Your First Month with Boldin: A Milestone Guide

Getting started with retirement planning can feel like a lot. This guide breaks your first month into 12 clear milestones — each one building on the last — so you always know what to do next and why it matters. You don't need to complete these in a set number of days. Work through them at your own pace. The goal is progress, not perfection.

Monday Welcome to Boldin with Coach Nancy 2:00 EST

Tuesday How to Use Boldin 2:00 EST with Coach Nancy

Tuesday Your Baseline Plan 7:00 with Coach Jennifer EST

Thursday: Scenario Planning 5:00 with Coach Debbie EST

Before your plan can work for you, Boldin needs to know who you are. Under your initial in the upper right corner, open your profile and fill in your name, age, and retirement goal. If you have a spouse or partner, add their information here too.

While you're there, review your plan settings — login and security, Boldin AI preferences, and subscription management. A complete profile means a more accurate plan from day one.

Watch: Get Started Day 1 — Tour

This is your foundation. Use specific, descriptive names for every account — it makes your charts and dropdown menus much easier to read as your plan grows. Link accounts directly using Boldin's connections feature, or enter them manually if you prefer.

Don't forget to enter accounts owned by your spouse or partner separately. Include personal property like vehicles or other assets, and add depreciation where it applies.

Watch: Get Started Day 4 — Assets and Debts

Boldin's investment feature gives you a complete picture of how your portfolio is positioned — and whether it's aligned with where you actually want to be.

Start by adding your investment positions. Enter your holdings across your accounts so Boldin can see exactly what you own, not just the total balance.

Then complete the risk tolerance survey. This short assessment helps Boldin understand your comfort with market risk — and builds your investor profile based on your answers, not assumptions.

Once your profile is set, compare your current allocation to your recommended profile. You'll see at a glance whether your portfolio is positioned too aggressively, too conservatively, or right where it should be — and you'll have the information you need to make confident adjustments.

Add every income source — current salary, self-employment, rental income, and any future income you expect. Include your Social Security estimates and any pensions. If you have a spouse or partner, enter their income sources separately.

Set income growth rates where applicable. The more complete your income picture, the more accurate your projections will be.

Watch: Get Started Day 6 — Income Planning

Your spending plan is your retirement plan. Enter your current monthly expenses by category, then add what you expect to spend in retirement — travel, healthcare, housing, and any large one-time costs like home repairs or helping family members.

Set healthcare costs separately so Boldin can apply the higher medical inflation rate to those expenses.

Watch: Get Started Day 7 — General Recurring Expenses

Watch: Get Started Day 8 — Healthcare Expenses

This is your first real look at your plan. Head to your Overview page and take in the key metrics:

Retirement chance of success tells you how likely your plan is to fund your goals all the way through your lifetime. We consider 80% or higher strong — but if you're not there yet, that's not a verdict. It's a signal telling you where to focus.

Safe spending target is how much you can sustainably spend each year in retirement without running your plan dry. Think of it as your green light number.

Net worth is everything you own minus everything you owe — your financial foundation in one number.

Tax location shows how your assets are distributed across taxable, tax-deferred, and tax-free accounts — and why that matters for what you actually keep.

Lifetime taxes shows the total you're projected to pay over your lifetime. It's one of the most motivating numbers in your plan.

​Retirement Withdrawals helps you understand your withdrawal rate, amount and source account.

Ask Boldin AI: "What does my chance of success tell me about where to focus first?"

Your plan is built on assumptions about inflation, rates of return, and growth. Understanding them — and making sure they reflect your reality — is what makes your plan trustworthy.

From the My Plan menu, open Assumptions and review your general and medical inflation rates, rates of return for each account, and Social Security COLA. If you're not sure which rate of return to use, Boldin's model portfolios take the guesswork out — just select the risk level that fits each account.

Consider adding rate changes to accounts where your allocation will shift as you get closer to or into retirement.

Watch: Get Started Day 2 — Assumptions

Social Security is one of the most important financial decisions you'll make. The Social Security Explorer lets you model different claiming ages side by side — comparing monthly benefit, lifetime income, and breakeven age — so you can find the strategy that fits your plan, not just a generic rule of thumb.

If you have a spouse or partner, model their strategy alongside yours.

Ask Boldin AI: "What's the best Social Security claiming strategy for my plan?"

This is where planning gets powerful. Scenarios let you duplicate your plan and test a decision before you make it — retiring a year earlier, spending more in your 60s, or seeing how a market downturn affects your outlook. Then compare your scenario to your baseline across every metric that matters.

Save the scenarios you want to revisit. Over time, your scenario library becomes a record of the decisions you've explored and the confidence you've built.

Ask Boldin AI: "What are the most important scenarios I should be modeling right now?"

Taxes are one of the biggest expenses in retirement — and one of the most controllable. Start by reviewing your lifetime taxes and tax location. Then open the Roth Conversion Explorer and look at the strategies available to you.

Compare your current tax rate to what you're projected to pay in retirement. That gap is often where the biggest planning opportunities live.

Ask Boldin AI: "Is a Roth conversion strategy right for my situation?"

Open Insights and find your safe spending target. Compare it to your current spending plan. Adjust your budget and watch your plan respond in real time — so you can spend with confidence, not guesswork.

This number isn't a ceiling. It's a compass. Knowing it changes how you make decisions every day.

Ask Boldin AI: "How much can I safely spend in retirement given my current plan?"

The best planners don't go it alone. Boldin offers a full suite of free support — and this is the milestone where you explore it.

Attend a live coaching class. Watch a recorded training session. Read or listen to a Boldin resource on a topic you want to understand better.

If you want personalized guidance, book a session with a Boldin coach. And if you'd like a professional in your corner, Boldin Advisors offers fee-only financial advice from credentialed planners.

A plan you check once is a snapshot. A plan you return to is a strategy.

Schedule a recurring time each month to review your plan. Update your data whenever something changes — a new job, a shift in spending, a change in the market. Run a new scenario whenever you have a big question. Track your net worth and savings rate over time.

The people who get the most out of Boldin aren't the ones who log in once. They're the ones who make it a practice — the way the healthiest people treat fitness. Not a destination. A habit.

Ask Boldin AI: "What's changed in my plan since I started, and what should I focus on next?"

Once you've worked through the milestones, consider these three ways to go deeper:

Coach review session — Book time with a Boldin coach for a personalized review of your plan. Non-advisory, judgment-free, and focused entirely on helping you plan with clarity.

Boldin Advisors discovery session — Ready for professional financial advice? Boldin Advisors connects you with fee-only, fiduciary financial planners who can work alongside your Boldin plan.

Retirement Readiness recorded series — A structured deep-dive into the topics that matter most: income, taxes, Social Security, healthcare, and more. Watch on your own schedule, at your own pace.

Ask Boldin AI anything — it has access to your plan data and deep financial planning knowledge. Or reach out to our support team via the Help Center. We're here every step of the way.