That question is at the center of a new conversation with Ryan Kittredge, President of ClearPath Financial Partners, who joined Radio Worcester to discuss the delicate balance between generosity and long-term financial security. “The biggest thing is having a game plan so that you can help without putting yourself at risk,” Kittredge said. “It’s kind of like the oxygen mask on the airplane—you need to put yours on first before you can help others.” Kittredge emphasized that the desire to help children—whether with college tuition, a wedding, or a first home—is natural. But without clear boundaries, that support can become unsustainable.

The discussion explored a range of real-world scenarios, from positive milestones like education and homeownership to more difficult situations such as addiction, mental health challenges, or failed business ventures. One example stood out: a client whose daughter, working as a social worker, was living in an apartment costing $3,600 per month. Kittredge used the situation to highlight the risks of open-ended financial support. Instead of continuing to subsidize an unsustainable lifestyle, he suggested a more productive approach—helping her find a more affordable living arrangement. Clear communication, he said, is critical. Families should clearly define whether financial support is a gift or a loan and document the terms to avoid misunderstandings or long-term conflict.

Kittredge acknowledged that these conversations can be uncomfortable but said they can be framed with long-term care in mind. “We’d love to help you,” he said, “but if it puts our own financial plan in jeopardy, we risk a future where we may need support ourselves.” He also outlined tools that can help families provide support more effectively, including tax-advantaged options like Roth IRAs and 529 plans. “Once you determine the support and the need, finding the right vehicles that have flexibility and tax advantages can really make it more bang for the buck,” Kittredge said. Ultimately, the message is one of balance: helping loved ones today should not come at the cost of financial independence tomorrow.

Kittredge explains that these final years are when retirement strategies should become fully mathematical, locking in income streams, tax positioning, and withdrawal sequencing. One client, he recalled, described the distinction simply: “The money that sits in my checking account, I call it my wallet. The money that I put with you guys is the safe.”

The conversation highlights how recent legislative changes have expanded opportunities for late-career savers. Provisions in SECURE Act 2.0 and the “One Big Beautiful Bill Act” increased contribution limits and delayed required minimum distributions, giving near-retirees greater flexibility to manage taxes and income timing. New “super catch-up” rules allow individuals aged 60 to 63 to contribute up to $35,750 annually, while delayed RMDs provide a longer planning runway before taxable withdrawals begin.

Beyond numbers, the episode also explores the psychological challenge many lifelong savers face when transitioning into retirement. Kittredge notes that those who spent decades accumulating wealth often struggle most with the shift to spending it. “It is those super savers that have the hardest time with going the other way with it,” he said.

One of the things Ryan wants people to understand is the importance of Long-term disability insurance. He tells us it is an underutilized form of personal insurance and vital in protecting one’s future earning ability. As Ryan notes “if you can’t afford to take a couple percent maybe of your income to buy that protection, how are you going to take a 70% reduction if you can’t work and you’re sick or injured?” Standard disability coverages, such as Social Security or employer-provided group plans, are often inadequate due to stringent approval processes, low payout caps, unfavorable tax treatment, and restrictive definitions of disability.

He also covers life insurance noting the need for life insurance is greatest for younger individuals with high future earnings potential and significant financial obligations (e.g., mortgages, dependents), and this need typically decreased as they approached retirement and built wealth. Kittridge pointed out the psychological “sunk cost fallacy,” where people hate to give up insurance policies they have paid into for years, even after the need for the coverage has diminished. As Ryan says, “insurance is one of those things that I’ve found at least that people hate to buy, but then once they own it, they really hate to lose it or give it up. It’s this weird psychology, but oftentimes the need for these insurances decrease over time.”

After several years of strong market performance, this can be a good time to rebalance investment portfolios, which may involve strategically realizing some taxable gains in the new tax year. New tax law changes, including an increased State and Local Tax (SALT) deduction cap and a new senior bonus deduction, offer significant planning opportunities.

Ryan advises it is more effective to focus on accomplishing one or two major financial goals for the year rather than trying to tackle a long list of resolutions. “If you set out to do, I don’t know, if you’ve got 10 big goals for this year, you’ll probably accomplish maybe around none of them, right? But if you have two big goals for this year and you write it down and you share it with a trusted advocate…you make that intention known.”

Andrew explained the importance of working with an independent insurance agency, which can shop policies among multiple carriers and advocate for clients when needs change. He also emphasized that the insurance landscape has shifted significantly post-COVID, especially in the auto market where rates have climbed and insurers have become more selective in policy underwriting.

One surprising trend: frequent switching can now negatively impact pricing. Loyalty matters more than it used to.

“It’s always the best time to ask those questions before the claim,” Andrew said. “Because once that claim happens, it’s going to be a problem.”

The conversation focused heavily on coverage strategy:

• Opting for higher deductibles may help keep premiums lower
• The savings can support higher liability limits essential as assets grow
• State minimum coverage often isn’t enough to protect financial well-being

Even a relatively small accident that requires an ambulance and hospital visit can quickly exceed minimum policy limits, putting future earnings and assets at risk.

Both Ryan and Andrew urged listeners to review their policies proactively, ensuring that insurance decisions support long-term financial stability.

An individual’s optimal asset allocation was not a one-size-fits-all formula. It depended heavily on specific factors like other income sources (pensions, Social Security), withdrawal needs, and personal willingness to withstand market fluctuations.

For some early retirees, it was appropriate to be more conservative in the years just before and after retiring, and then increase stock exposure later once other income sources like Social Security began.