Recorded live at MilMoneyCon, financial planner Tyler West shares practical guidance for families facing the rising price of higher education. As an associate at CL Sheldon & Company who works with military and veteran families, and a former soldier, university staffer at the University of Colorado, and college planning entrepreneur, Tyler blends experience from several worlds to challenge standard advice.
His core claim flips the usual script: families often obsess over which savings vehicle to use and skip the important work of asking whether the investment will deliver value. In Tyler’s view, the right path to affordable, meaningful higher education begins at the dinner table and in conversations that map a student’s goals to realistic funding choices.
Begin with goals: the conversation that shapes the plan
Instead of defaulting to an account-first approach, Tyler urges parents to have early, regular talks about careers and academic intent. Most teenagers have a narrow mental menu of career options, usually influenced by parental roles; expanding that menu through exposure to diverse jobs helps students choose programs that lead to clear employment outcomes. Use the reach/match/safety idea as an admissions and affordability tool: think of reach/match/safety not only as selectivity tiers but as cost scenarios. A program that looks prestigious but has poor completion or weak job placement may cost more per outcome than a straightforward in-state route.
Rethinking the 529 and the middle-class squeeze
The 529 plan remains a powerful tax-advantaged tool, but it is not a universal solution. Tyler highlights trade-offs: some states offer a state tax deduction for contributions, yet the plan’s limited investment choices and state-specific rules can reduce flexibility. For example, not every state follows the same rules on rollovers to retirement accounts; families should verify local tax treatment before assuming a smooth transfer. For higher-income households, the difference between accounts becomes less meaningful for financial aid calculations — beyond certain income and asset levels, many families pay close to sticker price regardless of the account used.
Another structural issue Tyler calls the donut hole — families who earn too much to qualify for need-based aid but not enough to comfortably cover sticker price. These households benefit from deliberate planning: consider commuter options, in-state public universities, and dual enrollment arrangements that save tuition and accelerate completion. Importantly, Tyler points to an often-overlooked metric: completion rate. Only 49% of students who start a four-year degree finish one, so choosing a program with higher graduation outcomes can be more valuable than chasing prestige.
Debt rules of thumb and the hazards of parent borrowing
Parent PLUS: an inexpensive-looking loan that can cost a family dearly
Tyler warns that Parent PLUS loans carry unique dangers. While they can cover gaps in college costs, these federal loans are obligations of the parents and can sap household savings and retirement potential if repaid over many years. A key rule he recommends: never borrow more than the student’s expected first-year salary. That simple cap aligns repayment pressure with realistic earning power and reduces the risk that parents will use prime earning years to service debt for a degree that may not yield commensurate returns. Also remember: there is no legal requirement that the student repay Parent PLUS loans, so repayment expectations can strain family relationships.
Graduate school and changing loan landscapes
Graduate school is where student debt can grow substantially, and recent policy shifts matter. Tyler notes new graduate school loan caps taking effect on July 1, and he cautions that professional and advanced degrees are often the biggest contributors to lifetime educational debt. Families should evaluate whether the projected earnings premium of an advanced degree justifies borrowing at higher levels. In many cases, targeted work experience, certificates, or employer tuition benefits provide lower-cost paths to career advancement.
Bottom line: the technical vehicle — whether a 529 plan, savings account, or loan — is a tool, not the strategy. Start with clear conversations about interests, likely career paths, and realistic outcomes. Combine that clarity with conservative borrowing rules, attention to completion rate, and a willingness to use pragmatic cost-savers like in-state options, commuting, or dual enrollment. When families let goals guide funding choices, the money they spend on education is more likely to produce the outcomes they expect.
