Show Notes

In this episode, I talk with Gerard Dawson, a former high school English teacher who took a unique and entrepreneurial path out of the classroom. Gerard's journey is a powerful case study in how to leverage a specific skill—in his case, writing—to build a whole new career. Before landing his current role as a Product Manager at Swivl, Gerard spent years as a successful freelance copywriter for edtech companies.

Gerard shares his "accidental" transition into copywriting, how he had to "unlearn" some of his academic writing habits, and why the fast, iterative world of startups was the perfect "opposite" to the bureaucracy of a school system. He offers an honest, practical perspective on why a career change isn't always a 90-day sprint but often a "five-year" journey of picking a direction and building experience.

• From Academic to Copywriter: Gerard discusses his transition from teaching English to learning the "brutally honest" craft of copywriting, and how the two disciplines were surprisingly complementary.
• The "Blank Canvas" of Entrepreneurship: Why the fast, iterative, and flexible nature of freelancing was a welcome "opposite" to the slower, more bureaucratic pace of the school system.
• The "Five-Year" Transition: Gerard's refreshingly honest take that a career change isn't always fast. He explains why his own non-linear journey took years and why patience is essential.
• "Pick a Direction": His core advice for teachers. Instead of applying for "everything" and getting no results, identify one specific skill you have (or want to learn) and focus on building experience in that single area.
• Your "Hidden" Experience: Gerard shares a great story about a teacher with a successful Etsy store, reminding us that educators are often running side businesses or managing complex projects that are full of valuable, marketable skills.

Episode Article

My guest, Gerard Dawson, is my first guest who forged his path out of the classroom by hanging his own shingle. A former high school English teacher, Gerard’s story is a brilliant roadmap for anyone who has a specific skill they want to leverage, but isn't sure how.

Gerard's transition began with writing. He was already blogging about his teaching experiences when he started to get "a small audience" and connect with edtech companies. This led to freelance article writing, but he quickly realized he needed a more marketable skill. He dove into the world of copywriting, taking online courses and, most importantly, practicing. He had to "unlearn" some of the rules of academic writing and embrace the more concise, results-driven style of writing to sell.

This skill became the key to his next step: entrepreneurship. Gerard spent several years as a freelance copywriter and consultant for dozens of edtech companies. He describes this as the perfect "opposite" to the parts of teaching that frustrated him. While the school system was often slow and bureaucratic, freelancing was a "blank canvas" where he could "make all of his own decisions," test ideas, and get fast feedback. He explains that this freelance period was a "shortcut" that allowed him to "compress a lot of learning" about the edtech industry into just a few years.

His core advice for teachers is built on this experience. He shares that he, too, "was applying for everything" at first and getting nowhere. His breakthrough came when he decided to "pick a direction." He advises teachers to "look at any past work experiences... what do other people tell you that you're good at? And what do you maybe find interesting? And maybe see how that maps to the business world as a starting point?"

He shares a fantastic story of a teacher who felt she had no experience, yet offhandedly mentioned running a successful Etsy store. Gerard's reaction? "You set up your own online store, you create the product, you deliver it, you got customers... you're running your whole business!" His point is that teachers are already entrepreneurs, project managers, and leaders. You just have to learn to "recast" those skills for the role you want.