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More on moving on

Plus, two quick items of follow-up for Release Notes listeners

👋 Release Notes listeners!

Charles Perry and Joe Cieplinski talked about my post from two weeks ago on the July 5 episode of their Release Notes podcast. Much to my surprise, too. Must have been a slow news week.

I listened to the show last night and there are two things I wanted to follow up on and one thing I want to add they might have missed.

More on being a “successful failure”

Charles and Joe thought I was unclear about why I defined my prior business as a “successful failure”. Joe says in part,

“He was a successful failure and it looked like a success from the outside but maybe it didn’t meet his expectations,. But it’s unclear if that’s from a money perspective where he hit a ceiling and couldn’t hit revenue or if he worked himself to the point where he couldn’t service his clients to the level he should. It’s not clear to me which he meant, but either one is kinda sucky.”

The answer is both.

The one part I take slight issue with is around 22:00 minutes in. Joe, again:

“He didn’t charge all that much for a high-touch service. If you’re paying $700 a month which is a lot more than the average person, you’re investing and trying to make an effort, but it’s not enough to pay him to do all the services I’m promising. So his approach was to approach customers for more money. Which is the classic strategy of ‘I’ll start off cheap and I’ll increase my prices.’ …the problem with targeting people is cost-conscious is they’re always cost-conscious.”

Long-time followers of my work my recall I sometimes joke about being ‘the cockroach of the internet’. Most people probably roll their eyes at that but I don’t think many people understood quite how serious I meant it.

I started pursuing clients in earnest when I was 19. I recall lots of people from that era circa 2006 who were doing the same kind of work around town. Coming from a small town to Indianapolis, Indy seemed “big enough” for me at the time.

We all enjoyed some measure of success but I quickly internalized the notion, “I’ll win because you want other things more than I do.”

Over a period of ten or so years all the people I was originally competing with went away. I followed-up with some of them and looked up others and realized they all took the same path: they got married. They had kids. They needed health insurance. Or they wanted fancy cars or vacations or a big house. In other words: life happened and other things became more important to them.

I didn’t have any of that. I went nowhere. I never took time off, and when I did I didn’t do anything. I spent no money. I had no debt, no credit card bills, no car payment, no student loans, and my highest bill was a $700 a month mortgage payment (to non-Hoosiers: yes, that number is accurate for a 3 bedroom 2 bath house. It was cheaper than renting, which is why I bought it.).

The first full year of my business made about $17,000, which was $4,000 more than I needed to live that year. I ate tuna sandwiches at least four times a week, often having half the mix for lunch and the other half for dinner. I was the cockroach among all those other business owners, surviving and winning simply because I didn’t have, need, or want any of the other things they fell into.

“Justin, how can you call that winning?”

Because of three things that are deeply ingrained in me:

  1. I’m unapologetically Midwestern in my approach to money. I hate spending it. Still do. To this day I won’t pick up cucumbers or tomatoes at a salad bar that charges by weight because those items are mostly water and expensive. It’s not some political statement or some weird fetish. It’s just how my brain is wired.
  2. The clients I bumped into and the network I had, particularly here around Indianapolis, weren’t going to support much else. I cared a lot about virtually all of them. They were and are good people doing their own hard things. When I asked to raise rates, it was because we were legitimately doing more. They knew that. But money was just tight, as it is for a lot of people.
  3. I told a colleague once, “There are a lot of people we serve who deserve a lot more. And I don’t understand how someone can charge them $10,000 for a $49 template.” That tactic, which I saw a lot pisses me off. A non-profit organization scraping by and pleading for money from every donor in town that thinks they’re getting a trustworthy partner to help them with their donor management instead gets a guy who charges them $5,000 or $10,000 for a $49 theme from ThemeForest and makes them write all the page copy can go to hell.

I never intended to start off cheap and then raise prices. That was never in my mind. I charged people what I thought they could afford and what seemed fair for the work.

The number one way I won over clients was by asking, “What’s your current website?” Then showing them the Dev Tools, opening Inspector, finding the CSS for the theme, Googling the name of the theme, and as the page popped up with a $49 theme asking, “How much did they charge you?” The reactions on people’s faces were one of quiet frustration. Like someone had just swindled them on tonic water.

I get why other agencies charge that much for so little. They have to because they all have those salaries to feed. They have a Hungry Ghost. I didn’t and actively avoided it. I lived like no one else I knew partly because I could and later because I had to.

But I was still an expense for clients. They felt the same way about increasing expenses you do when the light company says they’re going to raise rates. When I said I built the wrong business in the wrong direction, this is partially what I mean. Some agencies, particularly in SEO, just won’t work with anyone small because there’s no growth opportunity for them or you. I took on the people who had a little bit of money but not a lot, and every one of them was beyond challenging as a marketing problem.

“But Justin, how does this even happen?” Well, scope creep for one. And because it made sense at the time.

A common scenario would work like this:

  1. The client is ready for a new website for whatever reason.
  2. We’d talk about it and give a quote for some usual amount of services. Typically a website design, build, email campaigns, and maybe some ongoing work like design or writing. All the things some agencies “productize”, like saying, “You get two posts a month”. I didn’t, because I recognized some months were going to be busier than others. I thought about the whole year, not the month.
  3. Six months later they’d get an oddball request, like, “Wal-Mart wants to feature our product. We need to get them photos of all our products in this format at this size and at this website.” This is not anything anyone can productize beyond some hourly fee or generic “consulting”.
  4. Twelve months later the person who only wanted a website now needs a flyer for an event they’re co-hosting. And a sandwich board. And some Facebook graphics. None of these were expected.

These last two steps pose a dilemma. If I take them on, I have to do the work. If I ignore or pass on them claiming they’re out of scope they can and will find someone else. I know because it happened every time.

Inevitably the nonprofit that is partnering with another nonprofit will find someone at the other place who knows someone to “do something quickly”. And guess what, it’ll become your problem anyway. They’ll find someone who will do the signage and set the design tone for the event. And guess where the client wants all that stuff? On their website, which is still your problem.

This is how I found myself taking design direction from accountants and having to scrape together fonts and image assets that were low-quality, ugly, off-brand, copyright violations, or just plain crappy. Since the client website is the center of their digital universe, my request not to pay attention to the flyer and signs they wanted to tack up around town means someone else did, and now I have a 40MB PDF brimming with comic sans and nothing else to work with.

And this leads me to my final additional point about why I moved on, and something Charles and Joe might have missed: my reason for selling was a lack of depth.

Generalists vs. specialists and depth vs. breadth

Dave Epstein has this philosophy of “generalist vs. specialist” in his book “Range”. Epstein says people should be generalists because it gives people wider flexibility and more value because they can intersect ideas. I don’t disagree with that. But there’s such a thing as being “too generalist”.

My work became a sludge of random processes:

  1. Client wants to promote an upcoming event.
  2. Write a blog post about the event. I know nothing about anything. Need to talk to people about the event for research.
  3. Need a featured image for the post. They don’t have one. Need to illustrate or get a stock photo.
  4. Crop and edit image. Add to post.
  5. Set metadata and make sure keywords are good.
  6. Send to client for review. Client wants to change headline. SEO ruined.
  7. Revise and publish post. WordPress encounters an error.
  8. Investigate error. Discover issue with PHP version.
  9. Update PHP version. Some other plugin breaks.
  10. Investigate that bug, get fixed. “Ugh, the client just wanted this dang blog post.”
  11. Post added, prepare to schedule to Facebook, Twitter, LinkedIn, and probably some other place that won’t get any clicks.
  12. Make an email campaign. Send to client for review.
  13. Client wants to change three paragraphs. Edits prior Word Doc with changes, but didn’t track changes. Have to re-publish all material in the post and email campaign.
  14. Done.
  15. Client says someone in the office thinks the guy in the stock photo reminds them of a serial killer who might be their ex and has serious daddy issues about it. Need to change the photo.
  16. Find a new photo. Facebook OpenGraph cache is stuck, need to flush the cache. Email campaign was already sent.
  17. Done.
  18. Client wants to know why we can’t change the email campaign’s image. And Facebook is “still showing the old image”.
  19. Explain how email and Facebook work.
  20. Done.
  21. Client wants to delete the old post on Facebook and re-post.
  22. Reposts to Facebook and social media.
  23. Done.

I was over that simply because I could predict the whole situation before it happened and despite getting people to sign off on things and reviewing edits early and revising and padding time for people to change their minds, it always happened. There’s no professional growth for me or really anyone there. I could do and manage all those things with aplomb.

What I want now is depth. Like I said before, I’m a good designer, a good developer, a good salesman, a good client manager, a good project manager, and a good writer. But am I great at any of them? I dunno. That’s what I want to find out. Most people tell me my best skill is patience. I can’t imagine why.

So despite having a business that made about $100,000 a year and being able to pay most people something close to respectable, the business was fine. The work wasn’t up to what I wanted. So I’m taking all those generalist skills and moving into copywriting and research work.

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Photo of Justin Harter


Justin has been around the Internet long enough to remember when people started saying “content is king”.

He has worked for some of Indiana’s largest companies, state government, taught college-level courses, and about 1.1M people see his work every year.

You’ll probably see him around Indianapolis on a bicycle.

1 thought on “More on moving on”

  1. Good to see you on here. I think about you often and hope you are doing well. What I read here seems to point to life being OK for you. Stay in touch.
    Sorry if I wrote this in a section where it shouldn’t be, but you already know how computer illiterate I am.

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