A Silicon Valley client I hadn’t heard from in almost a decade sent an email asking about my availability.
I’m still in new daddy mode and dodging work like Wall Street dodges responsibility, but instead of a simple referral to one of my Bay Area copywriting friends, I found myself writing:
“I’d refer you to another copywriter, but over the last couple years the small handful of Bay Area tech/response copywriters I can personally vouch for have all been snapped up for regular gigs or fallen into Marketing Director jobs.”
“Feeding the online monster has become a fulltime gig at most organizations, direct response experience is more valuable than people admit, and these days it’s hard to argue with benefits.“
That’s more explanation than my contact wanted (in the interest of not whining I omitted the second sentence), but it does shine a light on an interesting question.
Are you planning to freelance until you’re dead?
Lots of friends ended up in the construction business, and while pounding nails is OK at 30, it’s a tough way to make a living when you’re 55. Some of them recognized that earlier than others.
I’m not sure how copywriters fit into that picture.
I like what I do. And I was working under the assumption I’d write (at least a little) until I toppled forward onto the keyboard.
But the marketplace — with its emphasis on change and youth — may not make that possible. I’m 51, an age that some have suggested disqualifies me from “regular” employment at an ad agency, the idea being I’m too impossibly old to form a truly creative idea or speak to younger audiences.
I’m not looking for a job and I can’t say I’ve suffered even a moment’s age discrimination, but in a decade, will clients trust their shiny new social media campaign to a 61 year-old copywriter?
I honestly don’t know.
It is harder to write a hundred headlines today than it was two decades ago, but I’d like to think a lot of hard-won wisdom more than fills any creative gaps.
And while I don’t tumble for every new digital media channel like some of the younger marketers, I also know the value of more traditional channels that newer marketers seem bent on ignoring.
Which is precisely why so much of my revenue comes from consulting.
I suspect that’s normal for freelance copywriters.
Still, in most of my small business consulting, we talk a lot about exit strategies and adding value to the organization beyond the founder.
Thinking which also applies to freelance copywriters. Is it time to start thinking about alternate revenue streams, or selling more than simply your time?
I’m not going to pretend I’m one of the last copywriters who started their writing career on a typewriter, but I do know it’s getting to be something of a distinction.
What happens when you’re fingered as one of the geezers who used to receive their checks in paper form, or when computers sat in big boxes under the desk instead of in your pocket, or when people actually typed copy?
What’s your plan for that day?
Keep writing (until you’re dead), Tom Chandler






I was talking about this with my wife the other day. I plan to keep on writing until I no longer can, but I will also train my sons so that if the employment situation for the youth in the UK doesn’t improve in the next 10-15 years at least they will have a skill they can fall back on. And, who knows, maybe they’ll be able to take on my client base and develop it as their own.
Alconcalcia(Quote) (Reply)
Interesting. Generational inheritance is pretty common in some industries, but I admit to never hearing of an instance in the freelance copywriting world.
Then again, maybe parents don’t want their kids to grow up to be writers…
TC(Quote) (Reply)
I’m hoping that the million dollar gig will come in next year and I’ll retire the year after and never touch a computer again… wishful thinking obviously. I’ve only done a “proper” job for three of the last 20 years so I guess I’m a dyed in the wool freelancer.
Derryck Strachan(Quote) (Reply)
There we go. 100 jobs at $1,000 each, or a single $100K gig?
I think a winning lottery ticket would ease the angst, the problem being that lotteries are typically taxes for those who are poor at math.
TC(Quote) (Reply)
>Are you planning to freelance until you’re dead?
You ask that as if there were a problem with it…
> will clients trust their shiny new social media campaign to a 61 year-old copywriter?
If you ask yourself this question often enough, you will probably paint yourself into a self-fulfilling prophecy. Happened to me in my last vocation.
>so much of my revenue comes from consulting. I suspect that’s normal for freelance copywriters.
Not for everybody.
How many of your readers are older than you are? How about a post that draws out the answers to some of your questions, like Alconcalcia’s perspective above? I think you’re on to something.
John White(Quote) (Reply)
Ageism is a very real thing in the ad agency game; I saw it from the inside in the 90s, and with the explosion of new digital media channels, I’m guessing it hasn’t improved over the years.
Simply put, I don’t envy a 50+ copywriter looking for a regular agency gig.
That said, I’m guessing ageism isn’t all that prevalent in the freelance universe, but anyone planning to freelance past their social security eligibility shouldn’t take the opportunity for granted.
I’m comfortable asking the question — as long as it’s a question, not an affirmation.
TC(Quote) (Reply)
This is quite a timely post for me as I recently applied for a fulltime copywriter position in Kuala Lumpur. Being self employed has its perks, but I’ve started to wonder whether I really fancy working from home for the rest of my life, and the anxiety of a fluctuating income, let alone paying for my own pension.
The opportunity came out of the blue and it’s for a great company with a Facebookesque corporate culture (no bosses! Yey!) in a fascinating new city for me to explore. They also have offices all over the world, so lots of scope for feeding my traveling bug. Still waiting to hear whether I managed to convince them to lure me in from the wilds of freelancing (I used my interview in working writers as one of my references:)), but if it falls through I think I’m going to keep looking.
If it doesnt work out I can always kickstart the Crucible again.
Matt Ambrose(Quote) (Reply)
Good luck. I started my career with a few freelance gigs, but went to a national ad agency gig almost immediately.
After leaving, I freelanced for a half-dozen years before I took another agency job; I was doing OK, but realized I didn’t know near enough about the business of advertising. I feared that when I spoke about the industry, I sounded like a 12 year-old boy discussing women.
Plenty to learn in each new situation. One of the dangers of freelancing is over-specializing yourself into a rut. Let us know, though if the job offer is somehow dependent on a Writer Underground blog post, I’m deeply concerned for your chances.
You should have picked a respectable blog.
TC(Quote) (Reply)
Not sure how things are in the UK compared to the US, but being a freelance copywriter can be a extremely lucrative career, affording many with lifestyles that others can only dream about. I can only imagine the same opportunities exist almost everywhere, and is mainly dependent on your mind state.
Many ad agencies are all about the “newest trend” and/or clever writing instead of EFFECTIVE writing. However, there is enough market share out there to ensure you never need to rely on an ad agency unless you want to, right?
Jarvis Edwards(Quote) (Reply)
Is it just my ear, or do a lot of copywriters leave comments that read like infomercials?
Marc(Quote) (Reply)
Ouch. But… yes.
TC(Quote) (Reply)