Episode #438

The Good, the Bad, and the Ugly of Working for Yourself

With Jeffrey Shaw

Often, one of the hardest parts of the learning curve of launching a speaking business is being self employed. Many would-be entrepreneurs have longed for a textbook that explains how working for yourself actually works. Fortunately, Jeffrey Shaw, speaker, author, and expert in the unconventional art of being self-employed, has written a book about just that. For Episode 438 of The Speaker Lab podcast, he spoke with TSL founder Grant Baldwin about honing in on your expertise and managing your own business. He also shares his time-tested strategies for mastering the art of storytelling, one of the most important skills in any speaker’s toolkit.

Many speakers overextend themselves trying to reach too many audiences. Getting in front of the group who values what you have to offer can be a long process. Jeffrey has done the hard work for you–he cycled through a variety of audiences before finding the place where his expertise could deliver the most value. While it’s not bad to try different things with different people, narrowing your audience helps you focus on your very best content, delivery, and presentation for the people who appreciate it most.

Jeffrey’s very first successful business venture was in portrait photography, which as you can imagine lent itself to a great talent for storytelling. His secret? He actually catalogs the stories he thinks will be useful for speaking as they happen to him. We’re big fans of creating and establishing systems within your speaking business, so this is a really important part of the conversation!

Finally, and perhaps most importantly, Jeffrey has a lot to say about the good, the bad, and the ugly of working for yourself specifically as a speaker. Constantly traveling, managing the ebb and flow of engagements, and running all the logistical aspects of a business is no joke! Fortunately, Jeffrey really is the expert–he’s never worked for anybody but himself–-and he offers constructive encouragement to those in the trenches.

You’ll also hear all about:

  • Why it’s normal for the iterations of your entrepreneurial career to be nonlinear.
  • Which people in your life are well-positioned to help you find your expertise.
  • How to decide if expanding to a particular audience is financially wise.
  • How to deal with feeling like your business barely survives day-to-day.
  • The “trust mantra” that can help you remain resilient in moments of self-doubt.
  • How using stories can make the same talk appealing to wildly different audiences.
  • …and so much more!

Want to know exactly how to find and book more paid speaking gigs?

Download our 18-page guide to the 6 proven steps you can use to book more paid speaking gigs in 2024!

About Jeffrey Shaw

From humble beginnings, Jeffrey Shaw became one of the most preeminent portrait photographers in the United States. His on-location style and fine craftsmanship made him the go-to photographer for families of C-suite executives of Anheuser-Busch, Twitter, and many others, Supermodel Stephanie Seymour, news anchors Jim Nantz and David Bloom, sports icons Tom Seaver, Pat Riley, and Wall Street executives too many to mention. His portraits appeared on The Oprah Show, CBS News, in People and O Magazine and hang at Harvard University and The Norman Vincent Peale Center.

After 35 years of exceptional service to his exclusive clientele, Jeffrey decided to share his knowledge of business, branding, and marketing to support self-employed and small business owners as well as progressive-minded companies. He’s an in-demand keynote speaker at conferences such as HOW Design, Growth Marketing, corporations the likes of Verizon and BMW, and institutions such as Florida Atlantic University and the Adams Center for Entrepreneurship. Jeffrey is also the author of two books, LINGO and The Self-Employed Life, a LinkedIn Learning instructor, and a regular contributor to various publications. In 2014, Jeffrey started a podcast, Creative Warriors, later rebranded as The Self-Employed Life which is amongst the top 15% of all podcasts.

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