Most writers have a closet full of clothes that don’t fit anymore. Mine holds a few hundred articles and at least one book.
The cringe is the best evidence I’ll ever get that I’m still improving. Writers who never feel it worry me a lot more than the ones who do.
Open something written ten years ago and the pages are exactly as clumsy as the day they were typed. The person reading them is the one who moved. He now has the eye to spot the padded sentences and the places where the writer explained something the reader already understood. Why would anybody want to lose that eye?
I’ve written 113+ books under my own name and ghostwritten 54+ for other people, and at least one of the early ones is a book I’d rather not open again. I’m glad of that.
Why does old writing make a writer cringe?
Your taste outran your skill, and it never stopped running.
Ira Glass, the radio host, gave a short talk years ago that writers still pass around. His point was that people get into creative work because they have good taste, and for the first few years their work falls short of it. The only way across that gap is volume. You write a lot of material, most of it disappointing, until one day the work starts matching what you hear in your head.
He didn’t dwell on the next part, and I think it explains the cringe. The gap never closes for good. Your eye keeps improving every year you write, so every time you look back, you’re judging old work with a better instrument than the one that built it. A sentence that read fine a decade ago can read like a mouthful of gravel today. The words didn’t change. The reader did, and the reader is you.
The writers who never cringe at their old work fall into two groups. Some stopped improving. The rest never look back at all, and I can’t decide which group bothers me more.
I deleted almost 200 pages of my own work
My friend Joe Rockey, who runs his own business, told me on a call that he’d built about 30 pages on his website and only four were still active. The rest no longer fit what he was doing. He said there was something about turning it all off, knowing how much time and energy he’d put into it, and watching it go dead.
“That’s normal,” I told him.
Then I told him what I’d done. “I deleted almost 200 web pages because they no longer are a business I’m in. I’m not a LinkedIn branding expert anymore, don’t want to be, so I deleted all the LinkedIn branding crap. I had hundreds of articles about it. And they’re gone. And they were articles that I made, this was before AI, so it hurt even more.”
That last part still gets me.
I optimized 100+ LinkedIn profiles in those years, and I wrote Focus on LinkedIn, and it sold 15,000 copies in three days. I wrote those articles myself, before any AI tool could have drafted a paragraph for me. Each of them cost me real work. Deleting them hurt.
I did it anyway, because I’d stopped being that person.
I’m a ghostwriter now, and the site needed to say so to every reader who landed on it and to every AI engine reading it to decide what I do. A page about optimizing your LinkedIn headline told both of them the wrong thing about me. Two hundred of those pages shouted it.
Whole websites follow the same logic. masterofworlds.com and richardlowe.com used to be separate sites, and today both of them point to thewritingking.com. I’ve written about this pattern in code too, where deleting work you already paid for feels like losing even when keeping it costs you more. The same instinct shows up in writers, and it’s just as wrong there.
If your old work doesn’t embarrass you a little, you’ve stopped getting better. – Richard LoweShare on X
The early book I’d rather not open
The pages I deleted were good work for a business I’d left. My early books are a different kind of embarrassment.
A book I ghostwrote in my early years came up on a call with Joe. “That book was one of my first,” I told him. “If I looked at it now, I’d probably throw up.”
I meant it.
I knew systems back then. I’d designed and written a project management system in the 1980s, a full computer system, so organizing information and laying it out in a logical order came naturally. Organizing information and writing a book somebody enjoys are two different skills, though. Plenty of capable people have the first and spend years catching up on the second.
Early books carry the same faults in almost everybody’s hands. The sentences run long because the writer is afraid of leaving something out. Every point gets made, then made again in case the reader missed it. The voice sounds like a manual because the writer hasn’t yet trusted his own voice. Chapters open with throat clearing, and transitions announce what the next section will do before it does it.
The first weeks after publishing teach their own lessons, and I’ve written about clicking publish and hearing nothing back. My early book descriptions were worse than the books. An affiliate marketer I looked up to told me to stuff them with keywords, and I did. They were junk. When I finally rewrote them, the books sold more right away. That one stings, because I listened to somebody who sounded confident and, as he admitted later, had tested nothing.
Should you delete old blog posts that no longer fit your business?
Yes, when they describe work you don’t do anymore. Keep the ones that still help a reader and still fit the business.
A website tells people what a business does. These days it also tells AI engines, and those engines decide whether to send anybody over. I told Joe on that same call that the way to become known now is to become known to AI. An AI reads the whole site. If it sees two hundred pages about LinkedIn and a few dozen about ghostwriting, it can easily conclude the owner is a LinkedIn consultant who dabbles in books. That’s the wrong picture, and the pages had to go.
Old posts in a lane you’re still in get different treatment. If an article from six years ago still answers a question readers ask, update it and leave it up. Fix the outdated facts, tighten the opening, and cut the parts that make you wince. Don’t delete a useful article because the prose embarrasses you.
Readers don’t care that it could be written better today. They care whether it answers their question.
So the test has two parts. Does the page describe a business you’re in? Does it help the person reading it?
Two yeses mean it stays and gets a cleanup. A no on the first means it goes, even if the writing is the best you ever did.
How do you decide what to delete from an author website?
Make a list first, and don’t delete anything in a bad mood.
Start with a backup of the whole site, files and database both, stored somewhere other than the web host. My website backup guide covers how. Then export a list of every post and page with its traffic over the last year and the number of outside sites linking to it.
An analytics tool shows the traffic, and a backlink checker or Google Search Console shows the links. Put the whole list in a spreadsheet with a column for the decision and mark each page keep, update or delete. Then work through the deletes in one batch, so the decision gets made once and not again every time the dashboard opens.
Pages with outside links get a 301 redirect to the closest current page on the site. Those links took years to earn, and a redirect keeps their value pointed at something worth reading. Pick the target by topic. Lazy redirects that dump every old page on the homepage drive me nuts. They tell search engines nothing, and Google treats a lot of them as soft 404s anyway. Pages with no links and no traffic can go.
As of 2026, Google drops both a 404 and a 410 from its index, and a 410 tells it the removal was deliberate. After the deletes, pull the dead pages out of the menus, the sitemap and the internal links. A link from a homepage to a missing page looks careless to readers and machines alike. Run a broken link checker a week later, because something always slips through.
Keep a copy of everything you delete. Export the posts before you remove them. Disk space costs nothing. Dead articles hold paragraphs you’ll want for something new.
What old writing should a writer keep?
Keep anything that still serves a reader.
Keep a private copy of the rest. Why throw away the record of where you began?
Most old work belongs in that second pile. It comes down off the website or out of print and goes into a folder you rarely open. I still have my copy of the 2,000-page autobiography I typed on a classic Mac in the late 1980s. Nothing else shows me so clearly where I started.
A closet works the same way. The suit that still fits stays, and maybe one old shirt stays too, because it reminds you who you were. Everything else goes to somebody who can use it. Old writing is easier to handle. Nothing has to be given away, and the old work just stops hanging where people can see it.
I’d never destroy the only copy of something because it embarrasses me. That’s a mood talking, and moods pass. A writer five years from now will want to see how far he’s come, and a bad draft can hide a story that deserves a better telling. Writers who burn their early manuscripts lose the record of their own improvement, and I think that’s a shame.
Label the private archive so it stays useful. A folder per year, file names that say what the piece was and where it ran, and a plain text note on anything that was published under a different title. Keep two copies in two places, one on a drive at home and one in cloud storage, so a dead laptop doesn’t take the whole history with it. Ten minutes of labeling now saves an afternoon of digging later.
Should an author rewrite an old book or leave it alone?
Rewrite it if the subject still matters to you and to your readers. Leave it alone if it belongs to a version of you that’s gone.
My cybersecurity book started life as Safe Computing Is Like Safe Sex, and it’s now Family Cybersecurity. Under the old title it sold nothing. A book about a subject you’ve left is a different case. Rewriting it means spending weeks on something you’ll never promote, and no reader is waiting for it. A ghostwritten book isn’t yours to rewrite at all. It belongs to the client.
If you do rewrite, treat it as a new edition. A changed title or subtitle means a new ISBN, and Amazon’s KDP has terminated accounts for having two versions of the same book live at once. Check the rules on your platform before you touch the metadata. I learned that one the hard way, and it cost me my KDP account.
And don’t rewrite an old book because you’re ashamed of it. Shame is a lousy reason to spend six months on anything. Write the next book instead, and put everything you’ve learned into that one.
Cringe is how growth feels from the inside
Plenty of writers treat their old work as a verdict on their talent. They read a clumsy chapter from years back and decide they were never any good, and some of them stop writing over it. It’s the same voice I wrote about in my piece on imposter syndrome. It lies to you. The clumsy chapter is a measurement, and the measurement says you’ve moved a long way since then.
A coach looks at old game film to find the mistakes his team has stopped making and the ones still hanging around. He doesn’t sit there feeling bad. Why should a writer treat old pages any differently?
Use the cringe the same way. Pick one old piece and write down the three things that bother you most. Then open your newest draft and check whether those faults still show up. If one of them does, you know what to work on next.
I’d be more worried if I opened something from my early years and loved every line. That would mean I’d learned nothing since. I’ve learned a hell of a lot, and the wince proves it.
Clean out the closet and keep writing
Go through your old work this month. Back it up first, then sort every piece into keep, update or delete. Redirect the pages that earned links and take down whatever advertises a business you’ve left, with a private copy of all of it in a folder you control. Then stop rereading it and write something new.
If you want help figuring out what your writing does well and where it still falls short, my writing coaching service works through your pages with you, and the writing hub covers the rest of the craft. Empty the closet without guilt. The clothes that don’t fit anymore are the best proof you’ve got that you grew out of them, and I’d much rather be a writer with a full donation bag than one still squeezing into the same damn shirt.
