Confessions of a RisingGen Leader (who is paralyzed by numbers)

 Written by: Torri Hawley

https://www.linkedin.com/in/torri-hawley/

The pressure of my daunting task looms heavy - my nervous system revs up as if a bear is approaching. But I’m not trekking in the wilderness, I’m simply gathering the right mix of bills from the ATM machine to pay my housekeeper.

"Hurry up! There’s someone waiting behind us…” my husband urges, just as my watch notifies me of my rising heart rate—with the deeply unhelpful suggestion: “Take a break!”

Surely, I — the confident and self-assured leader in my family, my job, my home life — can manage this task without a nervous breakdown.

I punch in the bills hastily and walk away from the ATM. I will not be admitting to my husband that I have to come back tomorrow.

If opening your banking app makes your stomach drop, or the idea of wading through your spending makes you cringe, this one is for you. Not because I’m going to offer a budget template or break down a financial plan, but because I’ve learned that what stands between most people and financial confidence isn’t knowledge. It's never having had a clear place to start.

There's something about numbers that makes some of us break out into a cold sweat. 

Layer in that money, while theoretically just numbers in a bank account, is inherently emotional and it's no wonder that less than half of affluent millennials feel confident about investing and retirement planning. Every financial decision I make—from extra guac at Chipotle, to leasing a car, to student loans (should we really be asking 18-year-olds to make decades-long decisions with little to no guidance?) feels steeped in judgment about who we are as people. The unfortunate message we often absorb is that our financial stumbles aren't the result of systemic failures in financial education, they're personal shortcomings.

If you are part of a family enterprise, as I am, that shame is amplified. You're surrounded by highly successful, incredibly smart high achievers - and admitting that thinking about finances gives you butterflies feels unthinkable. And in my work with those in the rising generation, I see this lack of confidence frequently, particularly among women. Messages or mindsets that you don't need to worry about budgeting because you have a trust, OR you'll always have the family safety net lingers in the background, inhibiting you from taking the same steps towards financial fluency that your peers may have taken. 

And these dynamics are compounded by the fact that many parents didn't receive appropriate financial education either. They came from parents and grandparents who didn't speak about money openly (while saying volumes through silence). Or they were “immigrants to wealth” themselves - the first in their family to build success, and extraordinary at creating financial success, but never developing the language for passing it on. In either case, the generation that follows sometimes inherits the assets without a roadmap for what to do with them. From there, a handful of family members rise into leadership and get trained on the numbers. The rest are left to figure it out alone.

It doesn't have to work that way! Real, lasting financial confidence follows a path. And the first step is simply Awareness.

For me, awareness started at my first job at a financial services firm. I was watching a colleague facilitate money stories activities with clients, helping other people examine their relationship with money, when I realized I had never examined my own. I was out in the world, paying my bills, functioning just fine on the surface. But I also felt money dysmorphia, unsure of my financial future, knowing I would someday be a beneficial owner, and in the meantime feeling like I had to keep up with the Instagram noise of wealth and consumerism. Working through my own wealth identity as a young person was the spark that changed everything. 

The night after that ATM moment, we went out for tacos with a group of friends. I grabbed the tab — yes, I am that friend who wants the credit card points and will fight you for the check — and went about my evening. The following morning, I woke up excited to sip my coffee while crafting AN AMAZING SPREADSHEET with detailed formulas for calculating tax and tip based on the number of margaritas consumed. My husband, a middle school math teacher, shook his head in confusion (and I sensed jealousy over my spreadsheet prowess). Was I not the same woman who had hyperventilated over calculating $175 x 2 the day before? 

Same woman. Different conditions. And that's a whole lesson about Confidence. Confidence isn't a personality trait you either have or don't. It's a muscle, and it grows when you give it something real to work with. It's built through practice, on your own terms, at your own pace. Low stakes. Breathing room. No one peering over your shoulder. You start with what's actually yours - your own accounts, your own spending, your own patterns and what you can control and you build from there. 

From there, Engagement becomes possible. Despite stuttering through accounting in my undergrad business degree, I went on to work in accounting for an embedded family office for nearly a decade. In that time, I got very good at spreadsheets. I now write curriculum that teaches others about personal finance, investing, and financial statements. I sit on the board of our family business. 

None of that happened because I was naturally gifted with numbers. It happened because awareness gave me a foundation, confidence gave me footing, and engagement gave me a place to show up — and keep showing up — even when I still had things to learn. 

For many people, Decision-Making is actually where the journey begins, not where it ends. A prenup negotiation. An inheritance. A seat at the table they didn't ask for but suddenly have. These moments have a way of arriving before you feel ready, and they have a way of revealing exactly what foundation is, or isn't, underneath you. It's overwhelming because it's meant to be built up to, not dropped into. But if the anxiety keeps you from starting, from practicing, from failing in small ways, from building anything at all, you risk arriving at the moments that matter most with no foundation underneath of you.

Imagine it the other way around. Imagine you've done the awareness work, you know your patterns, your history, your triggers. You've forgiven yourself for being "bad" with money or for not sticking to your budget. You've built confidence through practice on your own terms in low risk settings. You've engaged, shown up, and now when the moment comes, you're not scrambling. You're making complex, considered choices of your own. Buying a home. Building a financial plan. Asking the right questions of your advisor or in a board meeting. Not because you have all the answers, but because you trust yourself to be in the room.

There is a process waiting to be started. 

Awareness. 

Confidence. 

Engagement. 

Decision-making. 

You don't have to sprint through it. You just have to begin. You might even surprise yourself by the value you bring.