The Hidden 10‑Year Mistake Costing Executives Their Best Options

Answer Box: TL;DR

The biggest mistake many executives make is having a promotion plan, comp plan, and stock plan—but no 10-year life plan. In this video, Dan Pasone, founder of Tailored Wealth and former revenue leader, explains how high-achieving executives drift through their peak earning years on “work now, figure life out later,” only to realize in their late 40s or early 50s that tax windows, equity opportunities, and flexible career options have quietly narrowed. He lays out a practical, numbers-based 10-year purpose plan built on five pillars and “5P” framework—linking purpose, planning, portfolio, paycheck/taxes, and process—so you can turn today’s income and equity into work-optional freedom and a decade that you design on purpose instead of by default.

Key Takeaways

Most executives are over-planned for work—and under-planned for life.
- They have promotion plans, comp plans, and equity plans.
- But very few have a clear 10-year life plan that covers how they want to spend their time, energy, and attention.
- By late 40s/early 50s, many discover that key options (tax windows, equity timing, flexible career pivots) have diminished.
The core question: “If the next 10 years went perfectly, what would your life look like?”
- Not just “retire comfortably,” but:
  - How you spend your week.
  - Who you work with and what problems you solve.
  - How much time you give to kids, parents, health, and impact.
- Most executives can’t answer this clearly—yet this answer should become the North Star.
Reframing from “work life” to “work as purpose.”
- Work life model: Career dictates schedule, energy, and even identity; life is squeezed around meetings and comp plans.
- Work = purpose model: Work becomes one of several vehicles for purpose alongside family, health, community, and mastery.
- For many, the goal isn’t “never work again” but “work-optional, on my terms.”
The 5 pillars of a 10-year executive plan.
- Pillar 1 – Purpose & Vision:
  - Define what a great decade looks like in detail, not vague ideas.
  - Key question: “If you were fully work-optional in 10 years, how would you spend your week?”
- Pillar 2 – Income & Equity Strategy:
  - Map salary, bonus, commissions, and equity into a coordinated 10-year plan.
  - Use vesting events to pre-fund key goals: mortgage payoff, “freedom fund,” college, downshifting money.
  - Equity should be treated as a design lever, not random extra money.
- Pillar 3 – Tax Plan as Purpose Enabler:
  - Tax planning is not just compliance—it’s the engine that funds your choices.
  - Coordinate timing of income, option exercises, Roth conversions, and charitable giving to avoid six-figure leakage over a decade.
- Pillar 4 – Cash Flow & Lifestyle Design:
  - Answer: “Can I enjoy life now (trips, vacation home, generosity) without derailing the future?”
  - Separate core lifestyle (needs) from dream decade items (lake house, sabbatical, extended travel) and model the tradeoffs.
- Pillar 5 – Risk, Family, & Legacy:
  - Protect the 10-year plan against health shocks, market crashes, and single-stock blowups.
  - Use insurance, estate planning, diversification, and liquidity planning so one bad event doesn’t erase years of progress.
The “5P 10-Year Design” framework.
- P1 – Purpose: Define the decade you actually want—work, family, health, impact, non-negotiables.
- P2 – Plan: Turn that picture into numbers—target net worth, annual spending, and key funding milestones.
- P3 – Portfolio: Align investments with the plan, manage concentration risk, and emphasize risk management so you can emotionally stay the course.
- P4 – Paycheck & Taxes: Engineer cash flow and tax efficiency; integrate equity comp, bonuses, and tax-advantaged accounts.
- P5 – Process: Implement a quarterly decision rhythm so the plan adapts to job changes, comp shifts, markets, and life events.
Case study: the 47-year-old revenue leader.
- Profile:
  - 47, revenue leader at a high-growth company.
  - High W-2, large RSU exposure; ~60% of net worth in company stock.
  - Two kids (10 and 13), secret 10-year goal: consulting 2–3 days/week and summers at a vacation home by the water.
- Before:
  - No clear 10-year plan; stock treated like play money.
  - No exit strategy from full-time role; fear of crashes and tax surprises.
- After working with Dan:
  - 10-year purpose plan defined, with clarity on vision.
  - 5-year, tax-aware, systematic diversification schedule for company stock.
  - “Freedom fund” pre-funded to make work optional by mid-50s.
  - Vacation home and career transition modeled and timed; board conversations aligned to an advisory role.
  - Quarterly reviews keep execution on track.
Key mindset shifts Dan highlights.
- The biggest risk isn’t picking the wrong fund—it’s not deciding what you want the next decade to look like.
- Tax strategy around equity comp is often a six-figure decision disguised as paperwork.
- 10 years is the perfect planning window: long enough to be transformational, short enough that today’s decisions clearly matter.
- It’s not about slowing down for 10 years—it’s about rearranging effort around what matters most.
What Tailored Wealth offers in this context.
- Specializes in executives with complex compensation.
- Helps them turn income, equity, and taxes into a coherent 10-year purpose plan.
- Provides a “wealth clarity chat” to map out the plan without pressure or contracts.

Key Moments

(00:00) – The hidden 10-year mistake. Dan describes how most executives have comp and stock plans but no 10-year life plan, and how by late 40s/early 50s many best options have already narrowed.
(00:29–00:52) – The real question. He asks: “If the next 10 years went perfectly, what would your life actually look like?”—beyond just “retire comfortably.”
(01:18–01:38) – Dan’s own light bulb moment. As a former financial services revenue leader, he realized he was great at hitting targets but lacked a clear destination, which inspired Tailored Wealth’s purpose-first philosophy.
(02:00–02:21) – Work life vs. deferred life. Dan explains the default “work life” model where career dominates and life fits in the margins, often leading to regret and exhaustion by 50.
(02:21–03:09) – Work as one vehicle for purpose. He reframes money’s job as creating choice and emphasizes “work-optional” living as the true goal for many executives.
(03:09–03:30) – Why a numbers-based 10-year plan matters. Dan argues that guessing or hoping isn’t enough; you need a structured, measurable plan.
(03:30–04:02) – Pillar 1: Purpose & vision. He walks through defining a detailed 10-year picture, including weekly rhythms and time with family and causes.
(04:02–04:24) – Pillar 2: Income & equity strategy. Dan shows how to map pay, bonus, and equity to specific 10-year goals.
(04:24–05:16) – Pillar 3: Tax plan as purpose engine. He reframes tax planning as one of the highest ROI tools for funding choice over a decade.
(05:16–06:07) – Pillar 4: Cash flow & lifestyle design. Dan explores balancing current lifestyle desires with long-term security using modeling and tradeoff analysis.
(06:07–06:33) – Pillar 5: Risk, family, and legacy. He highlights how to protect the 10-year plan from being derailed by shocks.
(06:33–08:49) – The 5P 10-Year Design. Dan lays out the five Ps: Purpose, Plan, Portfolio, Paycheck & Taxes, and Process, including quarterly strategy sessions.
(08:49–10:41) – Case study: 47-year-old revenue leader. He shares a anonymized story of a high-growth exec using the 10-year framework to de-risk stock, grow a freedom fund, and move toward a consulting + vacation-home lifestyle.
(10:41–11:32) – Insights from those who nail it. Dan lists 4 key insights: clarity, tax planning, the power of a 10-year window, and rearranging effort.
(11:32–12:28) – Old vs. new model. He contrasts “grind and hope” with using wealth as a tool for purpose and work-optional freedom.
(12:28–end) – Call to action. Dan invites executives to book a wealth clarity chat at yourtailoredwealth.com and subscribe for more content on building a rich life on their terms.

Episode Summary

In this episode, Dan Pasone calls out a subtle but costly pattern among high-performing executives: they have detailed plans for promotions, compensation, and stock—but almost no plan for what they want their next decade of life to look like. As careers peak and comp packages grow more complex, many stay locked in “work now, figure life out later.” By the time they reach their late 40s or early 50s, critical opportunities—tax windows, equity timing, flexible career pivots—have quietly narrowed.

Dan begins by posing a deceptively simple question: “If your next ten years went perfectly, what would your life actually look like?” He wants specifics: how you spend your week, who you work with, what kinds of problems you solve, how much time you reserve for kids, aging parents, health, and impact. He shares his own transformation from a financial-services revenue leader chasing the next quarter to a purpose-led advisor who sees money as a tool for freedom, not just accumulation.

From there, he introduces five pillars of a solid 10-year plan. The first is Purpose & Vision, the foundation that defines a truly great decade in concrete terms. The second is Income & Equity Strategy, where he maps salary, bonuses, commissions, and stock vesting events into a coordinated system that pre-funds goals like mortgage payoff, a freedom fund, and kids’ college. The third pillar reframes tax planning as a major enabler of choice: by timing income, exercises, and conversions strategically, an executive can free up six figures of extra capital over a decade.

The fourth pillar, Cash Flow & Lifestyle Design, addresses a common executive tension: wanting to enjoy life now—vacations, second homes, travel with kids—without sabotaging long-term security. Dan separates essential lifestyle costs from “dream decade” items and uses modeling to see what’s possible, what needs to be phased in, and which fears are justified versus just noise. The fifth pillar, Risk, Family, & Legacy, focuses on protecting the plan through insurance, estate structures, diversification away from concentrated company stock, and ensuring liquidity when it matters.

He then introduces the 5P 10-Year Design framework: Purpose (define the decade), Plan (translate that into numbers and probabilities), Portfolio (align investments and manage risk), Paycheck & Taxes (engineer cash flow and tax efficiency), and Process (create a quarterly decision rhythm). Dan emphasizes that you don’t need to predict every twist in the next ten years; you need a repeatable process for recalibrating as comp, markets, and family circumstances evolve.

To bring the concept to life, Dan walks through a hypothetical case study of a 47-year-old revenue leader at a high-growth company with significant RSUs, heavy single-stock exposure, and two school-age kids. The client’s secret goal is to be consulting part-time within ten years and spending summers at a waterfront vacation home. Before working with Tailored Wealth, he treated his stock as play money, had no clarity on when or how to exit his role, and carried constant anxiety about market crashes and taxes. Dan’s team helped him build a 10-year purpose plan, implement a tax-aware stock diversification schedule, pre-fund a freedom fund, model the vacation home and career transition, and establish quarterly strategy meetings. The result is a clear timeline, less stress, and the ability to be more present at home.

Dan closes with four insights that separate those who nail this decade from those who drift: clarity about what they want, tax planning that turns income into retained wealth, the power of a 10-year window as the right planning horizon, and a willingness to rearrange effort around what matters most rather than simply grinding until 65. He invites executives who are ready to stop deferring life and start designing it to book a wealth clarity chat at yourtailoredwealth.com and to subscribe for more guidance on aligning wealth with a rich, purposeful life.

Full Transcript

Dan: Most executives have a promotion plan, a comp plan, and a stock plan, but not a ten-year plan. And here’s the dangerous pattern I see over and over: work hard now, figure out life later.

Dan: The problem? Later comes faster than you think. And by the time you’re in your late forties or early fifties, a lot of your best options—like tax windows, equity timing, and career pivots—are already gone.

Dan: If your next ten years work perfectly, what does your life actually look like? Not just your retirement account—your actual life. How you spend your week, who you’re working with, what problems you’re solving, how much time you’re giving your kids, your health, your impact.

Dan: Most executives can’t answer that beyond “retire comfortably.”

Dan: Today, I’m showing you how to flip from work life to work with purpose and build a ten-year plan that turns your income, equity, and tax strategy into the freedom to design what comes next.

Dan: Hi, I’m Dan Pasone, founder of Tailored Wealth. And before this, I was a financial services revenue leader with high pressure, complex comp, and always chasing the next quarter.

Dan: And one day I realized I was great at hitting targets, but I had no clear picture of what I was actually building towards. That was a light bulb moment for me, and it caused me to make the shift to build Tailored Wealth around the idea and the concept that money is a tool for purpose, not just accumulation.

Dan: And now I help executives and business owners to do the same thing: build a ten-year purpose plan to fund the life they actually want. Let’s get into it.

Dan: Here’s the mental model that most people operate in: work life. Everything is optimized around income, status, and output. Your career dictates your schedule, your energy, your identity.

Dan: Your life might include family, your health, and personal passions—and it gets fit in around board meetings, comp plans, and travel schedules. And look, I get it. You’re in your peak earning years. The money is real. The opportunities are real.

Dan: But here’s what I see happen: people wake up at fifty and realize they’ve been deferring life for two decades. The kids are almost out of the house. Their health took a back seat, and they’re exhausted, but they can’t articulate what they actually want next.

Dan: So, here’s the reframe: work equals purpose. Work becomes one of several vehicles for purpose alongside family, health, impacting community, maybe personal mastery.

Dan: And money’s job is to create choice, not just fund a date called retirement. For most clients I work with, the real aspiration isn’t “never work again.” It’s “work optional”—and on my terms.

Dan: Maybe it’s consulting three days a week. Maybe it’s board work, mentoring, or building something new. The freedom to say yes to the work that matters and no to the rest—that’s the shift.

Dan: And the way to get there is by designing a clear, numbers-based ten-year plan, not just winging it and hoping it works out.

Dan: So, what does a ten-year plan actually include? Let me break it into five pillars that business leaders actually care about.

Dan: Pillar one is purpose and vision. This is the foundation. What does a great decade look like for you? Not vague terms—specifics.

Dan: Who are you working with? What problems are you actually solving? How much time are you investing with your kids, aging parents, or the causes that you really care about?

Dan: Here’s a question I ask every client: if you were fully work optional in ten years, how would you choose to spend your week? Most people have never thought about it, but the answer becomes the north star for every financial decision that you make.

Dan: Pillar two is income and equity strategy. Now, we map your salary, bonuses, commission, and stock into a coordinated strategy.

Dan: Maybe you’ve got equity vesting over the next three, five, and seven years. How do those events pre-fund part of your ten-year plan? Maybe it’s paying off your mortgage. Maybe it’s building a freedom fund that allows you to downshift at fifty-two.

Dan: Maybe it’s funding your kids’ college so that’s off the table and you can focus on your next chapter. The point is, equity isn’t just extra money. It’s a lever for designing your next decade.

Dan: Pillar three is tax plan as a purpose enabler. Here’s the thing most people miss: tax planning isn’t just a boring compliance exercise. It’s the engine that funds your choices.

Dan: If you’re not strategic about when you realize income, how you exercise options, and how you sequence withdrawals, you’re easily leaving six figures on the table over ten years.

Dan: Some examples include timing RSU sales around low-income years or charitable giving, doing Roth conversions early in retirement when your tax bracket drops, and structuring bonuses and equity to avoid surprise tax bills that derail your cash flow.

Dan: This is where the difference between winging it and having a plan shows up in real dollars.

Dan: Pillar four is cash flow and lifestyle design. One of the most common questions I get: can I safely spend now while still hitting my ten-year target?

Dan: You want the vacation home. You want to travel with the kids while they’re still interested. And you want to give generously. But you’re also terrified of screwing up your future.

Dan: A real plan answers that. We distinguish between the core lifestyle—the stuff you need—and the dream decade items like the lake house, the sabbatical, the extended travel. Then we model it.

Dan: Can we do all of them? Do we need to phase one in later? What tradeoffs are real and what are just anxiety? That clarity is everything.

Dan: Pillar five is risk, family, and legacy. Finally, we protect the ten-year plan from being derailed: insurance, estate structures, liquidity, diversification away from the company’s stock.

Dan: Because the worst thing that could happen is you design this beautiful ten-year plan, and then one bad event—a health crisis, a market crash, a stock blowup—takes it all off the table. We don’t let that happen.

Dan: All right, let me give you a framework you can remember. I call it the five P ten-year design.

Dan: P number one is purpose. Define the decade. Clarify what you want work to look like in three, five, and ten years. What are the non-negotiables for family, health, and impact?

Dan: This is where most people get stuck because they’ve never given themselves permission to think beyond “grind until I’m sixty-five.” But once you get clear, everything else gets easier.

Dan: P number two is plan. Turn the purpose into numbers. Transform the vision into targets. What’s your target net worth? What’s your target annual spending? What are the key funding milestones—college, a new home, launching a business?

Dan: This is where our fully customized financial planning process comes in. We model it. We run the scenarios. We show you the probability of success and the tradeoffs.

Dan: P number three is portfolio. Make the money do the work. Align your investment strategy with the ten-year story. How much volatility can the plan handle? How do we diversify away from single-stock risk while still capturing the upside?

Dan: We emphasize active management and risk mitigation—not because we’re afraid of the market, but because staying the course emotionally is half the battle.

Dan: P number four is paycheck and taxes. Engineer cash flow and tax efficiency. Integrate equity compensation timing, bonus allocation strategy, and tax-advantaged accounts.

Dan: The goal: lower overall tax burden, smoother cash flow, and fewer surprise bills. Because every dollar you save in taxes is a dollar you can deploy toward the decade you’re designing.

Dan: P number five is process—quarterly decision rhythm. Here’s the secret: you don’t need to predict every detail over the next ten years. You just need to commit to a recurring decision process.

Dan: We run quarterly strategy sessions. We adjust as life changes—new job, new kid, market volatility, tax law changes. We adapt.

Dan: That’s what turns the plan from a one-time binder into a living system.

Dan: Let me bring this to life with a story. This is a hypothetical client that’s totally anonymized. Forty-seven years old, revenue leader at a high-growth company. High W-2, big RSU exposure, and about sixty percent of net worth is in the company stock.

Dan: Two kids, ages ten and thirteen. The secret goal: in ten years, he wants to be consulting two to three days a week and spending summers at a vacation home by the water.

Dan: But when he came to us, he had no plan. He was treating his stock like play money, had no clear plan for when to exit, how much to save, and how to step down from full-time executive work, and had constant fear of market crashes and tax surprises.

Dan: So, here’s what we did. In year one, we created his ten-year purpose plan and we got crystal clear on the vision, built a diversification schedule for his company’s stock over five years—systematic, tax-aware, no emotion—and pre-funded a freedom fund to make work optional by his mid-fifties.

Dan: In years two to three, we started modeling the vacation home purchase—timing, financing, tax implications. He adjusted his workload strategy and began having conversations with his board about transitioning to an advisory role.

Dan: Quarterly reviews kept him accountable and adaptive as his comp package changed.

Dan: Today, he’s on track. The stock diversification is happening automatically, and the freedom fund is growing. He knows exactly when he can make the shift.

Dan: And here’s what he told me: “For the first time in my career, I’m not just reacting. I have a plan. I know where I’m going and I can actually be present with my kids because I’m not up at 3:00 am wondering if I’m doing this right.”

Dan: That’s what a ten-year purpose plan does.

Dan: Now, let me hit you with a few insights that separate the people that nail this from those that don’t.

Dan: Number one, the biggest risk for executives isn’t picking the wrong fund. It’s deciding what they want the next decade to look like. Clarity is the unlock.

Dan: Number two, tax planning is often the highest ROI investment you can make. You’re already great at earning. The real win is keeping and deploying more of it, especially around equity comp. Those are six-figure decisions disguised as routine paperwork.

Dan: Number three, the ten-year window is perfect—far enough out to be transformational, but close enough that today’s decisions clearly matter. Retirement becomes a byproduct of good ten-year planning, not the main event.

Dan: And number four, I’m not asking you to slow down for ten years. I’m asking you to rearrange your effort around what matters most.

Dan: All right, let me bring this home. The old model is work over life. Grind, accumulate, and hope it works out when you’re sixty.

Dan: The new model is work equals purpose. Use your income, your investments, and your tax strategy to fund a ten-year chapter where work becomes optional—and you get to choose what it looks like.

Dan: Executives don’t need more products. They need three things: a clear ten-year picture, a financial plan engineered to that picture, and a quarterly process with a trusted partner to keep them aligned as life changes.

Dan: That’s what we do at Tailored Wealth. We specialize in working with executives with complex compensation and turn it into a coherent plan that funds the decade you actually want.

Dan: If you’re ready to stop deferring life and start designing it, head to yourtailoredwealth.com and book a wealth clarity chat. We’ll map out your ten-year plan. No contracts, no pressure—just clarity.

Dan: And if this was helpful, like and subscribe. I put out content every week for high earners that want to optimize wealth and live their version of a rich life.

Dan: I’m Dan Pasone with Tailored Wealth. Thanks for watching, and I’ll see you in the next video.

Resources & Concepts Mentioned

10-Year Purpose Plan: A structured, numbers-based plan that connects income, equity, taxes, and lifestyle to a clear decade-long vision.
Equity Compensation Strategy: Coordinating RSUs, stock options, and company stock around tax windows and life goals.
Tax Planning as a Lever: Using timing, Roth conversions, charitable strategies, and income sequencing to free capital for future choices.
Freedom Fund: A dedicated pool of assets designed to make work optional by a target age.
Quarterly Decision Rhythm: Ongoing strategy sessions to adapt the plan as compensation, markets, and life circumstances change.

FAQs

Why focus on a 10-year plan instead of just retirement at 65?

A 10-year horizon is close enough that today’s decisions clearly matter and long enough to be genuinely transformational. Retirement often becomes a natural byproduct of a good 10-year plan—not the sole target. It also gives you room to design a phase of work-optional living rather than an abrupt “full stop.”

What makes this different from traditional financial planning?

Traditional planning often centers on generic retirement goals and broad risk profiles. Dan’s 10-year framework starts with a clear life picture, integrates equity comp and tax strategy at a granular level, and uses a quarterly process to adjust as real life happens. It’s much more tailored to the realities of executives’ complex compensation and evolving goals.

Is this only for very high earners?

The specific examples focus on executives and revenue leaders with complex comp and significant equity exposure, because that’s where the stakes (and potential mistakes) are biggest. But the core concepts—clarity of purpose, tax-aware planning, and a structured process—are useful at many income levels.

What if I don’t know exactly what I want my next decade to look like?

That’s normal. Dan’s process starts with questions and exploration to help you articulate what matters most in work, family, health, and impact. You don’t need perfect clarity to begin—just enough to start shaping directions and testing scenarios.

Do I need to change everything in my life immediately to start this?

No. The idea isn’t to blow up your life; it’s to rearrange effort and decisions around what matters most over the next decade. Small shifts in equity strategy, tax planning, savings, and lifestyle choices—compounded over ten years—can dramatically expand your options.

Disclaimer

This video and written summary are for educational and informational purposes only and do not constitute financial, tax, or legal advice. They do not create a client relationship with Tailored Wealth or any related entity.

10-year planning, equity compensation strategy, tax planning, and investment decisions all involve risks and trade-offs that depend on your specific circumstances. Before making any decisions, you should consult with:

A licensed financial advisor or planner
A qualified tax professional (CPA or EA)
Legal counsel, where appropriate

Any examples or case studies are illustrative, anonymized, and not a guarantee of future results.

Next Steps

Write your 10-year vision: In a paragraph or two, describe what a perfect decade looks like for your work, family, health, and impact.
List major milestones: College, home purchases, debt payoff, career shifts, sabbaticals, and any “secret goals.”
Audit your equity & tax situation: Identify key vesting dates, concentrations, and potential tax windows.
Estimate your target “freedom fund”: The amount you’d need to make work optional by your desired age.
Set a quarterly review rhythm: Even if you do this yourself, commit to revisiting your plan every 90 days.
Consider a wealth clarity chat: If you want help building and stress-testing your 10-year plan, explore working with a specialist like Tailored Wealth.

Your income, equity, and effort are already significant. A clear 10-year purpose plan helps ensure they add up to a decade you actually want—not just a pile of numbers on a statement.