Freelancing, year 5.

As this new year kicks off, I’m pitching myself into it with a mix of optimism and pessimism. If I had to weight that mix, I’d put it at roughly 40% optimism and 60% pessimism. Here’s why.

I think the tilt toward pessimism is mainly due to the fact that I’m not a young man anymore. And the business world is enamored with young talent. This is nothing new. Young people are cheap to hire and they possess a naive exuberance about work that I sometimes wish I still had. That’s ok. A few failures down the road they’ll be wiser too.

Also, the freelance talent universe is expanding (regardless of the average age). And, the pool of freelancers on the market who will work for less is in abundance.

Then of course, there’s the pandemic horror show that won’t let up. That’s not helping. At all.

Let’s not forget about the stigma of the white male. And in my case, the 50-something white male. I’m theorizing that we’re all being lumped into a demographic profile that hirers are looking past.

So that’s my uneducated, unscientific guess as to the “why.”

I think this means 2022 has a good chance of being another year of under-employment for this stigmatized white guy. I cringe at the term “under-employed.” But, it’s fitting. I am one of those people ... the guy who was laid off and whose income or employment opportunities never really recovered … the guy who had a good job at a growing digital agency but account losses triggered layoffs and he became a statistic … the guy who has submitted hundreds of job applications but can’t get an interview. Yeah, I’ve become him.

That doesn’t mean I’ve given up. But it puts a busload of stress on the ego.

Mind you, it hasn’t been all dire straits. I’ve had freelance work each year, but it hasn’t exactly gotten us a dee-luxe apartment in the sky. And all the business relationships seem so fragile these days. I’m sure my clients — past and present — have all endured some level of Covid-19 instability the past two years. I’ve seen all types of upheaval on the client side since the pandemic started. Staff layoffs. Career changes. Maternity leaves. Reorgs. Early retirements. People who resign. A company is sold off, merged, or acquired and people get laid off due to role redundancies. A promotion (which usually leaves me at the mercy of the next marketing person to figure out who I am). It is, without question, really tough being on the outside always looking in, constantly asking for work.

And it’s not like I sit around waiting for jobs to land in my lap either. I’m very proactive about the process. I browse Upwork nearly every day. I cold email new clients every week — week after week, without fail. I circle back and email older clients with whom I’ve not worked in X number of months or even years. I connect with new people regularly on LinkedIn. I direct-message people sometimes too (though I think that’s a loss leader).

The other thing that continues to frustrate me year-over-year is the disappearance of the courtesy reply email. When exactly did this become the norm? People who are in a position to hire me simply won’t take 15-30 seconds to write a reply email. Or even to paste a stock reply into an email and hit Send (which would take about 3-5 seconds). Even amongst former clients, I usually get no reply if I send them a follow-up inquiry about work. I don’t really understand this behavior. I’d estimate that about 1% of all prospecting work I do via email gets a reply. The no-reply is unprofessional, in my opinion. But I guess it also points to the fact that most full-time employees are over-scheduled, over-worked, and dread having to wade through a stack of emails all day long.

One factor that I thought might be hurting my curb appeal was my website. While comprehensive, it wasn’t sharp looking or super well organized. So, last year I spent the entire 4th quarter completely overhauling my site’s UI and the work shown on it. I sunk literally hundreds of hours into it. (See my December 2021 “Year-End Productivity” post).

If you’re here reading this blog, maybe you’ve browsed my site. I hope you like it and appreciate the effort I put into it, not to mention the quality of the work itself. I’ve had a long career so far, and I hope there’s more to come. Otherwise, I’m going to have to seriously look at a career change. Then again, who’s hiring white guys in their late 50s?

Well, thanks for reading. Until next time, stay safe, do good things, and if you have a job, take a moment to appreciate it.