The Plight of The Cobbler



One day you woke up and said to yourself that you wanted to control our own destiny. No more listening to the man or long hours stuck in a cubical.

“This podcast said I could do it!” you shout. So you went to work.

You found your first few customers through friends of friends and that extra $500 going into the weekend was damn nice. Back then it was easy, because you were honest. You were honest with yourself and your customer.

“Hey, I’m just starting out with this whole web design thing, but I can do it for ya.” You didn’t know it, but you were setting the client to consultant expectation. Somewhere along the way you’ve lost that.

The Cobbler finds herself lost in the work and not in the journey.

The problem: You don’t know the why

When I’m talking to other consultants and boutique agencies, I’m always digging for the why.

Why did you get into this industry? Do you have a long-term goal that you’re trying to achieve or is this just bridging the gap for some short-term cash? This past weekend I wrote an e-mail to my newsletter about this very dilemma.

You might have a company mission statement, but does that get you up every day?

For me it’s about solving problems by building technology that hasn’t been built before. That could be by piecing together off-the-shelf WordPress plugins or writing completely custom web apps from scratch.

It’s the journey, not the destination, I’ve come to enjoy.

What about you? If you cannot define yourself and your purpose, how can you possibly define your goals? I’m confident that a majority of us fall into these character sets:

  • The Cobbler
  • The Artist
  • The Boutique Bossman
  • The Digital Maven

As my storyline progresses I’ll define each, for today, I’m focused on The Cobbler.

Pro-tip: You can read my original e-mail here. You might like where it’s going.

The Plight of The Cobbler



“A shoemaker who repairs shoes, rather than manufacturing them” – Wikipedia

Take in the definition and that photo for a moment. What thoughts come to your mind?

Cobbler’s love the work that they do. I mean, you’d have to really love your job to fix other people’s shoes, right? As you take this in, what are some of the things you’ve noticed about the Cobbler?

  • There are no assistants.
  • No front-end person.
  • He’s the owner and the technician
  • He’s surrounded by his work
  • He’s surrounded by his tools
  • He repairs shoes, rather than manufactures them.

It’s in the very definition of The Cobbler where failure begins to rear its ugly head.

Repair vs Manufacturing (A Freelancer vs A Business)

If you’re a Cobbler your committing yourself to fix one problem at a time for one client at a time. Where the shoe manufacturer is serving thousands, employing a team, and setting up a process of streamlined manufacturing. Along with that foundation, sales and support to keep the company chugging full steam ahead.

WordPress is a breeding ground for Cobblers

I am 110% guilty of this.It’s part entrepreneur brain, part love for WordPress, part love for the industry.

I can spend hours trying new tools, plugins, and themes. It’s part of my job to stay sharp and bleeding edge of all things web and WordPress. I’m also a product builder, so I need to know what other software companies are doing with their offerings.

All your tools are belong to us
All your tools are belong to us

Tell me if this sounds familiar:

You started a project with this great new theme that promises design for an amazing new website in less time than it takes your 8-cup Chemex to brew your coffee. The client is going to love it, it’s exactly what they want and be damned if you’re going to waste time coding this yourself — you’re going to make 8000% margin!

You set out and start to style the homepage and it’s looking great — the client gives you a thumbs up. Fantastic! You’re already planning your Super Bowl weekend.

Now you just have to touch it up by installing a contact form plugin, e-commmerce, lead gen, commenting plugin, bread crumbs, oh yeah and a gallery. Wait, they want a slider on the homepage, no problem! We can do that. We have the resources.

Deep breath. You dive into your toolbox of plugins.

What’s this fatal error I’m getting? Why doesn’t this product page look like it’s supposed to? Text fields don’t look the same across pages. Maybe I’ll just Google this…

Then it all starts to unravel. You find your colleagues recommending another tool to get the job done. “It’s the easiest thing since sliced bread!” they shout.

Yep, that’s what I need. I need this tool!

Back to square one. There you are, chipping away at the sole of this shoe with your tools and your fancy apron. Birds are chirping, it’s now April, and that project you were supposed to have done in a weekend has now taken you 65 days.

The solution

It's about the journey
It’s about the journey

Something that really burns me is when I see internet marketers using pictures of Lambo’s to represent success. An illusion that your business can go from 0 – 60mph in 3 seconds in the world’s most prestigious car is absolute bullshit.

It’s also unhealthy to think it’s that easy. It’s the journey that defines us.

Each failure, success, conversation, hard time, good time and client creates a fingerprint that no one else can replicate. That is how our business is defined.

How does the Cobbler become the Artist?

Define who you are. I Want you to define what you’re truly capable of and what really motivates you about this business. Write it out and say it proud. If you’re not a developer, recognize it and don’t call yourself one. If you’ve never studied emotions or color theory or have never sketched out a layout on a piece of paper — don’t use designer.

I’m neither. My only real power is connecting with people and seeing scale at a 30-thousand foot view. Wish me luck.

Define your toolset. This is an addiction, I know it. I always want to try something new on incoming projects. Here’s what keeps me grounded: We have a core set of tools that we use on each project, like our Conductor plugin for layouts and content.

When we’re faced with a decision of looking for a new tool or building the solution, I’ll look to see if this is something that WordPress can already handle OR if we build it, can we use it again? For example, content permission capabilities. WordPress has ‘roles’ built into core — do you really need the overhead of a complex membership plugin?

Give yourself R&D time to play with new technology. Keep your project workflow streamlined and only divert from the path when it’s absolutely necessary.

Become specialized. You want to become designed for a particular purpose. For me, I specialize in building WordPress solutions for content publishers. You’re not only defining a better marketing message, but this specialization will equip you to have better internal processes and make client engagements even smoother.

Theoretical bullshit.

Sure is. When you’re in the stage of The Cobbler your biggest obstacle is yourself.

Mentally preparing yourself for growth, confidence, and defining yourself is what brings you to the next phase. If you do not write this shit down and train yourself to reflect on your journey – You. Will. Fail.

You will fall deeper into the abyss of doing the work. Every new client is just a cash grab to keep you breathing above water. There is no consistency in your work and your client problems become your problems.

That’s not to say you become so rigid that you cannot expand on your core and move into a new direction. You must be agile and be aware that you explore new paths to become The Artist.

In a recent e-mail I sent, I asked you to define who you were. Tell me, are you The Cobbler, The Artist, The Boutique Bossman, or The Digital Maven? Find the definitions here. Leave a comment below.


7 responses to “The Plight of The Cobbler”

  1. “WordPress is a breeding ground for Cobblers.”

    What gives WordPress its advantage is also what makes it difficult for freelancers to build a business. It is easy to get started, but hard to focus on what will take to subsequent levels.

    When we get heads-down in The Work, that’s when we become directionless. Specialization, defining our ideal client, and saying NO to unfruitful work are steps out of that mire.

    Looking forward to the rest of this series.

    1. Thanks for stopping by, John. 🙂

      Totally agree, it’s an advantage and a struggle at the same time. We need to identify what works for us and roll with that.

  2. My Kid has no shoes.

    It is time for me to reflect and um “pivot”? Umm, no actually become more laser beamed.

    1. I know you will get there, Rusty 🙂

  3. Wow, I will have to read this a few times. Not completely know who I was or what I wanted to do was the main reason I shut my site off for a bit (i didn’t stop working) but i did start another company. I saw Dre’s status about the weekly challenge and was already thinking of spinning up my site again.

    What am I?

    If I had to only use those four definitions I would say Artist with a sprinkling of Cobbler.

    But really I am the fixer. People call me to fix things. I fix them then I tell them what to do next.

    1. Welcome, Loren. 🙂

      I think this will click with you a bit more once I release my definition of the Artist. Thanks for stopping by, hope to see you around more.

  4. I think this is all generally true but overstated when you identify the “cobbler” with “failure” and low fees. Someone with a local or regional clientele who does traditional print-oriented design, marketing collaboration, and/or web is not necessarily unfocused or unprofitable, or unprofitable because unfocused. They may in fact be artists and consultants, but a lot of their clients will only ever appreciate them as cobblers, which is not to say they are underappreciated. That is often how the culture of smaller markets go — a jack of all trades with a diversified clientele is viable, but a specialist is not.

    My advice would be to minimize on cobbling clients or keep them within a certain threshold if they pay well. But if you want to be a cobbler, go for it. A lot of people seem to make this model work and enjoy one thing after another. They like the diversity and learning. Scaling up their business without dramatically adding to their costs would be hard, but it may not be their goal, and it’s not impossible.

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