The Hard Truth About Freelancing: What I Wish I Knew 10 Years Ago

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Have you experienced this phenomenon before? 

You start learning a new skill and things are going pretty great at first.⁠

You feel super confident, capable, and almost like you were “made for this”. 

But then something crazy happens…⁠

You suddenly find yourself DEEP in a pit of despair.⁠

Full of doubt and limiting beliefs…⁠

And you just don’t think that you’re “cut out” for this thing you were once so confident about. 

⁠Sound familiar? ⁠

Well, I hate to break it to you, but…⁠

You’re not special. ⁠

This is something that happens to most people when they’re learning a new skill or trade. ⁠

It’s called the Dunning-Kruger effect, and I WISH I had known about it 10 years ago when I first got started freelancing. In this blog, we’re going talk about this crazy phenomenon…

What it is, why it happens, and most importantly – 3 tips for helping you move past it. 

Hey, Posse! What’s up? It’s Alex. 

Coming at ya this week with a fresh tutorial to help all my fellow freelancers and entrepreneurs crush it in their businesses and live a life that feels good to YOU

But first, if you’re new to the crew – welcome!

My blog is dedicated to teaching you everything and anything about copywriting, marketing, and entrepreneurship. 

From how to get in creative flow, to how to start and run your freelancing business, hot new digital marketing trends – and so much more. 

So if you’re ready to master the world of marketing, then make sure to subscribe to my newsletter.

Alright, let’s get right into the topic…

So The Dunning-Kruger Effect is something that I learned about relatively recently, and it absolutely blew my mind…

MOST of us have probably heard the term “imposter syndrome” a time or two – especially if you’re already knee-deep in the world of freelancing. 

Imposter Syndrome was first described like this by two psychologists in the 1970s

Impostor phenomenon occurs among high achievers who are unable to internalize and accept their success. They often attribute their accomplishments to luck rather than to ability, and fear that others will eventually unmask them as a fraud”.

Essentially – imposter syndrome happens when smart and extremely capable people underestimate their abilities.

They feel like they’re doing a terrible job, don’t deserve the recognition they’re getting, and will one day be exposed as a fraud…

…meanwhile all their clients, peers, and coworkers think they’re amazing!

And while this is definitely something that I think a lot of freelancers encounter during certain points of their career…

The more common phenomenon is actually the TOTAL OPPOSITE of imposter syndrome. 

Enter, the Dunning Kruger Effect

According to psychology, when you first learn a new skill, your confidence will be at an all-time high. ⁠This peak of confidence is called Mount Stupid (lol yes seriously).⁠

Image from Wikimedia

And plot twist…

The sky-high confidence you’re feeling is actually a FALSE SENSE of confidence that’s caused by your general lack of knowledge. It’s kind of like… you don’t know what you don’t know so you overestimate your skill level.⁠

But then, as time goes on and you begin to accumulate more knowledge, you realize that you didn’t know as much as you THOUGHT you did. ⁠

And that’s when you fall into…⁠

⁠The Valley of Despair. ⁠

This is typically when all those doubts, fears, and limiting beliefs rear their ugly heads. ⁠This is when you may start feeling like a fraud or like you’re not “cut out” for what you’re doing. 

But it has nothing to do with being an imposter… 

It’s just the uncomfy feelings that pop up when you realize, “Damn, this is harder than I thought it would be”. 

You know, because the more you know, the more you realize you know nothing. 

And folks – this is the hard truth about freelancing. 

You’re going to feel challenged

It will feel hard

You’re probably gonna feel like you’re doing a terrible job at times! 

Remember, learning a new skill is supposed to be challenging. 

And guess what else?


Despite how you’re feeling, this doesn’t mean that you’re failing, or stupid, or “not cut out for this.” There is nothing wrong with you! ⁠

You’re just a normal person learning a new skill and experiencing the rise and fall of confidence that comes along with that. ⁠

So the real question here is…


Well, as you might have already guessed, the only way out of the valley of despair is to move THROUGH it. 

You just gotta keep going, keep learning, and keep trying. 

But I get that feels unhelpful to have someone tell you “just keep going” lol. 

So I’m going to share 3 practical ways you can “keep going” allllll the way up the Slope of Enlightenment to the promise land… the Plateau of Sustainability…

#1 – Ask For Honest Feedback 

Hands down the best way to grow and get better at your craft is to receive honest, constructive feedback on your work. 

This can come in a few different ways…

First of all – never underestimate the value of a mentor or coach. Someone who is skilled and experienced in what you do and can offer you unbiased feedback.

Even if you only work with them for a few months, you’ll be surprised how much you can improve when you’re being told EXACTLY what’s lacking, what needing improvement, and what’s really great

Another way to approach this is to ask your clients for feedback on your work. 

Now, this one is a little bit more tricky… 

Because not all clients will know how to spot the difference between good and bad copy. And clients also tend to have biases. 

But it’s still worth asking. So once you complete a project, you could send them a follow-up email that says something super simple:

I’d love to stay in touch and hear how my copy performs for you.

This opens the door to having a conversation about your work – it includes the client’s personal thoughts about your work, it could involve metrics, or even feedback directly from their customers. 

And as a bonus, if the result and feedback are good, you can utilize it as a testimonial! 

Alright, on the next tip…

#2 – Join A Community 

Another thing that should never be underestimated in the world of freelancing… community

In this digital age, most of us freelancers work solo. And unless we’re part of a community, membership or mastermind, we probably don’t know, or interact, with very many people who are doing the same thing we’re doing. 

Not only can it feel isolating…

But it also makes it hard to GROW.

Being in a community is so valuable, because you can share wins with each other, get inspiration from one another, and something my Reignmakers do from time to time is…

Host pop-up workshops! Where they will come together on Zoom to workshop someone’s copy or brainstorm solutions to a problem. 

Now your next question is: “Yeah but how do I find a community, Alex?

Well, you’re already here! The Posse has a ton of great community resources, including private membership groups that you get access to when you join anyone of my programs.

Facebook also has hundreds of free groups you can join. Be active, be present, start conversations with people and go in with no expectation other than connection.

Alright, now on to the final tip…

#3 – Practice, practice, practice. 

Probably saw that one coming, huh? 😉

As plain and simple as the advice might be… practicing really is THE BEST way to improve your skills and grow your confidence. 

Remember: Courage comes first, then capability, then confidence. Not the other way around!

So take on all the projects you feel comfortable doing – get the experience, learn something from it, and keep repeating the cycle until you start to find your groove…

You can practice even if you don’t have any clients or projects!

One of my favorite ways to practice is by rewriting copy I find online. Ads, emails, sales pages – anything is up for grabs!

If you read something and think, “Hmmm, I could make it better.”

Then try it! Rewrite it and make it better…

Do it as often as you can and I promise you will keep getting better and better. 

And if you have a peer group, mentor, or coach – ask them for feedback 🙂  

Now, before we end here, I want to leave you with this. If you’re currently riding in that low “valley of despair” phase…


Your confidence will grow over time. I promise!⁠

⁠⁠I’m rooting for you. You got this!

Until next time. I’m Alex. Ciao for now.

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