Why You Sometimes Must Fail Before You Can Succeed (and How to Recover)

I hate pain! When the doctor has to draw blood, I wince and look the other way. If I know something is going to hurt, I generally go out of my way to avoid it.

However, sometimes you must fail before you can succeed as a freelancer–and failure hurts.

Don’t get me wrong. I’m not advocating failure for failure’s sake. I definitely believe in working smart. That’s one reason I share my experiences and knowledge here on Freelance Folder–to help other freelancers

But sometimes, failure is the best teacher. Did you know that failing can sometimes make you a better freelancer in the long run? When failure happens to you, here’s how to make sure you learn from it.

Acknowledge Your Hurt

It doesn’t do any good to pretend you’re not upset that you failed, because you probably are. Immediately after a failure is also not the best time to analyze your mistake. You’re probably not thinking as clearly as you should be, anyway. Give yourself time to work through your natural emotional reaction.

For some freelancers a failure means getting angry, for others it means crying or even grieving over the mistake. It’s okay, though. Remember that nearly every freelancer has made a few mistakes.

Now, find a trusted friend who would understand your experience. (Beware of venting online, though. Angry or upset words on the Internet can come back to haunt you. Remember to protect your online reputation.) Or, if physical activity helps you, go the gym or run or whatever it is that you do.

Make Amends, If Necessary

Once you’ve worked through your emotion and feel relatively calm, it’s time to do some damage control. If the mistake was your fault and resulted in a loss to a client or colleague, you need to try–to the best of your ability–to fix it.
First off, contact whomever it is that was affected by your mistake and apologize. I know it’s hard, but just swallow your pride and do it. Next, offer to fix your mistake.

Fixing a mistake might mean redoing a project for free, refunding a client’s money (I told you this would be painful), or offering them something else that makes the situation right.

Your mistake may have cost you a client, but making amends can keep you from losing your reputation as a freelancer.

Conduct a Project Post-Mortem

Once you’ve made amends, it’s time to put your analytical hat on. You really need to figure out what went wrong. Here are a few questions you may wish to ask yourself:

  • Was there a miscommunication between myself and the client? If so, at what point did the miscommunication occur?
  • Did I allow enough time to adequately complete this project?
  • Was my knowledge and experience as a freelancer complete enough to do this project well?
  • Did I have the proper tools to work on this project?

(I’m sure you can think of other questions to ask yourself, as well.)

If you’re still on speaking terms with the client, you should ask them what they thought went wrong. They may have an entirely different viewpoint about what happened.

Once you’re armed with the knowledge of what caused your failure, you can put processes in place in your work habits and in your business to ensure that you avoid making the same mistake again. (This is the part where you recover and start to succeed.)

Some of the processes might include (but are not limited to):

  • Getting a project description in writing
  • Having the client review the work at crucial stages of the project
  • Buying additional tools for your freelancing business
  • Taking training classes to learn a new skill

Of course, take the remedial steps that best fit the cause that you discovered. Your remedial steps may be different than the ones I listed above.

When Needed, Ask for Advice

Sometimes, when we make a mistake, we really have no idea how to avoid it. If this happens to you, You have nothing to be ashamed of–you may still be able to work out a way to solve the problem.

This is where having a strong peer network and/or a freelancing mentor comes in handy. Often, your mentor or your peers have faced (and solved) a similar problem and can share what they did.

You can also look for articles, forums, and other online resources for freelancers (such as the Freelance Folder blog) where good advice is given. Don’t be afraid to reach out to the freelancing community for advice.

Your Turn

What processes do you have in place in your freelancing to avoid problems? Have you overcome a failure?

Let’s learn from each other! Share your answers in the comments.

Image by rocknroll_guitar


  1. says

    Great advice, Laura! I especially appreciate the wisdom of acknowledging the hurt, giving yourself some time, and talking with a trusted friend. Acknowledging hurt is hardest for me, but I’ve found that when I do, I learn and grow so much more.

  2. says

    You must have been raised in a very sheltered environment. I learned not to touch the hot kitchen stove by touching it.
    Later, kitchen stoves were insulated and that is why you didn’t have the privilege of the experience. Of course maybe you weren’t allowed in the kitchen.

  3. says

    Great comments everyone!

    ccc–I’m sorry that you continue to fail.

    Bill Kerschbaum, I think if you try to move past the hurt too quickly you won’t be as effective doing the remaining steps.

    Gold–Great example that proves my point that freelancers can and should learn from failure. In your example the failure is that you got burnt. After you scream and put medicine on the burn, you examine what went wrong. What went wrong? You touched a stove when it was hot. What process can you adopt to avoid similar failures? In the future, make sure the stove is off when you touch it. See–same point, different illustrations.

  4. Nathan Rattray says

    Fail, Fail again and Fail better :) Had failed client’s approval hit me hard… am glad I failed otherwise I won’t improve at certain areas. Great post by the way :)

  5. says

    If you succeeded did you fail? Maybe you didn’t succeed. That may have been failure. But since you did succeed what is all this talk about failure?

  6. says

    Failure is the quickest way to succeed, there’s no doubt about it. Failure means you must re-examine your processes and research alternative methods of tackling a problem. I don’t always do everything right, sometimes I screw up bad in an area. You just have to take it apart and ask yourself how to “not” do that next time. :D

  7. says

    There are lessons to be learned with every client you have, whether you “succeed” or “fail” with them. The key is to open to learning new things and to changing the way you do business. The ones who truly fail are the ones who refuse to change. That’s why Einstein said: “Insanity is doing the same thing over and over again and expecting different results.”

  8. says

    Laura, thanks for your thoughts on this. I think a lot of people have problems seeing what the kind of highlights “failing” can do. It really is one of the quickest and easiest ways to learn lessons. We forget how important it is to continue to learn and from the things that seem to fall short. Thanks for sharing!

  9. says

    Failure in a good sense allows for self examination and additionally raises awareness for the prevention of repeated mistakes. A dash of good faith as well as courage in oneself will help tide through the waves.

    I don’t remember knowing anyone successful this day who has never fallen at least once.

  10. says

    I read your article a couple of months ago but didn’t comment then. I hope its not too late to comment now.
    I recently lost a major client and per your advice conducted a project postmortem. After a week of discontinued work I sat with my ex-client and asked where I had gone wrong. He pointed out my faults and I kept noting silently. I then asked if he was ready to listen to my side and he agreed. I gave him my list of points where his expectations had gone beyond our agreement. I also told him that losing his project was bad for business and we are now back working together on fresh contract.
    Thanks for writing a great post Laura!


  1. […] Why You Sometimes Must Fail Before You Can Succeed (and How to Recover) I hate pain! When the doctor has to draw blood, I wince and look the other way. If I know something is going to hurt, I generally go out of my way to avoid it. However, sometimes you must fail before you can succeed as a freelancer–and failure hurts. Source: freelancefolder.com […]

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