We were lucky to catch up with Jalyn Powell recently and have shared our conversation below.

Jalyn, appreciate you joining us today. Are you happier as a business owner? Do you sometimes think about what it would be like to just have a regular job?

Being a business owner is not for the faint of heart especially in those early years when you’re the HR department, the marketing team, the program manager, and everything in between. I am deeply fulfilled as a business owner, but happiness ebbs and flows. When things get hard, I remind myself of my why.

There are always moments when I think, “Maybe I should just get a regular job,” especially during tough seasons. I’ve even tried it and it never worked out. I realized God had me in this space for a reason. That understanding taught me to stop fighting the path and instead get more intentional and creative with growing my business and serving in every season.

I remember one night, exhausted from overlapping deadlines, realizing that people often see only the polished end product not the countless hours behind it. Entrepreneurship is unpredictable: there are seasons of uncertainty, questioning where the next check will come from, and seasons of abundance, when you can celebrate wins without even checking the price tag.

A few years ago, I bought my first home with income from my business, a huge milestone that came with new financial realities. A major contract unexpectedly ended due to shifting grant funds and political changes. I went from celebrating homeownership to feeling “house poor.” But as the business picked up again, I learned that entrepreneurship is a constant cycle of risk, reward, and resilience.

Through it all, I’ve learned that fulfillment doesn’t always mean comfort. I may not always feel happy, but I am purpose-driven and that knowing keeps me going.

Jalyn, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

I’m Jalyn Powell, founder and CEO of OUTLOUD LLC, a consulting agency, and OUTLOUD DE, a youth-centered nonprofit. My journey began with OUTLOUD LLC, which provides strategic support to youth and community-serving organizations. We help these organizations articulate their programs and impact through strategic messaging, grant writing and development support, and grassroots engagement strategies. Our work ensures that organizations can show up authentically, secure funding, and design initiatives that are equitable, sustainable, and community-centered, including programming that supports mental health, wellness, and holistic youth development.

OUTLOUD DE is our youth-centered nonprofit, where we create spaces for young people to lead, heal, and thrive through our two pillars: mental health and wellness and justice. Through these pillars, we equip youth to use their voices, advocate for change, and design projects that strengthen their schools and communities from the inside out.

What sets us apart is our commitment to showing up where the need is greatest. We operate on the principle that nothing about us should happen without us, youth and community voices are central to every strategy, program, and policy. We connect service with strategy, helping organizations strengthen their impact while uplifting the communities they serve.

Both arms of OUTLOUD have grown from a single idea into a movement. From supporting youth through wellness and justice work to helping organizations secure resources and build sustainable programs, our mission centers empowerment, healing, and equity. For organizations looking to maximize their impact, I want them to know that OUTLOUD is more than a consulting firm or nonprofit, it’s a movement that builds power, OUTLOUD. We equip youth, communities, and the organizations that serve them to lead, heal, and transform from the inside out, all with purpose, creativity, and community at the center.

Let’s talk about resilience next – do you have a story you can share with us?

I officially started my business in 2020, with the encouragement and support of my father. Even in uncertain times, he was my biggest cheerleader, always reminding me, “Did you talk to God about it? If you and God are with it, I don’t have to ask any questions.” His confidence in me gave me the courage to take risks I might not have taken on my own.

A year later, our roles shifted dramatically. I went from being supported by him to becoming his power of attorney as he fought for his life after being diagnosed with COVID. He passed away, and I lost not only my father but also my unofficial business partner, confidant, and cheerleader, the person I could share my wildest ideas with and know he would be all in.

That experience tested me in every way, emotionally, mentally, spiritually and professionally. I had to navigate grief while continuing to grow my business, make critical decisions on my own, and honor the lessons he had instilled in me. It was a profound exercise in resilience: I learned to trust myself, to lean on my faith, and to keep building even when it felt impossible. Today, I carry his words and belief in me into every decision I make for my business.

Can you talk to us about how your side-hustle turned into something more.

My business actually started as a side hustle. I formed an LLC in 2019 with the goal of getting paid for public speaking, but that first year I didn’t generate any revenue. Instead, I focused on building credibility, doing work for free, and showing up for the community.

In 2020, an opportunity came up that required a business license, and that’s when my focus shifted toward youth services. I took a leap of faith, left my full-time job at 23, and went full time. My first official contract was with a state agency, along with smaller contracts, and over the next few years, business grew steadily, I hit my first six figures within three years.

At 26, needing insurance, I returned to a job for the benefits, so my business became my side hustle again. Three years later, I felt a strong pull to go back full time. This leap of faith didn’t come with guaranteed contracts, but within three months, opportunities began to flow simply because we had consistently shown up for the community. My business is the epitome of “never let a crisis go to waste” by serving genuinely in times of need, opportunities found us in the middle of our service.

Along the way, our work in the community has been recognized by the Southern Poverty Law Center in 2022 and by Delaware Online in 2023 as one of Delaware’s Most Influential People. Those milestones reflect the power of consistent service, faith, and showing up even when it feels uncertain.

Contact Info:

• Website: https://www.outloudde.com
• Instagram: https://www.instagram.com/outloud_de/?hl=en
• Facebook: https://www.facebook.com/OutLoudDE/
• Linkedin: https://www.linkedin.com/in/jalyn-powell-ma-17b7b0167/