The Blind Spot That Almost Cost Her Everything: What Leaders Can Learn From a Financial Wake-Up Call

The Leadership Blind Spot That Was Hiding in Plain Sight

In the world of high achievers, financial acumen is often assumed. But what happens when your leadership blind spot shows up in the very area you’re expected to master?

That’s exactly what happened to Jacquette Timmons, an MBA in Finance, a Wall Street veteran, and now a highly sought-after financial behaviorist and speaker.

In a recent episode of The Enlightened Executive, Jacquette shared a deeply personal, and professionally pivotal, story that sheds light on a powerful truth: even the most seasoned leaders can be blind to the patterns that hold them back.

When a Single Question Reframes Everything

Back in 2003, Jacquette walked into her CPA’s office feeling proud. Her numbers were strong. Her business was thriving, or so she thought. But what happened next shook her.

Her longtime CPA paused, looked over his glasses, and asked a question that stopped her cold: “When are you going to stop mortgaging your life?”

It wasn’t about real estate. It was about her behavior.

Jacquette had been regularly transferring money from her personal savings to cover business expenses: dipping into reserves, selling securities, even increasing credit card debt. It was a pattern she hadn’t even recognized. But her CPA had. And he called it out…not as a reprimand, but as a wake-up call.

That moment launched Jacquette on a path of deeper inquiry, not only into her finances but also into the unconscious beliefs and emotional patterns that shaped her decisions.

Why This Matters for Leaders

As Jacquette put it, “I had access to the same information as my CPA. But I didn’t have the distance or objectivity to see what he saw.”

That’s the challenge with blind spots. They don’t come from ignorance. They sit right next to your strengths.

In leadership, they often show up as habits that once worked but now get in the way. They’re reinforced by success and easy to overlook.

You might be a sharp strategist who over-functions and stifles your team. Or someone generous and dependable who unknowingly undercharges, like Jacquette did.

Blind spots aren’t flaws. They’re patterns. And recognizing them is more than self-awareness, it’s a leadership essential.

The Science Behind the Shift

Neuroscience shows that the brain prioritizes patterns because they conserve energy. Once a behavior becomes automatic, your brain stops questioning it, even if it’s no longer helpful.

But under stress or transition (like Jacquette’s move from corporate finance to entrepreneurship), those patterns get louder. They show up in your financial decisions, your time management, your communication.

In leadership, the more senior your role, the less feedback you receive. Which means the more critical it becomes to intentionally seek out those patterns and interrogate them.

Action Steps You Can Take This Week

1. Ask the Hard Questions
   What’s a pattern you’ve rationalized as “just how I work”? Ask someone you trust: “What’s one behavior I repeat that might be holding me back?”
2. Use Proximity and Distance
   Just as Jacquette’s CPA offered an external view, consider who has enough distance from your day-to-day to see what you might be missing. Bring them into your reflection process.
3. Audit Your Financial Behavior
   Even if you’re financially savvy, revisit how you make money decisions. Are they based on logic, or driven by unconscious emotional patterns?
4. Normalize Pattern Spotting
   Encourage your team to identify leadership patterns in themselves. Use tools like the Enneagram to surface blind spots and shift from reflexive to intentional leadership.

Jacquette’s story is a reminder that success doesn’t immunize us from blind spots. In fact, it often conceals them.

But when you build the muscle of pattern recognition, when you train yourself to pause, zoom out, and name what’s really happening, you unlock a new kind of leadership.

Not just smarter. More conscious. More effective. More human.

Because the most enlightened executives don’t just fix problems. They see patterns. And they choose a better move.

For deeper insights on uncovering your blind spots, explore our Enneagram Applied program.