My Plan Keeper + Grace AI

Your retirement plan should listen and talk back.

Grace AI finds the gaps in your retirement plan, runs the math on your options, and builds a plan around your actual life.

Find my retirement gaps

Here's how it works

1

Tell Grace what's on your mind

Pick the retirement question that matters most to you right now.

30 seconds
2

She asks a few follow-up questions

Grace listens, learns your situation, and connects the dots you didn't see.

A few minutes
3

You get a personalized plan

A retirement clarity plan with specific steps, timelines, and dollars saved.

Yours to keep

Conversational AI for Retirement

Built by people who've sat across the table from thousands of retirees.

These are the questions that keep people up at night. Grace helps you work through them, by text, by voice, at your pace.

When should I retire?

See how different ages change your income, benefits, and readiness.

Will my money last?

Understand your income vs. spending picture across decades.

Am I paying too much in taxes?

Learn how withdrawal timing and account types affect your tax bill.

What about healthcare?

Navigate Medicare, coverage gaps, and out-of-pocket costs.

What will I actually do?

Purpose, health, faith, travel, and the life you want to design.

Ask anything, anytime.

New mattress, family money talk, or just venting. Grace is here for all of it.

Tell Grace what's on your mind. She'll build your plan.

Pick the plan that fits where you are. Grace takes it from there.

Most Popular

The big-picture plan

Retirement Clarity Plan

You're within a few years of retiring and the big decisions feel overwhelming. Grace finds the gaps in your timeline and gives you a clear 30-day action plan.

Your money confidence check

Financial Wellness Plan

Grace runs a complete financial health check, finds the weak spots causing you stress, and gives you a prioritized plan to fix what matters first.

Design what comes next

Purpose & Legacy Plan

You've got the money part figured out, but what will you actually do? Grace helps you design a life with purpose, meaning, and legacy beyond the paycheck.

Grace doesn't ask for your Social Security number or account numbers. She helps through conversation, and you choose what to share.

ElevenLabs Grants Recipient Encrypted conversations Your data is never sold

Featured Retirement Guides

Expert articles on the decisions that matter most. Free, fact-checked, updated for 2026.

Creating Your Retirement Paycheck

4% rule, bucket strategy, and guardrails compared.

When to Claim Social Security

Break-even analysis and spousal strategies by age.

Retirement Money Anxiety

Why you can't stop worrying and what actually helps.

Identity Beyond Your Job Title

Who are you when the business card goes away?

Browse our guides →

Voice Conversation

Hear Grace in action

Grace's voice is powered by ElevenLabs to deliver natural, emotionally precise speech.

Talk to Grace by Voice

Questions & Answers

Things people usually ask.

What is Grace AI? +

Grace is a retirement intelligence engine you can talk to whenever you are trying to figure out what comes next. She helps you think through Social Security, Medicare, income, and "will this actually last?" in plain language, not jargon. Grace remembers your numbers and your story so every conversation can pick up right where you left off.

What does my first day look like? +

On your first day, you will get a welcome email with a secure link to create your account. When you log in, Grace introduces herself and starts a short conversation, asking the right questions and recommending a plan journey with her where she will deep dive about your age, income, accounts, and timeline so you do not have to guess what to tell her. In about 10 minutes she will likely uncover a few gaps, turn them into a simple to-do list, and take on the follow-up, reminding you, breaking tasks into smaller steps, and picking up the conversation exactly where you left off next time.

Is Grace giving me financial advice? +

Grace helps you understand your options, spot patterns, and surface gaps, but she does not give personalized investment advice or tell you what to do with your money. She may break down trade-offs, run simple comparisons, and highlight hidden risks to discuss, yet all decisions should be reviewed with a licensed financial professional before you act.

Grace is powered by advanced AI models and can still make significant mistakes, so you should never rely on her alone for decisions that affect your finances.

Is my information private? +

Yes. Your conversations are private to your account. We don't sell your data. You can delete anything you've shared with Grace any time.

What if Grace can't answer something? +

She will tell you honestly and point you to the right resource or professional. Grace does not pretend to know what she does not.

What if I don't like it? +

We believe Grace should improve your retirement journey, help you see real savings or time saved, and feel worth using. If that is not true for you, email us and we will refund you. Our early adopters are founding members with us, and we take that seriously.

How does pricing work? +

The 30-Day Clarity Sprint is $49. You get full access to Grace for 30 days and your personalized plan is saved permanently. The Retirement Co-Pilot is $149/year at founding member pricing for a full year of Grace with proactive check-ins and plan updates as life changes. The annual plan renews each year unless cancelled. No hidden fees either way.

What does Grace help with? +

Grace helps with the logistics and the life side of retirement, not just the big headline questions. She keeps what you share in one place, spots patterns and gaps, and turns complicated transitions into smaller steps you can actually do before, during, and after you stop working.

  • Before retirement (pre-transition) Social Security timing logistics, including your options at 62, full retirement age, and 70, and what each means for monthly cash flow and break-even points.
  • Medicare and healthcare bridge Organizing the steps between employer coverage, COBRA, ACA plans, and Medicare, and flagging deadlines and penalties to talk through with a professional.
  • Account and cash-flow prep Mapping which accounts you have where, what is tax-deferred versus Roth versus taxable, and what moving money around would mean in practice.
  • Around your retirement date (the transition) First-year income logistics, turning "here's your plan" into plain-language steps for which paycheck stops when, which income sources start, and what needs to be set up.
  • Withdrawal order trade-offs Outlining pros and cons of different withdrawal sequences so you can review the approach with your tax or financial professional.
  • Rollover and paperwork Listing the actual tasks between "you should roll that over" and "the money is in the right place," including forms, custodians, and beneficiaries.
  • After you retire (post-transition) Ongoing cash-flow check-ins, comparing planned spending with what is actually happening and surfacing when something looks off so you can adjust.
  • Tax-aware prompts Reminding you when to revisit things like Roth conversions, RMDs, or estimated taxes with a professional and helping you prepare questions.
  • Healthcare and insurance gaps Organizing your coverage and assumptions and highlighting where there may be blind spots to discuss with specialists.
  • Lifestyle, purpose, and routine Daily and weekly routine, helping you sketch what a weekday looks like when you are no longer working full-time, including structure, flexibility, and guardrails on overspending or underspending.
  • Purpose and identity questions Prompting you to think about what you are retiring to, not just what you are retiring from, and where money supports or conflicts with that.
  • Family and legacy conversations Helping you get organized for talks with a spouse, adult children, or other family members about support, inheritance, and practical responsibilities.
  • Between you and your advisor Translating recommendations into tasks, turning an advisor's or planner's suggestions into an ordered checklist with dates, documents, and small steps.
  • Advisor-ready summaries Keeping a running summary of what has changed and drafting a concise "here's what happened since last time" note.
  • Clarifying responsibilities Separating what your advisor, employer, or benefits team handles from what is on your plate so nothing falls through the cracks.

Grace is designed to spot patterns and gaps, break complex decisions into smaller steps, and keep track of what you said matters, but she does not replace a qualified professional. She is powered by advanced AI and can still make significant mistakes, so anything that feels like advice about your investments, taxes, or legal situation should always be confirmed with a licensed financial professional before you act.

Do I need to download an app? +

No. Grace works by phone, text, or the web. Whatever is easiest for you.

Can I cancel any time? +

Yes. One click in your account, any time. Renewal stops right away. If you are on the annual plan and Grace is not the right fit, email us and we will refund you the same way we handle satisfaction: fairly and without runaround.

How does gifting Grace AI work? +

Visit myplankeeper.com/gift/mom, choose the 30-Day Clarity Sprint ($49) or Retirement Co-Pilot ($149/year), enter her email, write a personal message, and pick delivery timing (Mother's Day or today). She gets a welcome email with instant access to Grace. Her account is created automatically.

Our first gift promotion is Mother's Day: use code MOTHER2026 at checkout for $10 off the annual plan ($149 becomes $139). Valid through May 10, 2026. The code applies only to the annual plan. Enter it in the payment form where it says 'Add promotion code.'

Gifting is not only for mom. Grace is for any woman navigating retirement: your sister, a friend, stepmom, grandmother, aunt, tia, abuela, mother-in-law, or anyone ready for clarity on what comes next.

Grace AI retirement planning assistant

Your retirement is more than the numbers. Grace helps you figure out the rest.

Start a Conversation with Grace