There are seven retirement stages. Find yours.
Most people feel lost about taxes in retirement. Not because they're uninformed, but because the system is genuinely confusing. Our framework places you in one of seven stages and shows you exactly what to focus on next.
THE PROBLEM
Most People Don’t Need More Money. They Need More Wisdom About the Money They Already Have.
You've saved well. You've done the right things. But somewhere between accumulation and retirement, the rules change and almost no one tells you when, how, or what to do about it.
Time Stays Tied To Money
Most retirement plans focus on saving, not income.
Without a strategy, your paycheck disappears, but your expenses don’t.
Money Slips Away to Taxes
Tax preparation looks backward.
By the time your CPA sees the numbers, the planning windows that mattered most have already closed.
Decisions Happen too Late
Tax-smart retirement requires someone tracking the windows that open and close. Roth conversions, capital gains harvesting, RMD timing.
That’s the gap most people never see.
Wisdom Equals Freedom
THE FRAMEWORK
Seven stages. One clear path.
Every business owner, retired person, or person planning to retire in the future is on this seven-stage journey. The decisions you make at your stage shape the rest of your retirement. The mistakes that cost the most are the ones you don't know you're making, in stages you don't know you're in.
HOW IT WORKS
Three steps. Built around where you are.
We don't make you guess which service is right. The assessment does the sorting, so the next step becomes obvious.
Meet Dre Griggs, CFP®
Founder, Obsidian Wisdom · Tax-Smart Retirement Expert
I built Obsidian Wisdom for one reason. Most people planning for retirement deserve a guide who specializes in the actual hard part of retirement. The tax-smart income decisions that determine whether you keep what you've built or hand a meaningful share of it to the IRS.
The seven-stage framework comes from years of watching where pre-retirees, business owners, and those retired got stuck. What tax windows they missed, and what those misses cost. The work I do now is built around what I learned from those situations.
SERVICES
Four tiers. Each adds one specific capability.
Choose your tier based on your stage and how much help you want. There's no wrong answer. Only the right fit for where you are.
Portfolio Wisdom
Stages 1 - 2
$49/mo
Learn the right financial moves early
Stay in control of your decisions
Clear, practical financial education
Guidance you can actually use
Community that helps you grow
Foundation Wisdom
Stages 1-3 · $100K+
$149/mo
Professionally managed investments
Structured financial guidance
Clear strategy you can follow
Annual review to stay on track
Alignment between goals and actions
Partnered Wisdom
Stages 3 - 6
$499/mo
CFP and CPA working together
Active tax planning year-round
Smart income timing decisions
Long-term strategy fully aligned
Every move supports the next
Concierge Wisdom
Stage 7 · $2M+
$1,999/mo
Family office-style coordination
Advanced tax efficiency strategies
Legacy and wealth transfer planning
High-level decision guidance
Everything aligned with your vision
Not sure which fits? Take the assessment — your stage tells you.
Or start with the 1-Hour Financial Health Check ($250, credits toward a full plan).
REAL STORIES. REAL OUTCOMES.
What tax-smart retirement looks like in practice.
FROM THE WISDOM CENTER.
Tax-smart retirement insights, organized by stage.
START WHERE YOU ARE. GROW AS YOUR NEEDS GROW.
Find your stage in less than 5 minutes.
Your stage tells you what fits. Take the assessment, find out where you are, and the right next step becomes obvious.
BUILD → SHELTER → CONVERT → HARVEST → COORDINATE → PROTECT → TRANSFER
Copyright 2026 Obsidian Wisdom, LLC is a Registered Investment Adviser in the state of Florida