The Good, the Bad, and the Ugly of Working for Yourself with Jeffrey Shaw

Mar 21, 2023

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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!

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