Welcome to Write Bites, an audio series where we discuss writing, marketing, and freelancing during one of my daily walks around the neighborhood.

Audio Recording

In Episode #13, I explain how to develop more confidence as a freelance writer.



Transcript: How To Develop More Confidence As A Freelance Writer

Hey guys. Welcome to Write Bites, an audio series where we discuss writing, marketing, and freelancing during one of my daily walks around the neighborhood.

Today, I want to talk about confidence and how to have confidence as a freelance writer.

The reason I want to dive into this is because I feel like the prevailing advice on confidence is kind of shit. It’s like if you were playing a basketball game and your coach called a time out, got the team on the bench, and was like, “Alright guys. Here’s what we’re going to do: Play better.” That’s kind of what confidence advice is like. It’s like, “Hey, be more confident.”

I want to try to explain how you can become more confident, but in a way that actually works and allows you to take action towards getting there. To do that, we need to break up confidence into two different types:

There is natural confidence, which is what most people think of when they say, “Be more confident,” or ask, “How can I become more confident?”

That has to do with a general lens through which you view people in the world and situations. There’s a level that has to do with your own personal self-assurance, but there’s also part of it that just has to do with how willing you are to be bad at something, or how willing you are to fail and make mistakes.

Some people are really scared to fail, and it causes them to be very unconfident when doing something that they’re not good at. If you can shift your mentality, it may help you have more natural confidence across the board, but ultimately that’s not my advice for you, because I don’t know, frankly, if you can change that. I would imagine you can, but again, for me to say, “Hey, be more generally confident,” “Be more naturally confident,” isn’t really going to do anything for you.

The other type of confidence though is a different story, and it connects to a little bit to one facet of what I just mentioned, which is when you’re good at something.

So, there’s another confidence, which is what I call “situational confidence”.

To illustrate this, picture a group of your friends. Everyone’s different, but you have one person who’s maybe a bit more introverted, a little bit shy, not super expressive, not super outgoing, but in certain situations, maybe when a certain topic comes along or they’re engaging in a certain activity—something where they’re very experienced or knowledgeable or passionate—all of a sudden their personality shifts.

There’s a marked shift where they become more expressive, they become more energized, more outgoing, and it’s because it’s in their comfort zone. It’s sort of in this situational sweet spot for them where they feel very confident. Even if they aren’t naturally confident across the board, when we’re in this specific milieu, or we’re focused on this specific area, they now become confident.

And that’s what we want to do for freelance writing. We want to get you situationaly confident. The way to do that is to just do it a bunch of times. Whatever it is that you’re not confident about, you have to go engage in it and do it unconfidently enough times to where you become confident.

Whether you achieve that level of situational confidence is purely based on your own activity. If you power through and do it multiple times, you will become confident. You have to accept that, “Hey, I’m not going to be confident initially, but if I keep doing this, I’m going to become more and more comfortable and develop a situational confidence in this area.”

And that applies to many areas. It applies to writing. If there’s an area of your writing where you aren’t confident, keep doing it. Practice.

As I’ve talked about before, 90% of your learning is going to come through actually doing the work of writing—not reading about writing, not getting a certification on writing, not doing another course on writing—but actually going out and writing for a client. That’s where you’re going to learn. That’s where you’re going to develop your confidence.

In the same way, when we talk about pitching and sales calls, you’re not going to get confidence from another sales seminar, from another lesson on sales, or from another training on sales.

You can buy my Pitch Masterclass: It’s not going to make you comfortable or confident in pitching in sales.

What’s going to make you confident is actually going out and doing it. Doing it over and over, you’re going to start to become familiar with what you’re looking for; with how different clients respond; the unknowns are going to start to disappear over the course of doing this thing numerous times.

If you’re sitting there and you’re thinking, “Hey, I’m not really a naturally confident person,” the answer is not to just become a more confident person. I mean, maybe it is. Shit. Maybe someone out there has the secret to changing your personality. I sure as hell haven’t found it.

But what you can do is you can go make the choice—knowing full well that you’re scared or just unconfident going into these situations—and just make yourself do it until you develop that situational confidence.

And I want to give you a path to aim for and also a bit of a light at the end of the tunnel to know that this does get easier over time. You do become more confident over time. I’m one of those people who tend to be a more naturally confident person. It’s obviously been reinforced in many areas of my life with being able to be confident and receive positive feedback on being confident, which is actually a privilege that I’ve experienced by virtue of being me. But there’s something beyond that.

Even as a naturally confident person, I’m not fully confident in a new situation. I’m confident enough to be timid and to go into it while I’m timid, but even still—when I was first doing sales calls, when I was first doing these writing assignments—the same process is there for me, it’s just expedited. For more naturally confident people, we just get to the situational confidence a lot quicker—possibly sometimes quicker than we really deserved—and that can backfire…

But at the end of the day, it’s the same process for everyone, whether you are naturally confident or not naturally confident. It just comes down to repetition—doing it over and over, developing the specific experience and skills that come along with having done a situation many times. In the same way that to make more shots in the basketball game you don’t just click a switch in your mind and become a better player, you get in the gym and practice your shot over and over and over. I hope that kind of clears things up.

The last thing I would mention on confidence is that when it comes to things that a lot of us are timid about or things that we look at and feel, “Hey, I’m not super confident in this area,” a lot of times we leave it vague like that: “I’m just not confident.” “I’m just not confident in my writing.” “How do I know if my writing is good enough?” “How do I know if my sales pitch is good enough?” “I’m just not good enough.”

We leave it vague like that. But vague doubt never translates into growth.

So what I would encourage you to do in a similar vein is when you feel like, “Hey, I’m not stacking up here,” or “I need to continue developing here,” or “This area is holding me back,” don’t leave it vague. Dive deeply into “What specific aspect of this is holding me back?” “Why am I not confident?” “What specific thing here do I feel confusion about or uncertainty about?” That gives you a very specific objective to focus on in increasing your mastery, increasing your experience, and ultimately increasing your confidence.

Hope that helps. I will catch you guys in the next episode.

Share Your Thoughts

I hope this was helpful, and I’d love to hear your thoughts on this topic in the comments below.

Plus, if you have a question you want answered on a future Write Bites episode, ask in the comments, and I’ll add it to the schedule.

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