From Self-Doubt to Self-Trust: A Young Entrepreneur Journey
Does this sound familiar? You jump into business ownership excited and motivated, believing hard work and passion will be enough to carry you forward. Then reality sets in. Clients don’t appear overnight. Confidence wavers. You start wondering if you moved too fast, if you’re doing the right things, or if you’re truly cut out to do this on your own.
If you’ve ever felt overwhelmed, anxious about promoting yourself, or unsure whether you’re on the right path, you’re not alone. This episode opens up an honest conversation about what it really feels like to be early in entrepreneurship—and how trusting yourself, finding support, and letting go of perfection can help you grow both personally and professionally.
My special guest is Josalyn Bension
Josalyn is an independent esthetician who stepped into business ownership while still in college. Originally from Las Vegas, she moved to Milwaukee for school and unexpectedly found herself taking the entrepreneurial leap sooner than planned. Like many young business owners, Josalyn didn’t start with a large client base or a detailed roadmap—just a strong work ethic and a desire to build something of her own.
She shares openly about the challenges of being new to entrepreneurship, including self-doubt, anxiety around self-promotion, and the pressure of trying to “have it all together” at a young age. Josalyn’s story reflects the reality many early-stage entrepreneurs face and highlights the importance of resilience, patience, and self-trust as a business grows.
Even when confidence comes and goes, commitment keeps you moving forward.
In this episode, you will be able to:
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Discover why self-doubt is a normal part of the early entrepreneurial experience.
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Gain insight into how community and shared spaces can reduce isolation for new business owners.
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Learn how trusting your own pace can support sustainable growth.
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Uncover ways to navigate anxiety around self-promotion and visibility.
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Explore how resilience and adaptability build confidence over time.
Personal Growth Shapes Business Success
Personal growth plays a critical role in business development—especially in the early stages. Entrepreneurs who allow themselves to learn without constant self-judgment often make clearer decisions and experience greater emotional stability.
For Josalyn, being surrounded by other self-employed professionals has helped normalize the ups and downs of entrepreneurship. That shared experience reinforces the idea that growth doesn’t require perfection—only persistence and support.
The resources mentioned in this episode are:
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IMAGE Studios – A collaborative space for independent beauty professionals and entrepreneurs.
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Connect with other self-employed professionals through shared studio and community environments.
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Tune in to the Free Agent Podcast with Meg Schmitz for real stories of self-employment and business ownership.
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Contact Meg Schmitz to schedule a free, no-obligation call and gain insight into self-employment and franchise opportunities.
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Use the form on the Free Agent Podcast page if you’d like to be considered as a guest on the show.
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Click to Take the Leap into the full interview transcript of the Free Agent Podcast, Episode 7.26, with Meg Schmitz and her guest, Josalyn Bension
Free Agent Podcast with Meg Schmitz – Guest: Josalyn Bension – Founder/Owner of EstibyJos
Meg:
Welcome back to Free Agent with Meg Schmitz, your place for inspiring stories of real people who took the leap into business ownership, franchising, and freedom. If you know there’s more to life than a desk job and you’re ready to take control of your destiny, this is your podcast.
Why work for the boss? Be the boss.
Josalyn, thank you for joining me today.
Josalyn:
Yes, thank you.
Meg:
This podcast is called The Free Agent because, in my opinion, we’re all free agents—especially if you’re self-employed. You make your own rules, you build your own business, and it’s not always easy.
For people who are contemplating taking the leap into self-employment, I’d love to hear about your journey. When did the seed get planted that you wanted to be self-employed?
Josalyn:
I’ve been thinking about it for a long time. Even back in high school, I always knew I wanted to be an esthetician. I just didn’t know how it would go or where I would end up.
My dad owned a restaurant in Las Vegas, where I’m from, and I always looked up to that. He loved having his own business. I knew the esthetician industry is hard, and it’s difficult to find supportive environments.
I wanted to be the person who created a big space where people could come together, fresh out of school, learn more services, and build themselves up.
When I moved to Milwaukee and went to esthetician school, I realized how much I loved it. I don’t thrive working under people. I work fast, I like my own pace, and eventually I realized I needed to do my own thing.
Opening my own business happened faster than I expected, but it was worth it. When I first heard about Image Studios, I wasn’t even prepared. It came out of the blue. But once I jumped in, I wouldn’t change a thing.
Meg:
Are there moments of self-doubt where you think, “Oh my God, this is real”?
Josalyn:
Yes, definitely. Since it’s only my fourth month, it gets hard sometimes. I question whether I’m doing the right things. I’m shy, and promoting myself is uncomfortable.
But there are also moments where I know I wouldn’t have chosen any other path. I love this.
Meg:
That feeling never really goes away. But what I love about Image Studios is the collective energy. Everyone here is self-employed. Everyone understands what you’re going through.
Have you made friends here?
Josalyn:
Yes. I’ve met several people. There’s one woman, Char, who passes my room all the time and is just the sweetest person. Some people even hand out my cards to their clients.
It’s nice to have support, especially coming in fresh and not knowing anything about the business. Having people say, “It’s hard, but you can do it,” makes a big difference.
Meg:
One big part of your success going forward is pricing and understanding how many clients you need to hit your goals. Do you have a six- or twelve-month plan?
Josalyn:
Not really. This was such a surprise. I’m 21, still in college, and my priority is finishing school. I used to be very rigid with plans, but I realized life doesn’t work that way.
If things happen, it’s a blessing. If they don’t, I’m not upset. I don’t want to pressure myself and make this harder than it needs to be.
Meg:
You’re more mature than your years.
Josalyn:
A lot of people tell me that. I used to put so much pressure on myself to be put together at 21. But a lot of people don’t even know where they’re going.
Where I’m at now is a blessing. I’ve learned from every trial. When hard things happen and I get through them, I feel accomplished. I know I can handle it next time.
Meg:
Do you think your entrepreneurial spirit comes from your family?
Josalyn:
My dad definitely influenced me. My mom is a huge go-getter too. She’s gone back to school multiple times and never regrets it. My family always taught me to put everything into what I want to do, and if it works, keep going.
Meg:
The future is clearly bright for you. We’re so glad to have you here.
Josalyn:
I’m so glad to be here.
Meg:
What brought you from Las Vegas to Milwaukee?
Josalyn:
I came here for college. I was recruited to play flag football and ended up finding opportunities I wouldn’t have found anywhere else. Milwaukee opened a lot of doors for me.
Meg:
Thank you for sharing your story. It’s very relatable.
Josalyn:
Thank you for having me. I love opportunities like this.
Meg:
Thanks for listening to Free Agent. Every time you share the show, you’re potentially changing someone’s life. To get my free ebook on franchise ownership, visit megschmitz.com.
Free Agent Podcast with Meg Schmitz – Guest: Josalyn Bension – Founder/Owner of EstibyJos
Meg:
Welcome back to Free Agent with Meg Schmitz, your place for inspiring stories of real people who took the leap into business ownership, franchising, and freedom. If you know there’s more to life than a desk job and you’re ready to take control of your destiny, this is your podcast.
Why work for the boss? Be the boss.
Josalyn, thank you for joining me today.
Josalyn:
Yes, thank you.
Meg:
This podcast is called The Free Agent because, in my opinion, we’re all free agents—especially if you’re self-employed. You make your own rules, you build your own business, and it’s not always easy.
For people who are contemplating taking the leap into self-employment, I’d love to hear about your journey. When did the seed get planted that you wanted to be self-employed?
Josalyn:
I’ve been thinking about it for a long time. Even back in high school, I always knew I wanted to be an esthetician. I just didn’t know how it would go or where I would end up.
My dad owned a restaurant in Las Vegas, where I’m from, and I always looked up to that. He loved having his own business. I knew the esthetician industry is hard, and it’s difficult to find supportive environments.
I wanted to be the person who created a big space where people could come together, fresh out of school, learn more services, and build themselves up.
When I moved to Milwaukee and went to esthetician school, I realized how much I loved it. I don’t thrive working under people. I work fast, I like my own pace, and eventually I realized I needed to do my own thing.
Opening my own business happened faster than I expected, but it was worth it. When I first heard about Image Studios, I wasn’t even prepared. It came out of the blue. But once I jumped in, I wouldn’t change a thing.
Meg:
Are there moments of self-doubt where you think, “Oh my God, this is real”?
Josalyn:
Yes, definitely. Since it’s only my fourth month, it gets hard sometimes. I question whether I’m doing the right things. I’m shy, and promoting myself is uncomfortable.
But there are also moments where I know I wouldn’t have chosen any other path. I love this.
Meg:
That feeling never really goes away. But what I love about Image Studios is the collective energy. Everyone here is self-employed. Everyone understands what you’re going through.
Have you made friends here?
Josalyn:
Yes. I’ve met several people. There’s one woman, Char, who passes my room all the time and is just the sweetest person. Some people even hand out my cards to their clients.
It’s nice to have support, especially coming in fresh and not knowing anything about the business. Having people say, “It’s hard, but you can do it,” makes a big difference.
Meg:
One big part of your success going forward is pricing and understanding how many clients you need to hit your goals. Do you have a six- or twelve-month plan?
Josalyn:
Not really. This was such a surprise. I’m 21, still in college, and my priority is finishing school. I used to be very rigid with plans, but I realized life doesn’t work that way.
If things happen, it’s a blessing. If they don’t, I’m not upset. I don’t want to pressure myself and make this harder than it needs to be.
Meg:
You’re more mature than your years.
Josalyn:
A lot of people tell me that. I used to put so much pressure on myself to be put together at 21. But a lot of people don’t even know where they’re going.
Where I’m at now is a blessing. I’ve learned from every trial. When hard things happen and I get through them, I feel accomplished. I know I can handle it next time.
Meg:
Do you think your entrepreneurial spirit comes from your family?
Josalyn:
My dad definitely influenced me. My mom is a huge go-getter too. She’s gone back to school multiple times and never regrets it. My family always taught me to put everything into what I want to do, and if it works, keep going.
Meg:
The future is clearly bright for you. We’re so glad to have you here.
Josalyn:
I’m so glad to be here.
Meg:
What brought you from Las Vegas to Milwaukee?
Josalyn:
I came here for college. I was recruited to play flag football and ended up finding opportunities I wouldn’t have found anywhere else. Milwaukee opened a lot of doors for me.
Meg:
Thank you for sharing your story. It’s very relatable.
Josalyn:
Thank you for having me. I love opportunities like this.
Meg:
Thanks for listening to Free Agent. Every time you share the show, you’re potentially changing someone’s life. To get my free ebook on franchise ownership, visit megschmitz.com.
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