What do people really want to know about retirement, and what happens when they can get answers based on their actual plans whenever they need them?
Boldin, the financial planning platform with more than 100,000 paying subscribers, shared a new analysis of more than one million conversations with its AI assistant since launching the feature in January. The findings challenge conventional assumptions about retirement planning: among AI users, more people asked about taxes than about outliving their savings; more than half updated their financial plans after an AI conversation; and a majority of conversations take place when financial advisors are off-duty.
Unlike general-purpose AI tools, Boldin's AI assistant works directly with each user's financial plan. It can evaluate the potential impact of decisions, model alternatives, and help people translate financial questions into changes to their long-term plans.
Taxes dominated AI conversations
More than 555,000 Boldin AI conversations this year involved taxes. Among AI users, 73% have discussed taxes, well ahead of outliving their savings (51%). Fewer than 6% have discussed whether Social Security will run out.
Boldin AI users are focused on tax strategy. Among all AI users:
68% of users discussed Roth conversions.
68% discussed managing their tax bracket.
43% discussed required minimum distributions.
Tax concerns intensify after the paycheck stops. Among retirees, two-thirds of conversations involved taxes. Retirees also discussed required minimum distributions far more often than people approaching retirement (24% of conversations vs. 14%).
Tax planning isn’t seasonal, either. Taxes came up in more than half of conversations every month since February, with no spike around April’s filing deadline. Tax conversations also ran deeper, averaging nearly twice as many exchanges as other conversations.
“Most people think of retirement planning as one number: do I have enough? But what they really want to know is how much of their money they’ll get to keep,” said Steve Chen, Founder and Chief Executive Officer at Boldin. “What we're seeing is that people want to understand how to make the most of what they've saved. Taxes can change when you should retire, when you withdraw money, and how much you ultimately have available to spend. These are complicated decisions, but they're also decisions people can understand and manage when they have the right tools.”
More than half of users updated their plans during the AI conversation
Boldin AI users don’t just ask questions. More than half (52%) have updated their retirement plan during a conversation with Boldin AI, making more than 637,000 updates across nearly 280,000 conversations. For many, it’s an ongoing practice: 44% of those users have updated their plan in three or more separate conversations. Because Boldin’s AI works inside each user’s own plan, it answers questions with that person’s real numbers, typically in about 18 seconds.
Users test before they commit. Nearly nine in ten conversations that ended in a plan update included modeling at least one scenario first. Those conversations ran a median of 12 messages, compared with two for other conversations.
“What's most encouraging isn't that people are asking AI financial questions. It's that they're using what they learn. They're testing alternatives, updating their plans, and coming back as their questions and circumstances change. That's what financial planning should be — an ongoing process of understanding your options and making informed decisions,” said Chen.
Fifty-four percent of the AI conversations happen when human advisor offices are closed
More than 568,000 of Boldin’s AI conversations took place when advisor offices across the continental U.S. were closed: on weeknights, early mornings and weekends. Three out of four users chatted with Boldin’s AI outside business hours. On Labor Day alone, more than 3,700 people talked to Boldin AI about their retirement plans. More than half (55%) of conversations that led to a plan update also happened while advisor offices were closed.
“Financial questions don't follow office hours,” said Chen. “People think about retirement at the dinner table, while reviewing their finances over the weekend, or when a news headline raises concerns about their future. When you can get an answer at 10 p.m. on a Sunday, it’s meaningful.”
The Boldin Financial Planner enables anyone to create and manage their own financial plan. Subscribers have access to Boldin AI, a powerful assistant that reads each user’s full financial plan, runs real scenarios, and tells users what the numbers actually mean for them. Boldin’s coaches help users make sure their plan is set up correctly, and professional guidance is available from Boldin Advisor’s team of CERTIFIED FINANCIAL PLANNER® professionals. To learn more or start a free two-week trial, visit https://www.boldin.com/.
Methodology: Based on more than one million Boldin AI conversations started by consumer users between January 7 and October 19, 2026. Percentages of users reflect the share who raised a topic in at least one conversation. “Advisor offices closed” means outside 9 a.m.–5 p.m. on weekdays in every continental U.S. time zone; holidays were not counted as closed. Topics and concerns were identified by AI classification of conversation content.
About Boldin
Boldin is a retirement planning platform on a mission to make high-quality planning accessible to everyone. The platform helps people understand where they stand, explore their options, and make informed decisions about retirement, taxes, Social Security, healthcare, housing, investing, and more. Combining powerful planning technology and personalized AI with education, coaching, community, and access to fiduciary advisors, Boldin gives people the tools and guidance to build a plan they can understand, trust, and act on. Today, more than 100,000 subscribers use Boldin to plan their futures, representing over $247 billion in self-reported assets. Learn more at Boldin.com.
SOURCE: Boldin