Whimsy, On Purpose
what an inheritance movie taught me about creativity in planning ahead
Takeaways:
Creativity can help us recognize and reclaim our values and dreams.
Legacy planning involves more than money.
When “Whimsical” Caught My Attention
Recently, I attended a dinner party and, as a middle-of-the-table guest, I partook in two conversations. As an introvert, I mostly listened and offered a word or two in each direction as appropriate. However, when I heard “whimsical” to describe a professional project, I turned and paid attention and then engaged deeply, despite the blank and somewhat confused stares of my companions.
Wrestling with the Instinct to Eliminate Uncertainty
Most of the guests seemed to be like me, business/finance people with careers in banking, insurance, logistics — that is, not only non-whimsical but anti-whimsical. We want to identify known risk, protect ourselves against unknown risk, plan carefully for contingencies, and chart and fund our path from childhood to retirement and beyond. That is, we want to squash whimsy in favor of certainty and numbers-driven outcomes.
Yet, I felt attracted to this notion of whimsy — creating the conditions for unexpected and pleasant surprises. I became drawn to the person who spoke of such a happening, an artist who elaborated on her creative process as I listened intently.
An Estate Plan Designed with Imagination
Later I wondered: when it might be appropriate for a finance person to introduce whimsy into her work? That question reminded me of The Life List, a movie about estate settlement.
The main character is Alex, a young woman whose mother recently died of cancer. The daughter struggles to find her place in the world, a problem the mom wants to solve.
The mom engages an estate attorney and creates a plan encouraging Alex to complete her 13-year-old self’s life list. After each item is ticked off the list, the attorney shows Alex a video of her mom offering praise and commentary for the most recent accomplishment. At the completion of the list including a four-point checklist involving finding true love, Alex will receive her inheritance from her mother.
As Alex moves through the list, she reconnects with herself, and gains clarity and comfort about her life’s goals. Alex’s awakening is what her mother most wanted for her. It’s essential that Alex knows who she is and what she truly wants before receiving a life-changing inheritance.
Considering the artist’s vision and this mom’s estate plan, I realized whimsy and finance can work together!
Where Whimsy Fits in Real Life
A whimsical approach may not be routinely appropriate for an investment analyst, insurance agent, or banker. However, it could be an excellent tool for financial professionals, estate attorneys, and DIY planners. Consider using creativity to align formal plans with personal values to spark joy and discover what matters, just as the artist and Alex’s mom did.
How have you experienced whimsy? Has it helped you live a more satisfying and fulfilled life?


