From Corporate Setback to Creative Freedom: How I Built Dearest

By Kathy Ecke

After more than 30 years in corporate America, I thought I had seen it all — the highs, the pivots, the politics, and the pride that comes from building teams and leading growth. My most recent role was as a Senior Vice President, overseeing operations, merchandising, and marketing for a multimillion-dollar organization. I loved the work, the people, and the momentum we were creating.

Then, at 55, I was suddenly fired — without cause — after just eight months on the job. My first thought was my résumé. How would I, at my age, find another position with such a short tenure? I was told the company was being acquired and would be bringing in its own team. That wasn’t the truth — and that company is now navigating Chapter 11.

It was a moment that stopped me in my tracks. After decades of defining myself by my professional success, I found myself asking, what now? Instead of rushing into another corporate position, I made the unusual decision to pause — really pause — and permit myself to explore what truly inspired me.

At first, that quiet space was uncomfortable and lonely. I was used to being in motion, leading meetings, hitting deadlines, and solving problems. But as the noise of “what’s next” began to fade, a spark of something new began to form.

That spark became Dearest.

I founded Dearest with one simple but powerful idea: to help people capture the real essence of life’s celebrations — the laughter, emotion, and shared joy — through community. The platform allows friends and family to easily upload and share photos and videos from events through a single link. What makes Dearest unique is that we don’t stop at digital. We curate those memories into beautifully designed, photographer-quality keepsake books — tangible tributes to the moments that matter most.

I wasn’t a tech founder by training, and I didn’t have a big team or venture capital funding. In fact, I completely bootstrapped Dearest with my savings. But I had a vision, a supportive circle of friends and family, and an incredible contractor I found through Upwork who believed in the mission (thank you, Buri!). Together, we built Dearest from scratch — piece by piece, click by click — into a brand that feels both deeply personal and refreshingly modern.

There’s something magical about creating a company grounded in connection. I’ve watched couples, families, and friends use Dearest to relive their most meaningful milestones — weddings, milestone birthdays, vacations, and reunions. One of my favorite stories came from a daughter who created a “Tribute Album” for her father’s 80th birthday, gathering decades of photos and heartfelt notes from loved ones. It was thoughtful, emotional, and timeless — exactly what I had envisioned when I began. I remembered creating a similar album for a milestone birthday years ago and how profoundly it touched the recipient.

Starting over later in life taught me lessons no corporate handbook ever could. It reminded me that reinvention isn’t just possible — it’s powerful. Sometimes, losing what feels like your foundation is really the moment you find your freedom.

For anyone facing an unexpected career change or life shift, my advice is simple: take the pause. Step back before you step forward. That space will reveal what’s truly next for you. Because when you build something that aligns with your heart, success stops being about titles — it becomes about meaning.

Today, Dearest continues to grow, connecting people through the shared beauty of their stories. For me, that’s the greatest win of all. I love what I do — and I’m honored to play a small part in preserving people’s most meaningful memories.

Connect With Kathy

www.dearestevents.com

Instagram: dearest_events

LinkedIn: Kathy Ecke