“Stories and lessons from an unexpected journey in finance.”

It’s a season of big transitions in our household.

• Last weekend, we took our son back to Villanova for his senior year.
• Earlier this week, our youngest daughter started her first year at Scripps College.
• And in a few weeks, our oldest daughter heads to UCL in London for graduate school.

Three kids. Three schools. Three sets of tuition bills. And one proud (but emotional) CFO trying to manage the balance sheet of family life.

It’s amazing how quickly milestones pile up. Just a few years ago, our house was noisy, busy, and filled with overlapping schedules. Now, in a single month, it’s turning quieter than it’s been in decades. Pride and nostalgia. Excitement and a little melancholy.

But as I sat with it, I realized how familiar it all feels. These family milestones echo many of the transitions I’ve led in companies — whether entering a new market, integrating an acquisition, or shifting strategy. The themes are remarkably similar:

• Budgets never quite fit reality. Move-in week at Scripps felt a lot like an IT go-live: the spreadsheet looked perfect, and then reality arrived with extra costs, missing items, and unplanned adjustments. (For the record, yes, twin XL bedding is real. No, we didn’t budget for three sets.)

• The real investment is in people. Tuition, rent, and travel expenses feel steep. But like training employees or investing in culture, the return isn’t measured in a single line item — it’s measured in growth, independence, and the ability to take on bigger challenges.

• Leadership is letting go. In both parenting and business, one of the hardest things is stepping back and trusting. Whether it’s handing off a P&L to a rising leader or leaving your child at college, success is when they can thrive without you hovering.

• Every season has an end. Families change, markets shift, businesses evolve. Growth requires letting go, even when it’s uncomfortable.

I’ve come to believe that good leadership is really just good parenting, scaled differently:
➡️ Set direction.
➡️ Build confidence.
➡️ Know when to step aside.

Transitions are messy. They disrupt routines, test budgets, and push us out of comfort zones. But they are also proof of growth — whether it’s a family moving into a new season or a company moving into its next chapter.

As the “Accidental CFO” of both business and family, I’m learning that the spreadsheets, while important, aren’t the story. The story is in the people — how they rise, adapt, and carry things forward.

What transitions — at home or at work — are teaching you about leadership right now?

#leadership #accidentalcfo #growthmindset #business #family #inersec