We’re excited to introduce you to the always interesting and insightful Heidi Weinberg. We hope you’ll enjoy our conversation with Heidi below.
Hi Heidi, we’re so appreciative of you taking the time to share your nuggets of wisdom with our community. One of the topics we think is most important for folks looking to level up their lives is building up their self-confidence and self-esteem. Can you share how you developed your confidence?
I like to think of confidence and self-esteem as muscles, not traits you’re born with. The more you work them, the stronger they get. And like any workout, it’s uncomfortable, sometimes painful, and occasionally full of awkward missteps. But that’s the point.
I’ve intentionally put myself in situations that stretched me. Pitching clients I was terrified to reach out to, raising my rates even when I second-guessed my value, teaching live webinars before I felt “ready.” Spoiler: I wasn’t ready. But I did it anyway. Each time, that confidence muscle grew just a little stronger.
But it wasn’t always like that.
Earlier in my life, I didn’t have this “muscle” metaphor. I just had a few key people in my corner who saw something in me — my parents, my now-husband. They reminded me, often, that I was capable of anything. That belief plants seeds that grow over time into your own voice.
I also believe deeply in the idea that “you are the average of the five people you spend the most time with.” So I’ve made it a priority to surround myself with people who challenge me, inspire me, and raise the bar. Whether it’s my FAST students who blow me away with their tenacity or peers who are doing bold, scary, meaningful things… they make me want to level up every day.
So no, confidence didn’t show up one day and say, “I’m here!” It’s been a lifelong practice. (And yes, I still get nervous, doubt myself, and wonder if I have any idea what I’m doing!)
Appreciate the insights and wisdom. Before we dig deeper and ask you about the skills that matter and more, maybe you can tell our readers about yourself?
I run a digital education platform, podcast, and coaching community for fashion designers who want to break free from toxic jobs and build steady income as freelancers (doing what they love).
I didn’t go to fashion school. I didn’t have connections. I didn’t live in a fashion hub. But I figured it out the hard way. Now I teach others how to shortcut that painful, lonely path. Through my signature program, FAST (Freelance Accelerator: From Surviving to Thriving), I’ve helped over 1,000 designers worldwide build sustainable freelance businesses in fashion. Many of them are now earning 2x, 5x, even 10x what they were before. I’m all about real strategies, no fluff, and teaching the stuff fashion school never did.
The most exciting part is watching people come alive again. Seeing someone go from underpaid and undervalued and on the edge of burnout to landing clients who actually respect their time and talent… that transformation never gets old. The designers I work with are smart, scrappy, and so damn creative. They just need the tools and confidence to go from “I hope this works” to “I’ve got this.”
Lately, I’ve been obsessed with exploring how AI can support freelance fashion designers. Not replace them, but empower them. Whether it’s streamlining pitches, speeding up client work, or helping with moodboards and trend research, AI has huge potential to reduce the grunt work so creatives can focus on the magic. I’ve been testing tools, teaching strategies, and helping designers adopt AI without losing the human touch that makes their work so special. It’s a space that’s changing fast, and I want my community to be ahead of the curve, not left behind.
What’s next? I’m continuing to evolve my content, coaching, and tools to support the modern freelance designer. I’m working on a few AI resources, expanding our live coaching inside FAST, and building even more systems to help designers work less, earn more, and feel free in their careers.
Because that’s really the point. Freedom. Flexibility. And making fashion work for you, not the other way around.
Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?
Looking back, the three things that had the biggest impact on my journey were perseverance, learning to be okay with discomfort, and asking for help.
Perseverance is everything. So much of my journey was full of “this isn’t working” moments. I launched things that flopped. I pitched clients and got ignored. I questioned myself constantly. But I kept going. I always say that freelancing in fashion, or doing anything creative and entrepreneurial, is a long game. You don’t have to be the smartest or most talented. You just have to keep showing up. (That’s something I talk about a lot on my podcast, Fashion Designers Get Paid. We share real stories from designers who stuck it out, stumbled, and still made it.)
Discomfort was a tough one for me, but it’s where all the growth happened. Pitching clients, raising my prices, showing up on video, saying no to bad-fit projects. None of it came naturally. But every time I did something that scared the crap out of me, I came out stronger. One of the most terrifying (and transformative) moments? Getting on stage for a live hot seat with Ramit Sethi in front of 500 people. My voice was shaking, my palms were sweaty, but I did it. I walked away with a breakthrough that shifted how I think about money, mindset, and leadership. If you want to grow, you’ve got to get used to feeling uncomfortable. That’s where the magic happens.
Asking for help was probably the biggest unlock of all. I used to think I had to figure everything out on my own. Spoiler: I didn’t, and neither do you. Surround yourself with people who get it. Ask questions, share your struggles, and find a community. This is a huge part of why I built the FAST program, and why I started my podcast too. I wanted freelancers to hear that they’re not the only ones navigating tricky clients, pricing stress, or burnout. We all go through it.
If you’re early in your journey, here’s what I’d say. Be kind to yourself. Be patient. And don’t wait until you feel “ready,” because you might be waiting forever. Take imperfect action. Get uncomfortable. Ask for help. And keep going.
That’s the real secret.
What do you do when you feel overwhelmed? Any advice or strategies?
When I feel overwhelmed, the first thing I try to do is pause. I step away from the screen, take a breath, and give myself space. Even five minutes can make a huge difference. Whether I’m deep in writing a new lesson for FAST, stuck in client pitch feedback, or testing something new in AI, a short break helps reset my brain.
Then I break it down. Whatever feels big and scary — a huge project, a new strategy, even just updating a portfolio — I chop into smaller pieces so I can focus on just the next step instead of the whole mountain.
I also ask for help. Whether it’s my team, someone in my freelance community, or a trusted mentor, I’ve learned (sometimes the hard way) that I don’t have to figure everything out alone. Especially in fashion, where so many of us are used to doing all the things, it’s a game-changer to simply say, “I’m stuck.”
I remind myself: You’ve done hard things before. I’ve navigated tight deadlines, tricky clients, flopped launches, and more. I’ve always come out stronger on the other side. The pain or stress in the moment feels huge, but it does get better. The older I get, the more I see how true that is.
And honestly? No one has it all figured out. I hear this all the time from guests on my podcast, Fashion Designers Get Paid. These are incredibly talented, successful creatives. And they still deal with overwhelm, self-doubt, imposter syndrome, all of it. It’s something I hear firsthand from pretty much everyone I talk to. The messy middle is normal. You’re not behind. You’re just in the process.
Contact Info:
- Website: https://successfulfashiondesigner.com/
- Instagram: https://www.instagram.com/sewheidi
- Linkedin: https://www.linkedin.com/in/sew-heidi/
- Youtube: https://www.youtube.com/@SuccessfulFashionDesigner-sfd
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