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FINANCIAL PLANNING FOR WORK OPTIONAL


Work-Optional Lifestyle Planning – Eric and Kelly Case Study

ERIC (53) & KELLY (51)


Planning a Work-Optional Lifestyle: Eric and Kelly’s Case Study

Eric and Kelly lack clarity and a financial plan for making work optional. They are motivated to organize their financial life before leaving big tech.

They aren’t entirely sure when they want to “retire,” but they know they don’t want to stay with the same company until age 65. They want a better understanding of when they can leave their high-earning careers, whether that means pursuing early retirement, taking a sabbatical, or exploring new opportunities.

Eric and Kelly need help creating a financial plan for retirement. They’re not looking for every day to feel like Saturday. Instead, they are planning to enjoy financial independence without the need to continue working in big tech.

Background: Eric and Kelly’s Financial Journey


Eric is an account executive, and Kelly is a senior director at Dell Technologies.

They earn mid-six-figure incomes, save aggressively for retirement and investment accounts, and have no debt aside from their home mortgage and rental properties. They’ve also protected themselves with adequate insurance. Kelly has been fortunate to receive additional compensation in the form of restricted stock units (RSUs) and bonuses. Employer stock makes up about 40% of their investments.

For several years, Eric and Kelly have been interested in making work optional. Their growing nest egg, the rising stress of big tech, and a desire to pursue more meaningful careers have all contributed to this goal.

They envision lifestyle upgrades after stepping away from big tech, including traveling the world, volunteering, and spending more time with family. While they’re open to the idea of early retirement, they’re currently focused on transitioning into other passion-driven career opportunities that allow for virtual work.

With financial independence on their minds, Eric and Kelly value having a fiduciary financial advisor to help them make informed decisions with their money. They’re not retiring tomorrow, but they want to understand how to make work optional and how to do so comfortably.

Partnering with Safe Landing Financial


Eric and Kelly weren’t sure where to start, so they reached out to Safe Landing Financial (SLF) for a complimentary introduction meeting to begin planning for a work-optional lifestyle. As a trusted advisor, SLF starts every relationship by asking thoughtful questions and listening closely to understand each client’s unique financial situation. Here is how SLF helped Eric and Kelly gain financial clarity.


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How SLF Helped Eric and Kelly Plan Their Work-Optional Lifestyle


SLF gave Eric and Kelly the confidence to reach their goals by helping them visualize and discuss a customized financial plan tailored to their lifestyle.

Here are some of the ways SLF helped Eric and Kelly work toward financial independence:

  • Account Consolidation: SLF gathered information from retirement and investment accounts held at multiple firms and consolidated accounts where appropriate for easier management.
  • Scenario Planning: SLF stress-tested various scenarios for leaving big tech at different ages, exploring a range of career and retirement paths. Each scenario was evaluated to ensure a high probability of success, with funds projected to last throughout their lifetime.
  • Investment Strategy: SLF designed an investment strategy aligned with Eric and Kelly’s financial goals and risk tolerance. This included diversifying away from Kelly’s concentrated employer stock position, reviewing 401(k) plan options, and implementing an asset allocation and rebalancing strategy.
  • Savings Planning: SLF identified optimal account types for future contributions to help maximize long-term asset growth.
  • Employer Benefits Optimization: SLF helped Eric and Kelly take full advantage of available workplace benefits.
  • Tax Planning: SLF helped Eric and Kelly minimize taxes by evaluating RSUs, HSA and retirement contributions, Roth conversions, charitable giving strategies, Social Security timing, and retirement income distributions.
  • Professional Coordination: SLF worked directly with Eric and Kelly’s CPA, estate planning attorney, and insurance agent. This ongoing collaboration ensures the financial plan remains aligned with changing laws and that no important details are overlooked.

With their financial life organized and a clear plan in place, Eric and Kelly now have peace of mind. They feel empowered to move forward confidently with a work-optional lifestyle, free from the long-term stress of big tech and the fear of running out of money in retirement.

More Resources


2025 Important Planning Numbers (free PDF resource)

Mega-Backdoor Roth Guide

Backdoor Roth Guide

Deferred Compensation Guide + Case Study

HSA Guide + Strategy for Reimbursement

RSU Guide + Strategy After Vesting

How Far Could $1 MILLION Go in Retirement?

Forbes: 5 Steps To Take, In The 15 Years Before Retirement, To Make Sure You Don’t Run Out Of Money

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 financial 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.




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