Building Confidence as a Freelancer & Beating Imposter Syndrome

I've never done a “part two” in the 3+ year history of this blog, but there’s a first time for everything, right?

I want to continue the conversation we started last week about confidence. 

Last week we talked about writing confidence. But today, I want to talk about a different type of confidence.

Here’s where this is coming from…

Earlier this month was the release of Season 2 of the Creative Class podcast, which I co-host with Paul Jarvis. With each release, we share the written transcripts of those episodes. It takes our audio conversations and puts (them word for word) in written format.

When I started reading through these transcripts, I noticed a recurring theme: I kept using words and phrases that cut away my ethos.

My portion of the conversation was littered with interjections that clouded the thoughts I was trying to communicate. Sometimes, it even made me sound less confident.

It made me realize: You can be the most confident and skilled writer in the world, but if that doesn’t 100% translate into the communication around those opportunities--you’re actually working against yourself.

Let me show you what I’m talking about more specifically with an example from one of the transcripts.

This was one of my comments on the topic of using ‘me’ vs. ‘we’ as a freelancer:

“I guess social media management was kind of a headache. Trying to be myself and the brand--and the same was true for like when I wanted to go and write something--I was overthinking everything because I was trying to write as a brand rather than just writing something as myself. So across the board it made things a lot simpler and, I don’t know, that was just my personal preference. For everyone it’s going to be a little different.”

I’ve bolded the words and phrases that I’m referring to. I’ll call these “detractors.” 

Detractors are words and phrases such as:

  • Kind of

  • I guess

  • Like

  • Sort of

  • I don’t know

  • Basically

  • I think (as in, ‘I’m uncertain, but…’)

Why don’t we want these “detractors” in communication? 

For one thing, they’re wishy-washy. These words and phrases carry an air of uncertainty and doubt with them. They don’t sound confident. 

What do you do to fix this? Here’s what I’ve been doing...

1. Always get a transcript for audio/video interviews you do. 

By studying transcripts that illuminate the way you naturally speak, you can spot the detractors and set up mental triggers for yourself. If you notice you use the word “like” as a verbal comma, for example, make a mental note and be aware of the habit so you can eventually phase it out. 

Bad: “I noticed that they had, like, 4,200 words still unwritten on the project.”
Good: “They still had 4,200 words to go on the project.”

2. Be aware of how you’re communicating in email/phone conversations.

Often times, detractors end up creeping into our communications in less formal settings--like email and phone conversations. It’s important to be on the lookout here as well.

Women especially have a hard time with this (I say this from experience.) We tend to use emotion-based language and take on an apologetic tone in situations when it’s not entirely necessary. Communicating confidently in these settings means using strong, declarative sentences instead.

Bad: “I wish I could take on this opportunity, but I just don’t think I can right now--I’m so sorry.”
Good: “I’m currently booked and can’t take this on right now--but I do appreciate the offer.”

3. Ask people close to you what your conversational “tics” are.

Asking friends and family about the way you speak is a good way to learn about your bad habits (that you may not otherwise pick up on). The people who listen to you most can probably give you a shortlist of your speaking habits right off the top of their heads.

Do you frequently say things like:

  • “You guys” when referring to a collective of people?

  • “T-B-H” instead of “to be honest”?

  • “Um” or “you know” as a conversational pause?

Once you know what to listen/look for, start practicing speaking and writing without them. Screen your emails. Do an audio recording of yourself answering questions for a podcast before the real recording. Do a test run for a video and watch the playback to study how you speak on camera.

4. Rosie Chrome Extension

Val Geisler just shared this amazing tool with me via Twitter this morning. What is it?

Rosie is a Chrome extension that detects undermining language and suggests more confident phrasing to help people represent themselves as the professionals they are.

That's amazing. And simple. Thank you Val!
Working on this stuff won't always be fun (I always cringe a little when watching/listening to myself), but the practice will make a world of difference.
You and I can both start communicating more confidently. That means we sound smarter, share ideas more clearly, and generally become more interesting to listen to. And who doesn't want that?

P.S. Don't be too hard on yourself as you work on this. As a card-holding member of the hyper-critical-of-myself club, I forget this all the time. Progress takes time, and practice makes perfect.

This article originally appeared in my newsletter, A Cup of Copy. Sign up and get these free tips sent right to your inbox every other Wednesday.