7 Strategies to Support the Retirement Readiness of Your Employees

Executive Summary

The United States is experiencing the largest workforce retirement wave in its history. In 2025 alone, 4.18 million Americans will reach the traditional retirement age of 65.¹ Yet the vast majority of organizations remain focused on a single dimension of this transition: the financial plan.

This whitepaper presents seven evidence-based strategies for supporting retirement readiness across the dimensions that matter most to employees and organizations alike: purpose, identity, health, social connection, logistical clarity, and knowledge continuity. Each strategy is grounded in peer-reviewed research and national survey data from 2020 through 2026.

The core finding is clear. Financial readiness and life readiness are not the same thing. Companies that treat retirement as a life transition, not just a benefits event, will retain institutional knowledge longer, reduce replacement costs, and build a workforce that transitions on its terms, not by surprise.

The retirement cliff is here.

This is not a forecast. It is a census. The baby boomer generation, 76 million strong, has entered the peak of its retirement window. The numbers are unprecedented in scale and speed.

11,400

Americans are turning 65 every single day in 2025, the highest number on record.

Alliance for Lifetime Income, "Peak 65" Report, 2025 ¹

Between 2024 and 2030, a total of 30.4 million baby boomers will cross the 65 threshold.¹ The Bureau of Labor Statistics projects that this wave will push the U.S. labor force participation rate from 62% down to approximately 58% by the end of the decade.²

The replacement math is staggering. U.S. employers will need to hire more than 240,000 people every month for the next five years simply to fill the roles being vacated by retiring workers.³

30.4M

boomers turning 65
between 2024 and 2030

Ref. 1

240K

monthly hires needed
just to replace retirees

Ref. 3

<30%

of organizations have a
knowledge retention plan

Ref. 4

52%

of U.S. employer firms owned
by people aged 55+

Ref. 5

Yet most organizations are not ready for the knowledge side of this transition. Less than 30% of companies have a knowledge retention plan in place.⁴ Only 29% incorporate retirement forecasts into their knowledge transfer practices, and just 23% train their managers to identify and transfer critical skills before experienced employees walk out the door.⁴

The retirement cliff is not a theoretical risk. It is an operational one, unfolding in every department, every quarter, across every industry.

Financial readiness is not retirement readiness.

The retirement planning industry has spent decades perfecting one dimension of the transition: whether someone has enough money. It has built 401(k) platforms, target-date funds, and Monte Carlo simulations to answer the question of financial viability. That question matters. But it is not the only question, and it may not even be the most important one.

According to the 2025 NFP U.S. Retirement Trend Report, 55% of employees associate retirement planning with negative emotions, reporting that they feel overwhelmed, unprepared, and scared.⁶ Only one in three workers feels confident about achieving a comfortable retirement.⁶

"The savings are often there. The life design is not."

The non-financial dimensions of retirement readiness are well documented in clinical and longitudinal research. They include:

Identity and purpose disruption. A 2020 meta-analysis published in the journal Healthcare, spanning 11 studies and 3,019 retirees, found that 28% of retirees experience clinical depression.⁷ The risk is highest among those who experienced mandatory or forced retirement, and among individuals whose professional identity was deeply tied to their occupational role.⁷

Social isolation and loneliness. Approximately 43% of Americans aged 60 and older report feeling lonely.⁸ One quarter of community-dwelling adults over 65 are classified as socially isolated.⁹ A study from the U.S. Health and Retirement Study found that persistent loneliness is associated with a 57% increased risk of mortality.¹⁰

Health behavior collapse. The National Institute on Aging reports that social isolation significantly increases the risk of dementia (approximately 50% increase), heart disease (29%), and stroke (32%).⁹ Loneliness has been shown to accelerate arterial plaque buildup, promote cancer cell proliferation, and trigger Alzheimer's-linked inflammation in the brain.⁹

28%

of retirees experience
clinical depression

Ref. 7

43%

of adults 60+ report
feeling lonely

Ref. 8

57%

increased mortality risk
from persistent loneliness

Ref. 10

Gender differences compound the problem. A 2013 Canadian longitudinal study found a strong correlation between men's feelings of self-worth through employment and depression after that employment ends.¹¹ Men who retired from identity-central roles were significantly more likely to experience depressive symptoms than women in similar transitions.¹¹

Financial readiness is necessary. It is not sufficient. The organizations that recognize this distinction will be the ones that support their people through a life transition, not just a payroll event.

The cost of doing nothing.

The financial case for retirement readiness support begins with the cost of ignoring it. These are not hypothetical projections. They are documented, measured, and recurring.

The Hidden Cost Cascade

When retirement readiness is ignored, the costs compound.

Financial stress affects 48% of workers' mental health, 43% of family relationships, and 32% of physical wellbeing. These numbers come not from a wellness company but from the NFP 2025 U.S. Retirement Trend Report, one of the most widely cited employer benefits surveys in the industry.⁶

Replacement costs. According to SHRM, replacing a single employee costs between six and nine months of that person's annual salary. For senior or specialized roles, estimates range from 100% to 213% of annual compensation.¹² In 2023, U.S. companies collectively spent nearly $900 billion on employee replacement.¹³ Every unplanned retirement accelerates this cost.

Presenteeism. The cost of employees who are physically present but mentally disengaged is significant and often invisible. An American Productivity Audit found that presenteeism costs the U.S. economy more than $150 billion per year, a figure that is five to ten times higher than the cost of absenteeism.¹⁴ Pre-retirees who are anxious, uncertain, or emotionally checked out are among the highest-risk populations for this phenomenon.

Stress-related productivity loss. Job stress costs American companies more than $300 billion annually in healthcare expenditures, absenteeism, and reduced performance.¹⁵ Financial stress alone causes nearly one million workers to miss work every day.¹⁶

$300B

annual cost of job stress
to U.S. employers

Ref. 15

$150B

annual cost of
presenteeism

Ref. 14

$900B

spent on employee
replacement in 2023

Ref. 13

Knowledge drain. The loss of institutional knowledge compounds every other cost. When experienced employees leave without structured knowledge transfer, organizations lose not just a person but the relationships, context, and operational intuition that took decades to build. Only 29% of organizations incorporate retirement forecasts into knowledge transfer practices.⁴ The result is a pattern of reactive hiring, contractor dependency, and operational disruption that repeats with every departure.

What your employees actually want.

The good news is that employees are telling organizations exactly what they need. The challenge is that most organizations are not listening beyond the 401(k).

Goldman Sachs' 2024 Retirement Survey found that 77% of workers most desire retirement investing and advice from their employers, not just the investment vehicle itself.¹⁷ In their 2025 follow-up, 46% of plan sponsors acknowledged that they now prioritize personalized, holistic retirement planning advice.¹⁸

Three quarters of survey participants said they would save more for retirement if their plan provided digital tools that showed whether they were on track.¹⁸ And 90% said it would be helpful if their employer provided secure income-generating options through their workplace retirement plan.¹⁸

"The era of '401(k) and done' is over. Employees want guidance, not just a plan."

Perhaps the most telling statistic comes from Mercer's 2024 Global Talent Trends study: 84% of employees anticipate continuing to work in some capacity after reaching traditional retirement age, whether by reducing hours, phasing into retirement, or simply playing it by ear.¹⁹ A 2024 WTW survey found that 15% of U.S. workers over 50 are already phasing into retirement, while an additional 19% would like to.²⁰

Employees are not asking for a party and a pension. They are asking for structure, for clarity, for a thoughtful transition that honors the decades they invested. The organizations that provide it will be the ones they remember.

Proprietary Data Intelligence

What People Are Really Anxious About

Grace Intelligence analyzes thousands of real retirement conversations to surface the anxieties that surveys miss. This is not survey data. It is behavioral data extracted from how people actually talk about retirement when no one is scoring them.

34%

Running Out of Money

22%

Healthcare Costs

16%

Loss of Purpose

11%

Social Isolation

Market Volatility

Health Decline

Source: Grace Intelligence Behavioral Anxiety Detection, aggregated across all partner conversations. Updated continuously. See Live Data

The 7 strategies.

The following strategies are drawn from peer-reviewed research, national workforce surveys, and the operational experience of organizations that have moved beyond financial-only retirement support. Each strategy addresses a specific dimension of retirement readiness that traditional benefits programs leave uncovered.

Strategy 01

Start the conversation five years before retirement, not five months.

Most organizations engage with retiring employees reactively. The conversation begins when someone submits a retirement notice, and by that point, the knowledge transfer window has already closed.

Less than 30% of organizations have a knowledge retention plan in place, and only 29% incorporate retirement forecasts into their workforce planning.⁴ This means the majority of companies are caught off guard by retirements that were, in every demographic sense, entirely predictable.

Replacing a senior employee costs 100% to 213% of their annual salary.¹² A five-year engagement window reduces that cost by converting surprise departures into planned transitions with structured handoffs.

What to do

→Identify employees within five years of retirement eligibility using existing benefits data
→Introduce retirement readiness as a recurring conversation topic in annual reviews
→Assign knowledge transfer partners 24 to 36 months before anticipated departure
→Create a pre-retirement engagement timeline with milestones at 60, 36, 18, and 6 months

Strategy 02

Assess readiness beyond the financial plan.

Financial readiness scores measure one dimension of a multi-dimensional transition. They tell you whether someone can afford to stop working. They do not tell you whether that person has a plan for what comes next, whether they have designed their social life outside of work, or whether they have addressed the identity shift that retirement requires.

The evidence for this gap is substantial. A meta-analysis of 3,019 retirees found that 28% experience clinical depression after retirement, with the highest prevalence among those who retired involuntarily or whose identity was deeply tied to their professional role.⁷ Forty-three percent of Americans aged 60 and older report feeling lonely.⁸

Financial readiness without life readiness produces retirees who have the money and not the meaning. Assessing both dimensions gives organizations a complete picture and gives employees the support they actually need.

What to do

→Add life readiness questions to existing retirement planning workshops: purpose, health, social connection, daily structure
→Offer holistic readiness assessments alongside 401(k) reviews
→Use assessment results to personalize pre-retirement support (not one-size-fits-all seminars)
→Track both financial readiness and life readiness scores at the workforce level

Strategy 03

Offer phased retirement pathways.

The cliff-edge model of retirement, where an employee works full-time on Friday and is fully retired on Monday, serves neither the employee nor the organization. It eliminates knowledge transfer time, severs social connections abruptly, and forces an identity transition that most people are not psychologically prepared for.

According to Mercer's 2024 data, 36% of employers globally now offer part-time, flexible, or phased retirement options.¹⁹ A 2024 WTW survey found that 15% of U.S. workers over 50 are already phasing into retirement, while 19% more would like to but lack the option.²⁰

Phased retirement programs serve a dual purpose. For the employee, they provide a gradual identity transition and time to build the life structure that will replace the work structure. For the organization, they extend the knowledge transfer window and convert an abrupt departure into a managed transition.

What to do

→Design 12 to 24 month phased retirement programs with reduced hours, project-based roles, or mentoring mandates
→Formalize mentorship expectations: each phased retiree should be paired with one or two successors
→Ensure benefits continuity during the phased period (a key barrier to adoption)
→Communicate phased options proactively; employees who do not know the option exists cannot request it

Strategy 04

Address the purpose and identity gap proactively.

For many employees, particularly those in senior roles, professional identity is not separate from personal identity. It is personal identity. When that identity disappears on the day of retirement, the psychological consequences are measurable and, in many cases, severe.

Men are especially vulnerable. A Canadian longitudinal study found a strong correlation between men's self-worth through employment and depressive symptoms after employment ends.¹¹ The meta-analysis data confirms that mandatory or forced retirement produces the highest rates of depression, while retirement driven by aspiration and positive motivation produces significantly better outcomes.⁷

The implication for employers is direct: the circumstances surrounding the retirement decision matter as much as the financial readiness behind it. Organizations that help employees build purpose, legacy, and daily structure before they leave are not just being compassionate. They are reducing a measurable health risk.

What to do

→Introduce purpose-planning workshops 12 to 24 months before retirement: values clarification, volunteer matching, legacy projects
→Normalize the conversation about identity transition as part of the retirement planning process
→Connect pre-retirees with retiree alumni who have navigated the transition successfully
→Provide access to coaching or counseling specifically focused on life transition (separate from EAP)

Strategy 05

Integrate mental health and social connection support.

Loneliness after retirement is not a soft issue. It is a clinical one, with health consequences that rival smoking and obesity in severity.

The National Institute on Aging reports that social isolation significantly increases the risk of premature death from all causes, with specific associations including a 50% increased risk of dementia, 29% increased risk of heart disease, and 32% increased risk of stroke.⁹ Persistent loneliness is associated with a 57% increased hazard of mortality.¹⁰

The protective factor is equally clear. People who engage in meaningful, productive activities with others tend to live longer, maintain cognitive function, and report higher life satisfaction.⁹ The employer's role is to build the bridge between the social world of work and the social world that must replace it.

What to do

→Extend EAP (Employee Assistance Program) access for 12 months post-retirement
→Create retiree alumni communities with regular events, both virtual and in-person
→Offer peer cohort groups for pre-retirees navigating the transition together
→Include social connection and loneliness screening in pre-retirement assessments

Strategy 06

Deploy digital tools for personalized retirement guidance.

Generic retirement planning seminars, delivered annually to a room of diverse employees with diverse timelines, have limited effectiveness. Employees are telling organizations this directly.

Three quarters of retirement plan participants say they would save more if their plan provided digital tools that showed whether they are on track.¹⁸ Nearly half (46%) of plan sponsors now prioritize personalized, holistic retirement planning advice over generic education.¹⁸

The opportunity is to move from one-size-fits-all presentations to personalized, continuous guidance powered by technology. Digital tools can assess readiness across multiple dimensions, deliver sequenced decision support (Medicare enrollment windows, Social Security claiming optimization, RMD initiation), and provide ongoing nudges that keep employees engaged in their transition planning.

What to do

→Evaluate AI-powered retirement readiness platforms that assess financial and non-financial dimensions
→Provide personalized checklists and decision-sequencing tools tailored to each employee's timeline
→Integrate retirement guidance into existing benefits portals so employees encounter it naturally
→Ensure any digital tool meets accessibility standards for the 50+ workforce

Strategy 07

Measure retirement readiness as a workforce metric.

Organizations measure employee engagement. They measure turnover rates. They measure wellness program participation. Very few measure retirement readiness, and fewer still use that data to inform workforce planning.

Only 29% of organizations incorporate retirement forecasts into their workforce planning practices.⁴ Only a third add skills gap analysis to those forecasts, and less than a quarter educate managers on identifying and transferring critical skills.⁴

Retirement readiness is not a benefits metric. It is a workforce strategy metric. When tracked at the population level, it enables HR leaders to predict departure timing, identify departments at risk of knowledge drain, and allocate retention and transition investments where they will have the greatest impact.

What to do

→Add retirement readiness to your HR dashboard alongside engagement, retention, and wellness metrics
→Track both financial readiness scores and life readiness indicators (purpose, health, social, logistics)
→Use predictive data to identify high-risk departments and allocate succession planning resources proactively
→Report retirement readiness trends to the executive team quarterly, just as you would turnover or engagement

The business case.

Retirement readiness is not a charitable initiative. It is a business investment with measurable returns across multiple categories.

A 2025 study by Wellhub found that 95% of companies measuring the ROI of corporate wellness programs report positive returns, up from 90% in 2023.²¹ For every dollar invested in employee wellness, companies can expect an average return of $3.27 in reduced healthcare costs.²²

Companies with holistic wellbeing programs (those offering four or more integrated wellness offerings) and high employee engagement were the most likely to see returns of 150% or more on their investment.²¹

Cost Category	Without Readiness Support	With Readiness Support
Employee replacement	100% to 213% of salary per departure ¹²	Reduced through planned transitions and phased retirement
Knowledge transfer	Reactive, incomplete, contractor-dependent	Structured, mentored, 24 to 36 month runway
Pre-retirement presenteeism	5 to 10x higher cost than absenteeism ¹⁴	Reduced through engagement and purpose alignment
Stress-related health costs	$1,685 per employee per year ¹⁵	$3.27 return per $1 invested in wellness ²²
Succession planning	Reactive; 71% without retirement forecasting ⁴	Proactive; data-driven department risk scoring

Ninety percent of employers already believe financial wellness programs are effective.²³ The next step is extending that conviction from financial wellness to retirement readiness across all five dimensions: financial, purpose, health, social, and logistical.

Redefining employer responsibility.

The old model was simple: here is your 401(k), here is your match, good luck. That model was built for a workforce that expected a pension and a gold watch. It was never designed for a generation that will spend 20 to 30 years in retirement and needs a plan for every one of them.

The new model recognizes that retirement is not a payroll event. It is a life transition that begins years before the last day of work and continues years after. It touches identity, health, relationships, daily structure, and financial security simultaneously. Organizations that invest in this broader definition of readiness will retain their most experienced people longer, transfer knowledge more effectively, and build a culture where transitions are supported, not survived.

The seven strategies in this whitepaper are not theoretical recommendations. They are practical, evidence-based interventions that any HR team can implement within existing benefits infrastructure. The research is clear. The demographics are certain. The question for every organization is the same: will you lead this transition, or react to it?

Ready to close the Life Readiness Gap?

My Plan Keeper helps organizations assess and close the retirement readiness gap across their workforce. Our platform, powered by Grace Intelligence, provides personalized retirement readiness assessments, decision-sequencing tools, and population-level analytics for HR teams, financial advisors, and benefits platforms.

Talk to Grace Contact Us

Next in Series

The Growing Crisis: How Delayed Retirement is Costing Your Company $50,000 Per Employee

A data-driven analysis with 47 cited research findings across workforce aging, financial stress, brain drain, and behavioral science. Includes the RAP (Retiree Assistance Program) model for turning retirement from a termination event into a managed transition.

Read the whitepaper →

References

[1]Alliance for Lifetime Income & Protected Income. (2025). "The U.S. Has Reached the Peak of Peak 65." protectedincome.org
[2]Bureau of Labor Statistics. (2024). Labor Force Participation Rate Projections, 2024-2030. bls.gov
[3]ManpowerGroup. (2025). "Will Baby Boomers Break the Workforce? Preparing for a Long-Term Talent Shortage." manpower.com
[4]Risk and Resilience Hub. (2024). "Succession Planning and the Aging Workforce." riskandresiliencehub.com
[5]Gallup. (2024). "Most Small-Business Owners Lack a Succession Plan." news.gallup.com
[6]NFP. (2025). "2025 NFP U.S. Retirement Trend Report." nfp.com
[7]Arias-de la Torre, J., et al. (2020). "Prevalence of Depression in Retirees: A Meta-Analysis." Healthcare, 8(3), 321. PMC7551681
[8]National Academies of Sciences, Engineering, and Medicine. (2020). "Social Isolation and Loneliness in Older Adults." PMC7437541
[9]National Institute on Aging. (2021). "Social Isolation, Loneliness in Older People Pose Health Risks." nia.nih.gov
[10]Shiovitz-Ezra, S., & Ayalon, L. (2021). "Associations of Loneliness and Social Isolation With Health Span and Life Span in the U.S. Health and Retirement Study." Annals of Behavioral Medicine. PMC8514074
[11]Hershey, D. A., & Henkens, K. (2013). Impact of retirement transition on depressive symptoms: Gender differences in a Canadian longitudinal study. PMC9288177
[12]Society for Human Resource Management (SHRM). (2024). "Employee Replacement Costs." salary.com
[13]Gallup / Apollo Technical. (2024). "Employee Retention Statistics." apollotechnical.com
[14]Stewart, W. F., et al. American Productivity Audit. Cited in Enhesa (2024). "The Price of Productivity Loss." enhesa.com
[15]University of Massachusetts Lowell, Center for the Promotion of Health in the New England Workplace. (2024). "Financial Costs of Job Stress." uml.edu
[16]The American Institute of Stress. (2024). "Workplace Stress Statistics." stress.org
[17]Goldman Sachs Asset Management. (2024). "2024 Retirement Survey and Insights Report." goldmansachs.com
[18]Goldman Sachs Asset Management. (2025). "Retirement Survey and Insights Report 2025." am.gs.com
[19]Mercer. (2024). "Global Talent Trends Study: Reimagining Work and Retirement." mercer.com
[20]Willis Towers Watson (WTW). (2024). Survey on phased retirement among U.S. workers over 50. asppa-net.org
[21]Wellhub. (2025). "Study Reveals Strong Return on Investment for Corporate Wellness Programs." wellhub.com
[22]Baicker, K., Cutler, D., & Song, Z. Harvard University meta-analysis of wellness program ROI. Cited in Wellhub (2024). wellhub.com
[23]ASPPA. (2024). "Financial Wellness: An Ingredient in Retirement Readiness." asppa-net.org

Disclaimer: This white paper is published for informational and educational purposes. It does not constitute financial, legal, tax, or investment advice. Statistical figures cited represent publicly available research data and are provided for illustrative context. Organizations should consult qualified professionals for guidance specific to their workforce. © 2026 My Plan Keeper. All rights reserved.

261 N University Dr S-500, Plantation FL 33324