identity. This is what branding is all about, going much deeper than colors and logos.
A brand is a living thing, establishing the culture around you and should evolve as the immediate space and world changes—this is ongoing work that requires care and reflection.
Online communities have to be hosted somewhere and while there are countless options, the best one will depend on goals, the audience, and the desired community engagement model. Getting this right aids in the understanding and expectations for members. For Ela Conf in 2015-2018, Slack was the best option. Everyone was already there for their jobs, so there was no extra barrier nor learning curve to tackle. For Wiggle Work, it’s Discord. These folks are burned out with Slack culture, are generally already in other servers, and are rightfully suspicious of most technology. It has been a great platform for our casual “hang out all day and chat” approach to connecting.
I’ve been a member of spaces on Mighty Networks, Circle, and Heartbeat, which have been great as a more formal and structured approach. While it can feel overwhelming, matching your audience’s preferences with budget, values, and intentions should narrow this monster list down pretty quickly. So, be considerate in this choice but also don’t let it be a blocker to bringing people together.
As communities grow and mature, tracking becomes more of a priority and more difficult to do manually. Having a way to track individual member information can help you remember important details about their lives and foster a deeper connection. If the demographics shift, that’s something you’d want to pick up on in order to make adjustments to events, discussion themes, and marketing initiatives. While not at that level yet, my next tasks for Wiggle Work, for example, include a CRM style tool for members and an automated system for onboarding that will need to connect several tools—again, important, but not a blocker.
Depending on the platform, it can feel like an application process is unnecessary. This temptation is even stronger with free communities, but I’d argue this is where it’s especially critical, since now there are no barriers to entry. The problem with making something too easy to join is that it requires no consideration, opening the door to people that have no intention of sticking around and others that have maybe not taken the time to review expectations and rules.
This application process also allows for the gathering of important information and data. I like to ask (but not require, of course) about birthdays, since I think the idea of having a birthday without your friends knowing and passing along well wishes is quite sad. Additionally, I find it important to have a sense of job titles and what struggles incoming members are experiencing with during their remote working days. These questions will vary by audience and intentions, with the high-level point being that capturing these insights can help steer special initiatives, best explain the community to others, and help drum up sponsors when and if that time comes.
I also like to speak to initial expectations here so that there are no surprises or confusion. For instance, it’s very important that we do not have anyone under 18 in our group, so this is a way to confirm that. I also mention that new members should introduce themselves within a week of joining, and if that’s not possible, it would be best to join at a later date. This is to protect the intimate feeling of the space for existing members, as to not feel intruded upon, and help newcomers get those important, warm welcome messages as soon as possible and not risk abandoning a space before giving it a proper shot.
And finally, this document is a perfect place to reshare and confirm the acknowledgement of a group’s code of conduct.
Every community’s heart lies in its code of conducts, yet many simply copy them from other spaces. As the guidelines for behavior, values, expectations, and procedure, these are one of the most important first steps—before the very first person even shows up. A thoughtful, proactive codes of conduct is going to serve everyone so much better than one that’s reactive with endless addendum.
Establishing clear boundaries and rules of engagement will ensure your space is safe, and that there is an obvious path to conflict resolution if it arises—so, mapping out exactly what a victim of harassment, for example, should do and what to expect next. A code of conduct should have explicitly labeled enforcement and reporting sections, have transparency around accountability, and list exactly who to report issues to. I’ve also learned that anonymous reporting procedures and encouraging everyone to use their names over vague avatars can bring comfort and reassurance to the group.
There are also certain rules that you’ll want to consider after reflecting on your least favorite parts of other spaces compared to what you’d like to foster. For instance, link dropping. Link dropping is when someone only shows up to the space to share their own work, while not being present or engaging with others. This type of behavior, while seemingly benign at first, directly contributes to that sense of phoniness and distance we’ve all felt in online communities.
To truly enable people to connect and share, communicate from the start that your space is not the right place for only taking and not giving. While this is just a single example, there will be many others when you reflect on your favorite and least favorite spaces. An additional example is adding language around respecting member privacy and avoiding things like taking screenshots of conversations and calls without everyone’s knowledge and consent.
Code of conducts do not guarantee a frictionless experience, but having this guide and plan of action will better prepare you when issues arise and bring great relief to those deciding to join—it’s the only way to achieve inclusiveness. These documents should be publicly accessible so potential members can get a sense of the environment before committing. And finally, be ready to act on these promises since these carefully crafted documents are not just for show.
Finding and empowering founding members is another substantial initial step—they bring passion, energy, and commitment during the critical early stages, helping to establish the tone and culture that others will follow. Within your existing network, reach out to a few folks that you know embody the values and the mission you’ve established. Choose carefully, as they will be your greatest champions and collaborators, proving essential for growth.
To nurture founding members effectively, provide them with opportunities to contribute meaningfully, whether through leadership roles or decision-making input. Recognize their contributions publicly to reinforce their value and ensure they feel appreciated. Regular communication, such as private check-ins or feedback sessions, can help you better understand their needs and motivations. By fostering their development and involvement, you empower these individuals and establish the foundation for a thriving and enduring environment.