Freelancing • Entrepreneurship • Remote Work • Productivity

10 Unexpected Challenges Encountered By Freelancers And Their Outcomes

Forgot to bill a client for your hard work? Called a client by the wrong name? Didn’t proofread your writing? Freelance fails abound – and they happen to everyone. 

From failing to make an alternate plan to not building a brand, here are the top “Oh shit!” moments shared by 10 freelancers and what they did next.  

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Failed to Set Up a Backup Plan

One major freelance fail I have made in my business was not properly setting up a backup plan for our customer data. We had been collecting customer information for months but had not taken steps to ensure someone securely backed it up.

As a result, when our system crashed because of a power outage, we lost all of our customer data. We could only recover a small amount of the data and had to start from scratch to rebuild the rest.

After this incident, I quickly realized the importance of having a reliable backup plan in place. We immediately implemented a new system that backed up our customer data in multiple secure locations, ensuring that if any one system failed, our data would still be safe.

I also worked to educate my team on the importance of data security and regularly review our backup procedures to stay ahead of potential issues.

Ann Young, CEO, Fix The Photo

Forgot to Invoice a Client on Time

One of my most memorable mistakes was failing to invoice a client on time. This caused a strain on our professional relationship and resulted in an income delay for me. 

In the future, I am taking proactive steps to ensure that this kind of mistake does not happen again. For example, I use software to track invoices and set up automatic email reminders for when they are due. 

I also build reminders into my personal calendar to prompt me to enter dates and send out invoices within the agreed timeframe. It’s important for small business owners to remain accountable for their work and ensure that those who support them receive timely payments.

Jim Campbell, CEO, Campbell Online Media

Miscalculated a Project

One major mistake I have made in my business was a miscalculation on a project, which resulted in a significant financial loss. It was an expensive oversight that I should have caught, but didn’t.

In the aftermath, I took personal responsibility for the mistake, apologized to my team and clients, and worked to fix the issue as quickly as possible.

I learned from the experience and worked to make sure similar mistakes wouldn’t happen again by following up with additional training and checks to help ensure accuracy and proper procedures were being implemented by all members of my team.

I also use more detailed tracking and metrics to monitor and analyze our progress, allowing us to catch any mistakes before they occurred. This helped my team and clients feel better about the services we provided and enabled us to maintain our credibility.

Arkadiusz Terpilowski, Head of Growth & Co-Founder, Primetric

Showed Up at the Wrong Location

I freelanced for many years as a sports reporter on the weekends while my personal career took off. It was in the middle of high school basketball season, and there were quite a few games for the outlet to cover. 

My contact at the outlet told me to cover the game at a certain high school. I typically showed up 45 minutes early to each game so I could get properly settled in. Unfortunately, I showed up at the wrong high school. It was a very similar name, but all the way across town. 

I called my contact and asked where the game was because the gym was empty, and he informed me it was at another address. I quickly rushed over to that high school but missed the first quarter of the game. It turns out that while I went to a similarly named high school; they had also given me the wrong address. 

Always double-check your information to make sure it’s correct before starting an assignment. People make mistakes every day. It’s just human nature. After that, I double-checked each location.

Seth Newman, Director, SportingSmiles

Didn’t Get a Clear Scope of the Project

One major freelance fail I have made in my business was taking on a project without fully understanding ‌its scope. I had underestimated the time and resources it would take to complete the project, leading to delays and frustration for both me and my client.

After realizing the mistake, I took steps to correct it by communicating more clearly with my client about the timeline and expectations and by hiring additional resources to help with the project. I also took the time to learn from the experience and adjust my approach for future projects so that I would not run into the same problem again. 

This was a valuable lesson that has helped me become a better project manager and made me more aware of my strengths and weaknesses.

Tiffany Homan, COO, Texas Divorce Laws

Misquoted the Service Provision

Freelancing is all about flexibility and being dynamic. This also involves agreeing to what needs to be done, how it will be done, and how much the service costs. 

The service provider and the client agree before the deal can be closed. One of the mistakes I made was quoting a service provider fee that was way below the value of the service provided. The mistake revealed itself when the amounts hit my account after all the formalities had been agreed on and signed off. This set me back a week’s worth of wages to recuperate the lost amounts.

Yongming Song, CEO, Live Poll for Slides

Tried Doing It All on My Own

As a solopreneur, one of the major freelance fails I had when soundproofing my business was when I attempted to do it all by myself. 

Although the process was straightforward enough and the supplies were available, I hadn’t done a lot of labor-intensive work before, so what should have taken half a day ended up taking me two weeks. 

When someone finally came to inspect the finished product, they noticed some parts of my work that were not as soundproof as they would have liked and pointed out that if I had consulted a professional in the beginning, my money (and time) would have been saved.

It was an embarrassing moment for me but instead of shying away from it; I took it and learned from it—for future projects, I will get advice right away!

Ludovic Chung-Sao, Lead Engineer & Founder, Zen Soundproof

Failed to Set Boundaries

One major mistake that freelancers and solopreneurs can make in their businesses is failing to set clear boundaries between their personal and professional lives. This can lead to burnout, as I experienced firsthand. 

When I started as a solopreneur, I was so eager to make my business a success that I worked long hours and took on more than I could reasonably handle. Soon enough, the stress and fatigue took a toll on my physical and mental well-being. I realized I had to change something to keep going and stay healthy. 

So, I became more mindful of my time and energy and set boundaries between work and leisure. I started writing a daily schedule with plenty of breaks and took time every day for friends and family. Now, I take regular vacations and prioritize activities that are unrelated to my business. In the end, I’m much more productive and happy.

Burak Özdemir, Founder, Online Alarm Kur

Underquoted an Absolutely Huge Project

Perhaps one of my biggest freelance fails in my career was when I was asked to audit a large e-commerce store’s technical SEO.

I had been working with this client for some time, so I assumed they knew how much work our team put into each project and what it would cost them. But this particular job seemed so straightforward. So, without really thinking about it too much, I submitted my fee proposal at way less than the market rate.

It wasn’t until we got started that reality hit me: this project was enormous! It required days’ worth of analysis and meticulous execution from multiple members of our small team—not to mention research and implementation. We’d have to charge far more than originally proposed if we wanted to break even.

So, even though it meant losing out on potential revenue, we adjusted our pricing. Thankfully, they understood and agreed to pay us fairly for the full scope of work needed for their audit.

Jamie Irwin, Director, Straight Up Search

Became a Freelance Ghost Instead of Building a Brand

Not building a D2C (direct-to-consumer) brand first would be my biggest mistake. As I started in wholesale over 20 years ago, I did not build my retail brand until seven years ago. This has helped us connect directly with our customers and control the customer experience. 

By building a D2C brand, we can communicate directly with our customers and offer them a tailored and personalized experience to tell our unique family business story.

Now we built our own customer loyalty to drive repeat business. It helped us be less dependent on third-party retailers and now my phone won’t stop ringing for wholesale accounts to carry our successful D2C brand. So if you want to freelance, think about building your own brand vs. ghostwriting or white labeling your service!

Marc Werner, CEO & Founder, GhostBed

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