Building Flexibility and Security in Early Wealth

The Challenge

Even with strong savings habits, Jamie and Dylan had several key questions:

• Are we being too conservative with our money — and is that limiting us?
• How should we handle ongoing stock compensation from Jamie's employer?
• What should we do with Dylan's recent inheritance in a tax-efficient way?
• How do we prepare for a potential early retirement in our early 50s?
• How do we plan for a possible "gap year" in the future?
• What estate planning steps should we take to protect our family now?
• Clarity on real estate opportunities — and whether rental properties should be part of their long-term plan.

Our Approach

We built a flexible financial framework designed to support their current lifestyle, prepare for uncertainty in future income, and create a clear path toward early retirement — without requiring them to make aggressive or irreversible decisions today.

Investment Planning

Created an investment framework focused on flexibility for life changes and early retirement:

• Began selling Jamie's RSUs as they vest and reinvesting into diversified funds
• Built a larger emergency reserve due to startup income uncertainty
• Allocated excess cash into a diversified portfolio aligned with long-term goals
• Rental real estate education and pros/cons vs. passive real estate investing

Cash Flow Planning

We executed three key objectives:

• Establishing a system for managing excess cash through quarterly reviews and timely reinvestment
• Creating a framework for funding large future purchases
• Improving clarity around how cash flow can support both flexibility today and early retirement goals, so they can spend confidently today

Tax Planning

Focused on reducing lifetime taxes while increasing flexibility:

• Developed strategies to manage income timing and tax efficiency over time
• Created a structured plan for Dylan's inherited IRA distributions
• Evaluated opportunities to accelerate or defer income depending on life stage and planning goals
• Identified tax-saving strategies tied to potential gap-year planning

Benefits Optimization

Ensured they were fully utilizing available employer benefits:

• Implemented a Dependent Care FSA for annual tax savings (~$1,400)
• Reviewed and optimized healthcare coverage for Jamie and their child
• Identified underused benefits, including deferred compensation opportunities

Multi-Generational & Life Planning

As their financial foundation became more structured, the focus expanded beyond accumulation toward building a stable base for their growing family.

• Created a financial education timeline for their children, which Sage will help facilitate
• Created a plan for funding education for their current and future children
• Weighed the pros and cons of newer tax-deferred strategies for children vs. maintaining flexibility and financial independence for them as they become adults
• Helped them think through the financial and non-financial side of a potential future gap year — ensuring the decision would be intentional, not disruptive

Estate Planning

We worked with a local attorney to establish a trust and complete foundational estate documents to ensure:

• Their child is financially protected and supported if something happens to either parent
• Assets transfer efficiently without unnecessary delays or court involvement
• Their family has clarity during difficult situations
• We also organized all estate documents into a secure digital system to make future administration simpler for their loved ones

Risk & Insurance Planning

We reviewed their full insurance picture to close key gaps:

• Built appropriate term life insurance coverage to protect future income
• Reviewed disability coverage and integrated it into planning scenarios
• Optimized home, auto, and umbrella liability coverage
• Recommended a multi-million-dollar umbrella policy to protect against unexpected legal risk