This season of The Defectors is sponsored by The Defector Academy Suite, a series of coaching activities designed to help you discern your path. If you’re even thinking about a life beyond campus, explore the trio of options available to you to work through these thoughts and ideas with me as your co-pilot! Don’t want in, but still love the series?Consider donating to keep it going!

wooden post fence, surrounded by flowering trees, with "The Defectors: Women at Work" overlaid in white text

Today’s Defector Woman at Work is Neely Steinberg. She is a dating coach, personal image consultant, and former student life professional. Neely and I met when she served on a panel about dating in the digital age. I was fascinated by the path that brought her to that role, so it was a pleasure to hear more from her for this series. I love Neely’s story for an incredibly unique example of where skills and competencies gained from a life in higher education and student affairs, can take you.

This interview has been edited and condensed for clarity.

Neely, what drew you to the work of student affairs and higher education in the first place?

I loved the idea of being part of a campus and working with young minds. While I was getting a Masters in Counseling at BU, I was assistant coaching the men’s and women’s tennis teams at Babson College. I fell in love with the atmosphere there and really wanted to find something full-time when I finished up my degree. A position opened up in the program management/advising office and I jumped at the chance.

That’s been one of the most common paths that people take to doing campus-based work. So given that scope of enjoyment, how did you start exploring the path you’re on now?

While I was at Babson, I was doing a lot of things on the side. I was freelance writing about dating and relationships, a subject that I’ve long been fascinated by in my own life and as an observer of other people’s lives. Also at this time, I created and hosted two internet radio shows and an internet TV show on dating and relationships. I had my main job at Babson, and my side hustles!

I’ve always loved the idea of coaching and motivating people — it fuels me. And at one point I thought maybe I’d become a therapist. While I was at Babson, I saw all of these amazing young people attempting to start their own businesses and become leaders. I was attending lectures and workshops and panels on starting a business and becoming a leader. And it was at Babson that I eventually conceived the idea for my own business: A dating coaching company that would teach women how to be the CEO and enTREPreneur of their own love lives. I would use the principles of entrepreneurship and being a CEO to motivate women to create change in their love lives. I wrote a book about it: Skin In the Game: Unleashing Your Inner Entrepreneur to Find Love.

After 13 years at Babson and running my coaching business on the side for the last 3 years of my time there, I made the decision to leave (which also coincided with me having my first child).

I love that story! Especially how much you clearly took with you from not just the work you were doing, but the environment in which you were doing it. Even though you’d been doing a version of the work for a while, what challenges did you face in making the transition?

Not having a steady paycheck. Not having intellectual stimulation from adults on a daily basis. Feeling isolated.

And on the opposite side, what rewards or fulfillment have come to you since leaving?

I’ve been able to work with a lot more people and make a positive impact on so many women’s lives. I love the idea that this business is all mine. That I created it, have sustained it for 8 years now, and that it can be around for as long as I put in the effort and have the passion for it. I don’t have to answer to anyone (well, except for my clients). I don’t have to work towards building somebody else’s passion or ideas.

You’ve talked about this a bit already, but how has the time, energy, and experience you gained in your on-campus work, fueled you in your latest pursuit?

Again, the concepts and ideas I learned at Babson and the passion of the students fueled my own desire to create my own business. Also, my time working with MBA students gave me the opportunity to hone my advising and listening skills. Additionally, Babson offered so many incredible professional development opportunities, such as public speaking, communication, etc., that I do believe I gained increased confidence and the skills to do more public speaking in my business.

All great points, especially the bit about the confidence. It’s so necessary when making a leap, and I’m happy to know that your time at Babson afforded it to you. In terms of things that your experiences didn’t afford you, what do you wish you had known prior to making the jump away from campus-based work?

How lonely it can be when you’re working for yourself. How you really have to be your own motivator, day-in, day-out. I can’t rely on anyone to pick up the slack. It’s on me. That can be great (I can be a bit of a control freak), but also burdensome and exhausting.

Man, I feel that in so many ways. I’m similarly often working on my own, and I feel that exhaustion.
Given everything we’ve talked about, what you’ve done since leaving your higher ed career, I have to ask: would you ever consider going back? What would it take

Possibly. I would have to be really burned out from the dating/relationship/love coaching sphere and burned out from running my own business for me to go back. But I do think there are very few work environments I would consider going back to at this point, and higher ed (or some sort of campus work) would be one of them. 🙂

22770541_10154845461577116_7983986065627665527_o - Neely Steinberg

If you’d like to learn more about Neely and the work she’s doing now, or even benefit from her experience as a client, you can find her at, and on Twitter or Instagram.

Neely Steinberg is a dating coach & style/image consultant and founder of her multi-service dating coaching company The Love TREP ( She teaches and coaches smart, savvy, single, professional women (from ALL career backgrounds), ages 25-55, how to become the CEO, founder, and enTREPreneur of their dating and love lives, so that they are creating, shaping, and building their love story instead of waiting passively to be rescued by some elusive Prince Charming. Her ultimate goal is to motivate and inspire women to take ownership of their lives, to make their own rules, and to create their future instead of following insulting, generic dating rules and waiting for a future to come to them.

Takeaways from Neely’s Journey

  • Your existing interests, hobbies, and “side hustles” can help guide your decision to defect. Is there a market for the things you do on the side, enough so it can be moved to the center?
  • The students, faculty, and staff that you work with and alongside each day could inspire your next steps! What are they working on that piques your interest? Are there ways for you to learn more about it while you’re still in your role?
  • Neely’s expressed interest in maybe one day being a therapist, before she eventually turned to coaching, demonstrates that the skills we acquire in our work can be used in a number of other places. What other industries, roles, or gaps in the market need what you have?
  • The defection process can feel isolating at times, especially if you move into a solitary role and not into a new organization. Managing those feelings – through mastermind groups, coworking, networking, and other events to create community – can help you stay motivated and mitigate the shock of such a big change.