Hypothetical Case Study 1

CasEY & Jesse: Ages 35 and 38

Balancing Family and Career

The Challenge:

Casey and Jesse have thriving careers and two sons, age 3 and 5. Their challenge: Figuring out how to balance it all.

Casey is a marketing manager at a startup that recently went public and Jesse is a software engineer for a large established tech company. They both are doing well at their jobs, but the daily grind is wearing them out.

With their company going public, Casey is now holding onto some valuable equity that they hope can fund a new house for their growing family.

But they also worry that a large home purchase could tie them down to having to stay at their high-intensity jobs forever.


  • Figure out how they could work differently to create more time, flexibility and “breathing room” in their daily life
  • Make a plan for Jesse’s RSU income and Casey’s employer stock
  • Buy a bigger house with a backyard
  • Make sure they’re on track with saving for college and retirement

The Approach:

It was important to start with helping Casey and Jesse figure out what mattered most.

After many soul-searching conversations, some with their financial planner and some on their own, they decided that the best path to create a more manageable household was to have Casey leave their job and work as a part-time contractor instead.

Together they designed a plan that accomplished the following:

  • Calculated how much Casey would need to earn in order to maintain their lifestyle and stay on track for their goals
  • Prioritized savings to maximize tax-advantaged accounts, including a mega backdoor Roth for Jesse
  • Reduced their concentration risk with a systematic plan for selling their employee stock and reinvesting into a diversified investment portfolio
  • Determined how much house they could afford such that they’d not feel “stuck” having to earn a high income
  • Set up Casey’s business structure and a self-employed retirement plan to maximize after-tax earnings
  • Calculated their “work optional number” so they could start imagining new possibilities for their lives
  • Put a life insurance policy and estate plan in place to protect their family in a worst case scenario

The Results:

Life is still busy, but Casey and Jesse now feel like they have the freedom and spaciousness to enjoy their family and work.

Although they don’t intend on leaving corporate life any time soon, Casey and Jesse are excited about the possibilities of “work optional” and feel confident about being on the path to get there.

They rest assured knowing that their planner is monitoring their investments, keeping them on track with their plan, and ensuring they are taking advantage of any opportunities available.

Please note that this case study is purely hypothetical and does not pertain to any existing clients of Modern Family Finance. It is important to understand that no aspect of the content should be interpreted as a guarantee that you, as a client or prospective client, will achieve similar results or levels of satisfaction if you engage Modern Family Finance for financial advisory services.