The day the webmaster died: 9 crazy deadline personalities

I’ve seen a lot of crazy in my 20+ years in the marketing biz as a creative professional. But when a conversation begins, “Hello, our webmaster died,” you know you’re looking at a whole different level of crazy. Here’s how it went down, according to my design friend Susan:

“True story 1:30pm yesterday, a client I haven’t heard from in months calls up out of the blue and says, ‘Our webmaster died last year. How much would it cost to take down our site, create a new one and add e-commerce before our event in 10 days?’ I ask, what’s your budget? The client replies, ‘We don’t have one but we need to spend as little as possible.’ “

No matter how much you love your work, we could all do without the deadline nightmares. While there Β are those tough people are very good at saying no to unreasonable requests, many of us are afraid to say no lest we be labeled “uncooperative.” Frankly, nowadays it feels a little nuts to say no, no matter how crazy the deadline.

I have compiled this list of the worst deadline personalities because, as much as we may like our clients or colleagues, they drive us insane by the insanity of their deadlines. Whether you freelance or work full-time, you’ll recognize them–hopefully they are not you.

The Five O’Clock Shadow. This client or colleague waits until 4:58 sharp, right as you’re packing up to leave, to call or stop by and “give you a heads up” on a new project or the revisions you’ve been waiting for all day long.

The Bait and Switch. This project starts out small, quick or easy and before you know it, it evolves into a full-blown campaign with multiple components, themes, versions, viral videos, t-shirts and billboards. which means you would have approached it completely differently from the start. And it’s all still due tomorrow. This can also happen when the two-week due date flies out the window when you get the call, “We need it tomorrow.”

The Bargain Hunter. Budgets are tight these days, but these folks have come to think of creative work as “Let’s Make a Deal.” Your estimate is merely a starting point in the negotiation. Others think you are trying to rip them off. No matter what you charge, it’s always too much.

The UnderEstimator. To these folks, your job doesn’t require time, effort or expertise–perhaps you could be replaced by an intern or a monkey. Or they don’t quite understand what is entailed to execute a particular creative project. So they see nothing wrong with asking you to complete a six-week project in six days. When you explain exactly what is entailed in the scope, they are genuinely shocked–then they blink and say, “So, tomorrow then?”

The DIY. The do-it-yourselfer is convinced that they don’t need to pay someone to do something they can do themselves. These folks have not come to appreciate that while yes, everyone can use photoshop, not everyone is a graphic designer. Or that just because you can write doesn’t mean you can write a compelling sales pitch.

The Fiddler. They can’t leave well enough alone. They fiddle with the colors. Question the shape of the text box. Pick and fuss at the logo until it looks like a cat ate it and coughed it up as a hairball. They are endless “tweakers” of copy, changing words and phrases here and there, and there, and here, then making wholesale paragraph changes, or worse, rewriting everything on the final review, until suddenly you realize you are on Round 18 of revisions and you only budgeted for three.

The Spontaneous Genius. These are the creative sparks that pop up the day before an event or meeting that was humming along UNTIL…someone has an absolutely brilliant idea that, in normal people time, would require a team, equipment and a class or two. Instead, all you get is a “go for it!”, a mad search of how-to videos on YouTube and one all-nighter. When the clock is ticking and you hear things like, “Hey, I know!” or “Here’s an idea!”, RUN. You’re about to be hit with spontaneous genius.

The Mystery Meat Special. The conversation goes something like this:Β “We need something designed, we don’t have the details yet, but how fast can you get it done and how much will it cost?” Huh???

Brain Freeze. Whether you’ve had the project for 5 days or 5 minutes, sometimes your brain just…dies. Every idea you manage to come up with sucks and you start to wonder if it’s time to consider a career change. Ditch digger and Walmart Greeter comes to mind. This can happen because of any of the crazy deadline personalities above, but sometimes it just happens for no damn good reason. That’s when you call a trusted cohort and vent until you are laughing again and then the idea comes and you are relieved because you still have “it.” Until the next brain freeze.

Go ahead. Vent. What’s your worst deadline horror story?

109 thoughts on “The day the webmaster died: 9 crazy deadline personalities

  1. Awesome post! I relate to all of it. πŸ™‚ Although I am in IT and not in Marketing, I do maintain all our companies web projects. And the UnderEstimator is what kills me everytime. For example, I was asked to put a new website up for a company we just aquired and the want it done in 12 days from scratch??! with no direction on it and minimal content. Frustrating to say the least. They actually said “can’t you just copy and paste?” People just don’t get it sometimes.

  2. This was terrific. And I know them all. As a graphic designer myself who frequently commiserates with another friend who does the same, we periodically share our war stories about clients and their behaviors. I think you’ve neatly summarized them all.
    Great post.

    1. wow, thanks Chris! if we don’t find the humor in the insanity, what’s the point, right?! Jeanne, I’m glad you could relate; i can’t tell you how many times i’ve called up people i know to just say, can you believe this? or worse, can you top this? sometimes i just need to verify that i’m not the crazy one. John, currently i work in marketing for an it company, so i totally get it! that’s why this topic really spoke to me, it crosses over all industries, not just marketing. when i first started in the biz and everything was going digital, an art director half-joked that the agency owner thought if he wanted a picture on elephant, we could just press “e” and voila! the technology may change, but some attitudes never die!

  3. OMG… thank you for confirming that I wasn’t going insane. You hit the nail on the head on all points. I’ve been designing websites for the past decade and have encountered each and every one of the circumstances you’ve mentioned.

    Awesome post. Cheers!

    1. Samantha, sounds like another personality, what would you call it? Thanks Zen Assassin, sorry it’s all true, really, I’ve experienced every single one of these too. Craziness!

  4. Very nice. I had one boss that would constantly wait to the 11 th hour to tell us important information like “oh, the CEO of the company is coming tomorrow for a visit. The store needs to be ready.” Um, thanks. Really?

  5. This is a fantastic post! I have different kinds of deadlines where I work, but it doesn’t matter…the stories still translate over well. “Oh hey…I know I’ve been sitting in the office across from your cubicle all day and haven’t even said hello to you, but could you possible make all these recommended changes to your report by tomorrow morning? Yeah, I know you leave in half an hour. Bye!”


  6. Wow, you’ve really hit the nail on its head!! As a self-employed Web Designer, I can vouch for the truth of ALL you’re saying. This post should be required reading for everyone planning to hang out a shingle and work for themselves (and I suppose it wouldn’t hurt for those hoping to work for someone else, too!). Thanks for laying it all out in easy-to-understand form. Oh, and congrats on getting Freshly Pressed!

  7. Brilliant — I want to hug you. I have run into all of these. In fact, I leave at 4:30 p.m. on Fridays on a regular basis because I get the last minute folks who want stuff to be done on Monday morning CONSTANTLY!

    You don’t pay me to work on the weekends so I don’t work on the weekends. There you go. “I can have it to you by Wednesday.”


  8. very true! I know how you feel. I work at national TV as an audio visual editor and deadlines are my bestfriend, well.. maybe not bestfriend. But really, it’s everyday madness and when everything is over, you know you’ll going to face it again tomorrow. And all you can do is do it best because it’s the only way we enjoy our work and survive the crazziness πŸ˜€

    have a nice day and thanks for sharing..

  9. This story so hits the nail on the head…I could relate to almost every scenario.

    I had a start up ask me for some help with a web site and some marketing – asked me to put together a marketing plan with a budget. I did – came in WAY cheap (like a 1/3 of what a small marketing house would charge) because I liked the product, wanted it to succeed and thought there might be a future with this company when it takes off. She needed the plan right away so I worked hard to get it done before our next meeting.

    I call her a few weeks later and she tells me that she basically shopped my proposal to someone else that will do it for free – they are an IT company. Good luck with that – while IT is part of the online marketing process…IT departments rarely understand the marketing side as well as a seasoned marketer.

    You know sometimes you get what you pay for – Karma bites back. Web site still isn’t online…

  10. My favorite is the “I’m leaving the country. Today. At noon. Make the arrangements for me. kthxbai”

    I work in IT and usually handle our traveling employees who need mobile internet. This request kills me as most of Europe uses different standards than we do.

    Thanks for the post, great to add humor to the insanity. Congrats on FP.

    1. ishana, what would you call that personality? that sounds like a time zone nightmare! Kim, i’m sorry you went through all that. as funny as it can be much much much later, it’s not fun to go through all those hoops for nothing. i agree, you get what you pay for. barry, thanks much! and lisa, yeah, i think on some level we must like the craziness. or we must embrace the craziness. or we’re all just crazy.

      1. I think that would be the UnderEstimator, as they often don’t realize how much IT has to do in order to make sure they will have internet in Europe. It’s not a problem if they tell us a couple days ahead of time, but occasionally they’ll tell us while they are actually in the other country. In which case, we can’t do anything to help them.

        And I can vouch for Kim — IT doesn’t know much/anything about marketing.

  11. LOL this article made me laugh and it is very true. However I am lucky enough not to have crazy deadline stories but I can just imagine pulling a couple of all nighters to create an ecommerce site in 10 days.

    Banner Stands

  12. Great post and totally true. As far as number 8, the Mystery Meat special, inevitably when you come up with something the response is “I don’t know what I want, but I know this isn’t it.”

  13. Hahaha, that’s funny post! I related all the personalities you describe here about something in my job of graphic designer (working at home as a self worker) and I have a client who is a commercial printing shop in a small village, and we see any kind of fucked up people who think they are alone in this world asking for crazy deadlines because of their bad management.

    Recently, I had a client who pops up from nowhere, referred by two time by two graphic designer, the time goes by trough emails and for their Β« special christmas card Β» they rushes me to shoot a sketch in august and ask me that sketch in TWO days. Yeah Right !!

    Now that every body have a computer, everybody can do graphic design!! couple of years ago, A had more interresting work. Now, printing shop receives brochures made in Microsoft Word, Publisher, Photoshop, any kind of horror crap to print on press… I patch crap from other poeple most of the time now. that’s very disgusting. People want to save money and do their promotion themself. They don’t care about deadline, graphic specifications (like bleed etc..) and they think you only have to push the button PRINT.

    Sometime I think to do something else… pffff…

  14. I dont know how this relates, but as a college student I once had a teacher who swore that no assignment would ever be due the day after it was assigned. I remember, and this happened several times to me, when an assignment had not yet been assigned… but I would miss a single day for personal reasons and come back the following day to “time to turn in the project” – and to my astonishment the entire class had theirs ready and I hadnt even known the assignment had been given.

  15. My last boss was numbers 1,4,5 & 8 ALL THE TIME. Sometimes he was also # 2, but always # 4. Luckily I did a sidestep in career. He burned me out, but bills are bills. Now I’m in a much better situation. Love the article.

  16. I used to work in PR… I know about deadlines…lol… and what makes me laugh is that we knoe the deadline, the client knows the deadline…and still every single time EVERYONE leaves something crucial to the last minute… and then- next project it happens again…lol… out of the list The Fiddler is my worst nightmare- annoying and maddening enough to drive to the nearest bar at the end of the day…

  17. I’m in the information technology and security field. I have my set rate which is communicated at the very beginning. Next is the project plan which I can craft up in < 36 hours.

    They sign off on it, work starts. The plan includes change management (1 freebie, the rest bill at 1.5 times normal rate).

    Cuts down on the crap.

  18. I’m in the field of Pharma, and I can tell you that 99% of clients are exactly like either one, or all of the above examples! They seem to think that we can program their studies to the web overnight, despite the complexities involved with programming. Not to mention that it’s got to be tested by two different teams before the client even gets a first look – then, they expect us to field the study to Neurosurgeons in Zimbabwe in a week. Yeah, because Zimbabwe is just brimming with neurosurgeons! Sometimes I just have to laugh out loud and run the risk of looking like a nut job πŸ˜€

  19. Nice post! I loved reading about the nature of your job. I’m only in high school, but I’ve had a taste of the wrath of deadlines from being editor of the newspaper. If I decide to pursue journalism, it’s only going to get worse!

    1. hannah, so nice to hear from you. deadlines are a good thing, except when they are unrealistic. when people tell me my project deadlines is “whenever,” i shake my head and say, oh no, don’t tell me that. it will never, ever get done. good luck with your career, sounds like you have a fantastic future ahead of you, whatever road you choose. cheers!

  20. Love this article, and I can totally relate! I work at an agency and have dealt with every single one of these deadline personalities – probably all within the past week!

  21. Wow…sounds like you’ve really put some thought into this. perhaps too much as it fringes on the craziness you were writing about. Its funny and very true but that twinge of frustration in your pen tells me you might choke the next one that comes in! Just kidding but no seriously vacation! no tan lines will make it seem like this is another world to you!LOL!

  22. Really entertaining post. I experience the “Brain freeze” way to often. The quote at the beginning sound is frightening. Its interesting how some people equate working on a computer for a living with an easy job.

  23. I recognise all of these characters.
    I’ve encountered Bait and Switch many times. Initial request for a quote offers big numbers, which in my industry offers the option of a bulk deal. Actual purchase order is for significantly smaller quantities but they still expect the same price.

  24. The time I got pretty much an entire damn good looking website up in two days. They knew it was nuts, though — and I was very glad I keep a spare web design in my back pocket for things like this. In all fairness, I love working there and the people involved were incredibly impressed that I was able to do it. I’m still damn proud of that one.

  25. I love your succinct, humorous description of the clients we all know and ‘love’! Anyone in any kind of customer service will recognize themselves and their customer base here.

    It certainly is true in fashion retail! “I have this event tonight…it could be indoors or outdoors…cocktail or business casual…the invitation might have said Caribbean theme, or maybe that was tomorrow night…but I have to look IMMACULATE!! and, of course…above all…THIN.”

    Thanks for the giggles!

  26. I used to work in public relations and The Fiddler was why I got out of it. They’d hire us to write a press release or article, then they’d take it all apart, re-word it, kill all its saleability and creativity…and then refuse to pay us when the newspapers didn’t pick it up or want to do an article (this was back in the 1990s). Many of my clients were banks. I’d always want to say, ‘Why, you can hold a pen, so of COURSE you can write! That means that since I can count money, I walk into your bank and write my own mortgage, right?’

    Thanks for the great laugh!

  27. I do my own web design because I know flat-out I can’t afford to hire someone, but I can vouch that you get these kind of people in any creative venture. The part that always boggles my mind is the absolute cheapness of people who will not, and could not, do the work themselves. I make jewelry, and it’s astounding to get the value judgments of people who have no idea what the jewelry is made of, how much that costs, how much time went into it–not just the crafting but the designing, the breaking down and re-designing to get it right. Same with web design I suspect.. they think that the elements get there by magic, and that you didn’t spend half an hour tweaking a small part of a website to get it just perfect, let alone the time actually building site elements from scratch.

    1. Susan, I totally agree. I saw your post from yesterday about teaching yourself web programming and i’m impressed! i’ve come to realize that no one can be an expert at everything, nor should we be. i was talking with an artist about his blown glass art and he told me his process for one small piece–then laughed and said, probably seems like $20 for that is too much. and i was incredulous! i said, no, for all that work that went into it, it seems like it should cost far, far more. i’m not sure about other industries, but when it comes to our creative work, many of us do it because we love it. getting a living wage out of it would be the cat’s jammies, but, well, we do the best we can. nice to hear from you!

  28. This sort of thing always happens when there is any sort of dead-line, be it fast food, designing an ad or building a computer network from the ground up. The non-technical person making the contact may be fabulous as a “people-person” but they seem to universally lack a basic understand of the logistics of doing business

  29. The Day the Webmaster Died is an excellent article. I have people from colleges ask me what to look out for all the time because they want to become a web designer. I think that they should look at this article first! It is so very true and I have run into each of these types of clients. Thank you for validating what has happened to us in the past. I will be sending some of my potential clients to this blog post before they actually become clients. I may even say to them that if they start becoming one of these types of clients, they may get a refund so that we don’t have to deal with that. (we will suggest other web developers to them so that they are not totally lost, and explain to them why we are doing this, so they don’t do one of these things to their next web designer!)

    1. hi marc, i think it is good for everyone to be aware of these personalities so that they can prepare for them when they see them and how they will respond. while this is the first time i’ve ever put names to them or organized them all in one place, i think we’ve all either seen these things first-hand or been guilty of it ourselves. i always think my husband can get electrical work done around the house way faster than is humanly possible, for example. πŸ™‚ i’ve found that it’s helpful to educate those involved in what is required, so that if something is crossing a line or unrealistic, we can speak up immediately, before it becomes an issue.

  30. As someone who has worked on both sides, I have to add this:

    Each one of these personalities is also … The Client.

    We get into these situations & while yes, it’s natural to complain because we are so very misunderstood, we must also keep that one point in mind at all times. They are the client. & for as much as they do not always “get” what we are trying to do, we do not always get what kind of pressures they are under as well.

    & this list, as arguably right-on & humorous & “right? i mean, right?!” as this is … it’s just a way for creatives to vent. & trust me, for every valid complaint we have about them, they have equally valid complaints about us.

    1. hi niki, that’s a great point. i too have worked on both sides, and yes, there is often pressure or certain situations that necessitate unreasonable deadlines. that being said, it’s great if you have worked both sides of the equation, because then you understand better what each side is facing. venting about creatives is a whole other blog post, no? πŸ™‚ that being said, just because one is “The Client” doesn’t give one carte blanche in terms of deadlines, expectations, etc. Everyone has their limits and needs to know when to say no. There has to be give-and-take on both sides. it’s a delicate balance in any industry. i’ve been guilty of the UnderEstimator simply because of my lack of knowledge of certain aspects of a project, so I try to be aware of that when kicking off projects. we all have something we need to work on. πŸ™‚

  31. Damn, you hit them nails on their heads. I’ve worked in IT since ’68 primarily as a programmer and have seen it all. The two that stick out for me are:

    1- “Can you DO THIS?” … Well, yes with six months of lead time, $400K of dollars, and a year to make it work, YES WE CAN” I’ve responded on several occasions.

    2- Usually from the accountant at end of fiscal qtr on an excited phone call:

    “My computer is frits’ed and I’m running on a 3 hour deadline ….. how long will you take to fix IT?”

    >> Well, I don’t yet know what is wrong, so I can’t estimate a repair time”.

    “But, do you know how important my work is!!!!!!!”

    >> Yes, I do but … the importance of your job is NOT RELATED to the required time to repair your as yet, undiagnosed issue.

    1. rufus, no pressure there, right? I think people just get so panicked when something goes wrong, and it’s all the worse because you don’t know a damn thing about how to fix it. i’m sure on many IT people’s hit lists, to be honest. πŸ™‚

  32. Here is another one for you… At my job within the last couple of weeks I have had this happen to me. I have a number of tasks to complete during the course of my working day. They are all important to the company and must be completed in a timely manner. Often times numerous times a day. Sometimes priorities need to be shifted about, certain things need to be completed more immediately. There is nothing unique about any of this, in itself.

    But a few weeks ago all these tasks were so far behind that when I clocked on and began work, I was told to “make this a priority”, and to “make that a priority”, and to make “that a priority”. Ultimately, when my boss had finished setting my priorities for me, all my usual daily tasks were priority. I had to put everything in front of everything all at once. When all your normal tasks are of equal priority and none of them are not, is anything really a priority?

  33. This is awesome. Even though I am not in graphic design, I can see a little of each of the nine in any job I’ve ever had. Especially the bargain hunter (I worked retail). You say a price and a customer thinks they can talk you down, like we’re haggling in an market in India! One night, at my job now in hospitality, I had a guy try to get me to lower the price on a room for twenty minutes! I’m just the front desk person, I have no control on pricing!

    Great blog, Kudos!

  34. I am a tech writer, so I found myself nodding along with a lot of what you were saying…and I absolutely hate when someone says “Can’t you just copy and paste”?

    But, the worst offender has got to be the fiddler.Urghh…

    1. hi nishita; yeah, the copy and paste thing has a lot of folks spoiled, thinking it’s a simple solution. i used to play the organ when i was a kid and memorized “Fiddler on the Roof.” i wish i remembered it still, i’m kind of in the mood to hear it again. πŸ™‚

  35. All well observed nasties.
    The important thing is to make sure all requests/fiddles/new ideas come in an email – so you have a written record. Handy when it’s invoice time – or even interim invoice time.
    The wonderful resource to have is someone who can speak the language of marketers or customers AND designers or programmers – because very often they simply cannot communicate directly. That way people on either side can be told, politely, that they do/don’t need whatever, or that it is/isn’t worthwhile or cost effective.

  36. I love the sarcasm and hilarity in the way you write. I cant really relate to this as I havent started my professional life yet, but it made me laugh through and through. My favorite: the five oclock shadow πŸ™‚

    Do check out my blog if you get time.

    1. zainab, love your blog. “no one wants to see curvy women” infuritated me!!! as a curvy woman, i strongly beg to differ. i’m glad you enjoyed my writing, the sarcasm and hilarity is a family trait. some people get good looks and brains, i got sarcasm and curves. go figure!

  37. What a great post…

    My favourite is the Fiddler, I am blogger but also build websites for worthy causes…You know the ones, just starting out but with a board and committee of 15. Ringing you up every 15 minutes with “Another” great idea for the site.

    I’m sure these geniuses are thinking all along “I could be doing this myself on word, no problem…” Thanks for the laugh

    1. you’re so welcome! i feel like all we can do is laugh, and with the economy being so dour for so long, i was long overdue for some giggles. i think you’ve hit on another personality, robbo, “The Committee.”

  38. Great post!
    Every point hits the mark.
    Working with websites (marketing and communications) myself, I feel that we run the role of the middle man i.e. the person that has to translate the conversation between the over technical developers and the incredibly vague project managers.
    I highly recommend the blog

  39. Hi

    Love your work specially Diy and the under estimator. I would say the word Customer seems to be derived by the word complex as its very difficult to communicate them your idea. I think that they all have a obligation to come to us otherwise they never wanted.
    Nice work keep it up.

    Tamour Tahir

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