2026 Financial Wellness Calendar for Employees: A Benefits Manager's Guide
Your month-by-month roadmap to building a financially confident, healthy, and high-performing workforce in 2026.
January: Foundation Setting & Annual Planning
January sets the tone for your organization’s financial wellness strategy. This is the ideal time to assess employee needs, review last year’s metrics, and establish goals, budgets, and priorities for the year ahead.
- Financial wellness audit quiz: Quickly evaluate your organization’s financial wellness maturity and identify where to focus your 2026 strategy.
- How Do I Use Wellness Dollars?: Learn how to maximize wellness budgets and allocate funds to high-impact financial wellbeing initiatives.
- Bots & Benefits: How AI Will Transform Employee Wellness Forever: Explore how AI will reshape benefits education and enhance the impact of your employee wellbeing programs.
- 2026 Employee Benefits & Wellbeing Trends Playbook: Get a strategic overview of the trends shaping employee wellbeing and how they connect money, mind, culture, and performance.
February: Understanding Your Employee Demographics & Financial Stress Points
February focuses on analyzing demographic differences, identifying key financial stressors, and using employee data to tailor financial wellness programs that meet the diverse needs of your workforce.
- Financial Stress: The Unseen Crisis Affecting Your Workforce Learn how financial stress is impacting employee mental health, productivity, and organizational performance.
- 5 Shocking Facts About Your Employees’ Finances: Uncover data-driven insights about the hidden financial struggles within your workforce to better target program support.
- Deloitte Research Report: Financial Wellbeing in the Workplace: Deloitte’s research highlights how financial stress varies across employee groups and offers clear insights to help HR tailor more inclusive financial wellness strategies.
March: Tax Season Support & Financial Literacy Basics
March is the ideal time to provide tax-related guidance, strengthen employee understanding of pre-tax benefits, and build foundational financial literacy across your organization.
- Can I Withdraw Money from My Health Savings Account? Everything You Need to Know: Help employees confidently navigate HSA rules, qualified expenses, and smart withdrawal strategies during tax season.
- A Practical Guide for Employers: Building a Financially Literate Workforc: Learn how to create effective financial literacy programs that meet employees where they are and drive long-term wellbeing.
- Tax Time Savings & Financial Tips: Federal guidance that helps employees use tax season to build savings, reduce debt, and make smart financial decisions.
April: Retirement Planning Programs & 401(k) Optimization
April is the time to strengthen retirement readiness by maximizing plan participation and supporting employees with tools like auto-enrollment, auto-escalation, and personalized retirement assessments.
- Retirement Readiness: A Must-Have Checklist: Give employees a simple, actionable framework to evaluate their retirement preparedness and identify next steps for long-term financial stability.
- Why Baby Boomers Are Delaying Retirement—and What It Means for Employers: Understand the shifting retirement landscape and its implications for workforce planning, benefits design, and organizational strategy.
- Pete’s Retirement Calculator: Use this straightforward tool and this accompanying blog to help employees estimate retirement needs and make more confident savings decisions.
May: Student Loan Assistance & Debt Management Programs
May focuses on helping employees manage debt by offering student loan support, educating on forgiveness programs, and providing access to personalized debt counseling resources.
- Webinar: Student Loan Repayments
Get up-to-date guidance on repayment changes and equip employees with strategies to manage their student loan obligations effectively. - Student Loan Repayments Are Draining Employees
Learn how student debt is impacting your workforce and why targeted support can significantly improve financial wellbeing and retention. - Student Loan Resources for Borrowers: A trusted federal guide that helps employees understand repayment protections, borrower rights, and options for managing student loan debt.
June: Mid-Year Check-ins & Emergency Savings Programs
June is the ideal moment to assess program effectiveness, promote emergency savings habits, explore employer-sponsored savings options, and support employees facing summer financial pressures.
- How Much Emergency Fund Should You Have?
Give employees clear guidance on determining the right-sized emergency fund to strengthen financial stability and reduce unexpected stress. - Should You Use Savings to Pay Off Your Credit Card Debt?
Help employees make informed decisions by explaining when paying down high-interest debt should take priority over short-term savings. - Helping Employees Set Up an Emergency Fund
Provide HR teams with strategies to encourage consistent savings habits and support employees in building financial resilience. - 3 Ways to Evaluate the Effectiveness of Corporate Wellness Programs
Use this framework to assess mid-year program performance, identify gaps, and refine your financial wellness strategy for stronger outcomes.
July: Healthcare Cost Management & HSA Strategies
July is the perfect time to educate employees on healthcare spending, strengthen HSA utilization, clarify insurance options, and begin preparing for open enrollment communication.
- What is a Health Savings Account?
Give employees a clear, accessible explanation of how HSAs work and why they’re a powerful tool for managing healthcare costs. - Getting the most out of your HSA
Help employees maximize tax advantages, contribution strategies, and long-term savings opportunities through effective HSA usage. - Can I withdraw money from my Health Savings Account?
Equip employees with guidance on qualified expenses, withdrawal rules, and smart decision-making around HSA spending. - Understanding Your Employee Benefit Options: Provide employees with a simplified overview of plan types and coverage choices to support confident open enrollment decisions.
August: Work-Life Balance & Dependent Care Benefits
August is an ideal time to support employees facing back-to-school stress and the combined childcare and eldercare pressures of the sandwich generation.
- Dependent Care Flexible Spending Account – Ultimate Guide: Help employees understand eligible expenses, contribution strategies, and how to maximize tax savings through dependent care FSAs.
- Supporting Caregivers in the Workplace: A Practical Guide for Employers: Use this comprehensive guide to strengthen caregiving support by understanding employee needs, benefit design, and effective implementation strategies.
- Child Care Perks You Can Offer to Your Employees: Explore practical childcare benefit options that reduce employee stress and improve work-life balance for working parents.
September: Open Enrollment Preparation & Benefits Communication.
September focuses on building strong benefits communication strategies, developing decision-support tools, and equipping managers to confidently answer employee questions ahead of open enrollment.
- 8 questions to ask when shopping for a financial wellness benefit: Use this guide to evaluate potential financial wellness partners and ensure you choose solutions that truly meet employee needs.
- Create an Engaging Employee Communication Plan: Learn how to develop clear, targeted benefits messaging that boosts understanding and increases employee engagement.
- Podcast: How to Communicate Employee Benefits and Leverage Them for Engagement
Hear expert insights on simplifying complex benefits information and using communication to strengthen workforce participation
October: Open Enrollment Execution & Total Rewards Education
October is dedicated to running effective enrollment campaigns, helping employees understand their full total rewards package, and providing personalized support as they make key benefits decisions.
- ROI Calculator: Show employees the financial impact of their benefit choices by offering tools that help them visualize long-term value and savings.
- 47 Unique Company Perks to Promote Employee Wellbeing (Without Breaking the Bank): Highlight creative, low-cost perks that enhance your total rewards strategy and help employees see the full value of what your organization offers.
- How to make open enrollment a success and maximize benefits: A practical HR-focused guide on simplifying benefit explanations, increasing participation, and executing a smooth enrollment process.https://www.yourmoneyline.com/roi-calculator
November: Mental Health & Financial Wellness Integration
November highlights the connection between financial stress and mental wellbeing by encouraging HR teams to address financial anxiety, enhance EAP offerings, and support employees through holiday-related financial pressures.
- Addressing the Silent Struggle: Financial Stress and Mental Health: Explore how financial anxiety affects employee mental health and learn strategies to integrate financial support into existing wellbeing programs.
- Financial Stress and Mental Health Statistics: Understand the data behind how financial pressures influence emotional wellbeing, productivity, and workplace engagement.
- Feels Good Is Good: The Impact of Financial Stability on Your Life: Use this short video to show employees how improving financial stability positively affects mental health, stress levels, and overall life satisfaction.
December: Year-End Planning & Program Evaluation
December is dedicated to evaluating program effectiveness, gathering employee feedback, finalizing next year’s initiatives, and celebrating financial wellness wins across your organization.
- What’s the ROI of a Financial Wellness Program?: Use this calculator to quantify the organizational impact of your financial wellness initiatives and guide next year’s strategy.
- Breaking Free: Conquering Money Stress and Regaining Financial Wellness: Share this resource to help employees reflect on their progress, reduce lingering financial stress, and enter the new year with renewed confidence.
- Empowering Employees with Financial Wellness Tools: HR-focused article on how year-end is a strategic moment to optimize benefits, drive engagement, and embed financial wellness programs.
About Your Money Line
We guide employees through all their money challenges, big and small, to ensure they find financial stability and achieve their goals. We do this through our all-in-one solution, which brings together AI-powered software, certified financial guides, and world class education.
Your Money Line is used by hundreds of companies, school districts, and healthcare systems across the U.S. and serves hundreds of thousands of homes. See how Your Money Line can increase employee engagement, decrease turnover, and boost both employee & company financial health today.
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