How Jason and Ashley Planned a Work-Optional Lifestyle With $12 Million

Jason is a senior executive at Amazon Prime Video, where the demands of the role often bring long hours and high stress. While he is grateful for the career success, he does not want to feel tied to Amazon forever. His goal is to have a clear plan that allows him to leave when he is ready, whether that is at 45, 50, or beyond. He wants the option to pursue something less stressful, explore new opportunities, or simply enjoy more time with his family.

Ashley is a director at a local nonprofit dedicated to helping dogs, a role that reflects her passion for animal welfare and community impact. She loves her work, but she also wants the family’s finances to give them freedom: the ability to travel widely, contribute to causes they care about, and spend more quality time together.

Much of their wealth has come from Amazon restricted stock units (RSUs) that Jason has accumulated over the years, leaving them with a heavy employer stock concentration. In addition, they have built sizeable retirement accounts and opened several brokerage and managed accounts along the way. However, the accounts are scattered across multiple firms with no coordinated strategy.

Their biggest question is how to turn their $12M in investments into a reliable plan for living well at different stages of life. They want to understand how their wealth can support them if they step away from corporate work early, transition gradually, or wait until traditional retirement age.

Jason and Ashley reached out to Safe Landing Financial (SLF) for a complimentary introduction meeting for guidance. They wanted a fiduciary advisor who could organize their wealth, stress-test their options, and give them the confidence that whenever Jason decides to step away from Amazon, their lifestyle and long-term goals will remain secure.

SLF gave Jason and Ashley the clarity and confidence to move forward with a plan tailored to both their financial resources and their vision of an intentional, fulfilling lifestyle.

Here’s how SLF helped them:

• Account Consolidation and Organization: Brought together accounts from multiple institutions to provide a clear, organized view of their entire financial picture.
• Scenario Planning Across Ages: Stress-tested retirement and career transition options at different ages, including early 40s, mid-40s, 50s, and beyond, to show how long their wealth would last and what adjustments would be needed. This helped Jason see what leaving at different points could mean for their financial security.
• Lifestyle Integration: Factored in goals such as buying and maintaining their $3M home, extensive travel, supporting animal welfare initiatives, and dedicating more time to family and community involvement. Each scenario showed how these lifestyle choices could be funded sustainably.
• Investment Strategy – Reducing Concentration Risk + Tax Location: Reduced reliance on Amazon stock by building a globally diversified portfolio across asset classes. Applied a disciplined rebalancing strategy and aligned investments by tax location: conservative in tax-deferred accounts, growth-oriented in tax-free accounts, and tax-efficient in taxable accounts.
• Investment Strategy – Tax Efficiency and Management Style: Managed investments around high unrealized gains held in separate managed accounts (SMAs), balancing diversification with tax sensitivity. Prioritized tax-loss harvesting, long-term capital gains, and minimizing or avoiding unnecessary capital gains, while implementing a low-cost, transparent ETF portfolio with broad global exposure.
• Estate Planning Guidance: Introduced key concepts like wills, trusts, and charitable giving strategies, ensuring their legacy would reflect their values and protect their family.
• Insurance Planning: Reviewed coverage for their new home, considered umbrella liability protection, and evaluated life and disability insurance to safeguard their wealth and family’s future.
• Tax Planning: Built strategies around diversifying out of concentration risk, Roth conversions, charitable giving, and tax-efficient withdrawal sequences to extend the life of their investment portfolio.
• Professional Coordination: Partnered directly with their CPA, attorney, and insurance contacts so the plan was cohesive and adaptable to changes.

2026 Important Planning Numbers (free PDF resource)

Forbes: The 9 Keys To A Happy Retirement

Business Insider: How Much Money You Need to Retire at Every Age and Comfortably Live on Investment Income

The Balance: How to Retire Early and Manage Your Health Care Costs

Disclosure: The above planning for retirement case study is hypothetical and does not involve an actual Safe Landing Financial client. No part of this content should be taken as a guarantee that their household will experience similar results if Safe Landing Financial is chosen to provide financial planning services.