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9 lessons I learned failing spectacularly as a freelancer and how it is helping me succeed today.

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Many of you may not know this but I’ve tried to become a freelancer and failed three times already. 

There was a lot of pain and feeling like a huge failure. I’ve shed a lot of tears, and have questioned my purpose.

I didn’t realize that all of those failures would lead to the best lessons I would ever learn. More valuable than my college education ever taught me.

Here are the 9 lessons I’ve learned failing spectacularly as a freelancer and how it is helping me succeed today: 

1. I don’t want to travel for work. I want to have work that will allow me to travel. 

My first dive into freelance work was being a photojournalist. I was able to travel the world and go to remote areas where I photographed indigenous tribes.

My biggest goal was to work with the United Nations. And when I was given the opportunity by the UN to travel to China with 21 other artists to showcase my work, I realized that I accomplished what I set out to do and decided to leave at the “peak” of my career.

I realized that I needed to do something more to help the people I was photographing and constantly traveling for work was not sustainable.  I was burnt out. I left and didn’t touch my camera for 2 years.


2. Don’t get caught up in creating the perfect content. 

My second attempt to becoming a freelancer was to create a children’s website Lollie Tot. I produced how-to activity videos for parents with toddlers and provided in-person art classes.

I hustled hard, made the cutest videos, had the help of the most talented and supportive people. 

As a content creator, most of us are perfectionists’ and it can be really hard to publish your work when you feel like it is not “perfect”.

But, I realized that the more elaborate and complicated I made my work, the fewer people were interested. And the more simple they were, the more my audience was able to relate to the content.

One very simple video that I made in my kitchen-had almost 1 million views, while videos I made in a studio barely had a few thousand views.

Curious? See the video. 

3. Do the 80/20 rule when marketing. 

One of the most valuable lessons I’ve learned as a creator was the 80/20 rule in marketing (and pretty much everything).

Spend 20 percent on creating content and 80 percent in marketing your product. Make the 20 percent the best it can be and market the hell out of it.

I learned that no matter how good your content is if you have no audience – it will only ever be a hobby.

I failed with Lollie Tot because I was creating quality content, but did not market my work properly and had no clue how to make money. It was not sustainable. I was spending too much and not earning enough.

failing as a freelancer

4. Having supportive people around you is crucial to your success.

You will know true friendships when you become an entrepreneur and freelancer.

A few years ago, someone ones told me that in order to succeed I may have to let go of certain people and to always surround myself with individuals who truly support me because it can be a very lonely road.

I never truly understood those words until recently. I realized how crucial it is to let go of negative people and to embrace the ones who truly support you.

5. You have to be passionate about what you do. 

Aaron and I also tried selling promotional products. It was a complete departure from my interests and there was no passion behind this new business except to make money and learn sales.

Freelance work really showed me why passion for your work is so important. I became bored. I hated the tasks I was doing and I was questioning my life choices every day.

I was not happy. I gave up.

failing as a freelancer

6. Networking the right way. 

During our time as promotional marketers, we attended so many networking events and we were constantly exhausted. After 6 months of doing 3-4 networking events every week we learned a valuable lesson:

Most people will waste your time. Learn how to be more efficient and research the person you want to connect with.

Instead of going to an event, contact them and ask them out for coffee, this way you will have their full attention and you can create a real relationship.

7. Delegating is the key to growth.

There were so many tasks that needed to be done, that Aaron and I decided to hire an assistant.

We learned that we could not do everything ourselves, and if we could – we really didn’t want to. We were getting some sales from the business and we decided to invest some of our profits to hiring an assistant to delegate some of the tedious tasks.

Although our business did not work, we learned that delegation is key to growth and to always hire someone who will make your business more efficient.

8. Be careful who you collaborate with but be open to new ideas. 

If you have ever met me and Aaron, you will quickly realize that we are very trusting people. We believe that everyone is essentially good.

We learned the hard way that not everyone can be trusted and ended up partnering with an individual who cost us thousands of dollars.

To this day, we still believe the best in people, but now we are more cautious in who we trust.

9. Learn from your mistakes and never give up.  If it is truly what you want. 

Although the last freelance work I did was a departure from my interests, it has taught me the most.

I have learned from so many of these mistakes and I am bringing them with me in my current business, that now it seems “easy” and a lot of things are “no-brainers”. But then I realized how many failures I’ve had in order to learn these lessons.


“It doesn’t get easier, you just get better”

Don’t get me wrong. I am still learning every day. But now I have a better picture of what’s ahead and more prepared to fall while I am continuously climbing up.

There will be opportunities that will be presented to you, many may not be your dream job, but they may be the jobs that will teach you the most about yourselves and what you really want in your life.

I “failed” at all of these freelance jobs and had to go back to my day job.

Feeling defeated and being lost is not new or foreign to me. I know that it isn’t too many of you either. Some of you may have gone through it already, while many more of you may feel defeated every day. 

failing as a freelancer

As I look back and as I am transitioning to yet another freelance lifestyle I realized that things are different this time around and the reason is… I’ve learned from all of these “mistakes”. 

I know that diving into a freelance career is hard work, but so is having a day job. Nothing is guaranteed and a lot of the people I have interviewed for the podcast became a freelancer because they lost a day-job.


So whatever your decision is, whether to have a side hustle while you’re working your 9-5 or going into the unknown to become a full-time freelancer. Make sure it is the right decision for you at this moment.

Nothing is ever set in stone, and even if you have to go back to your day job, you can always try and try again. I am the living proof of that.

Embrace your failures. This is how life is educating you and it is worth more than any lessons you will receive in school. 

And always remember:


“You are not failing, you are learning.”





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2 comments on “9 lessons I learned failing spectacularly as a freelancer and how it is helping me succeed today.

  1. Lia Garcia says:

    This advice is spot on! My current full time gig as a blogger is actually my 3rd online venture too. The first 2 were just hobbies, but the lessons I learned from them allowed me to make the leap to full time this time around. I’ve also had a lifelong history of failing the first time and nailing it the 2nd time. Failure is a crucial part of my learning process!!

    1. debbie says:

      You are killin’ it girl! It’s amazing how all the failures really help us succeed in the long run. But what most people see are just the success. You definitely inspire me everyday.

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