How Do You Build a Writing and Speaking Career in Midlife? Maria Leonard Olsen on Side Gigs, a Shocking DNA Discovery, and 50 After 50

Episode SummaryAttorney and author Maria Leonard Olsen shows how women can build a fulfilling second career — as a writer, speaker, and podcaster — without giving up the financial security of their primary profession. After becoming a lawyer to please her immigrant mother, Olsen used the "side boat" of writing during a career break to eventually publish eight books, deliver two TEDx talks, host the podcast Becoming Your Best Version, and appear on CBS Sunday Morning, all while continuing to practice law full-time. The episode also covers a life-altering twist: a consumer DNA test revealed that the man who raised her was not her biological father, a discovery that became the subject of her upcoming book, Before and After the DNA Test. Listeners get a real, step-by-step roadmap — writing articles to build credibility, applying repeatedly for TEDx talks, posting daily on social media, and learning to say no — for turning a side project into a legacy-building second act.Key TakeawaysYou don't have to quit your day job to build something new. Olsen kept her law practice as a financial safety net while building her writing, speaking, and podcasting career on the side — proving a "side boat" and a primary career can coexist.Credibility is built in layers: articles first, then books, then stages. Olsen advises aspiring authors to write articles and build a "clip file" before pitching a book, because publishers and speaking bureaus want proof that others have already paid for your work.Consistent, low-effort visibility compounds over time. Daily posting on LinkedIn (which cross-posts to Facebook, X, and Threads) built the following and credibility that eventually led to a CBS Sunday Morning feature — after a producer found her simply by searching "bucket lists."Misattributed parentage from consumer DNA tests is more common than people think. Olsen's own 23andMe result revealed her father was not her biological parent, a discovery so disruptive that she spent a year researching it, wrote a book about it, and now warns others about the emotional and legal consequences of home DNA testing.Saying no to others is often saying yes to yourself. Escaping a lifelong pattern of people-pleasing — by asking "Do I really want to do this, or am I just trying to please someone?" — freed Olsen to focus her time on what actually aligns with her goals.Guest Bio: Who Is Maria Leonard Olsen?Maria Leonard Olsen is a practicing attorney in Washington, D.C., an author of eight books, and a two-time TEDx speaker. Her most popular book, 50 After 50: Reframing the Next Chapter of Your Life, chronicles the 50 new things she tried during her 50th year following divorce, sobriety, and becoming an empty nester — and became the basis for her TEDx talk, "Turning Life's Challenges Into a Force for Good." A graduate of Boston College and the University of Virginia School of Law, Olsen served in the Clinton administration's Justice Department before building a career in civil litigation. She hosts the award-winning podcast Becoming Your Best Version, where she has interviewed more than 300 guests about personal growth and reinvention. Her story has been featured on CBS Sunday Morning, and she writes for outlets including AARP's The Ethel. Her forthcoming book, Before and After the DNA Test, explores the emotional and legal fallout of misattributed parentage — a subject she researched after a consumer DNA test revealed her own father was not her biological parent.Frequently Asked QuestionsHow can I start a side career while keeping my full-time job?Start small and build proof of your work over time. Maria Leonard Olsen recommends writing articles first to build a "clip file," then using that credibility to pursue books, speaking engagements, and other opportunities — all while your primary job continues to provide financial stability.How do you get a TEDx talk?Getting a TEDx talk typically requires persistence and a track record. Olsen submitted twelve applications before she was accepted, and recommends building a platform and publication history first, since TEDx organizers vet speakers and often require coaching before the event.What are the risks of taking a consumer DNA test like 23andMe?Consumer DNA tests can reveal misattributed parentage, meaning the person who raised you is not your biological parent — a discovery Olsen experienced firsthand. She warns that these tests, often marketed as fun holiday gifts, can uncover unexpected family secrets with significant emotional and legal consequences, which is why she wrote Before and After the DNA Test.How do you stop being a people pleaser?Olsen suggests pausing before saying yes to any request and asking two questions: "Am I doing this because I want to, or just to please someone?" and "Does this bring me closer to who I want to be?" If the answer is no, she recommends politely declining without over-explaining, recognizing that saying no to others is often saying yes to yourself.Can you make money from writing books, speaking, and podcasting?It's possible, but Olsen describes it as slow going unless you're a skilled marketer. Speaking engagements at corporations can be lucrative, while books tend to build credibility and open other opportunities rather than generate direct income. She recommends keeping a primary source of income while building a following through consistent content and public speaking.Resource Stack50 After 50: Reframing the Next Chapter of Your Life by Maria Leonard Olsen Maria Leonard Olsen's official website (books, TEDx talks, speaking inquiries) — marialeonardolsen.comTEDx Talk: "Turning Life's Challenges Into a Force for Good" — available via her websiteBecoming Your Best Version podcast — Apple Podcasts | Spotify23andMe DNA testing service (referenced in the discussion of misattributed parentage) — 23andme.comWhere to Find Maria Leonard OlsenWebsite: marialeonardolsen.comInstagram: @fiftyafter50Facebook: @FiftyAfter50Podcast, Becoming Your Best Version: Apple Podcasts | SpotifyBook: 50 After 50: Reframing the Next Chapter of Your Life — available on AmazonForthcoming book: Before and After the DNA Test — available for pre-order via her websiteAbout Build Your Own BoatBuild Your Own Boat is a podcast series hosted by Janine Vanderburg — award-winning three-time entrepreneur and anti-ageism advocate — featuring women who have launched new entrepreneurial ventures in midlife and beyond. The series is part of a larger storytelling project that includes a Substack publication and a forthcoming book, all built ar...