Early on in the late-90s action movie “The Negotiator”, police negotiating expert Chris Sabian remarks:

“I once talked a guy out of blowing up the Sears Tower but I can’t talk my wife out of the bedroom or my kid off the phone.”

It’s a modern twist of the timeless proverb ‘the cobbler’s children have no shoes’. If you haven’t come across the term before, it refers to someone who, while perfectly capable in their profession, is unable or unwilling to help their family with whatever skill they’ve mastered (in this case, the cobbler can’t even give his own kids shoes).

Yellow wooden clogs

And it’s a phrase that’s been kicking around my head for the past few months.


Because recently, I took the plunge into solopreneurship.

Little did I know…

I tripped up. A lot. Surprisingly, the things I stumbled over weren’t what I expected. Sure, finances are a drag, but easy to keep on top of if you spend the time. Replying to potential clients pronto and having the right process — two of the ‘professional basics’ — were both things I picked up super-fast.

But the things that I helped clients with as a copywriter, and got great feedback and response almost every time? No problem… except when it came to my own business.

So, what were these ‘cobbler kid’ mistakes leaving my business high and dry? The list is a long one, but these were a few that particularly stung.

1. Not optimising for SEO

What went wrong

You’re probably asking, “How the heck does a copywriter not optimise their own site for SEO?”

And that’s a good question!

Simply put, I didn’t appreciate the value or importance of SEO. My introduction to the industry and priority for the last several years was direct response copywriting. SEO barely rates a mention in this field, as the focus is squarely on how to craft effective, persuasive messaging.

SEO is its own speciality and one that I only recently started to explore. And yes, I’m discovering some hard lessons.

Getting back on track

The first step to getting half-decent at any skill is to get a clue from a credible source. The clue, in this case, came from Kate Toon’s SEO course.

The next stages involve a lot more elbow-grease. Slowly revisiting my web pages to optimise them for SEO is a painful but necessary task, but building off-site SEO with things like guest posting (with the help of lovely people like Sandra!) and directory links have been the #1 priority over the past month.

2. Under-pricing your services

What went wrong

Any business who doesn’t charge enough is at worst going out of business and at best checking in for a long stay in Struggle Town. And it’s not just a matter of profit and loss. Cheap prices can be a red flag to many customers and earn you a reputation as a budget service provider.

And yet, from my very first jobs in copywriting — where I wrote blog posts for $10/hr — to even earlier this year, price has been a big problem for me.

Imposter syndrome and lack of self-confidence certainly played a major part in that. Getting much of my early work on an online freelance platform, where low-cost bidding is prevalent, also had a role. Plus, the simple fact was that I didn’t know industry rates for a lot of things I did… a very basic thing I needed to address.


Getting back on track

To be honest, I sometimes still struggle to charge a fair rate. Being in a Facebook community where others encourage you to charge what you’re worth has been one big way to put the Under-charging Monster back in its box.

Sick of the wild ‘I guess it’ll be $70 for a web page’ guesses, I also followed the SEO example and read up. Being a bit of a Kate Toon fan (if you haven’t noticed), I took her pricing course, which created a lot of clarity to what I charge these days.

3. Not doing enough marketing

What went wrong

If you’re a copywriter, you’ve probably done jobs where it’s been as much about the marketing as it is the copy. Even if I’m not giving marketing advice, I almost always talk to clients about how they’re going about marketing their business.

Oh, how I wish I could have had that conversation to myself twelve months ago (without appearing like a complete crazy to the world).

In my earliest days, I was completely oblivious to the marketing side of things. And while I’ve learnt a lot over the years, it wasn’t until I’d been running my business for some months that the need for marketing became painfully apparent.

Getting back on track

I’ve found marketing as much an organisational challenge as anything else. Carving time out of every week to spend just on marketing has started the wheels to slowly turn.

Experimenting with things like social media and pay-per-click ads has also been educational. There have been mistakes (like setting up a landing page but disabling the opt-in button, then spending a few hundred dollars driving traffic to a useless page) but the lessons have been valuable most times.

Content marketing — in which blogs play a big part — also rears its head. On top of being super for SEO, it’s a powerful marketing tool for many businesses and sits at the top of my marketing to-do list these days.

4. Spending too much time with prospects

What went wrong

I’m an introvert but can spend hours talking to almost anyone about a subject I’m a fan of (like marketing, copywriting, or AFL). It’s a weird paradox.

So, when businesses approach me, I’m always happy to have a chat.

The problems started when I took 1, 2 or even more hours out of my workday to talk to prospects. Regardless of whether I ended up with work, it quickly became an inefficient way of scoping a project.

Getting back on track

Today, I try to be more ruthless and protective of my time.

I’ll always be happy to help people out, but the investment is more carefully controlled. 60-minute chats can be cut in half (or more). The pre-work I used to do is now sidelined until a project is green lit.

Finally, to finish on a more personal note…

5. Getting snared in the distraction trap

What went wrong

When you’ve got writing to do, it seems like the perfect time to jump on Facebook. Check out LinkedIn. Re-tweet a few blog posts.

That’s never been my problem, luckily. When it comes time to write, the siren song of social media is one I can happily sail past. But… email is a different proposition, even though the problem is the same (as Sandra points out here).

The little dopamine hit you get when a new email lands in the inbox is all it takes to keep me checking email throughout the day, even though 95% of it is non-urgent, irrelevant of flat-out crap.

While it’s not a serious time sink, it does break your concentration. That momentum kill is enough to hinder your productivity for the next couple of minutes. Add that up enough times over the day, and you’ve just lost a big chunk to the nefarious inbox.

Getting back on track

Using an app like Freedom to block access during my writing time was an obvious first step (which reminds me, I’ve been slipping lately!).

The second thing was to give myself permission to let my inbox blow out a bit throughout the week. “Inbox Zero” is a tempting target to strive for, but it becomes more a distracting annoyance than liberating. Cleaning out emails once every week or two is more than enough, just to make sure it doesn’t get to this…


How about you? Are you selling your shoes in the market while your kids (AKA your business) run barefoot in the back streets? And if so, what can you do to bring the love back into your own ‘home’?

About the author

Owner of the imaginatively-titled Dean Mackenzie Copywriting, Dean is a freelance copywriter trained in direct response methods, with most of his work centring on landing pages, emails, websites and sales pages.

He also enjoys speaking about himself in the third person and a good cup of tea.

How to unwittingly hurt your writing business and how to fix it
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