Tax-smart retirement income strategies for people 45 and over, so you can stop worrying about money and start living on your terms.
I'm Dre Griggs, CFP® and founder of Obsidian Wisdom. A wealthy retirement isn't about age, it's about separating your time from your money.
Every week I break down:
✔ Retirement withdrawal order & tax strategy
✔ Roth conversions & bracket management
✔ Social Security & Medicare optimization
✔ Building multiple income streams
✔ RMD planning & business owner exits
→ Free Tax-Smart Retirement Stage Assessment:
obsidianwisdom.com/taxquiz
→ Free Retirement Income Fitness Score:
obsidianwisdom.com/incomequiz
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LinkedIn: linkedin.com/in/undregriggs
obsidianwisdom.com | Dre Griggs, CFP®
Wealthy Retirement w/ Dre Griggs, CFP®
We start with two stocks.
Stock A is the winner.
Stock B is the loser.
Stock A was bought for $50,000.
Now it is worth $80,000.
That gives a gain of $30,000.
At 15% capital gains tax, that means paying $4,500.
Stock B was bought for $40,000.
Now it is worth $28,000.
That creates a loss of $12,000.
That does not feel good.
But that loss can help.
Sell the losing stock first.
That recognizes the $12,000 loss.
Then sell the winning stock.
Subtract the loss from the gain.
$30,000 minus $12,000 leaves $18,000.
At 15%, that becomes $2,700.
That lowers the taxes owed.
If losses are greater than gains, you move the rest forward.
You can also take $3,000 as ordinary income.
Then move the rest into the next year.
Ready to optimize your retirement and keep more of what you’ve earned?
Take the Tax-Smart Retirement Stage Assessment and discover your next best move for a tax-efficient future obsidianwisdom.com/asssessment
#retirementplanning #taxplanning
4 days ago (edited) | [YT] | 2
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Wealthy Retirement w/ Dre Griggs, CFP®
Retirement isn't an age, it's a decision. The decision to work for something other than money.
You can work for purpose.
You can work for health.
You can work for enjoyment.
But you are not working for money.
#retirementplanning #financialfreedom
6 days ago (edited) | [YT] | 4
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Wealthy Retirement w/ Dre Griggs, CFP®
A simple way to manage raises is to split them. Half goes toward your future and half toward your life today.
This allows you to enjoy progress now while still building toward financial freedom over time.
#retirementplanning
1 month ago | [YT] | 4
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Wealthy Retirement w/ Dre Griggs, CFP®
Most people start their retirement planning with a 401k.
That worked very well when taxes were significantly higher than they are today.
But today we are at historical lows.
In the 1980s $100,000 could have been taxed around 60 percent.
In 2025 or 26 it might be closer to 22 percent.
Someone working then and retiring now would have paid much less taxes.
The question becomes what taxes will be 20 or 30 years from now.
#retirementplanning #taxplanning #financialeducation
1 month ago | [YT] | 4
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Wealthy Retirement w/ Dre Griggs, CFP®
Life insurance can protect a family business.
Policies on founders or key members provide cash to pay estate taxes or buy out shares.
This prevents forced sales.
A business creates its own economy.
Profits can fuel stock and real estate investments.
It also teaches kids financial literacy and responsibility.
#lifeinsurance #familybusiness #generationalwealth #estateplanning
2 months ago | [YT] | 2
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Wealthy Retirement w/ Dre Griggs, CFP®
Fixed strategies like the 4% rule use the same dollar withdrawal every year. When the market drops, that fixed amount becomes a larger part of your portfolio.
Proportional withdrawals work differently. You withdraw a fixed percentage of your portfolio each year so spending adjusts with the market.
Example. A $1 million portfolio with a 5% withdrawal equals $50,000. If the portfolio drops to $900,000, the withdrawal becomes $45,000. If it grows to $1.2 million, the withdrawal becomes $60,000.
You sell fewer shares in bad years and give yourself raises in good years. This flexibility builds natural guardrails into your plan.
#retirementplanning #retirementincome #investingstrategy #financialplanning #wealthstrategy
2 months ago | [YT] | 2
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Wealthy Retirement w/ Dre Griggs, CFP®
Most people work hard for their money.
Then their bank pays them almost nothing.
That is the problem.
Online banks are paying 10 to 12 times more than traditional banks.
Same money.
Very different results.
This is why I showed you these three options.
Not hype.
Just better use of your cash.
If your money is sitting still, it is falling behind.
Let it work harder.
#highyieldsavings #personalfinance #smartmoney #savingmoney #moneytips #financialeducation #retirementplanning
2 months ago | [YT] | 3
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Wealthy Retirement w/ Dre Griggs, CFP®
For many people, retirement spending starts at about 80 percent of their current salary.
That number makes sense because most people already invest part of their income into a 401k. They are already living on less than 100 percent.
Eighty percent also accounts for the cost of living where you live today. Some people will travel more and spend more. Others will slow down, do projects, and volunteer.
The number depends on lifestyle.
#retirementplanning
2 months ago | [YT] | 5
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Wealthy Retirement w/ Dre Griggs, CFP®
Your money can be replaced.
Your time can’t.
That’s why smart retirement planning isn’t about chasing returns.
It’s about buying back your time while you still can.
Use money wisely. Spend time intentionally.
#retirementplanning
4 months ago | [YT] | 4
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Wealthy Retirement w/ Dre Griggs, CFP®
Are you confident your retirement income can handle inflation, taxes, and market swings?
If you had to stop working tomorrow, would your income keep flowing?
Discover how prepared you really are for the future.
Find out your Retirement Income Fitness Score now incomefitnessscore.scoreapp.com/
4 months ago (edited) | [YT] | 5
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