Every successful freelancer has also, at some time, been a freelance failure. I know, I know, you’re all like, “What? It’s not just me?” Nope, it’s not just you. Believe it or not, even I have been the screwer upper of a thing or two.

It sucks, and as much as I would love to say “With the right preparation, it won’t happen to you,” that would be bananas. It will happen to you, probably more than once. So, today, I will lay out the common ways that freelancers fail, look at how to avoid these pitfalls, and discuss the ways to get back on track.

Face Your Freelancer Failure

Freelance Failure #1: You don’t get the contract

Almost half of deals are lost because of budget. Twenty-five percent are marked closed-lost because of timing. Lack of authority, time to review, and urgency are the third, fourth, and fifth most common reasons, respectively. (HubSpot)

Let me make this one very quick and easy for you: If every proposal you send out gets signed, you are pricing yourself too low. Think about it: if everybody you provide a contract to can afford your services, something is not right. Now, it could be that is your method. I know of a company that offers web design and development at incredibly low prices, but they make their money on the hosting fees you have to pay every month as long as you want that website. Most people don’t even see the ongoing monthly hosting fee on the contract and sign quickly. Incidentally, if you can find a method like this for your business, I would say go for it. It’s not unethical in my opinion (everything is written in the contract) and it works.

I have a closing rate of about 20%, which is higher than the average, probably because I’m only sending out about two per month. (Construction companies have a closing rate of less than 10%.) I find that many contracts close within one month and the work starts almost immediately, but about 1 in every 20 proposals that I send out close much later. Sometimes even years.

How to get over this failure?

1. Move on quickly. Set up a sales process that includes an hour a day (minimum) working on your sales process. This will keep you spread thin enough to not obsess over each proposal you send out. Included in the sales process should be time to follow-up (emails and phone calls), and you should limit the amount of follow up emails and phone calls so that you aren’t bugging the prospective client. Quick tip: always call and then follow up with an email rather than the other way around. If you warn a prospect that a phone call is coming, they probably will not pick up!

2. Make sure your proposals have everything that’s needed and that it’s all presented in the right order. Remember what the client wants to know is more important than what you want to say. They want to know the cost, the timeline, the process, and why you are best qualified. Try not to be wordy (this is the pot calling kettle black – I am Wordy Mcwordisson – so I provide a table of contents that allows prospects to jump to what they want to know) and always provide relevant case studies. Make the instructions to sign and return the contract as easy as possible.

Freelance Failure #2: You get fired

The worst. Abask was fired from the very first contract it ever got. Why? Because I got pregnant.
It’s a long story, but the shortened version is this: I hired someone to manage our client’s social media while I was in the hospital giving birth. That person went on vacation without warning me and posted erratic, nonsensical stuff to my client’s Facebook page while she traveled. I got a phone call letting me know that we had failed as a company while I was in the recovery room with my newborn.

How to get over this failure?

  1. Learn from it. I hired a friend that I still believe was experienced enough. However, she didn’t take the job seriously, probably because she was a friend and not someone I had vetted seriously. I will not make this mistake again.
  2. Be humble and apologetic. I offered free services, I made sure the client knew how seriously I took the mishap and how much I appreciated their business. I wasn’t able to save that contract, but less than a year later, they hired me to manage several PR campaigns, their new website, several sales presentations, and a proposal review. We continue to work together today.
  3. Move on quickly. Don’t obsess. Assess, learn, move on.

Freelance Failure #3: You take something offline accidentally.

To err is human, to admit it, superhuman (Doug Larson)

First, whenever possible, have a backup. Second, whenever possible, have a process for updates.

I use GoDaddy’s CPanel for websites and this offers a free backup on a daily, weekly, or monthly basis. I also have a day set aside for billing, checks, and dates. I check on my deadlines and my renewal dates at this time so that nothing will go offline without me knowing beforehand.

How to get over this failure?

  1. Make sure your contract covers you for any mistakes made by your client or third parties.
  2. If you can fix the problem in 15 minutes or less, do that first and then send an email to your client to let them know they were offline for 15 minutes due to a glitch, but thanks to the backups you keep, everything is fixed and right with the world.
  3. If the problem will take longer than 15 minutes, call the client and warn them. If possible, offer a temporary solution. Tell them how long you estimate the resolution will take and assure them they will not be charged for your time. Keep them updated and check in after to explain how this won’t happen again. Be friendly and courteous.
  4. Don’t blame someone else without reason. Sometimes our clients cause errors, like when one decided to bring in a family member to “help.” That family member was a liability. When a mistake was made, we needed to be sure it wouldn’t happen again. This was a good reason to place blame. Kindly though.
  5. Consider offering a discount or some service for free as compensation.

Freelance Failure #4: You miss a deadline.

If I could have one wish (presuming “another wish” is not an option), I would probably wish that I was on top form every day. But people get sick. People don’t get inspiration some days. People don’t always get the feedback they need on time. People quit on you and technology fails. All in all, shit happens.

How to get over this failure?

  1. Avoid this pitfall.
    Never commit to a deadline unless you can be sure you will meet it. We always “aim” for deadlines, but never “guarantee.” We make sure our proposals, contracts, and website policies page all say the same. I reiterate this in every kick-off meeting and provide it with the sign off for each portion.
  2. Maintain open lines of communication.
    If you are having weekly meetings with your clients, this should not be a concern. They will see the deadline looming and you can talk about what will, or won’t, be done.
  3. Recognize why you may miss it. If it’s something out of your control, be honest with yourself and your client, and move on. If it’s something you can control, get it right next time or allow more time for it!

Freelance Failure #5: You don’t get paid.

This isn’t exactly a failure, as much as a bad judgment call! Some clients overestimate their abilities, some fall on hard times, and some are just jerks. None of these things is your fault!

How to get over this failure?

  1. Avoid this pitfall.
    • Get a deposit. Be clear that this is nonrefundable once the work has started.
    • If you are on a retainer, expect to be paid at the beginning of a month prior to work starting.
    • Make sure your contract is clear on what happens when payment is late or nonexistent and have a page on your website that states the same as part of your policies.
    • Make it easy to pay you. Is your address correct? Can they pay by credit card? Sometimes you lose a percentage of your payment when paid by card, but it’s better than not being paid at all! I don’t haggle on this or add fees. My policy is basically: Pay however you want, just pay!
  2. Don’t get mad. Emotions sink more negotiations than we could count in a lifetime. Stay calm no matter what happens and weigh your options carefully.
  3. Figure out why you aren’t getting paid. Give your clients the benefit of the doubt and call your point of contact first. Perhaps the bill went to the wrong person. Maybe your point of contact hasn’t approved payment because it’s sitting on her desk. Be understanding and give a deadline for receiving the check if this is the case.
  4. Keep the lines of communication open. I have one client that was supposed to open a store in March. They opened in November and the money ran out long before opening. Everything in their contract was put on hold for a few months. Now they are up and running they are able to resume payment and we can pick up where we left off. No hard feelings. It may not be a perfect scenario, but everybody wins in the long run.
  5. Describe the leverage you have. “You will lose all work performed to this date…” This is usually enough to get things moving, but if not…
  6. Get legal. This is the final straw and should only be taken if the money owed is substantial and available. What do I mean? Lawsuits are expensive and there’s no guarantee you’ll win AND collect money. You could sink your life savings into a lawsuit, win and yet, still not collect money. Plus, if you know your client doesn’t have the money (see store above), what’s the point?
  7. Let it go. Sometimes you have to chalk one up to experience.

You will have little failures in your quest to build a successful enterprise and that’s ok. If I can offer one piece of advice about growing a business, it’s this: you can recover from a lot if you are well-liked or your work is exemplary. If you can’t guarantee the second, you’d better be sure about the first!


The End,
but it doesn’t have to be…