MY TOP 3 STRUGGLES • Lessons Learned - 6 Months Full-Time Freelancer

I worked in an office. I answered the phones. I did whatever projects that got laid on my desk.
Fluorescent bulbs washing me away. No window to the outside world.


Only a small wall of glass like I was a fish in a bowl.

“Here’s the office admin, watch her swim in circles all day long…”


Slowly the running joke that I was “in prison” started to feel more like my reality.

Getting “yard time” during lunch, having to find someone to watch the phone so I could pee, and breaking my bladder all too often.

Being followed around and trapped at my desk while some contract co-workers would vomit all their despair, drama and shit at me, no matter how much work I had to get done…
Almost 7 years and all the same weekly and annual routines started feeling like a really bad Groundhog Day movie remake.

But this was my second job at a desk with no window. So make it 10+ years.

I did my time.


Woa. Today marks 6 months since my last day with a boss.
May 8th to be exact. Which worked out awesome because my favorite # is 8. Easy to remember.

One month later I turned 30 so this is my version of a midlife non-crisis.
“What the hell am I doing and what do I want to be doing?”

I had the desire to make my art functional. To make something beautiful that is useful, in demand and empowered the customer who purchased it.

How could my art make a someones life better? To help make their dreams come true?

I became a Branding Designer and a Website Designer with knowledge of Online Business & Marketing Strategy.


Do you also have this feeling that you are not pro enough or qualified enough to be sharing your knowledge?
To be writing articles and providing content for your ideal audience?

Well I do. Marie Forleo and Jenna Kutcher have inspired and pushed me to walk the talk.

I really believe that our story and current “know-how” is going to be so valuable to someone else.
You don’t have to have it all figured out before you can provide valuable content to your audience.

So acting on my own advice and beliefs I want to share what my biggest struggles were in the first 6 months going rouge.
I think these are things we can all use and need to check ourselves on frequently.



Analysis paralysis is being so terrified of making the wrong decision that you put off making any sort of decision at all.
Dammit. Seriously. Decision fatigue is a thing.
I feel like no one can help if they don’t know all the details, courses, strategy and perspectives that I have gulped up.
So I buck it up & out alone, a lot.

I know this ache, so it’s my goal to be the flashing sign, the wall to bounce ideas off of and in-the-know friend for my clients.

Minimize decisions, remove distractions. Intentionally limit the amount of information you consume. Start before you feel ready.
Realizing how much my overthinking and over analyzing has made me think I’m busy all the time. Changing that “I don’t have enough time, I can’t do ALL THESE THINGS” mentality.

Deep down, I don’t want to make the wrong decision because I don’t want to fail. But the fact is, we all have failures and successes. You might not see them behind the Instagram feed. So forget what you think your success or progress should look like, let it just be natural.


If you know something is a good decision but “you’re not ready yet” Kick Ready in the freakin face.
Muster your 15 seconds of Courage and just do that thing. Send that email, buy that course, call that coach or designer.
If you feel yucky and sick to your stomach? Then listen. Something is not right. Don’t push through that and take a step back.

It might take months until you feel something is good enough but you will never have a business if: you don’t just publish that blog, start that marketing campaign, put out that product you have now, or just start serving people the best way you can, right now.

Read more and get into the science of: ANALYSIS-PARALYSIS & YOUR PRODUCTIVITY at



So you have a ton of decisions to make. In every aspect of your business. I sure did. Especially in the first 6 months.

Should you choose Squarespace for your website? What colors do you use for your branding? How do I choose social media channels for my business? What images do I put on my website and where do I find them? What tools and apps should I actually pay for? What can I get by skipping right now?

The more you read the more questions that seem to come up and choices that need to made. Am I right?
Then the big one’s surface. I am I doing this online business thing right? Will people like this? Will they like me? Am I worth what I am charging?

I have asked myself ALL these questions too. I still ask myself some of them today. Is someone going to find this article stupid? Am I boring or is it too long? Is my website be best it can be? Is that the wrong opt-in offer for my ideal audience?

This is an ever-evolving thing and we all have to go through these growing pains. Several times. It’s ok! Even the big league hot-shots think these too. It’s natural.


Feel your feelings. If your gut and first intuition is telling you something, listen.

Stop checking out the people who have been in business for years and years and then beating yourself up that you are not where they are. They were in your shoes once too and it could very well have been way more screwed up. That is where some big lessons get learned. In experiences and mistakes.

When you have a day that you feel like a badass and can take on a dragon. Write yourself a letter. Why are you doing this hard, uncomfortable thing? What powers do you have and how awesome are you?
You’re so awesome! You really can do this. Don’t give up. Keep going.



Starting out is hard. Much harder than when you get the word out and start attracting your ideal clients later.
Especially in a service based business. You’re working closely with the people that pay you and there is some form of back-and-forth going on.

In graphic, branding and website design this is a big thing. I am creating something to represent someone else and their ideas. I take that very seriously. It’s a process. They might have an idea in mind or might have no idea what they want.

My first 6 months of work came mostly from a few connections in Facebook groups, referrals and a platform called Upwork. No matter where you are finding your clients and customers everyone is going to have their opinion of how much this should be worth and how long it should take.

I have seen people offer $20 for a logo and get many freelancers desperate for work and doing a quick shoddy job. Sometimes even ripping trademarked images off Google!

These people would be climbing all over the job like it was a zombie feeding frenzy.

Although it was hard I stuck to my guns and tried to pick only the best projects that I could find to work with. Someone who valued my talent and time.
This gave me more quality work, happier clients and I think really made the difference in my start out success.

I give my ethics and stamina the credit for “Rising Star” badge on my profile in the first couple of months. And I now have a “Top Rated” 100% Job Success badge on my profile now.

I still fell into some situations that were not ideal and these things have taught me some awesome lessons. I’m very thankful for them and their outcomes.


  • The person you are working with should be the decision maker for the project.

  • Pick up an unfinished project can be a Red Flag & Sand Pit

  • Set a time frame and stick with it as best as you can. Be a firm as you can with it.

  • Even if the client is ok with it going over. (On and on…. it will probably go.)

  • Don’t start working with a client until you have everything you need (if you can help it).

  • Set the rules and workflow yourself. Clients want to be guided. You both are so much happier when everything is decided and explained before getting started.

  • Even if it’s slower, holding out for the best and doing things right is the path to pure success and more joy along the way.


I’m going to tell you a secret: My new understanding of life.

Despite your circumstances, to a large degree - YOU DESIGN YOUR REALITY.
Even if you’re still doing the 8-5 bit in the office with no window...

(I was there for a decade, I totally get it!) We can dream our dreams and design their realities.



I Design My Reality ↡
I Set Intentions ↡

Much of these past 6 months have been behind my computer and that’s ok.

Things are not going to happen overnight.


But even though I have not yet lived my passionate dreams of enjoying all this freedom as much as possible.

  • I have a desk with a window.

  • I don't have to wait for someone to cover the phone to pee.

  • I can wear T-shirts, Jeans and Yoga pants to work.

  • I have been able to see my family more and be there for them more.

Such amazing things need to be enjoyed and savored.

I’m still navigating how to balance work and life and let me tell you it is actually SO much harder now.
It’s a work in progress.

I’m a work in progress. You are too and it’s a beautiful thing. This fact gives me so much hope and joy.

Wherever you are keep dreaming and make a plan. Work each day, no matter how little, towards your dreams.
Book that trip, make time for you in the morning. Read for 15 minutes a day. Listen to a podcast on the way to work. Anything it takes.

What’s your favorite passionate dream you want to bring to life? Share it with me on Instagram! 


Hi! I’m Monica Fawn Orto.
A digital designer and brand strategist that specializes in custom branding and Squarespace websites.

Coming into digital design with a background as an artist strengthens my ability to to create original content, designs and be inventive to meet your needs.

With no consequences in life - I would live on Sushi and Italian Nachos.