From Dating Apps to Dating Advice for Women With Dating Coach Lily Womble

JF: At FinkDev, we define an Authentic Career as one that taps into your strengths, values, and interests. How does running Date Brazen create an authentic career path for you?

Lily Womble: Date Brazen has put me in the driver's seat of my career. I've always been very entrepreneurial-- from starting a recycling club in first grade to creating a local nonprofit in high school, to building Date Brazen-- strategizing to create solutions to deep-seated problems has always gotten me out of bed in the morning.  

Before starting my company, I was one of the top matchmakers at the largest firm in the country. While working there, I saw a need in the dating landscape for a more holistic, long-term approach to women's dating needs. I started Date Brazen after matching hundreds of individuals and realizing that with coaching, women could match themselves better than any professional ever could. 

Now, my mission is to transform the dating industry by helping women build fulfilling, joyful, successful dating lives on their own terms. Being in this leadership position is incredible, complicated, rewarding, scary, and very exciting-- all the things. 

JF: Tell us more about your company, Date Brazen, and your ideal clients.

LW: I work with single women around the world who are ready to transform their dating lives from a soul-suck to an act of self-care. 

Through my coaching experience, The Brazen Breakthrough, and live events around the country, I help women build badass dating lives that lead to amazing relationships. 

I also regularly train therapists on how to serve their dating clients more effectively. The work is multifaceted and so rewarding.

"My mission is to transform the dating industry by helping women build fulfilling, joyful, successful dating lives on their own terms."

JF: What do you see is the biggest obstacle getting in the way for your clients?

LW: One of the biggest obstacles for my clients is cognitive overload. Dating is overwhelming and discouraging for a very good reason: our brains literally can't handle all the options. I see most single people interpreting ghosting and overwhelm as just "part of the dating game." But that's not necessarily the truth.

The fix? A major mindset shift. I get to coach my clients from the mindset of: "It's a numbers game, I need to swipe and date as much as possible," to the more empowering, "What is meant for me will not pass me by. I'm for the few, not the many."

More tactically, I suggest clients swipe as little as possible. Try putting the app down before you get overwhelmed. You're not for the many, you're for the few. Try swiping like it.

JF: We both believe that values are a critical component of navigating your life in career and in love. How do you help your clients get clear on their values?

LW: The first step is reflecting on past relationships and how they impacted you. Exploring how you did and did not feel supported in those relationships is a great way to get in touch with your personal values as they relate to your dating life. 

I also love Brene Brown's exercise in Dare to Lead, which I also use in my coaching practice to help clients get in touch with themselves and their core values.

"I wish everyone knew that what is meant for them will not pass them by."

JF: What's one thing you wish everyone knew about finding a fulfilling relationship?

LW: I wish everyone knew that what is meant for them will not pass them by. 

So many of my clients are anxious that it's "too late" to find a good relationship and are frustrated by dating advice from family, friends, coworkers, etc. That advice usually looks like a prescription of well-meaning "solutions" based on that person's direct experience. 

The truth is how you will find your partner will look different than how anyone else found theirs. I encourage my clients to take some of the dating pressure off and make your own rules of engagement that truly feel aligned with your preferences and values. 

JF: How can we follow you and get connected to your dating advice?

LW: If you're interested in becoming irresistible to the right sort of people online, you can get my free Irresistible Dating Profile Guide at datebrazen.com!

You can also follow my journey on Instagram @datebrazen.

JF: It's super exciting that you've hit your stride in your business and are continually growing your community! Who would you most love to connect with, in the upcoming year?

LW: Love this question! I'd love to connect with single women who desire a more fulfilling, successful (and fun) dating life- those ladies are my people. 

I'd also like to connect with more therapists who need training on better serving their single and dating clientele.

I also love connecting with fellow female entrepreneurs- there's a lot of magic in the room when we get together.

Contributor Bio
CEO & Founder of Date Brazen | Dating coach & Speaker | I help people build fulfilling, joyful & successful dating lives

Connect with Lily
@datebrazen, or datebrazen.com


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1) Join Our Job Search Accelerator Membership. Our structured step-by-step process to clarify, attract, and land your ideal opportunities.

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