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  • Jenny Stallard

How to boost your confidence when you're self-employed

Updated: Nov 16, 2022

Confidence - do you feel it? Struggle with it? Feel you lack it? Wish you had it?

I genuinely believe that every self-employed person, freelancer, entrepreneur or small business owner faces crises of confidence or challenges to their confidence during the career and usually during each working day or week.

Even the most famous and well-known among the self-employed world will face those moments. From established podcasters who decide to write a book, through to people who run communities and agree to speak at events. A celebrity who steps onto a stage isn't always 100% confident. And neither is a freelancer who steps into a room full of new people at a networking event.

Confidence challenges us, and holds us back. It's also a force we can harness to move our business forwards, if we know how. I am on a mission to break down our freelance confidence issues into manageable actions we can address in our own time.

Confidence is a process we are always taking part in. I don't believe we are either 'confident or not', but, rather, confident in different freelance situations. You might be hugely confident in one, but that then overshadows another.

If confidence is holding you back in your freelance life, I'm here to help. Because when we're more confident, things happen. We find we are capable of things we assumed we weren't - our confidence grows.

These are my three steps to building your freelance confidence, and I'm creating workshops around freelance confidence, too.

Step 1: Focus on what brings you joy - and do things your way!

One of the biggest mistakes we can make as freelancers is to try and do things the way someone else is. Just because it's working for them, it doesn't mean it'll work for you. And it's important to remember that while they might come across as confident (for example, speaking at an event, or even at their own book launch), inside there will be many things challenging their own confidence as a freelancer. There might have been challenges for them on the journey to the place you see them in, too.

When we do things that bring us pleasure, we tend to feel more confident. For example, take video on Instagram. I'm sure I come across as super-confident, and, I will admit, I am fairly confident! I'm in my zone. It does bring me joy, so I focus on it more. One thing I do to make it feel like 'me' is to be honest and open, in the moment. I record video on the go on a dog walk, I might post a reel and say I'm trying something out. For me, that builds confidence as I'm saying 'this isn't perfect.

However, that confidence you see on Instagram isn't there on Twitter. I regularly write tweets and then delete them. I am actively scared of posting in case I get trolled, which is what I feel Twitter is about. So I lurk, I re-tweet, I post then close it down. I bet that's surprised you! But it's true - Twitter is not my confidence space. And I know that by not being there, I am probably missing out on opportunities for collaboration, community and clients.

Which leads me to Step 2.

Step 2: Do one thing at a time!

By thing, I mean the thing that challenges your confidence. If you're keen to try something on social media - perhaps posting on LinkedIn for the first time in ages, or a video on Instagram, focus on the one thing. Don't worry about where else you'll post it, or share it, or repurpose it.

So, Twitter challenges me. What isn't a good idea is to try and work on that while I'm also scrolling on Insta on my phone. What I plan to do is take some allotted diary time to look at Twitter, to curate who I follow and why, and to look at how what I offer might translate to tweets.

If your confidence challenge is networking, for example, don't try and go to five events in one week, or set up loads and loads of meetings with potential new contacts. Try one event, reflect, and see how it feels. See what comes of it. if you enjoy it, try another.

You might feel you need a confidence boost when it comes to pitching ideas to new clients, or editors. Sending loads out in one day, like throwing confetti, is going to lead to confidence confusion. Instead, send them out one by one, make a note (I have a Google sheet for this) of who you've sent it to and when.

Being in control of those emails means your confidence isn't also trying to grab hold of your brain as it careers ahead. If you're focusing on pitching (ideas, or yourself to new people), then try and focus less on pitching yourself elsewhere. That is to say, if you're emailing new contacts, don't also be scrolling on social. One thing at a time.

Step 3: Celebrate the confidence wins

When we do something that challenged our confidence, and we enjoy it, we often then move on to the next goal. Taking a moment to celebrate what you've done is really key - it's your moment, and you should enjoy it! Why not share your new post in a freelance group, or just send it to a freelance friend and say 'I did it!'

Check in with yourself, too. Take time to reflect on the feeling you have when you tipped from pre-confident to confident. What was it like to seize that moment?

And then think about what it's brought your business. Perhaps people have interacted with your post, or you went to an event that has brought new contacts.

To talk about how coaching with Freelance Feels can boost your confidence, get in touch!

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