How Organizations Can Close Retirement-Driven Skills Gaps

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Organizations across industries are navigating an unprecedented surge in retirements as baby boomers reach the age of 65. Experienced professionals are leaving the workforce in growing numbers, with many taking decades of institutional knowledge with them.

As long-tenured workers are stepping back from their roles, organizations simultaneously face challenges with responding faster to technological disruption, economic pressure, and changing customer and employee needs. Given these challenges, many companies are navigating significant skills gaps — and realizing traditional workforce strategies may no longer be effective to close these gaps. .  

This wave of retirements gives organizations an opportunity to rethink how talent is sourced and engaged and build a more agile, future-ready workforce model.

Retirement by the numbers 

In the U.S., 4.1 million Americans are turning 65 each year and will continue to do so until at least 2027 in what many experts are calling the “Silver Tsunami.” This means about 11,200 Americans reach retirement age each day, compared to 10,000 per day over the past decade.

The uptick in retirements isn’t only a challenge in the U.S. According to the United Nations, by 2050, one in six people globally will be aged 65 or over, nearly double the number from 2019.

Data published by the World Economic Forum projects that Korea, Japan, Germany, and Italy are most at risk of a shortage of workers due to a decline in working age populations. Japan is the most heavily impacted — taking the country’s working age population in 2000 as a base, this number is projected to be only 60% of its original size by 2050. 

This increasing number of retirements will impact organizations for many years to come. Forward-thinking companies need to develop strategies to address short-term skills gaps and maintain long-term business continuity. 

The modern retirement paradox

In the past, retirement often meant a complete exit from the workforce. However, reaching retirement age is now seen by many as a time of career transition — without necessarily leaving professional life behind. 

Many retirees want to continue working, but on different terms, such as reduced hours, project-based work, advisory roles, or mentorship. Some even have no plans of retiring in the foreseeable future. 

According to a 2024 survey of about 10,000 adults distributed by Transamerica Center for Retirement Studies, 36% of employed workers say they plan to retire at age 70 or older — or have no plans to retire at all. Additionally, 53% plan to continue working in retirement. Among self-employed workers, 56% expect to work at least part time in retirement, while 37% indicated that they dream of doing paid work during retirement.

Data from the Pew Research Center also found that labor force participation among Americans over the age of 65 has nearly doubled since the late 1980s. Several factors likely contribute to this shift, including rising costs of living, longer life expectancy, and an interest in staying mentally or socially engaged — even if this isn’t in a full-time capacity. 

Additional challenges impacting skills gaps 

Retirements aren’t the only factor creating workforce skills gaps. Organizations are also addressing challenges related to disruptors such as AI and other technology-driven change, disengagement, and economic uncertainty. Despite perceived immediate needs, the solution to closing these skills gaps shouldn’t be putting more tasks on existing workers’ plates. 

A 2024 survey of 2,500 workers distributed by The Upwork Research Institute found that 65% of workers reported struggling with employer demands on their productivity. Additionally, 81% of global C-suite leaders indicated that they increased demands on workers in the prior year.

This data points to a reactive mindset — stretching employees thinner instead of building resilient, skill-diverse teams. However, this approach can lead to reduced morale, missed deadlines, turnover, and diminished creativity and innovation.

4 strategies to address skills gaps 

The following strategies can help your organization address skills gaps by thinking beyond traditional methods to retain company knowledge and engage and train workers. 

1. Proactively capture company knowledge

An often overlooked risk of mass retirements is the loss of undocumented knowledge. While roles can be backfilled, professionals who have been in a role for some time typically have additional knowledge about company goals, processes, and processes. 

Institutional knowledge may include familiarity with client communication styles, best practices for team collaboration, how certain tools or systems work most effectively, and expertise about historical projects — such as timeline, budgets and roadblocks.  

To capture and protect this knowledge, companies need to act intentionally and proactively. Steps companies can take include:

• Conduct knowledge audits. Identify roles at risk of near-term retirement — or turnover for other reasons — and assess where critical expertise resides. This helps prioritize which skills, relationships, or insights are most urgent to capture before individuals exit the organization.
• Create documentation frameworks. Establish consistent methods for capturing knowledge internal spreadsheets or playbooks. Standardized frameworks and processes can make key processes and decisions transparent, transferable, and easy to update over time.
• Invest in knowledge-sharing platforms. Use knowledge base tools such as Confluence, Haystack, or Tettra that make it easy to store, search, and access institutional information across teams. Centralized systems such as a company intranet or employee engagement platform reduce duplication, minimize onboarding friction, and prevent expertise from being trapped in silos.
• Encourage storytelling and recorded walkthroughs. Invite longer-tenured employees to share the context behind how things work — via recorded demos, written narratives, informal interviews, or expert-guided standard operating procedures (SOPs). These stories often contain nuanced insights that traditional documentation may miss. 

These efforts help preserve past knowledge while also accelerating onboarding, supporting compliance, and improving decision-making company-wide.

2. Engage freelancers to address immediate skills gaps

When a worker retires, the role may remain unfilled for months, causing critical projects to stall. Even once the role is backfilled, it may take a few additional months for the new team member to be fully onboarded and productive. 

Organizations can’t afford to put high-priority initiatives on pause while waiting to backfill a role. An effective solution is engaging freelancers, which enables organizations to avoid overburdening existing team members, access specialized expertise as needed, and reduce costs compared to making a full-time hire. 

According to the Upwork’s 2025 In-Demand Skills report, 49% of full-time employees surveyed rely on freelancers to help meet their goals and 51% of C-suite executives said their business would struggle to operate without freelance support.

Freelancers are often highly specialized, offering deep experience in focused domains — including supply chain management, data migration, and artificial intelligence engineering. These specialized, in-demand skills enable freelancers to fill urgent gaps without the long ramp-up times often associated with full-time hires.

3. Upskill and reskill internal talent to build resilience

While freelancers address short-term needs, internal capability building is essential for long-term sustainability. Offering upskilling and reskilling opportunities and building a culture of continual learning can help ensure existing team members’ skills remain relevant and support shifting business needs.

A 2025 survey of 937 learning and development and HR professionals distributed by LinkedIn Learning found that 91% of respondents believe continuous learning is more important than ever for career success. Additionally, 88% of respondents are concerned about retention and cite learning opportunities as a key solution.

Prioritizing upskilling, reskilling, and talent development isn’t only beneficial to business continuity. Investing in workers’ growth can also make workers feel more valued, which can drive higher employee engagement and retention. 

Ways for companies to offer upskilling and reskilling to current team members include:

• Access to online learning platforms
• Performance reviews
• Skill and talent assessments
• Stretch assignments and experiential learning
• Mentorship opportunities
• Reimbursements for professional development events and courses

4. Rehire or retain retirees in flexible roles

As the Transamerica Center for Retirement Studies survey shows, many adults approaching retirement age want to continue working in some capacity rather than leaving the workforce entirely. Identifying opportunities to keep existing workers on board in a part-time or flexible capacity can help maintain their institutional knowledge, such as their familiarity with internal systems, people, and processes. 

Ways to retain or reengage retirees may include:

• Project-based consulting. Retirees can offer their expertise on high-stakes initiatives such as audits, sales proposals, customer presentations, or vendor negotiations.
• Part-time advisory roles. In an advisory capacity, retired workers can share their high-level strategy knowledge for priorities such as business planning, compliance reviews, or training design.
• Mentorship programs: Matching retirees with high-potential workers can provide effective succession planning, which can help ensure institutional knowledge gets passed on to workers who will eventually fully take on retirees’ roles. 

This approach is mutually beneficial, as organizations can retain access to trusted expertise, while retirees stay connected and continue to contribute — without committing to a traditional, full-time schedule.

Setting expectations and boundaries when reengaging retired workers is important. Providing clearly defined scopes, timelines, and desired outcomes can support a smooth working relationship without expecting retired workers to contribute in the same capacity as they did in full-time roles. 

Build an agile workforce to close skills gaps

The retirement wave is only one of the many examples of how workforce structures and team member expectations are shifting. How organizations respond will shape their ability to compete, adapt, and succeed for decades to come.

Forward-thinking companies will build agile workforces by moving away from traditional hiring models — such as exclusively hiring full-time, in-house workers — to engaging freelancers and upskilling and reskilling existing team members. 

As you look to address skills gaps at your organization, Upwork is here to help. Search for experienced freelancers with more than 10,000 skills on Talent Marketplace™. Or, upgrade to a Business Plus plan to access the top 1% of freelancers on Upwork and shortlist top talent based on your specific business needs. 

If you’re retired, considering retirement or semi-retirement in the near future, or looking for flexible opportunities to earn income, search for jobs on Upwork that align with your skills and experience. 

Get started today — create an Upwork account or log in to your existing account. 

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