I did not start freelancing until I was in my late 30s. The beauty of this is that I made enough mistakes in my past careers that I did not enter into this world with unrealistic expectations or an overly romanticized vision of what this life might look like—besides being able to work from home in my PJs. I find that because I have launched a successful second career, people my age, and older, are intrigued by the idea of being a freelancer over the age of 40.

I tell people that the first time we do anything can be daunting. Even if we are well prepared, there is always the “what if” question that lingers. I recently had a virtual conversation with a witty older man who wants to be a freelance writer. He primarily uses his Facebook statuses as microblogs. With a strong following and positive feedback, he is ready to launch a public blog. His primary concern is that people outside of his immediate social circle might not “get him”. My advice to him was to write in a way that is authentic and true. The most successful writers are ones who are honest or even vulnerable.

I told him that I struggle with people who use language not as a bridge to bring about greater understanding, but as a barrier. Unfortunately, there was a time in my life when that person was me. I wanted people to know that I was smart so I would intentionally use archaic words and revise my sentences to make them more complex and more convoluted. This was a carryover from my days as an academic. Yet, what worked in academia did not work in the blogosphere.

Lesson One: Transitioning to freelancing may require a new approach to your craft.

Like many people who desire to speak or write for the public domain, I underestimated how much connecting with my audience mattered. I thought it was about me, my ideas, and my purpose. When this happens, and it happens too often, I think, we tend to see audience members as consumers and not conversants. Yes, public writing is intended to be consumed—especially if a blog is monetized or a book is for sale—but, it is also supposed to be a conversation, albeit imaginary, between the writer and the reader.

Lesson Two: Not all projects will be right for a more mature freelancer.

Whether it is a light hearted topic or something more serious, there are times when a writer’s age is a disadvantage; conversely, there are times when it is an advantage. Every once in awhile, I am asked to contribute to an outlet whose target audience is millennials. Obviously, I am not a millennial—I have taught them; I mentor a few; and there are several in my family.
My experience of writing for them is not the same as writing as one of them.

I made this clear to one editor and she told me that I probably wouldn’t be a good fit because she needed someone with intimate knowledge about their everyday lives. I also did a pitch once for an outlet that wanted an article about the nuances of first time homeownership. Albeit, it’s been a while, but I was a first time homebuyer 17 years ago. Needless to say, I didn’t get any extra brownie points or that writing gig.

Lesson Three: You have a lot to share.

Having the diverse life experiences that often come along with being older coupled with a willingness to speak openly about more complex topics is definitely an asset. So when I was pressed further by my 40+ year old FB friend about the advantages of freelancing, I told him to draw from his wealth of knowledge.

He asked me what should he do if “his truth” is difficult for others to accept. I responded that he should keep writing. Eventually he will find an audience that will embrace him and his writing style. The alternative—never writing for the public—is not an option. Of course, he, like others who are newer to freelancing, will grow along the way and he may even discover that he’s not that hard to get after all.

And that’s the real beauty of being an older freelance writer. We can paint with a broad stroke or use the most intricate of brushes to tell stories, share experiences, and inform others.
What we can’t do is pretend to be people who we are not which leads to the best advice that I can give to anyone launching a second career as a freelancer: Make sure that the voice that you use is your own. Eventually, everything else will fall into place.


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