The response to my post two weeks ago, Why I Left a Well-Paying Corporate Job Before Making a Penny From Content Creation, inspired many of you to either reach out to me personally or leave a comment about how you, too, are dreaming of moving away from what you’re doing now and jumping into something that feels more aligned with your passions and lifestyle. Thank you for sharing all of your stories with me and being vulnerable about what’s holding you back. After looking through dozens of messages it became clear to me that we should talk about confidence and fear of failure or judgment.
Doubt Kills More Dreams Than Failure Ever Will
There are two quotes I come back to whenever I find myself wavering:
“Doubt kills more dreams than failure ever will.”
“We suffer more in our imagination than in our reality.”
That first one ran through my head on a loop when I took the leap into content creation. It still plays when I launch something new—an e-book, a new platform, or bigger projects (more on those soon!). Importantly, there’s a difference between believing in yourself enough to move forward and having complete confidence in your business idea. The truth is that very few people feel completely confident before they start.
Whether you subscribe to “fake it till you make it” or believe in keeping small promises to yourself as a path to confidence, both strategies have one thing in common: action. Confidence is built through doing.
And just to prove that it wasn’t all smooth sailing for me from day one, here is one of the first recipe reels I ever shared. In my first year of posting consistently, I gained only 700 followers. My “pay” came in the form of free protein powder and peanut butter. I even pitched brands offering to create content for free—and still got turned down!
I share this not to discourage you, but to remind you that confidence isn’t built from immediate success. It’s built by showing up, again and again, even when no one is clapping yet.
Find the Fun in the Early Stages
One thing that has always helped me push through moments of doubt is focusing on the parts of a new venture that light me up. When I start spiraling into thoughts of this will never work, I take a step back and redirect my energy into the fun parts of the process. For me, that’s branding and creative—imagining how my community will experience something for the first time, dreaming up names, colors, and visuals.
Once I’m reinvigorated by the vision, I have the energy to power through the less glamorous parts—operational plans, financials, logistics. Confidence comes when excitement outweighs fear.
The Myth of Overnight Success
At first glance, it can seem like successful entrepreneurs were always successful. They built a buzzy brand, and suddenly they’re gracing magazine covers. But success stories rarely unfold that way.
Amazon took nine years to turn a profit, and Jeff Bezos made multiple bets that nearly ruined the company. Phil Knight didn’t set out to build Nike into the giant it is today—he just wanted to create a high-performing running shoe. Slack started as a video game company before pivoting, and Samsung was originally a grocery store. These founders didn’t have everything figured out from the beginning. They started, they listened to market feedback, and they adapted.
And that’s the key: If they hadn’t taken that first leap, their businesses wouldn’t exist today.
If you’re looking for more stories like this, I highly recommend listening to Guy Raz’s How I Built This, or Steven Bartlett’s The Diary of a CEO. Seeing the messy, uncertain beginnings of now-iconic brands can be a powerful reminder that no one starts with all the answers.
Your “Unfair Advantage”
A few of you mentioned wanting to go into content creation but feeling like the space is already oversaturated. How can a new creator possibly stand out?
This is where I encourage you to lean into your “unfair advantage.” For me, that was struggling with acne for most of my life and learning how to nourish myself in a way that wouldn’t inflame my skin. Years of research and trial and error led me to develop the cooking style I share today. That personal experience—the deep knowledge that only I could bring—became my differentiator.
So what’s your unfair advantage? Maybe it’s a unique life experience, a skill set, or even just a perspective that others haven’t heard before. Lean into it!
Perfection Is the Enemy of Progress
One of my favorite mantras: Perfection is the enemy of progress.
There is never going to be a perfect time to launch. No one is going to wake up one morning and beg you to start your dream business. There’s no perfect name, logo, or messaging to wait for. There isn’t even a perfect product.
The only way to build confidence and clarity is by starting.
And remember—some of the biggest, most successful companies in the world completely changed direction after they launched. They could only pivot because they were already in motion. The same has been true for me. After every e-book launch, we do a postmortem and adjust for the next one. Most recently, I pivoted my entire Substack strategy based on feedback and a bigger vision.
Surround Yourself With the Right People
This might be the most important piece of advice I can give: Build a community of people who believe in you.
Find fellow dreamers—the people who see possibility and potential. The ones who encourage you to keep going when quitting feels easier. Surrounding yourself with the right people will help you stay the course, even when doubt creeps in.
There is no perfect roadmap for starting a brand new business. But confidence isn’t something you wait for, it’s something you build by moving forward, one step at a time.
If you have any advice for aspiring entrepreneurs, please share it in the comments. I’d love to hear what has helped you take the leap!
Olivia!! You sweet angel. I started a budgeting/wellness IG back in July and just hit 500 followers last week. I am so focused on my vision to help people and trust themselves enough to dream bigger for themselves. Your story is so inspiring and gives me hope! I think of you constantly when I feel defeated or that I still haven't had a video go viral yet. I am working with a social media strategist now and that is already helping with my commitment and confidence. Thank you!!
I love this!!! So proud and grateful to have you and the community you’ve created!❤️