For Women Who Refuse to Be Underestimated, Underpaid and Undervalued

I once represented a woman whose exact counterpart at a sister subsidiary, same parent company, our firm represented them both, had less experience and a smaller budget than she did and was paid three hundred thousand dollars more. We knew it because we had both contracts sitting in front of us. My client wanted to ask for parity. She was terrified because she already knew what would happen if she did. I convinced her to ask anyway.

Her request was rejected. The president screamed at me on the phone and told me his company would never do business with our firm again. His actual words about her were that she was lucky to have the job at all. No one ever said that about her male counterpart, the one with less experience, a smaller budget, and three hundred thousand more dollars. The message to her was not subtle. Play by the rules we set for you. Don't ask questions. Be grateful. He was, incidentally, fired not long after for sexual harassment, unrelated to any of this, but I will admit I enjoyed the timing more than I probably should have.

Here is the part I keep coming back to. My client's fear was not irrational. It was not a confidence problem or a distorted sense of risk. She was right. We got punished exactly as she predicted we would. So what was the actual mistake? Asking the wrong person. See the Lesson below for what happened to my client next.

This week's guest on Takin' Care of Lady Business, Caroline Dell, built an entire company on the idea that the right ask, made to the right person, is what actually moves a career forward, and that most of us are sitting on more leverage to make that ask than we realize.

With Love & Lady Business,
JJ 

In today’s edition:
1. The Women Who Get Ahead Aren’t Smarter. They Ask. - with Caroline Dell
2. Asking the Wrong Person Is the Mistake
3. TJD Power List
4. Lady Bits

1. The Women Who Get Ahead Aren’t Smarter. They Ask. - with Caroline Dell

Caroline Dell spent years building community and access for women in leadership as an early employee and executive at Chief before she left to found Goodword, a relationship management platform built on the idea that your network, not your resume, is your most valuable professional asset. She found her own technical co-founder through a single warm introduction and raised her first half a million dollars almost entirely from her personal network before she had a product or a co-founder to show for it. This episode is for anyone who has ever assumed the right opportunity would find them without ever picking up the phone.

In this episode you'll learn:
— Why the human brain can only meaningfully track around 1,500 relationships, and what that means for how you manage your own network
— Why women often wait to be asked instead of asking directly, and what that costs over a career
— The exact moment Caroline knew it was time to leave a company she helped build, and how long it actually took her to act on it
— How AI can preserve the human context that makes a relationship usable, instead of replacing the relationship itself

🎧 Listen here: Spotify | Apple | YouTube
Explore Goodword: goodword.com — use code FRIENDOFJJ for $25 off

2. Asking the Wrong Person Is the Mistake

Here is what happened to my client after that call. She stayed. Then she followed that same president to another company when he moved on, because he had, in his own way, become her patron, and patronage can feel like security even when you already know exactly who it is protecting. When he was eventually fired for sexual harassment, the same pattern catching up with him a second time, she was fired right alongside him. Collateral damage in someone else's reckoning.

He landed another job within months. He had the network, the clout, and enough people willing to vouch for him that one scandal barely slowed him down. She did not have any of that, not because she hadn't earned it, but because she had spent her capital building a relationship with one powerful man instead of building a reputation and a network of her own that existed independently of him. When he went down, there was nothing under her.

This is the real lesson, and it is not the one I expected to be writing. Asking for what you deserve was never the mistake. Who you ask, and whose approval you organize your entire career around, is where the actual risk lives. My client asked the right question. She just kept asking the same one person for permission to exist professionally, long after that question should have been distributed across a dozen relationships instead of concentrated in one.

Research confirms my client's fear of retaliation was not paranoia; it was an accurate prediction: women anticipate real social and professional penalties for negotiating assertively, and that anticipated cost is often correct, not distorted.

Here is what I would tell her now, and what I tell every client since:
1. Never let one person become your only source of professional oxygen. If a single relationship, boss, mentor, benefactor, is the entire reason you have a job, a reputation, or a network, you do not actually have those things. You have access to his.
2. Build your reputation with people who have nothing to do with him. Every professional relationship that exists independently of your patron is insurance you can't buy any other way. The moment he falls, and powerful men protecting bad behavior eventually do, those are the only relationships still standing.
3. Ask yourself who would still take your call if he disappeared tomorrow. If the honest answer is almost no one, that is not a reflection of your talent. It is a reflection of where you have been spending your relational capital, and it is fixable starting today.
4. Loyalty to a person is not the same as loyalty to your own career. You can respect someone, even owe someone, without tying your entire professional survival to their continued good standing.

REAL TALK
My client did everything right the day she asked for equal pay. Where it went wrong was every day after, when she kept asking one man for her worth instead of building a reputation that didn't depend on his answer. Ask boldly. Just make sure you are not asking the same person for everything.

Have a decision you're navigating and need a second set of eyes? Reach out to The Justice Dept.

3. TJD Power List: Gail Becker

Gail Becker Bet a Career on a Vegetable Nobody Asked For

Gail Becker left a corporate career, one that had already taken her through Warner Bros., Edelman, and the U.S. Department of Health and Human Services, because her sons have celiac disease and she was tired of not finding a cauliflower crust pizza worth eating. She launched CAULIPOWER in February 2017 with thirty stores at Whole Foods. She funded the early days herself, maxing out credit cards and selling her own clothes, because the capital she needed did not show up on the terms she wanted.

It worked. CAULIPOWER became America's number one cauliflower crust pizza and a top ten frozen pizza brand overall, and Forbes named it one of the world's most innovative food companies. She did all of that in an industry, food manufacturing, that had no reason to expect a former communications executive to understand supply chains, co-packers, or grocery buyers, and she disrupted a category that had not meaningfully changed in years.

She joined me on this podcast once before, back in 2023, to talk about exactly this. If you want to hear more of her story in her own words, listen to that conversation here. And that is why Gail Becker lands on this week's TJD Power List.

💋💋 Lady Bits

🤯 Women literally helped calculate the trajectory that put a man on the moon before they were legally allowed to get a credit card in their own name.

🤖 Stanford researchers built an AI model that can identify whether a brain scan belongs to a man or a woman with remarkable accuracy, based purely on how different brain regions talk to each other. Turns out the wiring really is different.

💵 The administration just drafted a new childcare subsidy that pays married couples up to $9,000 a year, but only if one spouse doesn't work. Single parents don't qualify. Guess which parent everyone assumes is staying home.

🤰 Doctors call it a "geriatric pregnancy" if you conceive after 35, the same clinical term used for patients over 75. The actual biology tells a very different story about who's aging faster.

Hi, I’m JJ

Since starting the Justice Dept, we have increased women's wealth by over $100MM in just over 5 years. Want to know what inspires me to do this work, other than making women money? My clients' surprised reaction when we manage to get them much better terms for themselves and their companies, whether via talent agreements, employment, severance, partnerships, asset sales or investments. They often admit that they never thought they could get that result. Not even hoped. This blows my mind. As we know at The Justice Dept. you are all worth everything you ask for and more. Reach out and we’ll show you how!
x TJD