One Year In: Cracking Open a Whole New Chapter

A year ago this week, I took a leap that had been quietly building for years… and launched Lisa Ratner Matchmaking & Coaching. It’s hard to believe it’s only been 12 months, because in many ways, I feel like I’ve lived a dozen lives in that time. And at the same time, I know I’m just getting started.

Leaving Corporate (and the Heels) Behind

For more than two decades, I was in the corporate world—pitching deals, building partnerships, and walking into high-rise office buildings in a cute suit with a practiced smile. Some days I felt fully present. Other days, I’d look around a boardroom or walk out of a client meeting, get in the elevator, and hear the Talking Heads playing in my head: “How did I get here?”

The truth is, I was good at what I did. I liked parts of it. But deep down, something didn’t fully fit. For years, I always felt like I was wearing someone else’s clothes, or playing the part of “girl in an office”, or “girl at a conference”.

So I decided to take everything I’d learned, about people, connection, relationships, influence, and apply it to the area I’d been quietly fascinated by for years: modern love.

A Winding (and Very Human) Path

As an environmental studies major, I never imagined I'd end up in the corporate world, let alone matchmaker. I thought I'd be in the woods somewhere leading nature programs, not helping singles navigate dating apps and first date nerves. But life has a funny way of connecting dots you didn’t even know were part of the picture. Am I right?

Looking back, it makes sense. I’ve always been a connector. Making friends easily and deeply in every chapter of life—school, camp, family friends, UVM, Santa Barbara, San Francisco, DC. I’m grateful to count many of those people as close friends today. I’ve always been drawn to understanding people and creating community.

But when it came to romantic connections? I encountered more bumps than I can count. There were years of dating where it felt more like job interviews than joyful discovery. I was guarded and didn’t know it. I looked for “resume matches” rather than real compatibility. And I 100% know now that I’m not alone in that.

What I’ve Learned This First Year

This first year of founding a business has been full of aha moments, stumbles, wins, and endless conversations with my “personal board of directors” (you know who you are). Here are some of my biggest takeaways:

1. Everything is a learning opportunity. Every conversation, every first date debrief, every “no” or “not yet, it’s all data. Staying in a mindset of curiosity and growth is what keeps me grounded.

2. Everything takes longer than you want it to, and everyone cautioned me about this. Progress isn’t linear, and neither is building a business. Patience is a muscle I’ve been building up.

3. Focus is a daily challenge. As a business owner, you wear every hat. I’m constantly learning to identify the highest-impact tasks and quiet the noise of all the things I could/should be doing. (this one is HARD)

4. Relationships are everything. I’ve been blown away by the support and wisdom from other matchmakers—both veterans and newcomers. People have shared knowledge, opened doors, and reminded me that this industry is full of heart, wisdom, and camaraderie. Thank you to the generous leaders, industry veterans, and fellow newbies, who’ve lifted me up and let me learn from their experience. (You know who you are, and I’m endlessly grateful.)

Behind the Scenes: The Village That Got Me Here

This milestone wouldn’t mean nearly as much without acknowledging the incredible community behind me.

To my family and friends who’ve cheered me on, referred clients, offered advice, sent encouraging texts, and celebrated every win—thank you. Your belief in me, especially in the early messy days, has meant the world.

To my business coach and accountability partners, my brilliant brand and web designer, and everyone who’s shared their time and guidance, you helped bring this dream to life in ways I couldn’t have done alone.

And to my husband—my #1 fan—thank you for your unwavering support, your belief in my vision, and for gently (okay, sometimes not so gently) pushing me to approach strangers in real life (or doing it for me) who might be perfect for a client. You remind me every day that love is real, and that the best matches can happen when we’re willing to be bold.

Finding My Voice (and My Purpose)

Selling myself and my services hasn’t come easy. After years of selling and managing multimillion-dollar deals on behalf of my employers, it’s a different story when the product is you. 

But here’s what’s different now: I feel alive. I feel aligned. I feel real. I feel like I’m doing exactly what I’m meant to be doing. For the first time in my professional life, I know in my bones this is the right path.

And I’ve realized—starting something new at 50 isn’t a risk. It’s a gift.

What’s Next

As I move into year two, I’m focused on growing my network of singles across the country, supporting coaching clients who are navigating dating post-divorce, and continuing to refine the services I offer, from Match Me to Coach Me to free Date-A-Base membership. I’m also excited to build more partnerships with fellow matchmakers to support clients in a more holistic way.

If you’ve been a client, collaborator, cheerleader, referral partner, or friend—thank you. Truly. Your support has meant everything.

Here’s to year two! Bring on more love, more learning, and more connection!

XO, Lisa

Questions? DM me on IG or FB @lisaratnermatchmaking

Or if you want to chat, I offer free intro calls, no pressure, just real conversation. Click here to schedule a time with me.