Why Is Asking for Help With Money So Hard?

When a woman finally brings me a money question she’s been sitting on, it often comes with a disclaimer. She’s sure she should already know the answer. These are women who run teams, negotiate contracts, build businesses, and are the go-to person when something goes wrong. They aren’t lacking intelligence, and they usually aren’t lacking information either. What they’re missing is a room (or a Zoom) where it's safe not to know.

The more capable she is elsewhere, the harder it becomes to ask for help with money. When you’re the one with the answers at work, saying “I don’t understand how my equity is taxed” or “I’m not sure what my advisor actually did with that account” can feel like putting your competence on the line. So she nods along in her accountant’s office, files the question away, and tells herself she’ll figure it out later. I don’t see that as a knowledge problem. I see it as a skills gap that was never given a safe place to close, and that’s something we can change.

“No, and I Don’t Know What That Is”

Before every Financial Insight Session, my clients fill out a pre-questionnaire. One question asks whether she has a high-yield savings account, and one answer option is “No, and I don’t know what that is.” I wrote that option on purpose. Most financial forms assume you already know the vocabulary, and a woman who doesn’t is left to guess, skip the question, or check whichever box makes her look like she has it handled. Putting the honest answer right there on the list tells her, before we ever meet, that not knowing is an expected place to start.

When a woman chooses that answer, we cover it in session the same way we cover everything else: plainly and without commentary on why she didn’t already know. A high-yield savings account pays a higher interest rate than a traditional bank savings account, and online banks usually offer them, which is part of why they can pay more. You link it to your regular checking account and transfer money. Many let you create separate buckets for an emergency fund, a trip, or your business. That’s the whole explanation, and no one should feel embarrassed for never having been taught it.

Why Asking for Help With Money Gets Harder as Your Life Gets More Complex

Many of us grew up in families where money simply wasn’t discussed, and some of us were taught that it was private, even at home. A girl who learns that money isn’t talked about doesn’t suddenly start asking questions about it when she grows up. She learns to figure things out on her own, quietly, and to keep what she doesn’t know out of sight.

That habit grows heavier as life becomes more complex. The higher your income and the more layered your finances, the more you assume you should already understand them. Equity compensation, a K-1 from a partnership, a business with its own accounts, and a divorce with real assets to divide each come with professionals who speak fluently about them and quietly assume you can keep up.

In Positive Intelligence, the part of us that ties our worth to our performance is called the Hyper-Achiever. It’s one of the saboteurs I see most often among the women I work with, and it treats not knowing as a verdict on who you are. For a woman who has earned her seat in every other room, a question about her own money can feel like evidence that she doesn’t belong there. So she doesn’t ask, and the gap grows quietly beneath an income that makes everything look fine from the outside. I make sure she understands that she is worthy, even without all her achievements, and that her net worth is not a reflection of her self-worth.

The Question More Than One Client Has Asked Me

More than one client has stopped me mid-session to ask what a brokerage account is, usually after we’ve started discussing her 401(k) or IRA. It’s a fair question because the account types sound alike and the differences matter. In general, a traditional 401(k) or IRA lets your contributions reduce your taxable income now, and you pay taxes when you withdraw in retirement. A Roth account works the other way: you contribute money that’s already been taxed, and qualified withdrawals, including growth, are tax-free. Both generally carry penalties if you withdraw before age 59½, with some exceptions. A brokerage account has no tax advantages, but the trade-off is flexibility, since you can take your money out whenever you need it.

Many accomplished women have a polished answer for terms like these. When I ask whether something makes sense, the first response is often that she’s familiar with it. I’ve learned to gently ask whether that’s intellectual knowing or something she can actually use to make a decision, because the real question is usually waiting beneath the polished answer. And when a client asks me something I don’t know, I tell her. A safe space works in both directions. I don’t need to have every answer, and neither does she.

What Being “Wildly Seen” Actually Looks Like

Calling something judgment-free is easy. Making it feel that way takes intention, and it starts before we look at a single number. I open every Financial Insight Session by telling my client that it’s a shame-free, judgment-free zone, that what she shares stays private, and that I expect her to jump in with questions. Then we do a short Positive Intelligence grounding exercise to get out of our heads and into our bodies, and I do it with her. We start with her money history rather than her accounts, because much of what shows up in her numbers today was learned long before she had any money. When we reach the numbers, she knows she can ask for a break at any time, and we treat every figure as information rather than a grade.

Sometimes I’ll suggest she look at her numbers as if they belonged to a friend and ask what she’d tell that friend. That creates enough distance for her to be curious rather than critical. I also remind women that needing support isn’t a sign that something is wrong with them. Coaches have coaches, and professional athletes have coaches. Asking for guidance on something you were never taught is simply what capable people do.

One client described the experience in a review as “wildly comforting to feel so seen in such a vulnerable space like personal finances.” Being seen makes questions possible, and questions make change possible.

If you’re the person everyone else turns to for answers, and you have money questions you’ve never asked, nothing is wrong with you. You likely grew up in a world where people didn’t talk about money, and you’ve built a life more complex than anyone prepared you to manage. Asking is a skill, and like any skill, it gets easier with practice and with someone who makes it safe to ask.

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If you’re carrying money questions you’ve been too embarrassed to ask, especially about finances that have grown more complex than anyone taught you to handle, I invite you to schedule a free Money Conversation. Bring every question. I expect them.

Book Your Free Money Conversation

Financial Coach Sabrina

Insight Financial Coaching

Know Yourself. Know Your Money. Claim Your Financial Agency

Serving high-earning midlife women carrying the financial load on their own in Austin, TX, and nationwide via Zoom