Do the Hard Thing: Eleanor Roosevelt’s Guide to Speaking, Having Conversations, and Being Brave

Eleanor Roosevelt – Sendy Spotlight Episode

Oh my goodness—writing about Eleanor Roosevelt is overwhelming! There are so many books, documentaries, articles, and stories written about her that trying to capture her life in a single week (or let’s be honest, a few days) feels impossible.

But that’s not what my Sendy Spotlights are about. Instead of trying to sum up someone’s whole life, I like to focus on a few powerful quotes or stories—moments that spark something in me—and share those thoughts with you. These are not necessarily Eleanor’s exact beliefs or messages, but they’re what I’ve learned by looking closely at her life. I hope, as we reflect on her story, we each find something to help us grow a little more into the courageous, resilient women we’re becoming.

And wow, was Eleanor Roosevelt ever a sendy woman.

I feel a real kinship with her—as a mother trying to do her best, as a woman learning to speak up, and as someone constantly curious about people. During her time in the White House, she invited all kinds of people to stay—even strangers off the street. She never dined alone, but also rarely dined with her husband. They had an interesting relationship that seemed to involve mutual respect if not a romantic love. They did have 6 children, with 5 of them surviving to adulthood. The family was in politics and the armed forces most of their lives. This was stressful. Franklin lost the use of his legs after contracting infantile paralysis just before his presidency. Eleanor became his legs because she could go places more quickly and could get the minds of the people. He felt people held back with him but were not afraid to speak their truly feelings to Eleanor. Franklin often asked Eleanor for help to understand issues. She had strong opinion that she was not afraid to defend. Although she never took credit for any of his policies, she was surely instrumental in many of the policies of the day. She was always talking, always listening, always learning. She wanted to understand people’s minds, and she made them feel seen.

A Little Background

Before we dive deeper, let’s clear up the Roosevelt family tree. It’s a little… tangled.

The first Roosevelt in America was Claes van Rosenvelt, who immigrated from Holland in the 1640s to what’s now New York City. He had two sons—one line became the Oyster Bay Roosevelts (that’s President Theodore Roosevelt’s side), and the other became the Hyde Park Roosevelts (Franklin’s side).

Theodore Roosevelt—yes, the one the teddy bear is named after—was Eleanor’s uncle. Be sure to listen to the Sendy Mom episode on Margarete Steiff who was the inventor of the teddy bear for more information on that. Eleanor’s father, Elliott Roosevelt, was Theodore’s younger brother. Eleanor and Franklin were actually fifth cousins. So yes—she was a Roosevelt before she married Franklin Roosevelt, who was also a Roosevelt!

Eleanor was born in 1884, named Anna Eleanor after her mother. Her mother came from a wealthy, socially powerful family, while her father, Elliott, had a kind, warm heart but struggled deeply with alcoholism. Eleanor adored her father. She later said he was the love of her life.

Tragically, her mother died when Eleanor was just eight. Two years later, her beloved father died after a seizure, following a suicide attempt. After that, Eleanor and her younger brother Hall were raised by their maternal grandmother. Hall became almost like a son to Eleanor, especially after she and Franklin married.

The Shy Girl Who Became a Voice for Millions

Eleanor was shy. Painfully shy. She didn’t think she was pretty. She didn’t think she was a good speaker. She didn’t love being in public. But she trained herself. She learned how to hold a conversation by listening to others and picking up bits of knowledge she could repeat. She said:

“More and more as I grew older, I used the quickness of my mind to pick the minds of other people and use their knowledge as my own… Few people were aware of how little I actually knew on a variety of subjects that I talked on with apparent ease.”

She considered this a bad habit. Maybe she thought it was dishonest. But I actually think there’s something sendy about it—listening, learning, being curious. Using what you hear not to impress but to connect. Being curious about topics you have little understanding of is a great way to start a conversation with someone who might know more than you. People love to share what they are passionate about. Let your questions lift the other person to talk about what makes them feel sendy.

Learning to Speak—and Listen—with Heart

One of the most moving parts of Eleanor’s story for me is her honesty about struggling to communicate, especially with her children. When emotions ran high, she shut down. She said she’d “clam up,” thinking it made her strong. But it often created distance—especially with her daughter Anna.

Eleanor told a story about how, one day while reading to her sons, she suddenly began sobbing. She was overwhelmed with grief over how disconnected she felt from her daughter. That same day, Anna came to her, and they finally had a raw, real conversation. From then on, they became close friends.

That moment speaks to so many of us. It’s hard to know when to speak and what to say—especially to our children. We don’t want to say the wrong thing, but silence can hurt too. What I’ve learned is: it’s not about having the perfect words. It’s about being open, honest, kind, and curious. Ask questions. Share your experience. Listen with love.

Most children (and everyone really) don’t really want advice, they want validation, connection, and acceptance. When someone comes to you with a problem? Instead of telling them what they should do, try asking, “How would you solve it?” Help them discover their own answers. That’s when real growth happens. You can keep rephrasing that question until they come to the answer themselves. Sometimes I’ll share things I’ve learned in my life or what seems to be working right now, but usually they already know the answer, just be a safe place for them to work it out.

Facing Fear and Finding Her Voice

Eleanor said she was not a natural speaker—and yet she gave hundreds of speeches. One of Franklin’s friends, Louis Howe, helped her early on. He pointed out that she laughed nervously after serious remarks—and how distracting that was. Ouch. But she took the feedback. She got better. He told her:

“Have something to say. Say it. And sit down.”

Simple. Sendy.

Hard Relationships and Lessons in Control

Her relationship with her mother-in-law was complicated. Franklin’s mother was strong-willed, controlling, and used money to keep her family close. When Eleanor and Franklin tried to raise their children to be independent, she often undermined them. One time, their son wrecked his car. They wanted him to face the consequences—but Grandma bought him an even nicer one.

Eleanor admired her, but they clashed. This reminds me: Money can be a tool—or a weapon. Don’t let money control you. And don’t use it to control others. It is fun to be generous, but it should come from love, not leverage.

A Champion for Equality and Peace

One of the things I love most about Eleanor Roosevelt was how she treated everyone as worthy of dignity and attention. She dined with royalty and regular folks with equal grace. She pushed for civil rights, inviting Black Americans to the White House and advocating for change. She was her husband’s eyes and ears—traveling, observing, connecting with people he couldn’t reach.

She hated war. After living through two, she made a personal vow to do everything she could to promote peace:

“I kept praying that I might be able to prevent a repetition of the stupidity called war… but the progress the world has made towards peace seems as the crawling of a little child, halting and slow.”

She knew how slow change could be. But she didn’t give up.

Why Eleanor Is a Sendy Mom

Eleanor Roosevelt did uncomfortable things every day. She spoke when she was afraid. She loved when it was hard. She got better, not bitter. And she challenged herself—and all of us—with these words:

“Do one thing every day that scares you.”

That’s sendy. That’s brave. That’s a mom who kept showing up, even when it was messy.

And that’s what we’re all trying to do.