As the largest wealth transfer in history reshapes financial services, advisors have a unique opportunity to build trust with clients across generations.
In my first article in the Generational Practice Management series, I wrote about the unprecedented opportunity for advisors as wealth shifts from Baby Boomers to younger generations.
This second installment focuses on what we at New York Life call the Financial Confidence Gap: the space between where clients and prospects feel they are financially and where they want to be. It’s a challenge that shows up differently for Generation X, Millennials, and Generation Z, but the opportunity for advisors is the same: to bridge that gap with insight, guidance, and trusted advice.
According to a New York Life Wealth Watch survey from September 2024, Baby Boomers (49%) remain the most likely to seek professional financial guidance. By contrast, Millennials (39%) and Gen Xers (24%) rely more heavily on internet searches. Gen Z (32%) also turns to social media, a trend likely to evolve further with the influence of generative AI. These behaviors shape how people make decisions about life annuities as well as life, disability income, and long-term care insurance. Advisors who understand these generational dynamics and how they connect to confidence will be best positioned to help close the gap.
Generation X: Balancing pressures without a plan
Generation X – born between 1965 and 1980 – numbers more than 65 million and stands to inherit significant wealth in the near term. Yet this group faces perhaps the most immediate financial confidence gap. Many are simultaneously supporting aging parents, funding children’s futures, and catching up on their own retirement plans.
The September 2024 Wealth Watch survey shows Gen Xers carry the highest average debt of any generation. Among those nearing retirement, 70% expect to work longer than planned or never retire at all. And while more recent data from 2025 shows nearly half of Americans ages 50 to 65 work with an advisor, 39% of Gen Xers still lack a formal financial strategy. That disconnect between high engagement with money and low confidence in a plan is the gap advisors can help close.
To help Gen Xers build confidence, advisors can start with practical, empathetic questions:
- What pressures are you experiencing from caring for both children and parents?
- If you inherited money tomorrow, would you prioritize debt, retirement, or emergencies?
- What’s your backup plan if you can’t work as long as you expect?
- How are you preparing for your parents’ potential long-term care needs and your own?
- Do you feel confident in your retirement savings strategy?
By uncovering where confidence falters, advisors can provide the structure and reassurance Gen Xers need most.
Millennials: Seeking confidence beyond retirement
Millennials – those born between 1981 and 1996 – are the largest generation in today’s workforce, but their financial confidence has been shaped by the turbulence of the 2008 financial crisis and the COVID- 19 pandemic. Debt remains a major hurdle: in 2025, more than one in four Millennials said credit card debt had the most significant impact on their finances.
Despite that, Millennials are also disciplined savers. Forty percent of adults ages 30 to 49 work with advisors, and many are contributing consistently to retirement accounts. But confidence in their retirement readiness lags: 43% of Millennials expect to delay retirement, often by up to a decade. The top reasons include lack of savings (51%), inflation (46%), and economic uncertainty (32%).
For this generation, the financial confidence gap comes from trying to reconcile competing priorities: paying down debt, saving for retirement, and managing near-term financial stress. Traditional accumulation-focused strategies aren’t always enough. Advisors who can acknowledge these trade-offs and offer flexible planning stand to build long-term trust.
Questions that can spark confident planning conversations include:
- How are you balancing debt repayment with saving for retirement?
- Do you have a plan if inflation continues to outpace wage growth?
- If you expect to work past 65, how are you preparing for income in retirement?
- Beyond retirement savings, have you considered long-term healthcare or caregiving costs.
Millennials want more than products and plans. They want confidence that they can move forward even in uncertain times.
Generation Z: Building confidence early
Born after 1996, Gen Z is just beginning its financial journey, and their financial confidence gap is especially wide. Having grown up through recessions, student debt debates, and pandemic disruptions, Gen Z is cautious and sometimes skeptical about traditional financial advice.
The numbers confirm this. The College Savings Foundation reports that as of 2024, 35% of Gen Z are already using 529 plans for education savings. Thirty-eight percent have shifted money out of equities into safer vehicles such as savings accounts, CDs, or bonds. And 42% say a career change has prompted them to seek financial guidance, while 20% point to buying a home. Yet, like Millennials, 38% already expect to delay retirement.
For Gen Z, the financial confidence gap is less about knowledge and more about trust. Many rely on social media for financial content, and nearly half already bank with digital-only institutions. Advisors who meet them in these digital spaces, provide clear education, and demonstrate transparency can help narrow the gap before it widens further.
Thought-starters for engaging Gen Z include:
- How do you prefer to receive financial advice: online, via social platforms, or in person?
- Which content creators influence your views on money, and why?
- How do you validate financial information you see online?
- What risks are you comfortable with today to build long-term stability?
- What safety nets do you think your generation will need that your parents didn’t?
Helping Gen Z build confidence now can establish loyalty that lasts decades.
Bridging the gap across generations
Whether it’s Gen X struggling with competing financial pressures, Millennials balancing debt and retirement, or Gen Z cautiously entering adulthood, the common thread is clear: no matter the generation, clients feel stuck between today’s financial realities and tomorrow’s goals.
The wealth transfer ahead offers advisors a critical chance to bridge that gap, strengthening relationships and guiding clients across generations toward greater financial security. Advisors who proactively engage these groups — on their terms, with empathy and actionable strategies — can bridge the Financial Confidence Gap. Doing so strengthens client trust, expands practices, and helps families face the future with greater certainty.
Philip E. Caminiti is vice president and head of third-party distribution at New York Life.
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