The Worst Project Proposal In History (Case-Study)

I’m going to tell you about the worst project proposal ever written by yours truly.

By the end of this post, you’ll know exactly what NOT to do when writing proposals – saving yourself a large amount of time and money.

But first – let me ask you this: do you remember your first kiss?

I’ll remember mine forever. I was eleven years old, and I kissed the beautiful Sarah, who lived in the apartment above ours.

I was really insecure and didn’t know how to act…

My heart was pounding like crazy, my throat was dry, my lips didn’t know where to go and our noses kept hitting each other.

It was the worst kiss ever…

Worst kiss ever

Despite all that, it was very romantic, and I was sure Sarah and I would be together forever, for good times and bad and in sickness and health.

Well… Sarah had different plans. She dumped me a week later to go out with Dan from the other class. He was taller than me, with longer hair and a better tan. I don’t think it was because of the kiss, but I guess I’ll never know…

Many years later…

I recently went through my Gmail and came upon the first project proposal I’ve ever sent a client. That project is another thing I’ll never forget. Except in this case, there was nothing romantic about it. In fact it was one long nightmare:

  • I wasn’t compensated properly. I actually lost money (and time) on the project.
  • I worked much harder than I ever thought I would.
  • The whole thing took twice as long as expected.
  • It ended with a foul relationship between me and the client. He too felt like he overpaid, never got what he was after, and that it was a mistake to hire me.

the worst project proposal ever

All of this despite the fact that at the end of the day, the client received a fully functional, beautiful website which received great responses!

Meanwhile I lost money, time, and earned myself a very unhappy client who will never recommend me to anyone – and a ton of headaches.

How did the whole thing start? From the worst project proposal in history.

I want to share this proposal with you, analyze it and show you why it was so bad and what made it into one of the reasons why this project didn’t work out well. I’m big on learning lessons and I believe learning what not to do is just as important as learning what you should do.

Learning from those mistakes is what got me where I am today (look ma, no hands!)

The world’s worst project proposal

Dean, a friend of a friend, needed someone to develop and design a website for a non-profit organization. At the time, the organization already had a website and it was ugly as hell. I was hired to revamp and refresh the old website.

After four phone calls and 19 emails (I counted!) here’s what I sent Dean:

worst project proposal ever

The email I got back only read: “Sounds great. Let’s start!”

At this point you’re either laughing your ass off, or, what’s worse, have gone back to Facebook.

If you’re still reading this, you might be in the same situation I was in a few years ago. You have no idea how to write proposals, or even worse – you don’t even understand what is wrong with my proposal to Dean, or why I call it the worst in history.

Well let me explain. And don’t worry – the joke’s on me.

Let me go step by step, explaining what’s so bad about the proposal.

worst project proposal ever

1 – Sending the proposal via email

Sending a project proposal via email is a horrible mistake. Think about yourself for a minute. Where do you read emails? In your office, on your desktop? Well good for you. But where else? In the kitchen while eating cereal? In bed, before even waking up? On the toilet? Yep.

Well your client reads emails the same way, and that’s how seriously they will take your proposal.

About half of all email correspondence is read on mobile devices these days. Every notification can interfere with the reading, so while your client is reading your proposal, they might receive a Twitter or Facebook notification and lose focus. Better send your proposal as a PDF, which shows seriousness.

My punishment

– In hindsight I realized the client didn’t remember most of these clauses – probably because he was reading them with very little attention, for two minutes, on his Blackberry, in a traffic jam.

– He saw me as an amateur, meaning he could pay me less and push me around as much as he pleases.

[bctt tweet="The Worst Project Proposal In History..."]

2 – Using a vague project description

“I’ve given thought to everything we talked about” – oh, woopty doo. Nice project description.

Nowhere does it say that we’re talking about a WordPress site, that it needs hosting, that some of the functions I’m intending to create require wordpress plugins.

That means the client hardly knew what he was paying for (nor did he take an interest at this stage.)

Nothing is said about site maintenance once it’s online either, or about how the site will look on mobile devices. These are all things the client took for granted.

My punishment

– The client believed he was getting X, and I believed I was doing Y. Once the website was ready (as far as I was concerned), you can imagine how big the client’s disappointment was – while I was expecting nothing short of a standing ovation.

– When I began talking to him about hosting and further costs, I heard a lot of awkward and angry silences over the phone.

3 – Leaving unpriced gaps

“This proposal does not include QA or moving the content from the old website” – I was sure I was being a total pro for mentioning what was not included in the deal. The only thing I didn’t realize was that this means I will not be able to negotiate for those missing bits later.

Releasing a website without QA – whether for design or development – is something that will hurt both the client and myself, so I won’t have a choice but to do it anyway, for whatever price the client will consent to.

My punishment

After many arguments, the client finally paid me an extra $500 for those two items, even though they took me over 90 hours. In other words, I worked for $5.5 an hour. Damn.

4 – Creating unreasonable schedules

“Beta version within a month, final version within two months”

Can you guess why this schedule makes no sense?

Well, for one, because it’s unclear when the clock starts running. Today I know how important it is to clarify that the project begins after the client is done sending me all necessary material. In this particular project, almost two months passed before I even got the images he wanted for the homepage slider(!)

Secondly, “one month” is not a very well-defined term.

  • Is it a calendar month? A business month? What if there are bank holidays in the middle (unfortunately for me, there were.)
  • What about the time it takes for the client to go over the beta version and give me their feedback? It took this client a whole month to do this, during which I couldn’t move forward with the project.
  • What about QA time?

etc etc.

My punishment

– The project took almost six months from start to finish. Since the client remembered me proposing to do it in two months (the one part he did remember), he kept reminding me I’m behind. And honestly? He was right. Never mind that many of the delays were because of him – he didn’t send me the material on time, he took forever with his comments, he asked for tons of revisions – it’s still a delay, and it’s my responsibility, because I led him to believe it will only take two months.

– I was stuck with the project for much longer than I had wanted, which kept me away from other projects, and left me with a headache even on days when I wasn’t working but waiting for feedback from the client.

5 – Not specifying content well enough

“New pages for the website, just like the ones that exist on the current website”

Wow. I just can’t believe what an amateur I was being. When the original website was created, Facebook and Twitter didn’t even exist yet. It wasn’t customary to ask visitors for their email addresses. Those are just two small examples for things that were not included in the original site, which of course the client expected to see in his new site. At my expense, naturally.

Today I know that I have to specify the project’s content as much as possible, and maybe even include it in an appendix with a prototype or a list of all items, including pages, buttons and required functionality.

As I said, the client and I made four phone calls and wrote 19 emails. The client’s demands were either specified verbally – so there’s no record of them – or in emails, where trying to even begin and understand who said what to whom would make some lawyer very, very rich.

My punishment

– I worked way, way more than I thought I’d have to.

– The client was very unhappy to learn that many things he thought were standard – like a mobile-friendly version – were not available in my beta version.

6 – Pricing the project wrong

Deciding my asking price for the project took me ten minutes. I thought I’d be more than happy with $30 an hour (I was working only part-time as a freelancer, and it was one of my first gigs so I didn’t aim very high.)

Since I thought about it less than 10 minutes, I saw no reason for it to take me more than 100 hours. So the math is pretty simple – $3K.

The most ironic part of all is that when he wrote back “sounds great, let’s start,” I was sure I was superman. I was so excited about how he didn’t even negotiate.

My punishment

What actually happened (my frustration led me to measure everything as so to make it easier for myself to self-pity later):

  • Using WordPress and designing the website: 90 hours (fairly close to my initial assessment)
  • Endless calls, emails, fights with the client, presenting the site in his offices three times: 80 hours
  • Requests for revisions, and a third, fourth and fifth version (about two months in total): 120 hours
  • Mobile-friendly version and other extras which were not included in the original proposal (about a month in total): 60 hours
  • Moving in the old content plus QA: 90 hours

Total: 440 hours. Which, had I received $30 an hour, would have been $13,200 – more than four times what I had asked for!

As I mentioned earlier, this took me almost six months in working part-time. Or in other words, I worked for just under $7 an hour. It hurts even to just say it.

Not a day has passed since where I haven’t recalculated these numbers, realized what an idiot I was being and kicked myself. And that’s before going into the headache and heartache that were a big part of the project.

[bctt tweet="The Worst Project Proposal In History..."]


If you’ve come this far, there’s a good chance something similar happened to you too. Maybe you’re even going through a similar nightmare at the moment.

So much money and time was wasted and why? Because I was lazy, and because I couldn’t be bothered to put in more than 10 minutes in writing my proposal. Because I emailed it as is. Because I started the project before everything was clear.

This project was a nightmare for my client too. And for many of the things that went wrong along the way I can’t even blame him – I can only blame myself.

He thought it would only take two months; he didn’t expect to work with a whiny, frustrated freelancer who will go on and on about how ‘this wasn’t in the specifications!’ and ‘we should have been done long ago.’ But how was he supposed to know about being mobile-friendly or about hosting costs? He knows nothing about these thing. I’m the one who’s supposed to explain it to him.

Yeah, I know, writing detailed proposals is annoying. Who even has the time for it?

But next time you submit a project proposal, think long and hard about what you’re doing, and what expectations you’re creating for yourself and for your client. For what should have taken me five hours of serious work, maybe even a day, I ended up paying four months.

Many years and projects have passed since then. I learned how to write excellent proposals. Ones that price the entire work, and even explain to the client why I deserve that much more money. I learned how to ask for more and how to get the client to the finishing point with a big smile on their face. 

What about you? What’s your story?

Post by Lior Frenkel

Lior is the head of fun and CEO at Bold & Creative. He is a mentor at the Designer's Pricing Class and the author of 'Pay Me.. Or Else!'

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