TL;DR Answer Box

Most high earners optimize salary, equity, and promotions—but never define what they actually want the next 10 years to look like. A decade plan turns “more money” into more choice by aligning your purpose, milestones, portfolio timeline, tax strategy, and quarterly decision rhythm. Use the Five P Framework (Purpose, Plan, Portfolio, Paycheck & Taxes, Process) to build a system that makes work optional on your terms—before burnout forces the issue.

Last updated: February 12, 2026

If the Next 10 Years Go Perfectly, What Does Your Life Actually Look Like?

I was on a call last week with a revenue leader who had just closed the best quarter of her career. She’d negotiated a promotion, maxed her 401(k), and had a clear path to VP in 18 months.

I asked her a simple question: “If the next 10 years go perfectly, what does your life actually look like?”

She paused. Then laughed. “I have no idea. I’ve been so focused on the next promotion, I’ve never actually thought about what I’m building toward.”

She’s not alone. Most executives I work with have optimized their comp plan, their stock plan, and their promotion timeline. Very few have a clear picture of what a great decade looks like.

Today, we’re fixing that. By the end of this article, you’ll know how to design your next 10 years so work becomes optional, money creates choice, and you stop reacting to what’s next and start building toward what matters.

🎯 The Question Most Executives Cannot Answer

Most executives have a promotion plan. They have a comp plan. They have a stock vesting schedule.

Very few have a 10-year life plan.

Ask yourself right now: If the next 10 years go perfectly, what does your life actually look like?

Not your net worth. Not your title.

Your life. How you spend your week. Who you work with. How much you travel. Time with your kids. Your health. Your impact.

Can you describe it clearly in three sentences?

If not, you’re not alone. But here’s the problem: you would never run a business on quarterly targets alone without a long-term strategy. Yet most executives are doing exactly that with their lives.

📍 The Real Risk Is Not the Market

The biggest risk for high earners is not picking the wrong fund or missing a market rally.

It’s never deciding what they want the next decade to look like.

It’s letting lifestyle expand without intention. Missing tax planning windows because there was no framework. Staying overconcentrated in company stock too long. Waiting until burnout forces a decision instead of designing the transition.

I’ve seen executives lose hundreds of thousands of dollars in avoidable taxes, not because they didn’t have good advisors, but because they never had a clear 10-year picture to plan around.

The unlock is not more complexity. It’s clarity.

When you know what the next decade should look like, every financial decision gets easier. Equity sales have a purpose. Tax planning has a target. Spending stops feeling guilty.

💰 The Five P 10-Year Design Framework

Here’s how to build your decade plan. I call it the Five P Framework.

P1: Purpose

Define the decade.

What does work look like in 3 years? In 5 years? In 10 years?

What are the non-negotiables for your family, your health, your impact, your flexibility?

Anchor question: If you were fully work optional in 10 years, how would you choose to spend your week?

Most executives tell me they’d work 2 to 3 days per week on projects they care about, spend more time with family, travel without guilt, and have space for health and hobbies.

Great. Now we have a target to engineer toward.

P2: Plan

Turn the vision into numbers.

What’s your target spending range? What net worth or asset base gets you there? What does your freedom fund need to be?

What are the major milestones? College funding. Mortgage payoff. Vacation property. Sabbatical year.

This is where modeling matters. You’re not guessing. You’re running scenarios in professional planning software to see what happens if you downshift at 52 versus 57. What happens if you take a lower-stress role at 80% of current comp.

The plan shows you the tradeoffs before you make the decision.

P3: Portfolio

Align investments with your time horizon.

This is where Life Driven Investing comes in. We organize money into four bands: 0 to 2 years, 3 to 5 years, 6 to 10 years, and 10 plus years.

Risk is not volatility. Risk is not having money when you need it.

If you’re planning to buy a lake house in 4 years, that money doesn’t belong in a 100% equity portfolio. If you’re planning to go part time in 7 years, you need a freedom fund prefunded so you’re not forced to sell in a downturn.

This also means addressing concentration risk. If 60% of your net worth is in company stock and you want flexibility in 5 years, we need a systematic diversification plan starting now.

P4: Paycheck and Taxes

Tax planning is a purpose enabler.

For high earners, taxes are often the largest controllable expense. Multi-year tax projections matter more than single-year optimizations.

Key ideas: timing equity sales around lower income years, Roth conversion windows when you step back from full-time work, asset location across taxable accounts, pre-tax retirement accounts, and Roth.

I’ve seen clients save six figures over a decade simply by planning equity vesting, bonuses, and withdrawals with a 10-year tax roadmap instead of winging it year by year.

P5: Process

The secret is not predicting 10 years perfectly. It’s committing to a quarterly decision rhythm.

Every quarter, you review: upcoming equity events, tax projections, spending adjustments, portfolio alignment, career transition timing.

The plan is a living system, not a binder you build once and forget.

This is how you stay aligned even when markets shift, your career changes, or life throws you a curveball.

⏱️ The 47-Year-Old Executive Who Got Clear

Let me show you what this looks like in real life.

A 47-year-old revenue leader came to us last year. High W-2 income, heavy RSU exposure, 60% of his net worth in company stock. Two kids, ages 10 and 13. He wanted to shift to consulting 2 to 3 days per week by 57 and spend summers near the water.

Starting state: no diversification schedule, no clear downshift runway, constant fear of a market crash or tax surprise.

What changed: We built his 10-year vision. Then we engineered a 5-year systematic diversification plan for his equity. We prefunded a freedom fund for his transition years. We modeled vacation home timing against his tax situation. We helped him start advisory transition conversations with his network.

Quarterly reviews created accountability. He’s not reacting anymore. He knows where he’s going.

His quote: “For the first time, I feel like I’m driving instead of being driven.”

✅ The 30-Minute Executive Exercise

You don’t need a full financial plan to start. Here’s what you can do this week.

• Step 1: Write your ideal 10-year week. What does a perfect Tuesday look like in 2036?
• Step 2: List 5 decade milestones. What needs to happen financially for that life to work?
• Step 3: Map the next 12 months of decision moments. Vest dates. Bonus timing. Tax filing. Benefits elections. Career inflection points.
• Step 4: Schedule your first quarterly strategy session. Block 90 minutes every quarter to review progress and adjust.

This exercise takes 30 minutes. Most executives tell me it’s the most clarifying thing they’ve done in years.

🧠 Making Sense of Your Money on Decade Planning

Before: Grinding toward a vague “retirement” goal. Reacting to comp changes and market swings. Making isolated financial decisions without a cohesive framework. Background anxiety about whether you can safely spend now or need to keep saving.

After: A clearly defined picture of your next 10 years. Work becoming optional on your terms, not abruptly stopped by burnout. Money creating choice and flexibility. Reduced anxiety because every decision ties to a purpose you’ve actually designed.

At Tailored Wealth, this is what we do. We build professional-grade financial operating systems using advanced planning technology that connects everything: cash flow modeling, tax projections, equity strategies, scenario testing for career changes or hybrid retirement moves.

We use our Life Driven Investing framework to align portfolios with your actual timeline, not generic benchmarks.

We model what happens if you downshift at 50 versus 55. We show you the tax impact of selling equity now versus later. We prefund your transition years so you’re never forced to sell in a downturn.

We’re the partner who keeps the system updated and in motion. We sit between you and the complexity. We translate your 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.

The plan is not a one-time binder. It’s a living decision engine that adapts as your life changes.

Ready to design your next 10 years? Watch my video on The Hidden 10-Year Mistake Costing Executives Their Best Options to see how this framework works in action.

As always, I hope this helps you to Prioritize Your Version of a Rich Life.

Until next week!

Key Takeaways

• Most executives have a comp plan, not a life plan. Clarity on your ideal decade makes every financial decision easier.
• The biggest risk is drifting. Lifestyle creep, concentration risk, and missed tax windows often come from not having a 10-year target.
• Use the Five P Framework. Purpose → Plan → Portfolio → Paycheck & Taxes → Process turns “more money” into “more choice.”
• Risk is timeline mismatch. Match money to when you need it (0–2, 3–5, 6–10, 10+ years) so you’re not forced to sell in a downturn.
• Quarterly reviews beat perfect predictions. A consistent rhythm keeps the plan aligned as markets and life change.

FAQ

What’s the difference between a “comp plan” and a “decade plan”?

A comp plan optimizes what you earn (salary, bonus, equity). A decade plan clarifies what you’re building toward and aligns your money, taxes, and portfolio to create options—like downshifting, taking a sabbatical, or making work optional.

Do I need a full financial plan to start a decade plan?

No. Start with the 30-minute exercise: define your ideal 10-year week, list 5 milestones, map 12 months of decision moments, and schedule a quarterly review. The goal is momentum and clarity, not perfection.

What is a “freedom fund”?

It’s money earmarked to fund transition years—like going part-time, starting a business, or consulting—so you’re not forced to sell investments at a bad time or accept the next job out of panic.

Why does concentration in company stock matter so much?

Because it can create a single-point failure risk. If a large percentage of your net worth is tied to one company, both your income and your wealth can drop at the same time—exactly when you may need flexibility most.

How often should I review my decade plan?

Quarterly is the sweet spot for most executives. You review upcoming equity events, taxes, spending, portfolio alignment, and any career changes—then adjust before small issues become expensive surprises.

Disclaimer

This information is provided for educational purposes only and is not intended as individualized investment, tax, or legal advice. You should consult your own financial, tax, and legal professionals regarding your specific situation.