Learning from Taylor Swift
How to Build a Community-First Membership Strategy
Summary
I love music and I love strategy. Though I don’t know Taylor Swift’s music very well, I do love the way she approaches her craft. She acts with courage, respects her fans, and successfully bridges art and commerce. She obsesses over quality, delivers best-in-class content and experiences, and creates loyalty that sustains her music and her business.
I think it’s important to look outside of associations for inspiration. It’s where we can find fresh ideas and creative ways of doing things. This article is based on the book There’s Nothing Like This: The Strategic Genius of Taylor Swift by Kevin Evers. What can we learn from Taylor Swift? How might we apply her business model to build evergreen relationships, offer great content, and become timeless and indispensable?
I lead the product community, a product development learning community designed specifically for associations. Let’s compare ideas and build something great.
Fan-First Philosophy: Member Obsession
“The most important thing to me is always customer obsession. It’s always about the founder talking as much as possible to customers, understanding them, and going really deep with them. If you really asked me for a metric, it would be something along the lines of the number of customer conversations they have per day. It literally should be per day. It should be a habit happening every single day or every single week, whether it’s conversations, reach-outs, or meetups in some shape or form.”
Michael Batko
I think it’s important for us to look beyond associations for ideas, inspiration, and creative models of practice. For instance, I recently wrote an article about community-led revenue that showcased Milk Street and Peloton. Taylor Swift is a force; although we are not influential songwriters, we do hold the keys to our destiny.
Swift’s core genius lies in being fan-obsessed and understanding the jobs her fans want done. This obsession has intensified as her popularity has grown, creating a strong bond between artist and audience. As I’ve written many times in this newsletter, we are wise to take this same member-centric philosophy. This means moving beyond surface-level satisfaction surveys to develop an intimate understanding of what their members truly want and need, but it also means surprising them and pulling them on a journey.
This means conducting rigorous, high-touch research into the real jobs members are hiring us to perform, whether that’s career advancement, networking, skill development, industry insights, or advocacy. Just as Swift uses lyrics that gives fans insights into her emotions and experiences, we can create content and experiences that speak directly to the unique challenges and aspirations of our professional communities. The goal is to build empathy, make members feel seen, and create deep trust relationships.
Though we excel at events, we might consider evolving from traditional gatherings into longitudinal extensions of our missions, in which we think about pathways more than siloed experiences. Rather than the standard conference, we could create immersive experiences that embody our values. Transcending the typical networking reception is important, but it’s even more important to deliver follow-up events with succeeding value that pulls our members onto a continuous journey. It’s not solely about the experience, it’s about the connection the experience creates so our members feel compelled to engage.
Continuous Engagement Strategy
“Creating connections in public spaces, particularly inter-group interactions, requires an intervening force or structure: a cultural norm, a social institution, or just something you sign-up for. In shaping the built-environment, this means the biggest opportunities for connections are the bookends of a typical design and construction process: the upfront community engagement, or the subsequent programming and operations.”
Eric Higbee
Swift abandoned the traditional music industry model of releasing albums every two years in favor of continuous dialogue with her fans. As Spotify’s co-founder Daniel Ek noted, successful artists in the streaming age realize “it’s about creating a continuous engagement with fans” through constant storytelling and ongoing dialogue. Swift embraced this reality, releasing 49 tracks in just 15 months and maintaining a steady flow of content that kept fans constantly engaged.
Associations traditionally operate on outdated cycles that resemble the old music industry model: annual conferences, quarterly magazines, and sporadic communications. This leaves yawning engagement gaps. We could consider mirroring Swift’s model of continuous value delivery by creating a steady stream of educational content, industry insights, networking opportunities, and professional development resources.
This means thinking beyond the traditional conference-centric model toward a continuous learning ecosystem where members receive valuable content weekly, engage in meaningful virtual events monthly, and experience new initiatives quarterly. The key is creating anticipation and ongoing engagement rather than relying on a few high-intensity moments (that typically only engage a 30% or so of the membership!) throughout the year.
Strategic Reinvention While Maintaining Authenticity
“Your thinking about strategic choices should be oriented heavily toward creativity and uniqueness.”
Roger Martin
Perhaps Swift’s most remarkable skill is her ability to completely reinvent herself across different musical eras while remaining authentically Taylor Swift. From country teenager to pop superstar to indie folk artist, each transformation has felt both surprising yet inevitable, maintaining her core identity while reaching new audiences and staying culturally relevant.
Though associations generally struggle with reinvention, we can apply this principle by, first, committing to a strategy that defines clear yet connected strategic eras (see my article on successive board chairs using the three horizon model). Rather than gradual, incremental changes, we could embrace transformations that embolden our missions by refreshing our programming, visual identity, and engagement strategies. A marketing association, for example, might evolve from a Traditional Marketing Era focused on established practices to a Digital-First Era emphasizing online strategies, and then to an AI Integration Era that positions artificial intelligence at the center of marketing practice. The key is staying true to our core identity as we evolve to meet new demands.
Each era can feel like a reinvention that creates anticipation while strengthening connection, generating excitement, and renewing interest from both existing and potential members. Evolving from a core focus deepens our commitment to our values and vision while preventing us from becoming predictable.
Innovation for Connection
“Strong brands earn innovation permission—the right to expand into new territories because customers trust the worldview behind the expansion. This isn’t about brand extension or licensing existing assets. It’s about the exploitation of systematic opportunities from the base of a coherent worldview.”
Paul Worthington
Swift uses innovation to maintain deep connections with her audience. For instance, she embeds hidden meanings and clues throughout her work. We could use this concept to create anticipation and hype. Though our members may not be as rabid, we could create buzz by offering exclusive insights, allowing members to preview content, or providing insights on industry intelligence. This could encourage members to pay attention, dig deeper, and contribute ideas.
Swift has also perfected the art of the parasocial relationship, where fans feel a genuine connection to her despite never meeting her. We can foster similar connection by sharing behind-the-scenes industry trends, decision-making processes, or strategic thinking. This sense of insider access could gives membership a feel of exclusivity.
Swift’s community also thrives on member-generated content, with fans creating theories, artwork, and interpretations that expand her brand’s reach. We can create a similar system by enabling members to create and share resources, case studies, and thought leadership within the association’s platform. The hope is to help evolve mailbox members into active contributors.
Building a Self-Sustaining, Indispensable Community
“Culture shock is constructive. It’s the growing pains of a broadening perspective. It just needs to be curated. You set up experiences and then you provide a forum for people to share and compare notes. We call this reflection. On my ideal tour, I’m not the teacher; I’m just the facilitator.”
Rick Steves
Swift has created something remarkable: a community where fans actively promote, defend, and expand her brand without direct compensation. This self-sustaining ecosystem makes her immune to traditional competitive threats because her audience has become emotionally and socially invested in her success.
We can create a similar dynamic by helping members evolve into advocates who actively recruit new members, not because they’re asked to, but because they genuinely believe in the unique value we provide. This requires systems where experienced members naturally mentor newcomers, where member-led special interest groups flourish, and where the association becomes central to our members’ professional identity.
The ultimate goal is to create network effects where we become the undisputed hub for industry decision-making, trend identification, and professional advancement. We become indispensable when membership becomes essential for career success and industry influence and when leaving feels like losing access to a professional ecosystem.
We achieve this by developing multiple interconnected value streams that create switching costs and deep integration into members’ professional lives.
Practical Implementation
“Ideas are easy, implementation is hard. The best startups aren’t the ones with the flashiest pitches, they’re the ones that deliver results. Keep your eye on the ball and prioritize doing over dreaming.”
Guy Kawasaki
Taylor Swift’s strategic principles provide a foundation for transformation; implementing them in an association is a different animal. We hold strong to predictable rhythms and are generally risk-averse and cautious. It would take a systematic, phased approach that respects the unique constraints and opportunities of associations.
Unlike Swift, who can pivot quickly as an individual artist, we need to navigate board governance, member expectations, budget cycles, and established organizational cultures. This deliberate approach can actually strengthen the transformation by ensuring each phase builds sustainable capabilities rather than creating temporary excitement.
The journey from traditional association to Swift-inspired professional community demands both strategic patience and tactical urgency. This takes deep member intelligence, ongoing relationship-building, and systematic engagement that builds and sustains authentic community. Properly implemented, this could result in a strategic reinvention that keeps us agile, relevant, and ready. As each phase builds upon the previous one, we can mirror the kind of indispensable ecosystem that Swift has created in the entertainment world.
Phase 1: Member Research & Understanding
Engage members to learn about their professional needs and challenges
Identify the emotional and practical jobs they’re hiring your association to do
Map member journey and identify engagement gaps
Phase 2: Continuous Engagement System
Develop weekly content calendar with valuable, actionable insights
Create monthly virtual networking or learning opportunities anchored by pathways
Launch quarterly releases of new resources or initiatives
Phase 3: Community Building
Establish member advocacy programs
Create peer mentorship systems
Develop industry influence through thought leadership
Phase 4: Strategic Reinvention
Define 3-5 year strategic eras based on infinite value and program refreshes
Maintain core mission while dramatically evolving delivery methods
Create anticipation and excitement around each transformation
By adopting Swift’s approach, we can transform from transactional service providers into indispensable professional communities that members actively promote and defend. This can make us as central and influential to our industries as Swift is to the music world.
There’s Nothing Like This
“I hope you know that you’ve given me the courage to change.”
Taylor Swift
My respect for Taylor Swift deepens.
Yes, associations are not influential chart toppers or the best selling music artists of all time. But we do have pluck, courage, and stick-to-it-ness. We have the built-in advantage of serving a niche and can utilize our creativity and community-building skills to navigate what’s coming. As I have said repeatedly in this newsletter, our unique value proposition is our community.
This is where we can challenge the status quo, push for interesting change, and make new connections to grow our reach. Testing and applying models from different worlds – like Taylor Swift, or Milk Street, or Peloton – will open us to new possibilities and new opportunities.
Thanks for reading.
I lead the product community; we are a learning community because we believe great relationships help us create the value our members want. Remember, product-led growth fuels connection. Join the product community and flip your destiny.
About the Author
James Young is founder and chief learning officer of the product community®. Jim is an engaging trainer and leading thinker in the worlds of associations, learning communities, and product development. Prior to starting the product community®, Jim served as Chief Learning Officer at both the American College of Chest Physicians and the Society of College and University Planning. Please contact me for a conversation: james@productcommunity.us