So you screwed up a freelance job. Now what?

March 31, 2017

“Oops! I don’t supposed you have any scotch tape, do you?” Image credit — Jilbert Ebrahimi via Unsplash

I love talking to Smart Freelancer subscribers. And one thing I always ask is, “What are some of the challenges you’re struggling with?”

Here’s an incredible response I got back in February:

“Actually starting. Like, the physical process of going out there and trying to find clients. It’s not so much where do I find clients as can I actually help them? What do I, as a n00b, have to offer them? What happens if someone decides they want to work with me and I screw it up?”

“What if I screw up?” is the sort of question you will never stop asking. Once you have some experience under your belt, it’s not that bad. But when you’re just starting out, it can be paralyzing. Heart-stoppingly terrifying, even.

So this week, we’re going to look that fear in its non-existent eyes, stare it down and call it awful names until it slinks back into the farthest corner of your mind and sobs itself to sleep. That’s the plan, at least.

But first, let’s acknowledge that it’s real. And it will come true.

I wish I could tell you, “Don’t worry! Just make sure you do X, Y, and Z, and you will never, ever mess up a project. Ever.” But then my pants would vanish in a white-hot inferno, because I’d be lying.

(Just kidding, I’m not wearing any pants.)

You said it, random picture I found on the internet!

Whether you’re n00b or a seasoned pro with 20+ years of experience, you WILL screw up.

It’s not a question of IF. It’s a question of WHEN, and how often.

You will make small mistakes that will seem terrifying at first, because you’re just starting out.

You will also commit fuck-ups so monumental that your only desire will be to curl up in a ball and die of shame. Either that, or to google “how do i fake my own death and disappear forever.”

But here’s the good news: it’s totally, honest-to-goodness fine. The best freelancers I know (and I don’t even include myself in their number) have all made mistakes. And they continue to make them. What makes them the best is that they don’t let those fuck-ups get in the way of doing great work.

They own them, they fix them, and they make sure they don’t do it again. Not as often, anyway. And in today’s post, we’ll discuss how you can do the same. By the end, you’ll have a step-by-step process for fixing any screw-ups you will inevitably make as a freelancer.

But first, confession time!

Forgive me, o freelancing gods, for I have sinned.

Hoo boy, have I sinned.

No, not like that, Tyrion! Jeesh…

For the past 8 years of making a living as a copywriter, I have:

– Missed deadlines more than once. In one memorable case, for a full year. I’ll tell you about it sometime when there’s more alcohol in my blood.

– Botched countless first drafts for everything from emails, to product pages, to sales copy, to blog posts, to advertising scripts, to some stuff I don’t even remember writing.

– Lost motivation right as I took on a project, couldn’t bear to finish it… so I bailed at the last moment, giving the client a refund.

– Handed in sub-par work — and amazing work that still failed miserably to deliver any results.

– Sent invoices for the wrong sums, and had to give refunds later, apologizing profusely.

– Completely forgotten to follow through with a client, repeatedly.

And I’m not even counting the small stuff, like the occasional typos and grammar errors in my copy, or having to push a deadline because I underestimated how long a project would take.

Of course, most of this stuff happened when I was a 20-year-old shithead who didn’t take his freelancing business (or anything in life) seriously. But if you think I have stopped messing up, I have to disappoint you.

Just 4 months ago, I fucked up a 1st draft so hard the client was so mad at me they couldn’t muster any coherent feedback. I spent 40 minutes of the phone with them, all stiff upper lip and sympathetic ear, trying to tease out what exactly I did wrong — and the next 2 hours fixing it.

Hell, I had another screw-up just last week, which I’ll tell you about shortly. But enough embarrassing confessions (starting to feel self-conscious here). Instead, let me share with you the lessons I’ve learned, and how you can apply them to your own freelance business.

Lesson #1. It’s always your fault

When you screw up, it’s your fault. And when the client screws up… it’s also your fault.

Your client is a fallible human being. They don’t always know what they want, aren’t necessarily great at communication, and they can freak out easily. Hell, they probably know less about working with freelancers than you do!

Because of that, even your client screwed up, they will often have no self-awareness to admit, “It’s all me. I didn’t give you enough information / imposed unreasonable demands on your work / failed to account for X, Y, and Z. Sorry!”


That’s why you want to recognize how you contributed to the situation, and go from there.

For example: just last week, I wrote a high-stakes blog post for a client. They had a big promotion planned for it, with a big-name partner, who created part of the content.

I wrote the draft, the client and the partner signed off on it. I handed it over to the blog editor, and they pressed “Publish”. Then, several things happened at once:

  1. Too late, I realized I got the dates of the promotion wrong.
  2. The partner came back with a bunch of last-minute edits that were never in their initial draft.
  3. I discovered an embarrassing formatting error in the post that the editor overlooked.

Only #1 was my screw-up. But all that was my fault. Why? Because I could have easily avoided #2 and #3 just by doing a better job as a freelancer, like:

  • Asking for feedback and clarifications more often, instead of writing a rushed draft.
  • Taking initiative and bugging my client’s business partners myself, instead of relying on second-hand information.
  • Getting the damn login credentials for the blog beforehand, to have a plan B just for this exact situation.

I spent all day calling the CEO (who was on a 5-hour flight and couldn’t take my calls), emailing the editor (who didn’t check their email that day), and bugging everyone who could have access to the blog (no one did).

In the end, I fixed the situation — but all the while, I was thinking, “What an easily avoidable clusterfuck!”

While I did my job to the letter (except where I got the dates wrong), I failed to do everything in my power to help my client succeed. And that’s on me.

And that’s what I mean when I say, “It’s always your fault.”


Lesson #2. Making *a* mistake is fine. Making the same one repeatedly isn’t


It sounds obvious. But it’s the kind of lesson that’s hard to internalize when you’re just starting out. When I started freelancing in 2009, I saw two conflicting points of view with seemingly no middle-ground in between:

1. Don’t make mistakes, ever. That’s the kind of advice I would read online, where everyone didn’t miss deadlines, always turned in stellar work, and never ran into any issues with their clients. The way they told it, anyway.

2. Clients don’t really respect you — they want to have shit done for the lowest price possible. If they don’t pay you well, why should you make an effort to do your best?

Embarrassingly enough, I used to believe this bullshit. It never occurred to me that it’s possible to screw up occasionally, but remain a a proud professional. The key is in the relationship.

Your freelance business lives and dies by the relationship you have with your clients. If they can trust you to do what you say you will do, your partnership will live through occasional screw-ups. But if there’s a continuous pattern of mistakes, with no sign that you’re learning from them, it will come back to bite you in the fleshy bits.

I learned this lesson the hard way — after I lost a $20,000/year client due to missing a deadline one too many times. That client was 100% right to cut me off. I crossed the line by abusing their trust, and I paid the price for it.

After that, for the last two years and 200+ jobs, I haven’t missed a deadline once.

Bottom line is: don’t do what I did and lose like $40,000 in guaranteed client work to learn this very basic lesson. I have no doubt that you’re a much faster learner than yours truly, so you will definitely do better!

Lesson #3. “It’s not the mistake — it’s what we do with it”

I wish I could take credit for this quote, but I can’t. I heard it from a project manager I admire. She didn’t say this to me, but to another copywriter — someone brilliant but relatively new, freaking out over a typo in her otherwise great copy.

Every time I fuck up, I think about that phrase, and then ask myself, “What can I do with this to make it right?” And there’s always something you can do.

We’re freelancers, not brain surgeons. Lives aren’t hanging in the balance. Barring something extreme, like deleting your client’s email list by accident, you can almost always clean up your mess. The way you handle your screw-ups tells a lot more about you than if you were a shining paragon of humanity, who never stumbles, has perfect posture, and farts odorless rainbows.

And if you have a solid process in place for fixing your mistakes in a way that doesn’t cost you clients — and actually improves the relationship in the long run — you will always land on your feet. So let’s talk about said process, shall we?

There are 4 steps to it — or 5, depending on how you want to look at it.

Because Step 0 is this

Here they are…

The simple 4-step process for fixing your freelance mistakes

Step 1. Apologize (duh)

Fixing any kind of mistake, freelance or not, starts with a solid apology. It’s a gesture of goodwill that will keep your client from spiraling out of control. You want your apology to do three things:

– Take full responsibility for the mistake.

– Reassure the client that you will fix it.

– Define what the first step to doing so look like.

For example, when I botch a 1st draft, and the client tells me as much, here’s what I might write in response:

“Hi [Name],

I understand that this initial draft is not even close to what you had in mind. It’s my fault, and I apologize for that.

I am 100% committed to giving you nothing less than my best work, and I want you to know that. I will do everything I can to make sure that the finished piece is aligned with your vision, and helps you achieve your business goals.

That said, for me to help you, I will need specific feedback on everything you would like me to improve for the next draft. I’m also prepared to do an additional round of revisions after the final, 3rd draft is done.

You can send me the document with your comments and feedback, or we can jump on a call to discuss any revisions you have in mind — I’m happy to do it in whichever way works best for you.

Let me know?


Oleg “

After that comes the hard part: finding out what exactly went wrong.


Step 2. Extract specific feedback

Sometimes you make an obvious screw-up, like missing a deadline.

In that case, you don’t really need to get feedback. Instead, do this: reassure the client that you’re prepared to give them a full refund, which is part of how you do business… but first, you really want to make it up to them. Ask what it would take, and proactively make a suggestion of your own (we’ll get to that in Step 3).

Most of the time, you won’t know exactly how you fucked up, unless the client tells you. And that’s the tricky part. In my experience, clients are terrible at explaining why they are unhappy. It’s your job to get them from, “No, this isn’t what I asked for at all, everything is terrible!” to “OK, here’s a list of everything you need to fix, and how.”

The easiest way to do this is by getting on a call — and it’s my preferred method. You will notice that I’m suggesting it as one possible option in that example email from Step 1.

But sometimes, for whatever reason, talking things through is not an option. In that case, you can give the client an example of the type of feedback you want. Staying with my “botched first draft” example, here’s what I might tell the client:

“You can add the feedback in the document I sent, using the MS Word comments function. Select the copy you would like to be revised, and write the comment for it.

The more details you can add, the better — e.g., instead of saying I should expand a section, write “Can you list 3-4 examples here?” or “Could you also mention our satisfaction guarantee?” That way, I’ll be able to implement your suggestions quickly and accurately.”


Step 3. Clean up your mess

There are two things you want to do in this step:

1. Implement the client’s feedback. So, it we go with my example, it means I would turn in a much better 2nd draft.

2. Offer something to make up for your misstep (I’ll give some examples below).

Depending on what your mistake was, and how bad you messed up, you might need to do only #1, or only #2, or both. I tend to work with clients for the long term, so I usually go with the last option. That way, I’m less likely to lose their business — and even if it’s the 1st time we are working together, I want to do everything I can to get them to come back for more.

There are lots of things you can give to the client as a gesture of goodwill. In the example email for Step 1, I went with an extra round of revisions. But here’s some more ideas for you:

1. A partial discount, to offset the loss of time / money / opportunity on your client’s part. Personally, I prefer not to discount my services, even if I screwed up — it sets a bad precedent. But it can be an option if you’re out of ideas.

2. An extra value-add you can throw in free of charge. For example, if you were hired to write 10 articles and you missed a deadline, you can do article #11 for free. I did this exact thing on my 3rd-ever freelance project, and the client loved it.

3. In extremely dire cases, a full refund. While it will sting in the short term, sometimes it’s the only way to keep someone’s business in the long run. But the good news is, most good clients appreciate the gesture and respectfully decline. It’s in their interests to keep working with you, and they know it.

Step 4. Clean up your act

Finally, you want to minimize any similar screw-ups in the future (remember Lesson #2). For example, here’s a running list of things I try to do whenever I take on a new project, to safeguard myself an the client against any unpleasant surprises:

– Whenever possible, do an early discovery call.

– If I’m not sure how long a job would take, I bill hourly — or add 20% to my quote.

– Add 2-3 extra days on top of any deadline I have in mind.

– If the client sets the deadline, I try to find out if there is any wiggle room, and push it back 2-3 days.

– If the deadline is non-negotiable, I check my schedule and book specific time slots to work on the project.

– If it looks like the project will take much longer than anticipated, I check in with the client and we talk about changing the fee or pushing the deadline.

– If there’s more than one point person involved, I get the contact details for all of them. So even if one person falls off the radar, I can still get in touch with somebody else.

– Before starting on a project, I send an email spelling out what the final result will look like, what the deadline is, and ask the client to give me the green light.


When something happens (like that password snafu I mentioned back in Lesson #1), I update my list. That way, I mostly make new mistakes, instead of repeating the old ones. Which is the best any of us can hope for, really.

And there you have it — the exact process you can use to make sure that you always do a great job… even if you screw up!

Now, I’d love it if you shared something with me. But this time, I’m asking about something completely different…

What’s one embarrassing mistake you’ve made as a freelancer?

You must have noticed by now that most freelancers aren’t very transparent about all the times they’ve screwed up — even though we all do. But you’re better than most freelancers, or you wouldn’t be reading this, trying to learn something new.

So, if you’re OK with sharing something like this, I would love to hear about the times you made a mistake… and how you handled it. Could you do that for me?

Leave a comment and let me know!
P.S. While it’s nice to be able to bounce back after screwing up, it’s much better to minimize your freelance mistakes in the first place. If you want to learn how to nail your first freelance job, I highly recommend this article. It’s written with writers in mind, but the principles can be applied to any kind of freelance work. And they are solid.


  • Reply Lindsey Hayward March 31, 2017 at 5:30 pm

    I absolutely loved this, Oleg. And I can absolutely identify with lesson #3. :p

    In addition to turning in not just one but TWO copy assignments with typos – to the same client… within 24 hours of each other – I’ve also completely blown a deadline. Ironically, for 10 articles.

    I’m a bit newer, so I’m still feeling things out, figuring out how to charge, how long projects take me, etc. For this particular assignment, I didn’t realize the scope of the project (my fault), and also underestimated how much time it would take (also my fault), as well as charging less than I should have (yet again, my bad). But thankfully the client was gracious and understanding to the point of practically apologizing for the situation (a few of the articles turned out to be about 5x bigger than anticipated). And after explaining my concerns on fees, I was able to negotiate a better rate easily.

    I know I’ll be screwing up as I go along, and especially while I’m still wading in the shallows, having just fully submerged my feet. But it’s invaluable to have your sage advice on some corrective and preventative actions – so thank you! 🙂

    • Reply Oleg Starko April 5, 2017 at 3:00 pm

      You’re welcome, Lindsey!

      Do you mind sharing how you negotiated a better rate? I’m sure I’m not the only one who’s curious about that. 🙂

  • Reply Mouka Mezonlin April 2, 2017 at 8:50 pm

    I really love this post Oleg. I must reckon I started freelance writing not long ago but, that mistake I remember is this: I submitted my outline and plan instead of the real copy.
    I didn’t know how it happened but the next thing I heard from the client is this: ” if you can kindly write the article, I’ll be grateful. I’m paying you for an article, not some mere list and plan. If I had time to write it, I’d have done it myself.”
    I apologized but after I submitted the article, he didn’t get back and I’m not missing him either. Yes that was a low paying task.

    • Reply Oleg Starko April 5, 2017 at 2:59 pm

      Thanks for sharing, Mouka! 🙂 I’ve made a few mistakes like that in the past, always by accident like you. The best thing to do there is to just acknowledge it, apologize, and move on. In your case, it’s a good thing that your mistake exposed a toxic client you wouldn’t want to be working with anyway!

  • Reply Joel Boomer April 6, 2017 at 3:33 pm

    The timing of this post is crazy (at least for me). Last weekend, I sent the first draft for a client and it bombed…real hard. When I saw his message my stomach tensed up and could hardly bear to read the rest. Fortunately, he did leave specific feedback. I apologized, got back to work and turned in a new draft. I waited for a few days to hear some feedback from him with crickets. Talk about a dreadful experience. I had the idea to just give him a refund and learn from the mistake. I got a message last night that seemed reassuring. After my apology and the new draft, he seemed willing to continue to work on the project. We’ll see how he feels about the new work, but it goes to show that saying, “sorry, I screwed this one up” goes a long way.

    Cool to finally find your website, Oleg, and thanks for the “you’re gonna be alright” article!

    • Reply Oleg Starko April 6, 2017 at 8:08 pm

      I love this, Joel! What a brilliant comment — kudos to you for sharing this story.

      I hope that your client comes around. Most people are very understanding when it comes to 1st drafts — they understand that feedback is crucial, and it can always be fixed in revisions.

      Have you isolated the reason why the draft bombed so hard? In my experience, it’s usually because of miscommunication with the client. A good creative brief and a short call go a long way to foolproof a project.

      > Cool to finally find your website, Oleg, and thanks for the “you’re gonna be alright” article!

      You’re welcome, and I do hope you stick around, Joel. 🙂

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