Kirk, a great addition to the list. And a prevalent problem.
I’ve known you a long time, my friend (can it really be 22 years already?). One thing I know is that you can do this. You have a stellar background. You have the talent. Now it’s time to hone the business side.
I hate seeing you struggle because I know it just takes lining up the right things to get you to where you want to be.
You had the right idea with the political blog. Now take that to Twitter. And LinkedIn. Market by networking. You, my friend, can network with the best of them. I know you’ve got this.
So you want to take this to the job-hunting level. Do this: remove all dates from your resume. Seriously, nothing that goes back farther than ten years should be revealed. We live in a world in which age shouldn’t matter, but does far too much. It’s illegal to discriminate based on age, but prove it. It sucks.
Your goal should be to befriend those who have the ability to get you hired. Show your stuff. You are NOT “nothing special” except to yourself. Your unique skills and talent are needed. Don’t let that harpy on your shoulder convince you otherwise.

Thanks, that helps too 🙂

She is one-of-a-kind, isn’t she?

Thanks, Paula. I still expect to do freelance writing on the side when I come across opportunities “organically,” so to speak. But I’m giving up on feeling guilty whenever I read on this blog about my friend Lori’s remarkable self-discipline.

Hi Kirk – I’d rather be happily underemployed than unhappily gainfully employed, too. I’m glad you found a gig you love.

Acceptance can be great because it alleviates a lot of pressures that we put on ourselves, but don’t totally discount the idea of still freelancing on the side.

There are ways to help cope with rejection. Mine is to put the query out of mind as soon as I hit “send.”

I was reading your bulleted list of people who probably are not cut out to be freelance writers, waiting in vain to see the one that resonates with me. So here is a suggested addition: People who struggle to cope with rejection.

And here’s another: People who have a hard time staying productive when nothing in particular has to be done TODAY.

The two together explain why I can’t do what you do: market myself continually to build a business.

It’s taken me years to come to terms with the word “can’t” in that sentence. (“Of course you can, you lazy coward. You just need to develop a thicker skin and some self-discipline. You give up too easily.”)

I know I’d be better off as an employee than as a freelance. I can be very productive when someone I know expects something from me, and that very expectation means I’ve already fundamentally dodged rejection.

But job-hunting bumps up against exactly the same issues as trying to build a freelance business. I’ve been unemployed or underemployed for more than a decade now, thanks in part to the Great Recession and some medical challenges. I’m about to turn 61. I’m good at what I do, but I’m nothing special — there are a lot of people in their 30s and 40s who can do as well or better. Faced with two comparably qualified candidates, even I would hire one of them rather than me.

I’m actually in a much better emotional state than the foregoing suggests. It’s come from recognizing that at some point, “giving up” is indistinguishable from “accepting reality.”

Right now I’m happily underemployed as a writer/editor for a small religious magazine that focuses on my own denomination. It’s (nominally) part-time, no benefits, and pays a bit more than a fifth of what I made at my peak. But it’s better pay than I’ve averaged since 2009, and I like the work and the people. I get to work from home, and I wake up in the morning eager to get to my desk.

Before that I was driving for Uber, and if the magazine gig falls through, I’m more than willing to drive for Uber again. It’s not the career I had in mind 40 years ago when I graduated from Princeton. But I’ve been a lot happier since I’ve accepted that this is just the way things turned out.

Anyway, reading your blog over the years has played a part in this evolution, so thank you. I’d say keep up the good work, but I already know you will.

The one thing that just might get through to some of those people who try to diminish your value is simply turning it around on them with something like that, or “Once your budget improves, you know where to find me.” That’s a polite way of reminding them that aren’t the big fish they’re pretending to be.