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Writing as Generosity: Brenda Ueland’s Message for Lawyers

By Kevin O'Keefe on May 11, 2025
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In 1938, a writer from Minneapolis named Brenda Ueland published a seminal book on writing. Her message was simple: everyone is creative, everyone has a voice, and everyone should write.

That book, If You Want to Write, has stayed in print for over 80 years—not because it teaches structure or grammar, but because it invites people to be honest, unafraid, and human when they write. Ueland believed that good writing comes from truth, not performance.

Guy Kawasaki—former Apple evangelist, bestselling author, and Silicon Valley thought leader—has called If You Want to Write “perhaps my favorite book of all time,” because it helped him overcome self-doubt and embrace the power of honest, fearless creativity across all forms of work.

It was Kawasaki’s naming of Ueland’s book as number one in his Inc. Magazine list of top four books in 1999 that turned me on to If You Want to Write. At the time, I was trying to figure out how to write—a necessity—while starting LexBlog.

How could I break from twenty years of writing as a lawyer—and begin writing better? I thought good writing meant mastering structure and grammar, ala The Elements of Style by Strunk & White (not that there’s anything wrong with it). But Ueland pointed to something more meaningful.

She taught that writing isn’t just about showing off what you know or have read—it’s also a bit about being yourself, something only you can do.

Sure, the law needs to be there, but Ueland believed writing should feel like a conversation with someone who cares about you and wants to understand what you’re feeling and thinking. That kind of writing isn’t about proving anything. It’s about connection. It’s about generosity.

That message feels timely in the world of legal blogging where it can be easy to slip into writing for search engines, leads and metrics. There’s nothing inherently wrong with wanting visibility—but voice matters more. And the best legal bloggers I’ve seen are the ones who write with the kind of clarity, candor, and care that Ueland would have cheered for. They know that writing is not a performance but an act of generosity.

You don’t need to be perfect to write something worth reading. You don’t need to have all the answers or the cleanest grammar. What matters is showing up with honesty and care. And in a profession that often prizes precision over presence, that may be the most generous act a lawyer can offer: to share what they see, what they know, and what they wonder about.

Photo of Kevin O'Keefe Kevin O'Keefe

I am a trial lawyer, turned legal tech entrepreneur, now leading the largest community of legal publishers in the world at LexBlog, Inc.

I am a lawyer of 39 years. Wanting to be a lawyer since I was a kid, I have loved…

I am a trial lawyer, turned legal tech entrepreneur, now leading the largest community of legal publishers in the world at LexBlog, Inc.

I am a lawyer of 39 years. Wanting to be a lawyer since I was a kid, I have loved almost every minute of it.

I practiced as a trial lawyer in rural Wisconsin for 17 years, representing plaintiffs, whether they were injury victims and their family members or small businesses.

In the mid-nineties, I discovered the Internet in the form of AOL. I began helping people by answering questions on AOL message boards and leading AOL’s legal community.

I later started my own listservs and message boards to help people on personal injury, medical malpractice, workers compensation and plaintiff’s employment law matters. Though we were green to technology and the Internet, USA Today said if my firm “didn’t stop what we were doing, we would give lawyers a good name.”

In 1999, I closed my law firm and we moved, as a family of seven, to Seattle to start my first company. Prairielaw.com was a virtual law community of people helping people, a sort of AOL on the law, featuring message boards, articles, chats, listervs and ask-a-lawyer.

Prairielaw.com was sold to LexisNexis, where it was incorporated into Martindale-Hubbell’s lawyers.com.

After a stint as VP of Business Development at LexisNexis, I founded LexBlog out of my garage in 2004 (no affiliation with LexisNexis).

Knowing lawyers get their best work from relationships and a strong word of mouth reputation, and not promoting themselves, I saw blogging as a perfect way for lawyers to build relationships and a reputation.

When I could not find someone to help me with my own blog, I started a company to provide what I needed. Strategy, professional design, platform, coaching, SEO, marketing and free ongoing support.

As a result of the outstanding work of my team of twenty and my blogging, the LexBlog community has grown to a community of over 30,000 legal professionals, world-wide.

Publishing my blog, Real Lawyers, now in its 18th year, I share information, news, and commentary to help legal professionals looking to network online, whether it be via blogging or other social media.

Blogging also enables me to think through my ideas – out loud and in an engaging fashion.

In addition to my blog, I liberally share others’ insight on Twitter. Feel free to engage me there as well on LinkedIn and Facebook.

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