The Next Era of Strategic Giving: Pairing Tax Strategy With Accountable Workforce Mobility
- kkelley271
- Jul 8
- 11 min read
A collaborative perspective from Tax Solve, pepelwerk, and the Free to Work and Learn Fund on connecting strategic tax review, charitable planning, and measurable education-to-employment outcomes.
Philanthropy is entering a new accountability era, and we believe donors should not have to choose between thoughtful tax planning and measurable social impact. Donors want to understand whether their capital is helping people move from uncertainty to capability, from learning to work, and from temporary support to durable economic participation. That requires collaboration between advisors who help donors evaluate the financial and tax context before capital is deployed and partners who help measure whether that capital produces meaningful progress after the gift is made.
For donors and advisors evaluating year-end giving, donor-advised funds, foundation grants, or prior-year tax patterns, the strategic question is no longer only “How much should we give?” It is “How can we work together to use tax insight and impact infrastructure so charitable capital is deployed with purpose and measured for progress?”
Executive Perspective
The charitable sector has more tools, more capital, and more urgency than ever. In 2024, Americans gave an estimated $592.5 billion to charity, with roughly 14 percent directed to education and 14 percent to human services—about $83 billion to each category, or approximately $166 billion combined across two areas closely tied to learning, employment, and economic mobility. At the same time, governments continue to allocate hundreds of billions more through education, workforce, unemployment, and social-support systems. The issue is not that the country lacks capital for education and employment. The issue is that too much of that capital is deployed through systems that cannot clearly show whether people actually moved forward.
Consider the math. If the estimated $166 billion in annual charitable giving to education and human services were treated as deployable human-capital funding, it would represent about $41,500 for each of roughly 4 million U.S. eighth graders in a single grade cohort. If the same pool were viewed against the approximately 7 million unemployed people reported at the end of 2024, it would represent about $23,700 per unemployed person.
Those figures are not a recommendation to redistribute funds in that way; they are a leadership lens. They show that the country already has enough capital flowing through education- and employment-adjacent systems to fund meaningful pathways—if the dollars are organized around outcomes, not just institutions, programs, or annual reports.
The donor math also matters. A donor in a 37 percent federal marginal tax bracket who contributes $100,000 to a qualified charitable vehicle may reduce federal income tax by up to approximately $37,000, depending on itemization, AGI limits, asset type, state taxes, and the donor’s full tax situation. If the contribution is made with appreciated long-term assets, the donor may also avoid capital gains tax that could have applied if the asset had been sold first. That means the same capital can potentially create three forms of value: a tax-planning benefit for the donor, deployable charitable capital for the community, and measurable progress for the people served.
This is also why trust matters. National giving data continues to show generosity, but participation and confidence have become harder to sustain when donors cannot see whether their giving produced durable change. Many donors are not giving less because they care less; they are hesitating because they do not trust vague impact claims, delayed reports, or disconnected program metrics. In workforce development, that skepticism is rational. Enrollment is not employment. Attendance is not advancement. A certificate is not economic mobility unless it connects to real capability, demand, and opportunity.
A donor-advised fund can help donors time and structure giving more strategically. In this collaboration, Tax Solve provides the strategic tax review that helps donors evaluate prior-year returns, income patterns, appreciated assets, and planning opportunities before a charitable decision is made. pepelwerk and the Free to Work and Learn Fund help connect charitable capital to measurable workforce and education outcomes after the decision is made. Together, we offer donors a more complete path: review the tax opportunity, structure the giving strategy, and deploy capital through an accountable workforce-mobility model.
Donor-Advised Funds Are Not Just Tax Tools. They Are Timing Tools.
A donor-advised fund is often described as a charitable savings account. A donor contributes cash, appreciated stock, real estate, or other eligible assets to the fund, may receive an immediate charitable deduction, and then recommends grants to qualified charities over time. In plain language, the tax benefit can happen when the donor contributes to the fund, while the giving can happen on the donor’s schedule.
For high-income individuals, business owners, families, foundations, and donor-advised fund holders, the strategy may be especially useful in years with higher income, liquidity events, appreciated assets, or a desire to bunch several years of giving into one tax year. The result can be a more intentional charitable plan: give when the tax timing is strategic, grant when the community need is clear, and use the remaining time to decide where the dollars can create measurable outcomes.
The Tax Strategy Is Only the Beginning
Immediate charitable deduction: A donor may be able to deduct the contribution in the year it is made, subject to applicable limits and the donor’s specific tax situation.
Appreciated asset planning: Contributing long-term appreciated assets directly to a donor-advised fund may allow the donor to avoid capital gains tax that could apply if the asset were sold first.
Bunching strategy: A donor may contribute multiple years of planned giving in one year to potentially exceed the standard deduction threshold, while still recommending grants over time.
Tax-free growth inside the fund: Assets held in the donor-advised fund may be invested and grow tax-free before grants are distributed to qualified charities.
These strategies are not one-size-fits-all. That is why Tax Solve’s strategic review of prior-year tax returns can be useful. Looking backward can reveal giving patterns, missed planning opportunities, appreciated asset exposure, income spikes, carryforward issues, and whether a donor-advised fund strategy should be considered as part of a broader charitable and tax plan.
The Real Donor Question: Did It Work?
Most serious donors are not skeptical because they lack generosity. They are skeptical because they have seen too many initiatives overpromise, under-measure, or report outcomes long after the opportunity to improve has passed. They want to know whether capital reached the intended people, whether it funded the right intervention, and whether the work produced measurable movement.
That is the leadership opportunity we see together. The next generation of philanthropy should not ask donors to choose between tax efficiency and accountability. It should give them a coordinated model that supports both: strategic tax review on the front end through Tax Solve and measurable workforce progress on the back end through pepelwerk and the Free to Work and Learn Fund.
Why This Matters Financially
Charitable capital is large, but it is not unlimited. Recent national giving data estimates U.S. charitable giving at roughly $592.5 billion in 2024, with foundation giving above $100 billion and donor-advised fund assets exceeding $327 billion. Those dollars represent enormous potential, but potential is not the same as impact. The financial question is not simply how much money is available; it is whether each dollar is deployed through a system that can prove progress, reduce duplication, and connect funding to measurable outcomes.
When strategic tax review and accountable workforce deployment are connected, donors can improve the return on philanthropic capital. Through this collaborative model, a donor can evaluate the tax-planning context, support learning, work readiness, access to opportunity, and career advancement, and gain visibility into participation, progress, completion, placement, and continued engagement. That means fewer blind grants, fewer fragmented reports, and stronger evidence that dollars are moving people toward self-sufficiency.
Why This Matters Economically
The labor market is changing faster than traditional education and workforce systems can respond. Artificial intelligence is reshaping career pathways, particularly for workers without four-year degrees and for entry-level roles that once served as stepping stones into higher-wage work. The World Economic Forum’s 2025 Future of Jobs research estimates that 39 percent of workers’ core skills will change by 2030, while AI, big data, networks, cybersecurity, and technological literacy are among the fastest-growing skill areas. If philanthropic capital continues to fund isolated programs without a connected accountability system, communities risk spending more while helping fewer people reach durable economic mobility.
pepelwerk is designed to help funders support a more adaptive workforce system. It connects people to career intelligence, education options, work opportunities, and measurable next steps. For donors, the economic value is clear: better capital deployment can help reduce underemployment, improve talent alignment, strengthen local economies, and lessen long-term dependence on social support systems.
Why Education and Work Must Be Aligned
For too long, education and employment have operated as separate systems. People are told to choose a school, select a major, borrow or spend money, complete a credential, and then hope the labor market rewards the decision. That approach assumes the job market will wait for the education system to catch up. It does not.
Funders have an opportunity to help create a freer, more accountable market for education and learning resources. In that market, learning providers compete to deliver relevant, adaptive, results-oriented options; individuals can access the learning they need when they need it; and employers can signal what skills, capabilities, and experience are actually required for available work. The goal is not to eliminate traditional education. The goal is to stop treating college-first as the only default path and start funding learning that is aligned to real employment demand.
pepelwerk supports this shift by connecting people, learning resources, work opportunities, and measurable progress in one accountable system. That makes it possible for donors to fund proactive employment support, not just tuition or program participation. It also gives funders a way to support continuous learning as the labor market changes rather than waiting until people become unemployed, underemployed, or disconnected.
The Problem With the Traditional College-First Plan
The traditional college-first plan is no longer a reliable enough workforce strategy on its own. The Federal Reserve Bank of New York reports that labor market conditions for recent college graduates remained challenging at the start of 2026, with unemployment around 5.7 percent and underemployment around 41.5 percent. In practical terms, roughly four out of ten recent graduates were working in jobs that typically do not require a college degree.
The trend is important for funders because it shows that degree completion alone does not guarantee employment alignment. The Federal Reserve Bank of St. Louis found that young college graduates experienced a larger increase in unemployment between 2019 and 2025 than older college graduates or young workers without a bachelor’s degree. That suggests the early-career labor market is becoming harder to enter even for people who followed the conventional education path.
This does not mean college has no value. It means the funding model must change. If donors continue to fund education without requiring alignment to jobs, skills, employer demand, and measurable progress, they may unintentionally subsidize pathways that leave graduates underemployed, indebted, delayed, or disconnected from the work the economy actually needs.
From Tuition Support to Proactive Employment Alignment
College-First Funding Model | pepelwerk-Aligned Funding Model |
Funds education first and employment later. | Funds learning and employment support together from the start. |
Assumes a credential will translate into opportunity. | Connects learning decisions to current and emerging labor market demand. |
Measures enrollment, completion, and institutional outputs. | Measures progress toward work readiness, job alignment, and economic movement. |
Limits choice to approved programs or legacy institutions. | Creates access to a broader free market of education, training, coaching, and learning resources. |
Responds after people become unemployed or underemployed. | Funds proactive support before people fall behind. |
Often separates the learner, school, employer, funder, and data. | Connects the person, learning path, work opportunity, funder, and accountability system. |
For donors, this is the difference between paying for hope and funding a system that can adapt. A free market of learning resources allows capital to flow toward what works: shorter pathways where appropriate, alternative credentials where valuable, coaching when needed, employer-aligned skill development, and continuous learning options that can change as jobs change.
Why This Matters Socially
Employment and education are not only economic issues; they are dignity issues. When people cannot see a path to work, learning, income, or advancement, families and communities feel the strain. Donors who fund access to career mobility are helping people build agency, confidence, and participation in the economy.
The social value of pepelwerk is that it helps replace charity-as-rescue with capital-as-access. The goal is not to label people as needy; it is to equip people with the tools, information, and opportunities they need to move forward. That distinction matters to donors who want to preserve dignity while still addressing inequality, disconnection, and opportunity gaps.
What pepelwerk Gives Funders That Traditional Grantmaking Often Does Not
Traditional Funding Approach | pepelwerk / Free to Work and Learn Fund Approach |
Funds programs and waits for reports. | Funds access and tracks movement through education, work readiness, and employment pathways. |
Measures activity, enrollment, or participation. | Measures progress, completion, alignment, and movement toward economic outcomes. |
Relies on fragmented vendors and disconnected data. | Uses a connected marketplace and accountability system. |
Supports one intervention at a time. | Supports a person’s ongoing journey across learning, work, and advancement. |
May fund what sounds compelling. | Funds what can be tracked, verified, and improved over time. |
What Decision Makers Get in Return
Confidence: A clearer view of whether funded individuals are progressing toward work and learning outcomes.
Accountability: A system that helps connect funding to participation, completion, matching, and movement.
Efficiency: Reduced duplication across disconnected programs and vendors.
Strategic visibility: Better information for boards, trustees, donor advisors, and family decision makers.
Reputational strength: A credible story of measurable impact in workforce, education, and economic mobility.
Legacy: A way to fund systems-level change rather than short-term charity alone.
The 20-Year Choice: Deploy Capital Differently or Watch the Gap Widen
Twenty years from now, the difference between accountable capital deployment and traditional disconnected giving could define whether communities adapt to artificial intelligence or fall further behind. AI will continue to change job tasks, eliminate some entry-level pathways, create new occupations, and reward people who can continuously learn and reposition themselves. Education systems that remain slow, expensive, and disconnected from labor market reality will leave many people unprepared for work that did not exist when they entered school.
If capital is not deployed differently, the likely future is one of wider inequality, more stranded workers, more expensive remediation, and more communities competing for fewer pathways into stable income. Donors may spend more money responding to symptoms: unemployment, underemployment, disconnected youth, adult retraining gaps, and social instability.
If capital is deployed through a more accountable workforce and education marketplace, the future can look different. Funders can help people identify viable careers sooner, access relevant learning faster, connect with employers more efficiently, and move through measurable pathways over time. In that world, philanthropic dollars are not merely spent; they become catalytic capital for economic participation because they are used to align education, learning, and employment before people are left behind.
Why We Are Working Together
We are working together because donors need more than a compelling cause and more than a tax idea. They need a coordinated path from financial review to charitable deployment to measurable impact. Tax Solve brings the tax-planning lens by helping donors and advisors review prior-year tax returns, identify planning opportunities, and evaluate whether tools such as donor-advised funds may fit the donor’s broader strategy. pepelwerk brings the workforce-mobility infrastructure by helping funders connect charitable capital to learning, work readiness, employment alignment, and progress tracking. The Free to Work and Learn Fund provides the charitable pathway for donors who want their capital to support people directly while maintaining visibility into how that support moves individuals forward.
Our shared goal is to help donors move from isolated decisions to coordinated strategy. Through Tax Solve, donors can begin with a clearer understanding of the tax and planning context. Through pepelwerk and the Free to Work and Learn Fund, donors can move from asking “Did we give?” to asking “Did people move?” Together, we believe that is the accountability shift philanthropy needs.
Suggested Donor Message
Your capital can do more than fund good work. It can be reviewed strategically, deployed intentionally, and measured responsibly. Tax Solve helps donors understand whether their tax history, appreciated assets, and giving patterns point to a more strategic charitable planning opportunity. pepelwerk and the Free to Work and Learn Fund help turn that charitable capital into access for people to find work, learn what matters, and move toward economic independence. Together, we help donors pair smart planning with a measurable system of accountability for the future of employment and education.
An Invitation to Think Differently Before the Next Giving Decision
For foundations, family offices, donor-advised fund holders, business owners, and major donors, the next step is not simply to give more. It is to evaluate whether prior giving patterns, prior-year tax returns, appreciated assets, foundation goals, and workforce-impact priorities are aligned. Register for the webinar to learn how Tax Solve, pepelwerk, and the Free to Work and Learn Fund are approaching this work together. Donors may begin with a strategic tax review through Tax Solve to evaluate whether a donor-advised fund or related charitable strategy may fit their situation. If workforce mobility is part of the giving priority, donors can then explore how pepelwerk and the Free to Work and Learn Fund can help deploy charitable capital into measurable education-to-employment progress.
This article is provided for educational purposes only and does not constitute legal, tax, investment, or accounting advice. Tax Solve provides strategic tax review services, and donors should consult their own tax, legal, and financial advisors before implementing any charitable giving strategy. pepelwerk and the Free to Work and Learn Fund support workforce-mobility and impact-accountability objectives and do not provide tax, legal, investment, or accounting advice. The organizations’ work together is intended to help donors evaluate planning opportunities and consider accountable pathways for charitable impact.