TL;DR Answer Box

Benchmarks don’t fund your life—cash flow does. If your portfolio isn’t mapped to when you’ll need money (1, 5, 10+ years), it’s not a plan—it’s hope. The fix is a four time-band system that assigns every dollar a purpose and a date: (1) 0–2 years cash safety, (2) 3–5 years conservative income for near goals, (3) 6–10 years moderate growth for midterm needs like college, (4) 10+ years aggressive growth for retirement and legacy. Then optimize asset location across taxable, pre-tax, and Roth accounts, and protect against sequence-of-returns risk by pre-funding the next 3–5 years of spending so you don’t sell long-term assets in a downturn.

Last updated: February 9, 2026

Introduction

If your portfolio isn’t mapped to your next one, five, and 10 years of life, it’s not a plan. It’s a hope.

Benchmarks don’t pay for college. They don’t fund your lakehouse. And they definitely don’t cover your sabbatical when you finally decide to downshift. Cash flow does.

I see this constantly: smart, high-earning executives with diversified portfolios, good savings rates, and decent returns. But when I ask, “What’s this money for—and when do you need it?” there’s a pause.

Their advisor built a portfolio to beat the S&P 500. They filled out a risk tolerance questionnaire. They rebalance once a year.

And somehow, they’re supposed to trust that this generic allocation will show up exactly when they need it for a down payment in three years, tuition in six, or retirement in 12.

That’s not a strategy. That’s rolling the dice and hoping the market cooperates.

Today, we’re fixing that. By the end of this article, you’ll know how to build a portfolio from your life backward so your money actually shows up when you need it.

🎯 What Risk Actually Means

Here’s what drives me crazy about traditional portfolio management: most advisors build portfolios to beat a benchmark and use a feelings-based questionnaire to set your allocation. On a scale of 1 to 10, how do you feel about volatility?

Here’s the reality: volatility isn’t your real risk.

Your real risk is not having money when you need it. Your real risk is having to sell long-term investments during a downturn because you didn’t plan for short-term needs. Your real risk is failing to meet a commitment—your kid’s tuition, the down payment on your vacation home, or stepping away from work on your terms.

Risk is personal. It’s whether your money shows up on time for your life.

📍 The Four Time Bands That Cover Your Financial Life

At Tailored Wealth, we call our process TAMI: Time-Horizon Asset Management Integration. We start with four time bands.

Band One: 0–2 Years (Current Needs)

Cash management sleeve. Six to 12 months of living expenses, emergency fund, upcoming purchases. High-yield savings, money markets, Treasury bills. Zero drama.

Band Two: 3–5 Years (Short-Term Goals)

Conservative income sleeve. Lakehouse down payment, home renovation, business expansion. Short-to-intermediate bonds, laddered Treasuries or munis, high-quality credit.

Band Three: 6–10 Years (Midterm Goals)

Moderate sleeve. College tuition, phased retirement, work-optional experiments. Diversified equity, quality bonds, maybe buffered ETFs. We’re growing this money—but we know when we need it.

Band Four: 10+ Years (Long-Term Goals)

Aggressive growth sleeve. Full retirement, legacy planning, generational wealth. Global equity, and for high earners with long time horizons, select alternatives like private equity, private credit, and real estate.

Here’s the key question we ask for every single dollar:

What’s the cost to access your money? Not just the asset class—what’s the account type, who owns it, what’s the tax treatment, and what’s the withdrawal schedule?

💰 Getting Tax Smart About Where You Hold What

Once we know your time bands, we get tax smart about where we hold what. This is called asset location, and it’s one of the biggest levers you have.

Taxable Accounts

• Cash management and short-term bonds for liquidity
• Muni bonds if you’re in a high bracket
• A diversified equity core with tax-loss harvesting opportunities

Pre-Tax Accounts (401(k), Traditional IRA)

• Income-heavy investments that would create ordinary income in taxable accounts
• Core bonds and income sleeves you’d least like to pay taxes on annually

Roth Accounts

• Your highest-growth, longest time-horizon bucket
• Tax-free compounding for decades
• Typically more aggressive positioning because growth is never taxed

The withdrawal strategy depends on your situation:

• Maybe we use a cash-first refill approach: spend from the 0–2 year sleeve and refill annually from longer-term sleeves.
• Maybe we blend taxable withdrawals with partial IRA distributions to fill your bracket efficiently.
• Or maybe we’re in sequence defense mode: pausing long-term sales when markets are down and pulling from short/intermediate bands.

⏱️ Why Sequence of Returns Risk Matters

Meet Investor A and Investor B. Both have $2 million portfolios. Both average 7% returns over 10 years. Both withdraw $100K a year. But the order of returns is different.

Investor A returns (early losses): -20%, -10%, +5%, +12%, +15%, +8%, +10%, +7%, +6%, +18%.

Investor B returns (same, reversed): +18%, +6%, +7%, +10%, +8%, +15%, +12%, +5%, -10%, -20%.

At year 10, Investor A has $800K less than Investor B. Why? Investor A was forced to sell assets in years one and two when the market was down. Those dollars never recovered.

Here’s the Life Driven difference: Investor B had three to five years pre-funded in conservative sleeves. When the market tanked early, they didn’t touch their long-term portfolio. They let it recover.

That’s not luck. That’s planning.

✅ How This Works in Practice

Meet Jen (45) and Mark (47). Combined income: $900K. Mark has RSUs that vest quarterly. Two kids, ages eight and 12. Lakehouse in three years. College in six and 10 years. Financial independence by year 12.

When they came to us, everything sat in a balanced 60/40 portfolio. No time-horizon mapping. No tax strategy. No equity comp playbook.

• We funded their 0–2 year band with living expenses plus emergency fund.
• Built the 3–5 year band for the lakehouse with laddered munis and short-term bonds.
• Positioned their 6–10 year band for college with diversified equity and bonds.
• Kept their 10+ year band invested for long-term growth with some alternatives.
• On the RSU side, we automated sales, rerouted cash into the right bands, and harvested losses when available.

The result? Money for the lakehouse was never at the mercy of a bad quarter. College funding is on autopilot. They have clarity on what they can spend today without jeopardizing tomorrow.

🧠 Making Sense of Your Money on Life Driven Investing

Before: Your portfolio is a collection of funds that may or may not align with when you actually need cash. Every market dip creates anxiety because you’re not sure if you’ll be forced to sell at the wrong time.

After: Every dollar has a job description tied to a date and a purpose. Near-term needs are protected. Long-term growth compounds without interruption. When the market drops, you don’t panic because your next three to five years are already funded.

At Tailored Wealth, we build professional-grade financial operating systems using advanced planning technology that connects everything: cash flow modeling, tax projections, equity strategies, scenario testing.

We organize money into four time bands. We optimize asset location across taxable, pre-tax, Roth, and HSA accounts. We integrate equity compensation into the structure. We manage portfolios at the group level—so your family’s accounts are coordinated together.

We’re the partner who sits between you and the complexity. We translate life goals into clear strategies—and we give you a system that works even when you’re busy running your business or leading your team.

Key Takeaways

• Benchmarks don’t pay for life. Cash flow does—so your portfolio must be mapped to time and purpose.
• Volatility isn’t the real risk. The real risk is needing cash at the wrong time and selling long-term assets during a downturn.
• Use four time bands (0–2, 3–5, 6–10, 10+) to assign every dollar a job description.
• Asset location matters. Put tax-inefficient income in pre-tax accounts and maximize Roth for long-term growth.
• Sequence-of-returns protection comes from pre-funding near-term needs so you can leave growth assets alone.

FAQ

Isn’t this just “bucket strategy”?

It’s similar in spirit, but the focus is tighter: time horizons + tax location + cash flow integration across all accounts (taxable, pre-tax, Roth, HSA) so decisions are coordinated at the household level.

How much should I keep in the 0–2 year band?

Many high earners target 6–12 months of expenses plus any known large purchases due within two years. The goal is to avoid forced selling when life happens.

Do I sacrifice returns by holding safer assets for near-term goals?

You may reduce upside on that slice—but you also reduce the risk of needing the money during a downturn. The objective is not maximizing a benchmark; it’s funding commitments on time while protecting long-term compounding.

Where do RSUs fit into the time bands?

RSUs become cash flow when they vest and you sell. A life-driven system routes RSU proceeds into the correct band (lakehouse, tuition, retirement) instead of letting them float into a generic “investment account.”

How often should I revisit the bands?

At least annually, and whenever your goals change (new home, kid planning, career pivot, liquidity event). Many executives benefit from a light quarterly check-in because cash flow and equity events can be lumpy.

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Ready to see what this looks like for your situation? Schedule a Wealth Strategy Call and we’ll walk through your time bands, tax strategy, and equity comp integration.

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Disclaimer

This content is for educational purposes only and is not tax, legal, or investment advice. Tax rules vary by state and change over time. Consult your CPA and other professional advisors regarding your specific situation.