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5 Lessons Learned From A Horrible Freelancing Failure

5 lessons from a freelancing failure

The initial process of starting something new usually comes with some anxiety, even fear that things will go wrong. Sometimes we end up overanalyzing and come up with every possible worst case scenario that could occur.

In reality, things will be fine.

Well, my first freelance marketing gig was a failure.

I didn’t completely destroy a business or ruin someone’s reputation. It wasn’t that bad.

I took on a client whom I didn’t know anything about and whose industry I wasn’t familiar with nor interested in.

He’s a screenwriter and novelist and has published some novels on Kindle, but he had almost no online following. He wanted to hire me to grow his social media following and get readers.

This meant I would have to read his books to learn his voice and understand who exactly I was going to be marketing. On top of that, I would have to learn about the screenwriting and publishing industries and find an angle to generate interest in him.

There were already obvious challenges laid out, but I encountered even more challenges.

Despite already juggling three unrelated projects, I decided to take him on.

It wouldn’t be too bad, I thought. I’ve handled multiple projects before. I just need to manage my time wisely.

Mistake #1: I didn’t properly assess what I was getting myself into.

The idea of social media is relatively simple. Engage with people and join conversations to build relationships and, hopefully, readers.

However, I didn’t fully consider the idea of performing my due diligence. Again, that mean researching his industry and his previous works and learning how to write in his voice.

I underestimated the work the project would require and the extra income sounded nice.

I was eager to sign him on for three months of work. He wanted a month as a test.

Looking back, I’m glad I didn’t sign for three months.

Lesson learned: Even though you know how much work needs to be done, realize that there’s likely to be even more work than that. Consider everything you’re already doing and if you’re willing to commit the time to your client. Don’t say yes just because you want the extra income. It’s not worth it.

Mistake #2: My ego took hold.

My client had asked for me to manage his Facebook fan page and Twitter profile. I began building a list of tweets and Facebook posts. These bite sized pieces of content included quotes from his books, links to buy his books on Amazon and short excerpts from his bio to help people learn more about him as a person.

I began following people on his Twitter account in hopes that they would follow back.

Then I realized that he wanted readers, not superficial followers. So advised a different approach without social media. I created a timeline of a campaign to get exposure for his Kindle books and get readers.

I really jumped into the project.

I created a strategy to distribute his books via Amazon kindle to as many outlets as possible. Running short free ebook campaigns to get people to download his most recent book and, hopefully, talk about it.

I talked about redesigning his website to push people to download his books. I talked about SEO and Google rankings.

My ego was talking. It was subtle. It could easily be seen as me just wanting to do the best I could for my client. But I completely moved away from what my client had initially hired me for–social media work. Instead I talked about marketing strategies that he didn’t understand. By doing this, I confused my client.

There I was talking about book distribution and growth hacking books when all he wanted was to get readers and followers.

Lesson learned: Don’t stroke your ego. I realized that it’s often not about doing what you think is best for your client. Freelance work is about making your client happy, even if it’s not what you would do for yourself. In the end, it’s not your call, it’s theirs. They didn’t hire you to tell them what to do. They hired you to help them get what they want.

[Tweet “When doing freelance work, it’s not about what you think is best. It’s about what the client wants.”]

Mistake #3: I hired before I knew what I was doing.

Since I didn’t know the industry, I didn’t feel I was well-equipped to handle the marketing on my own. I recruited a friend who had an understanding of public relations and screenwriting to help.

I should have learned from working on The UP Lab [link] that hiring too quick is detrimental to getting shit done.

Because I didn’t know what I was doing, my partner was confused about what exactly he got himself into. Remember earlier how I didn’t even know what I got myself into? That lack of clarity was amplified.

We figured it out as we did research into the client and after about two weeks of confusion, we produced some great results.

Here’s the part that still irks me. Not much happened in those two weeks. We met up one day and got everything done in six hours.

The process–or lack of it–wasn’t efficient by any means.

Lesson learned: Don’t hire if you don’t have to. If you do hire, make sure you know what you’re doing. Without goals or a plan, little action will be taken. When no one knows what’s going on communication is going to be ten times as difficult. Have a solid plan, then hire.

Mistake #4: I undervalued my services.

The rate that I charged my client was already low to begin with and my partner and I split that down the middle.

However, I felt so bad that my partner and I were inefficient in our work and offered my client the second month of our services free of charge.


This scenario is another example of my ego taking control. Although I felt bad, I didn’t have to provide the free month. I didn’t feel confident in my capabilities and felt the need to act on those insecurities. It was more for myself to feel better than for the client.

If your client is on a flat fee contract, then he doesn’t care how inefficiently you worked. He only care about the results. It’s a different story if you’re getting paid by the hour.

Lesson learned: Do not EVER undervalue yourself or your services. As long as you demonstrate to the client that you got results, there’s no reason to lower your rates.

Mistake #5: I didn’t commit.

After those two months, I discussed the situation with my partner and we agreed to cancel the contract.

There were many reasons for ending the commitment. 

I had other projects on my plate. I wasn’t interested in his industry. I wasn’t willing to dedicate time to read his books. I’d rather read other books. I didn’t enjoy the process of working on his campaign.

I decided to focus on achieving my own goals before helping someone else achieve his. By doing this, I was able to focus my energy and get my dream job.

This all could’ve been avoided if I had initially thought through what I was getting myself into.

Lesson learned: If you do your due diligence in the beginning and know what you’re getting yourself into, it’s easier to commit and you’ll avoid ruining the relationship with your client.


It”s important to be really picky with who you work with and what you work on. Otherwise you’ll end up unmotivated

[Tweet ” Be really picky with who you work with and what you work on. Otherwise you’ll end up unmotivated.”]

I realized that my attitude of saying yes to everything had its drawbacks. In this case, I got really excited about what I could do for my client. I was so excited about what I would do that I hardly paid attention to who and what I’d be marketing. So I ended up marketing for a client that I had almost no interest in.

It could’ve been worse. It could’ve been a huge client who ended up disappointed and spread the word that I’m not reliable. That would’ve been horrible.

Luckily that wasn’t the case.

I could say that I would’ve done things differently. In reality, I wouldn’t have taken my client in the first place. I would’ve done my due diligence and thought through what the work would entail. I would’ve been more humble with how much I could do each day. I would’ve asked myself if I even care about who and what I would be marketing.

Live and learn.