
The Retirement Planning Question 99% Of Advisors Never Ask
Many financial advisors will give you a portfolio… Not a plan.
60% stocks. 40% bonds.
Congratulations. You're now retired...
Here's The Problem
The problem is, money has no idea what it's supposed to do.
Most retirement plans are just asset allocation.
Your advisor tells you where your money sits. Growth bucket. Income bucket. Safe bucket. They never tell you what your money does.
That's not a plan. That's a spreadsheet with predictions.
And here's what happens when your money has no purpose:
You don't know if you can take that trip to Europe.
You don't know if spending $50K this year hurts your retirement at 85.
You don't know which dollars are for living and which are for legacy.
You're guessing. Hoping. Anxious.
After 40 years of building wealth, you're still uncertain about what you can actually do with it.
The Distinction Nobody Explains
There are two types of retirement planning:
Cookie Cutter: "Here's your diversified portfolio. 60% equities, 40% bonds. Rebalance annually. Hope it lasts."
Intentional: "This $500K funds your annual travel for the next 20 years. This $2M generates your guaranteed lifestyle income. This $1M compounds tax-deferred and creates a tax-free legacy for your children."
One tells you WHERE your money is.
The other tells you WHAT your money DOES.
See the difference?
Cookie cutter planning assigns financial function only. "This is in stocks. This is in bonds."
Intentional planning assigns function AND purpose. "This money grows through equities and funds your adventure. This money protects and generates your daily income. This money compounds and secures your family's future."
Every dollar has two jobs:
1. How it works (financial function)
2. What it enables (life purpose)
Why This Actually Matters
When your money has no assigned purpose, you make every spending decision in a vacuum.
"Can we afford this vacation?"
"Should we help the kids with the down payment?"
"Is it safe to spend $10K on that thing we've always wanted?"
You have $5 million but you're still asking "can we afford this?" because nobody told you what each dollar is for.
That's not wealth. That's a prison with a bigger balance.
Here's what changes with intentional planning:
You know your travel fund is $500K growing at 7%. You can spend $35K per year on travel forever without touching principal.
You know your lifestyle income is $120K annually from guaranteed sources. Market crashes don't touch it.
You know your legacy fund is growing tax-deferred and will transfer tax-free to your children. Spending on yourself doesn't steal from them.
Every decision has clarity because every dollar has purpose.

How Intentional Planning Actually Works
Let's break down a real example.
You have $5M in retirement assets.
Cookie Cutter Approach:
$3M in stock index funds
$2M in bond funds
Withdraw 4% annually
Hope it lasts 30 years
Spend conservatively to be safe
Intentional Approach:
Replace It ($2M): Guaranteed income of $120K per year from optimized income sources. This covers your baseline lifestyle. Market volatility doesn't touch it. You never worry about running out.
Protect It ($500K): Tax mitigation strategies save you $50K annually. Those savings don't disappear—they redirect into other parts of the plan. Risk management frees capital instead of just reducing loss.
Grow It ($1.5M): This money compounds uninterrupted at 7-8% annually. You never touch it. In 20 years it's $6M+. You're spending and your wealth is still growing.
Leave It ($1M): Tax-deferred growth transferred tax-free to children through optimized life insurance. They receive the full amount with zero tax burden. This is locked in—your legacy is secure regardless of what you spend.
Enjoy It (Everything Else): With income replaced, risks mitigated, growth compounding, and legacy secured, you have complete permission to spend without guilt. The math proves you can live fully without running out.
See how every dollar has both function and purpose?
The $2M isn't just "bonds for safety." It's your lifestyle freedom, guaranteed.
The $1.5M isn't just "stocks for growth." It's proof that wealth increases while you spend. The $1M isn't just "life insurance." It's your children's secured inheritance that frees you to enjoy now.
The Five Pillars Work Together
Here's what most people miss:
The pillars aren't separate goals. They're an integrated system.
Replace It creates the foundation. Guaranteed income means you can't run out. That removes fear.
Protect It doesn't just reduce risk—it creates fuel. Tax savings of $50K per year redirect into growth and legacy instead of disappearing to the IRS.
Grow It enables everything else. When $1.5M compounds to $6M while you're spending $120K annually, you prove that enjoyment doesn't deplete wealth.
Leave It removes guilt. When legacy is secured through optimized life insurance, spending on yourself doesn't mean stealing from your children. You can gift while alive and watch them benefit instead of waiting until you're gone.
Enjoy It becomes possible only when the first four are in place. You need proof that income is replaced, risks are mitigated, wealth is growing, and legacy is secured before you can give yourself permission to truly live without anxiety.
Each pillar makes the others stronger.
Protection creates fuel for growth.
Growth enables spending without depleting legacy.
Secured legacy removes guilt from enjoyment.
Guaranteed income provides foundation for everything.
That's the difference between a checklist and a system.
The Side-By-Side Reality
Let me show you what this looks like in practice.
Starting Point (Both Plans): $5M in retirement assets $120K annual lifestyle need 30-year retirement horizon
Cookie Cutter Plan: Year 1: $5M portfolio, withdraw $200K (4% rule) Year 10: $4.2M remaining (after market volatility and withdrawals) Year 20: $2.8M remaining (anxiety increasing) Year 30: $800K remaining (if markets cooperate)
Outcome: Constant worry about running out. Spending conservatively. Checking portfolio daily. Stress for 30 years.
Intentional Plan: Year 1: $5M allocated across five pillars, $120K guaranteed income, $50K travel fund from growth returns Year 10: $6.2M total assets (growth outpaced spending), $120K income still guaranteed, zero anxiety Year 20: $8.1M total assets (compound growth continued), spent $2.4M on lifestyle, wealth still increased Year 30: $10M+ total assets, enjoyed three decades fully, left larger legacy than expected
Outcome: Certainty. Freedom. Wealth grew while living fully. Zero regret.
Same starting capital. Radically different results.
This Isn't About Having More Money
This is about assigning purpose to the money you already have.
You don't need a bigger portfolio. You need a deliberate plan.
Cookie cutter is defaulting to industry standard: "Here's what everyone gets."
Intentional is designing for your life: "Here's what your money does for YOU."
Generic works for coffee. Not for your retirement.
You didn't build wealth for 40 years so it could sit in a diversified portfolio doing nothing but existing. You built it to serve a purpose.
The question is: What purpose?
Most people can't answer that because nobody ever asked them.

The Question Nobody Asks
Here's the question your advisor should have started with:
"How do you want to spend the rest of your life?"
Not "What's your risk tolerance?"
Not "What's your time horizon?"
Not "How much do you have?"
How. Do. You. Want. To. Spend. The. Rest. Of. Your. Life.
Because that answer determines what every dollar needs to do.
If you want to travel six months per year, your plan needs a travel allocation with growth returns funding it.
If you want to watch your grandkids grow up without work constraints, your plan needs guaranteed income that doesn't require your involvement.
If you want to gift to your children while you're alive instead of waiting until you're gone, your plan needs optimized legacy structures that free capital now.
Your life vision determines your financial architecture.
Not the other way around.
The Possibility Planning Session
Here's what we do in 30 minutes:
We start with that question: How do you want to spend the rest of your life?
Then we map what's possible with intentional planning for your specific situation.
Not generic. Not cookie cutter. Not "here's what everyone gets."
We look at your actual assets, your actual goals, and design the architecture where every dollar has both function and purpose.
You'll see:
What guaranteed income you can create
How your wealth can grow while you spend
What your legacy looks like with tax optimization
Where you have permission to spend without guilt
The side-by-side comparison of generic vs. intentional for YOUR numbers No obligation. No pressure. Just clarity.
Because after 40 years of building wealth, you deserve to know what it can actually do for your life. Not what it CAN'T do (which is all cookie cutter planning tells you).
What it CAN do.
Book Your Possibility Planning Session
30 minutes.
We map what's possible when every dollar has both function and purpose.
You'll leave with clarity on:
How much you can actually spend without running out
What your wealth will look like in 10, 20, 30 years while living fully
How to secure legacy without sacrificing lifestyle
The specific numbers for your situation (not generic projections)
[Book your Possibility Planning session here]
The bottom line:
Your money should have a job.
Not just WHERE it sits. But WHAT it does.
Cookie cutter tells you the allocation. Intentional tells you the purpose.
One creates anxiety. The other creates freedom.
Your move.




