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How do you break into speechwriting? (And why?)

Veteran freelance speechwritist Hal Gordon used to lobby me, when I ran the Speechwriters Conference, to do a session on "How to break into speechwriting—and how to bust out!" It would be a guide for communication generalists eager to find their way into this relatively lucrative and prestigious corner of the communication business. And it would be an escape guide for speechwriters who feel pigeon-holed in the specialty, and golden-handcuffed to powerful speakers who demand all their time. I never did it, because though the best conferences contain lots of reality, conference brochures are built on hope. Who wants to come to a conference where half the practitioners are trying to learn how to get out of the profession? But I thought of Hal's worthy idea the other day when I got this note, from the friend of a colleague:

Your time is precious I know, and likely worth a whole lot more than mine.

To the point: Is there a way I can break into or gently ease up to writing speeches for others?

I'm confident in my skills, but how and to whom do I convey that "give me my first break" pitch without falling flat on my face?

It's hardly the first time my precious time has been taken up trying to answer this question. The advice I usually give is: Do some speeches pro bono, for local politicians or the directors of nonprofits who could use the help. Use those speeches as clips to show to to other organizations—preferably organizations whose industries you understand and are interested in—in hopes you'll get one assignment, then, two and three. But there's nothing gentle or easy about that, and I always think: Isn't there anything else I can tell this person? Speechwriters, I put it to you: How would you advise this man of questionable sanity who wants to break into the speechwriting game? I'll point him here for your suggestions. —DM