We recently connected with Ashley Lester and have shared our conversation below.

Ashley, thanks for joining us, excited to have you contributing your stories and insights. If you could go back in time do you wish you had started your business sooner or later

If I could go back in time, I don’t think I’d change the timing of when I started True & Timeless.

I’ve always been a natural curator. Ideas, aesthetics, and experiences have a way of coming alive in my head long before they exist in real life. Creativity is just how I move through the world. Over the years, that’s led me to try a lot of different things. I’d dive in wholeheartedly, build something beautiful, and then realize my passion didn’t truly live there. At the time, that pattern felt like failure. I carried shame for not “sticking it out” or finishing what I started.

But now I see it differently. I was refining my purpose. Each venture taught me something about who I am and how I’m wired. Those “false starts” weren’t failures; they were foundations.

True & Timeless was meant to be a slow build; something I nurtured quietly behind the scenes while balancing my corporate career and motherhood. The plan was to take a few clients, build a portfolio, and announce it when everything looked polished. But life had other plans. When I made the decision to step away from my corporate role to be a stay-at-home mom to my three children, one of whom has special needs, everything shifted. Suddenly, waiting for the perfect moment didn’t make sense anymore. So I decided to go all in.

There’s no such thing as perfect timing, only purpose and obedience. Launching my business in this season of life has stretched me, but it’s also been incredibly freeing. I wouldn’t change it. Every lesson, every detour, and every tear has shaped the way I lead and serve my clients today.

In addition to my wedding planning business, I also founded a nonprofit organization called SIP Community — a women’s ministry designed to help women discover their God-given purpose through Jesus. It’s another extension of the same heartbeat: helping people uncover the beauty, meaning, and legacy that already exist within their stories.

Ashley, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

I’m an Ohio girl with a deep love for storytelling, design, and all things beautiful.

My journey into wedding planning wasn’t a straight line; it was more like a collage of creativity, experiences, and lessons that all led me here. I’ve always been drawn to planning, organizing, and creating meaningful, aesthetically intentional moments. But it wasn’t until my own wedding day, when I faced a few unexpected hiccups, that I realized how deeply I wanted to help others experience something different – a day that truly feels like them.

After leaving my corporate role in September, I knew there was no better time than now to go all in. That decision gave birth to True & Timeless, a full-service wedding planning company built around the idea of legacy and helping couples craft a moment that will be felt for a lifetime.

I specialize in elopements, intimate weddings, and mid-scale celebrations that maintain a sense of intimacy and authenticity, no matter the size. My clients often come to me because they’re struggling to find individuality in a world full of trends. They want their day to feel personal, to reflect their story, not a Pinterest board.

What sets True & Timeless apart is my focus on what I call “wedding branding.” Just like a brand evokes emotion through its colors, tone, and aesthetic – I help couples develop a signature look and feel that represents their relationship at its core. When guests experience their wedding, I want them to know the couple’s essence without ever seeing a name or logo. It’s beyond trends. It’s legacy work.

I’m most proud of simply starting. For years, I dreamed and hesitated, but stepping into this season of life with courage has been my biggest accomplishment. Knowing I’ve found a passion that won’t fade. One that I can pour my creativity and heart into every single day, is incredibly fulfilling.

At the end of the day, my clients’ vision is the blueprint. I’m just here to elevate it, refine it, and bring it to life in a way that’s effortlessly timeless — a reflection of their story that will be remembered long after the last dance.

Have you ever had to pivot?

My biggest pivot came when I transitioned from corporate life to becoming a full-time stay-at-home mom, and unexpectedly, a full-time business owner.

I spent years in new development property management, overseeing everything from operations and marketing to client relations, policy creation, and community outreach. It was fast-paced, structured, and demanding, but it taught me how to manage large-scale projects, communicate with diverse clients, and bring big visions to life with precision.

When I made the decision to step away from my career to focus on my family, it felt like an ending at first. But it quickly became a new beginning. I realized that all those skills I had refined in property management translated beautifully into wedding planning: organization, creative direction, communication, and experience design.

That pivot forced me to reimagine success. It reminded me that purpose doesn’t disappear when life shifts; sometimes it just changes form.

Any stories or insights that might help us understand how you’ve built such a strong reputation?

I believe my reputation has been built through authenticity, excellence, and the way I create experiences that truly connect with people. Before launching True & Timeless, I poured a lot of my energy into my women’s ministry, SIP Community, which exists to help women discover their purpose through Jesus.

One of the most impactful things we do is host events that bring women together for community, worship, and breakthrough. In March 2026, we’ll be hosting our fourth annual women’s brunch, and each year it continues to grow in both beauty and impact.

These gatherings aren’t just aesthetically beautiful; they’re intentional. They’re designed to fill women’s cups, to help them leave lighter, encouraged, and seen. I think the way we’ve presented those events with professionalism, heartfelt purpose, and a refined sense of design has given people a glimpse of what they can expect from True & Timeless as well.

That same standard of excellence, attention to detail, and care for the overall experience carries through everything I do, whether it’s a women’s brunch or a wedding day. It’s not just about making things look beautiful; it’s about making them feel meaningful.

Contact Info:

• Website: https://www.trueandtimelessvow.com
• Instagram: TrueandTimelessVow