Congratulations to Neil Frank for Winning the August 2022 Barefoot Writing Challenge! (Your $100 prize is on its way!)

The challenge was to write an essay that answered this prompt:

Pull out your persuasive writing skills and write a letter to your partner, spouse, parent, or best friend to help them understand why copywriting is the right career choice for you.

Neil shared a touching letter about his lifelong pursuit of writing. Enjoy his winning submission:


So you’re skeptical that my becoming a copywriter at age 89 is a good idea.

Well, I hope to persuade you that it will indeed be an excellent move for me — and for us.

As you know, writing and editing have occupied a huge chunk of my life from my early years right to the present day.

And, I’m proud to say, in all that time I have always been known as a “good writer.”

If I may refresh you — 

My writing career began as a junior high and high school editor; progressed to various newspaper reporting gigs in the U.S., Australia, and Europe; and saw me become a high-level public relations writer with prestigious firms in New York and Los Angeles.

And to this day, of course, I’m still deeply involved in writing and editing as a self-employed executive recruiter and career coach here in L.A. 

So I think I can claim to be a strong writer (or, perhaps I should say, an able editor with strong writing skills).

With that experience to draw on, I’m sure I can retool myself as a contemporary copywriter — and thrive in the process.

(You know I’m never so contented as when I’m up to the hilt in reading, writing, editing, or otherwise immersed in the fascinating world of words.)

Apart from the satisfaction I hope to get from copywriting, let’s consider what it could mean for us in dollars and cents.

We know that although I certainly don’t want to give it up, my current consulting practice is in decline.

Adding copywriting to my professional menu will give us a decent shot at increasing our income.

And since we’ll both continue working from home, our day-to-day life would not change substantially.

So will copywriting be an easy road to riches, let alone a more satisfying work life?

Unfortunately, no.

I see three daunting challenges to cope with in order to make this work.

Chief among them has to be my age.

No matter how well I present, no matter how capable I am, no matter my “young” demeanor, my age can’t be concealed.

And we know from unpleasant experience that for many I must deal with, this will be an automatic turnoff.

Another problem is that, despite my wealth of writing experience, I’ll be learning a new trade with new techniques and technology to master.

Finally, there’s the ever-present chore faced by any independent consultant: getting business.

In my case, this task will be particularly difficult since as a brand-new copywriter, I’d be venturing into largely unfamiliar territory.

But enough of this cold water!

If I’ve done nothing else, I’ve switched gears successfully many times in my career — and with your support, I know I can do it again as a copywriter.

What do you say?