I specifically recall that at my first few jobs out of college, I was required to sign an employment agreement that prohibited me from discussing the terms of my employment, including my salary, with other employees.
This was the early 2000s and I didn’t think much of it until I found myself in a job where I felt grossly underpaid, working side by side with a colleague of the same age whom I suspected was paid more.
Instead of getting coffee with him and breaking the contract by flat-out asking what he was getting paid, I followed the company rules and buried my thoughts, leading to immeasurable resentment and anxiety, some of which I took out on him. (David, if you’re reading this, I’m so sorry!)
As bad as that experience was for me, it also helped shape my values around transparency. More on that in a sec…
In a recent NY Magazine interview with Sherri Shepherd, former co-host of The View, she credits Rosie O’Donnell’s generosity and transparency for earning her millions more than she would have settled for had O’Donnell not intervened. Shepherd shared:
“Rosie O’Donnell called and was like, ‘Let me tell you what everybody’s making — I make $2 million, Joy Behar makes $500,000, Elisabeth Hasselbeck makes $500,000…you need to ask for $2 million.’”

Considering the network had offered Shepherd just $400,000, O’Donnell’s transparency gave Shepherd a competitive edge in negotiating her pay throughout her seven years on The View.
“I eventually made millions, too. I always will credit Rosie O’Donnell for being free with that.”
Shepherd also shared that O’Donnell inspired her to pay it forward to others coming up behind her.
“I was very thankful to Rosie for what she did for me, and to this day, if there’s a woman who does a talk show, I’ll let her know what I make.”
Like Sherri Shepherd, I also had people in my career–a colleague, a headhunter, and a mentor–give me the gift of transparency, helping me reach my full financial potential.
No more questioning. No more resentment. No more struggling.
This is why I’ve brought transparency into The Upside community. When we share what we charge and are transparent about our pricing and not ashamed to discuss it, everyone is lifted, especially us.
Members of The Upside have access to these discussions plus hundreds of searchable real-world pricing case studies from members, open conversations on pricing, 1:1 support on pricing, and a cohort of similar colleagues to cross-check their ever-evolving pricing.
So, if you’re not already an Upside member and you ever find yourself wondering if you’re charging the right amount, reach out to someone you trust and say,
“I trust your opinion so much. Would you be willing to share feedback with me about an important proposal I’m pricing out?”
Transparency: It has become one of my core values in life and a competitive edge for our members.
I hope Sherri Shepherd’s story inspires you to incorporate transparency into your values and leverage it as your competitive edge.
You’ve got this!