Confidence in Pieces? Here’s How to Start Rebuilding

Hi Friend,

During a recent coworking session, a few of us swapped stories about the moments our self-confidence didn’t just wobble, it plummeted off a psychological cliff—arms and legs flailing—and exploded into a confetti of doubt on impact. Think less “small stumble” and more “Humpty Dumpty on a bad day meets base-jump with no parachute.”

Prefer to listen to this post? Hit the play button and you can hear me read it out.

This picture will make more sense in a few paragraphs Photo by Nick Karvounis on Unsplash

And let’s be honest, unless you’ve got the misplaced bravado of a self-help writer who pens an 800-word blog post and thinks “Yep, this can be a best-selling 200-page book, no problem,” you’ve probably been there. I know some of you have because I’ve been there. And while I am an acquired taste, I’m not exactly a rare specimen. (I believe the word some people would use is “basic.”)

Confidence crashes can come from anywhere:

• A project doesn’t land the way you hoped

• A client writes you the dreaded “This isn’t working” email

• The head of the company you’re head of content for gets you to write a plan to incorporate AI into your job, then lays you off and replaces you with AI to save money (ask me how I know)

• A potential client ghosts you after your first meeting

• You hit a wall and can’t see your way to a solution

• A social media post you thought was brilliant lands with a thud

The thing is, freelancing—like skydiving, race-car driving, and diffusing bombs while blindfolded—requires a solid foundation of confidence (along with a healthy tolerance for risk). Without it, everything stalls. You stop marketing. You freeze in meetings, like a cat on the kitchen counter when you walk into the room and he knows he’s not allowed to be there. (Hasn’t evolution taught them they aren’t invisible under fluorescent lights?)

You fumble your words, doubt your ideas, and spiral into a vortex of “Why did I ever think I could do this?” All the negative self-talk you’ve quietly tucked away comes roaring back, thirsty for revenge after being locked up for all that time.

Blame it on our brains

The problem is, our brains are annoyingly efficient at collecting evidence that confirms our worst fears. Make one mistake? Forget one detail? Your brain’s like, “Aha! I knew it! Proof you’re terrible at this. I will never let you forget it.” Meanwhile, all the wins, praise, and progress quietly slip through the cracks. If you’re not careful, you start scanning for reasons you’re failing instead of looking for signs you’re learning, growing, and doing pretty damn well. That’s why it’s so important to interrupt the pattern—to find ways to retrain your thinking so you stop looking for proof you’re not good enough, and start building a case for the opposite.

And sure, there’s no shortage of advice out there for when your confidence tanks. Power pose in the mirror like a superhero (who has the time?). Repeat affirmations until your teeth hurt. “Just be positive!” they say, as if that’s a personality setting you can toggle on. Or my personal favourite: fake it till you make it. (Because nothing builds lasting confidence like pretending you’re fine while your insides are staging a full-blown identity crisis.)

Look, if those tricks work for you, great. But for many of us, they feel as useful as painting a crumbling wall. Sure, it’ll look okay for a minute or two, but the cracks are still underneath, and they’re not going to fix themselves.

So what can you do to help your confidence?

If you’re looking for longer-term solutions to your crisis of confidence, here are some places to start.

1. Create an “I Am Awesome” folder.
This is exactly what it sounds like—a folder (digital or physical) filled with nice things people have said about your work. Glowing emails from clients. Compliments from colleagues. Feedback from an instructor. The random LinkedIn comment that made you feel like a genius for a full 30 seconds (an eternity on social media). If you don’t have one yet, get started now. Go back through your inbox and pull out anything remotely encouraging. Reread the testimonials on your website. It’s not self-indulgent—it’s a tool for truth-telling when your brain is lying to you.

2. Separate your work from your worth.
You are not your invoice total. You are not your last draft. When freelancing wobbles, it’s easy to spiral into “I’m a failure at this so I must be a failure, full stop.” Push back on that. Think of how you show up for people in your life—how you’ve supported a friend, helped a family member, or made someone laugh on a terrible day. Your value isn’t confined to client feedback loops.

3. Make space for your feelings, but don’t let them take over the whole house.
Be nice to yourself. Confidence crashes sting. You’re allowed to feel disappointed, frustrated, or downright heartbroken. You might be tempted to ignore them, but if you try to power through without acknowledging those thoughts, they tend to sneak back in louder and more chaotic than before. Acknowledge them. Process them. Then start gently, and intentionally, rebuilding your confidence. And start looking for the wins, because I know you have them.

4. Reconnect with your why.
Why did you start freelancing in the first place? What kind of life or work did you want to build? When confidence crumbles, it’s easy to forget that you had a vision—something bigger than just finishing this one project or landing that one client. Revisit your goals, your values, and the kind of work that makes you feel proud. Let that anchor you while you find your footing again.

5. Start a win streak—tiny wins count.
Confidence builds through action, not overthinking. Pick something small and doable: send one pitch, follow up with one client, or write one social post. Celebrate taking action, rather than obtaining a specific result. Don’t wait to feel confident before you act. Act first. Confidence tends to show up once it realizes you’re already moving and it has to keep up.

6. Aim for neutral.
If “I’m amazing at this” feels like a leap, don’t force it. Go for neutral. Remind yourself: I’ve done this before. I’ve met deadlines. I’ve solved problems. I’ve delivered results. You don’t need fireworks and self-hype—you need a calm, grounded reminder that you can do what you say you do. Objective evidence beats empty affirmations every time. This is where writing a list of your accomplishments can help. Not a list of how great you are, but an objective list of things you’ve accomplished in life, related and unrelated to work.

7. Take yourself out of it.
Sometimes the kindest way forward is to pretend you’re not the one going through it. What would you say to a friend in the same spot? You wouldn’t tell them they’re terrible or hopeless—you’d remind them of everything they’ve done, everything they bring to the table, and how one rough patch doesn’t define their worth. Try offering that same kindness to yourself. You might be surprised how different (and reasonable) it sounds when you’re saying it to someone else.

You aren’t doomed

Remember: things that don’t go well aren’t signs you’re doomed—they’re opportunities to learn. You’re not going to get it 100% right every time. Not every client will be a great fit. Not every project will run smoothly. That’s not failure. That’s life. No one bats a thousand. You might be an adult, but you’re still learning.

These moments? They’re part of the freelancing experience. And if you treat them as chances to learn, adjust, and gather insight—not as reflections of your worth—you’re far less likely to take them personally. Confidence isn’t about never messing up. It’s about knowing you’ll figure it out when you do.

If your confidence has taken a hit lately, you’re not alone—and you’re not broken. You’re navigating a tough, unpredictable career path with heart, skill, and grit. That matters.

I’d love to hear from you: What’s helped you rebuild your confidence when it’s been shaken? Hit reply or share in the comments—I read every one.

You’ve got this, even if you don’t always feel like it,

Heidi