Month of Letters Strategic Plan for 2026-2030

Hey there LetterMoians! A quick message from the Month of Letters Admin Board! Over the past year, we’ve crafted a Strategic Plan for LetterMo over the next four years. The plan comes out of a need for a strategic direction for our operations, financial needs (to keep the website running and secure), and to ensure a sustainable growth of the community. The Strategic Plan is a living document, not set in stone. We have committed ourselves to take your feedback on an annual basis through our Annual Participant Survey, which you’ll hear more about later in February!

Introduction

Purpose of the Plan

The LetterMo Strategic Plan is a living and guiding document designed to chart a clear, intentional path for the organisation over the next four years. As LetterMo explores formalisation as a nonprofit and deepens its year-round engagement, this plan serves as a roadmap to align efforts, clarify goals, and ensure the long-term sustainability and vibrancy of the community. It reflects our shared commitment to preserving the joy of handwritten connection while embracing the opportunities of thoughtful growth.

Planning Process

The strategic planning process was shaped by focused conversations with board members, volunteers, and community participants who have kept LetterMo thriving. Input was gathered through one-on-one interviews and a participant survey to ensure that the resulting priorities are rooted in both experience and vision. This inclusive and consultative approach ensures that the plan honours the voices of those who have built and nurtured the community over the years, and invites the whole community to participate in shaping what comes next.

Vision, Mission & Values

Values: Community, Creativity, and Connection

Mission: We foster connection and creativity by encouraging people around the world to write and send personal correspondence throughout February and beyond. This challenge, and its supportive community, celebrate art, joy, and the enduring power of personal correspondence.

Vision: To create a global community where personal correspondence continues to inspire creativity and connection in a digital age.

Current State Overview

Organisational Snapshot

Founded in 2011 by author Mary Robinette Kowal, LetterMo, short for “A Month of Letters,” is a global initiative that invites participants to send a piece of mail every day the postal service runs during February and to respond to every letter received. What began as a personal challenge has blossomed into a vibrant, volunteer-led community that celebrates the art of handwritten correspondence.

Since 2016, a dedicated team of volunteers has managed LetterMo, overseeing its operations and nurturing its growth. Since 2023, a renewed volunteer board meets monthly throughout the year and weekly during January and February to ensure the smooth running of the challenge. Their responsibilities include maintaining the website, moderating forums, engaging with participants, and fostering a welcoming environment for all members.

LetterMo’s online platform serves as the central hub for its activities, offering resources such as planning calendars, letter trackers, and participant badges. The community thrives on its forums and blog, where members share experiences, tips, and stories, further strengthening the bonds formed through letter writing.

As of 2025, LetterMo boasts a membership of approximately 950 individuals worldwide. The organisation continues to explore avenues for growth and sustainability, including the potential incorporation as a nonprofit and the expansion of year-round engagement opportunities.

The Administration Board

Christy Shorey, Chair
@weylyn42
Christy is an academic librarian from Florida who loves to write. She and her partner are owned by 4 cats, all of whom try to help with the letter-writing process as much as possible. Christy has served on the LetterMo Admin board for a couple of years, helping transition the LetterMo to its new website and new leadership. With an eclectic mix of hobbies, Christy is unsure exactly how she has time to do anything.

Adam Yates, Vice-Chair and Director of Technology and Operations
@yatesa01
Adam is a priest in the Anglican Church of Canada, and lives with his husband and their beagle in Vancouver. He enjoys the pace of sending letters and cards by mail and the joy of opening his mailbox to find a letter or postcard waiting there. Adam first started participating with LetterMo in 2018 and became a part of the board in 2023. He tries not to feel too guilty about the stack of letters awaiting his response.

Miriam Fernandez, Treasurer
@mirichan
Since joining LetterMo in 2024, February is Miriam’s favourite month. Passionate about travel, art, and reading, she loves connecting with people and learning from them and their cultures, fountain pen in hand! Currently based in the UK, she works in the financial services industry and drinks way too many cups of tea every day.

Caitlin Córdova, Director of Member Relations
@soupercaitlin
Caitlin has been part of LetterMo since 2022 and assists with member engagement and community connection. She regularly attends Postcrossing meet-ups, stamp and fountain pen shows, and other correspondence-adjacent activities. She is a high school instructional technology coach and enjoys reading, strength training, and dancing with her husband (when not glued to her Kindle or dumbbells).

Ahmed Jaffer, Director of Strategy and Development
@ahmedj25
With a passion for lifelong learning and adventure, Ahmed aims to create transformative experiences both through his travels and by welcoming others into his world. His approach combines personal growth with community service, meaningful connections, and charitable giving. Ahmed’s journey is guided by a dedication to continuous education, cultural exchange, and creating lasting positive change in communities worldwide.

Key Challenges & Opportunities

Administration Board

Engagement Drift: All directors agree that LetterMo’s strength in February doesn’t carry through the rest of the year. Monthly prompts, badges, and themed events are commonly proposed to sustain interest and community bonds.

Volunteer Fragility: Every director cited burnout, confusion, or lack of clarity in their role. Without onboarding materials, defined responsibilities, or task-sharing, volunteer participation is unsustainable.

Structural Consensus: While each director expressed different governance preferences, all support a move toward clearer board roles and succession planning, reflecting a shared desire for accountability and professionalism.

Tech Friction: Website plugins, outdated tools, and inconsistent support systems are cited as barriers. Directors want stable, intuitive tech with support resources like FAQs and tutorials to help users navigate independently.

Communication Demand: Across interviews and the survey, email newsletters were the top-requested format. There’s a clear appetite for centralised, proactive communication—especially for reminders, updates, and storytelling.

Major Findings from the Participant Survey

Engagement Gap: There’s a strong correlation between participation length and willingness to support LetterMo financially; newer members need more convincing about the value proposition.

Leadership-Community Disconnect: Current board members are highly enthusiastic about nonprofit status and governance, but general members are much more hesitant or need education.

Motivation Crisis: The number 1 challenge is staying motivated, which directly correlates with requests for year-round engagement and better communication systems.

International Opportunity: 15% of respondents are international, suggesting untapped growth potential, though they show lower donation willingness (likely due to tax complications and foreign exchange fees).

Volunteer-Donor Pipeline: There’s an 85% correlation between volunteer willingness and donation readiness – people who invest time will invest money. They also want to see structure and accountability for their time and money.

Strategic Priorities

Priority 1: Infrastructure & Governance

Objective: To create a solid foundation for the creation of a legal entity (nonprofit or otherwise).

Key Results

Expand the Board’s Capacity: Recruit and onboard new Board Members as needed while ensuring proper succession planning for future growth.

Policies & Procedures: Create working policies and procedure manuals (finance, volunteer onboarding, moderation, data protection).

Volunteer Roles: Define and codify all volunteer roles and responsibilities in a detailed document.

Incorporation: Complete and approve bylaws and articles of incorporation before registering LetterMo as a legal entity (nonprofit or otherwise) in a single jurisdiction.

Priority 2: Community Growth & Engagement

Objective: To maintain a year-round member engagement plan enabling meaningful yearlong member participation.

Key Results

Social Media Engagement: Increase social media engagement (likes, shares, comments) by 50%.

Email Newsletter: Create and maintain an email newsletter with a 25% subscription rate and a 30% open rate.

Increase Forum Use: Find ways to tangibly increase forum replies on LetterMo.com by 10% annually.

Annual Participant Survey: Gather member feedback and publish an annual community feedback report.

Priority 3: Financial Health & Sustainability

Objective: To create a financial plan which maintains diversified income sources that allow for the upward scalability of the LetterMo movement

Key Results

Financial Planning: Develop and approve a 3-year financial plan and operating budget for 2027-20230.

Financial Reporting: Implement transparent annual financial reporting, published to members by March of each year.

Fundraising: Create an annual February fundraising campaign in addition to product sales.

Finance & Fundraising Committee: Establish and maintain an FFC that makes non-binding recommendations to the LetterMo Board on financial matters.

Implementation

To ensure a detailed and effective implementation of the strategic objectives, the Board of Directors will utilise project and performance management tools, such as Trello or other tracking platforms, to document and monitor progress on each Objective and Key Result (OKR). Each Key Result will be assigned to a specific board member or committee lead, who will be responsible for providing updates. Progress will be reviewed quarterly at board meetings, where committees will present short updates highlighting achievements, challenges, and any adjustments needed. To maintain transparency, a condensed OKR tracker will be included in the Board’s Annual Report, using clear indicators to communicate progress to the community. If a Key Result falls significantly behind schedule or becomes less relevant, the responsible director or committee will propose adjustments, which will be discussed and approved by the Board to ensure accountability and alignment with the mission. In addition, updates will be shared with the wider community through quarterly blog posts, inviting feedback and reinforcing engagement. Finally, at the end of the 2026–2030 strategic cycle, the Board will conduct a full review of all objectives and key results, measuring overall impact, identifying lessons learned, and setting the stage for the next strategic plan.