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Full Transcript:

Note: This is an original transcript–edited for sense, length, and clarity.  If you have any questions or concerns, please email our host, Doria Lavagnino, at doria@sheventurespodcast.com.

Intro: 

Doria Lavagnino: This woman’s career started with a brief stint in the music and entertainment industries. She found her passion in teaching and decided to pursue a master’s degree at NYU in general and special ed. She taught at a charter school in New York City, and while she loved teaching her students, she found herself becoming increasingly depressed and anxious. After some soul-searching, she quit her stable teaching job to pursue her first entrepreneurial venture, a tutoring business called “Teacher on the Go.” About a decade ago, she founded her current business, “The Non-Nine-to-Five,” to help, primarily women, transition to find their true purpose. I would like to welcome Jen Shultz. Jen, welcome to SheVentures.

Jen Shultz: Thank you so much. What a beautiful introduction. Just hearing all those details was really amazing

Doria: It’s all you.

Jen: It is.

Doria: After college — I found this really intriguing because I also did things right after college that ended up not being my passion — you worked briefly in the music and entertainment industries. What did you do?

Jen: I worked for a record label. I don’t remember exactly what my title was, but I did marketing. It’s really interesting to think back to then [it] was in the early 2000s when we were using CDs.

Doria: When you said that I was envisioning, you remember, The Virgin Megastore store on 42nd Street.

Jen: Yes, and the Virgin store on 14th Street in Union Square. I went to it all the time. I’d be dancing in the aisles. I’d be listening to music there. I loved that store and I was so sad when they closed it down.

Doria: I know. It was really sad. You did that for a while, and you decided that it wasn’t for you. How did the calling happen to go back to school?

Jen: Several years after I was in music, I worked in a different music company. I was doing artist management and I was a booking agent. I left there and ended up going to a company that did marketing for Broadway musicals. I was their marketing and promotions coordinator. I think that was my role. 

At that point, I had several jobs and nothing was a match for me. Funnily enough, I ended up getting fired from that job. I was not upset. None of the jobs were really a match for me, and I just couldn’t figure out what was wrong with me.

Doria: Can I ask why you got fired?

Jen: I am the type of person who wants to do a good job. If I’m working at something, I want to do a good job. Inside of myself, I was feeling so mismatched with the job. I was underperforming and it showed in my work. Honestly, I don’t know if I’ve ever said this to anyone — especially in an interview — I wanted to get fired. When they called me into their office, I thought they were going to fire me. It opened up the door to leave the country and I ended up backpacking in Australia for four months.

Doria: I’m envious of that. I wish I would have done that.

Jen: It was a really amazing experience and journey. I’m so grateful that I had the opportunity to do it. When I came back home to New York City in 2006, I thought about teaching. My mom had always said, “I think you’d be a really great teacher. You’re great with kids. You’re so natural with them.” I said, “Let me try this out.” 

In the summer of 2006, I interviewed for a very part-time job with a nonprofit that was looking for a teacher’s assistant. They gave me the job. By the second or third day, I knew in my heart that the next step was for me to teach. I applied for my master’s degree at NYU, which was another dream for me because it was a school that I had always wanted to go to. I think I graduated with a 3.9 GPA, and I was so proud of myself and I started teaching.

Doria: Good for you. Amazing. It sounds like at each step of your life, you were able to find what you wanted to do next.

Jen: It is interesting — when I look back at the path that I’ve been on up until this point without realizing it — I was always following my heart and intuition, even when it felt really painful. That’s what ultimately had me leave teaching to pursue entrepreneurship.

Taking a Step Toward Entrepreneurship

Doria: Some of our listeners might wonder, because they’re not in New York City, about what a charter school is like. You taught at-risk youth. You said that you loved your students and then you talk about that period of depression and anxiety that many of us go through. I was wondering if you could kind of give some color to that time in your life?

Jen: That’s such a great question because it probably wouldn’t be clear to a lot of people and it wasn’t clear to me at that time. To work at the charter school felt like a dream come true. This charter is massive all over New York City now. I’m so appreciative of the work that they’re doing. 

As a teacher for a charter school, it’s very rigorous because you are putting in very long hours but you have resources at your fingertips [that] when I was teaching at a public school I didn’t have. There’s so much more structure and rigor. The type of folks that are hired to do this job are [a] high-caliber of person. They really want to be there and are willing to go the extra mile, which I was. 

I think what happened for me was that it wasn’t a match for the type of person that I am. I was exhausted from waking up at 5:00 am, walking to the subway, taking two subways to get to the stop, and walking to the school in the dark. I didn’t leave the school until it was dark outside. I rarely left the school during the day to see the sun, and it started to take a toll on me.

Doria: It was like your whole life was revolving around the school completely.

Jen: Yes, and lots of things start to set in for me mentally and physically. I started to become exhausted. When I’m feeling that low, it can start to lead to really negative thoughts about who I am. I had thoughts of “I’m such a loser. Why can everyone else wake up this early and go teach? Why is this such a problem for me? Why do all the teachers seem better than I do?” 

All of this just started to snowball to where I thought I was horrible. As all of this is happening, there’s this tiny, little, very calm, positive voice saying, “You are a really great teacher and you care about your students. Maybe the structure of this just doesn’t fit who you are.” That seemed like an absurd thought to me. I thought, “If you teach, you’re a teacher in a classroom.” There’s no other way that you teach, but that way. I was willing to entertain this little voice that was kind of nudging me — my intuitive voice or a voice connected to something greater than myself. 

In December 2010, I followed that voice. I walked into the school on a Monday morning, and I gave my two weeks’ notice. I think it’s really important for me to share that this was not a moment of empowerment with my head held high and my shoulders held back. It was a real moment of, “Wow, I am such a loser because I’m letting the school down, I’m letting the staff down, and I’m letting these students down.” These kids were used to people coming in and out of their lives all the time and they didn’t have that stability.

Doria: You’re shouldering all of that guilt even though it wasn’t necessarily yours to take. I think that’s what happens to so many of us when we enter that negative spiral. When I’m listening to you, I hear partial Imposter Syndrome and partial exhaustion. Tell me if I’m correct in thinking that you’re a perfectionist? Did you have very high standards for yourself at that time?

Jen: Yes, at that time. Perfection is something that I have worked on for years and it’s also something that I support my clients with, too. Many of my clients fall into having high standards, which is not a bad thing, but there’s also a time to realize, “This is good enough, I am good enough, and I’m going to move forward with this.”

Doria: Yes, it’s so true. I have the battle of perfectionism myself. One of my daughters is a perfectionist. She is now learning how to pace herself. For her to say, "I may not do so well on this psychology test," is a really big deal for her. In the scheme of things, it’s such a small thing, but when it’s in your head and life, it seems much bigger.

Jen: Yes, absolutely agree. 100 percent.

Doria: So you went there? How was the principal? Was he or she supportive?

Jen: No, and I love that question because no one has ever asked me that before, and you bring me back to a very specific moment. Probably somewhere between when I gave my notice to a couple of days before my last day, I was at the school quite late. It was probably around 5:00 or 6:00 pm when I walked out of my classroom and I shut the door. I saw her down the hallway and I went to wave and she looked at me and just turned around. You could say, maybe she didn’t see you but having worked at that school, she wasn’t that far away from me, and she was quite upset. In her defense, she was a very new principal at the school, and this was the first charter school opening in the Bronx. All the schools had been in Harlem. She was a brand new principal, and I don’t know what her feelings were that she was feeling.

Doria: Right or the pressures?

Jen: Exactly pressure and feeling let down. Everyone handles that differently. It was very hard to receive, but I wouldn’t want to say, “Oh, she’s such a bad person.” It was very hurtful for me, but I don’t know what she was feeling inside either.

Doria: Right, and that is such an important place to get [to] I still work on that myself. It’s not necessarily about me — it’s about what that person might be going through and honoring that. You ended up leaving, and then what happened next is that you did some soul-searching. How did that all come about?

Falling Forward

Jen: I left in December of that year. It was a couple of days before the holidays and the school holiday break, so that was really tough. Christmas Eve in my family has traditionally been a large Christmas Eve with lots of family members. People would ask how school was going and how’s work going. 

What happened next was a bit of soul-searching. Things fell into place in a way that I could have never imagined, which speaks to the power of taking a risk, the power of taking a leap, and going against all safe norms when you are following your heart. 

I linked up with a private tutoring agency located in New York City, and wonderfully enough, it was owned by a woman. I was fascinated by the fact that this was owned by a woman, because it’s a whole other world to think about businesses that were owned by women, especially where I was at. In 2010, I wasn’t rubbing elbows with other women-owned businesses. I had no idea about that.

Doria: Absolutely, and [it’s] so important to remember that we’ve made progress, but we still have a long way to go. It’s a little bit more common, but it really is uncommon today and so I get that.

Jen: I was so wowed and blessed because I had a special education background, and tutors and support teachers were more in demand. She had students that she could place me with, so I was basically an independent contractor. Probably a week after the first of January, I was placed with my first student.

Doria: Incredible.

Jen: I traveled to a school and I worked with a student there. What was so awesome about it was that I got to go to the student’s classroom, take him from his class and read, and go into the school’s computer room where there was no one else. It was quiet and I got to focus on what the student’s needs were. Then, this agency gave me a second and third student and suddenly I had three students. I was making a pretty decent hourly rate because of the background that I had, and while not super enough to make a living, I was kind of getting by. 

Also, I was living in New York City, so I was paying New York City rent prices. Even 12 to 13 years ago, rent was still very expensive in New York. It’s at a totally different place now.

Doria: Yes, very expensive and that makes a huge difference, but you were able to fall forward.

Jen’s Father’s Words of Wisdom

Jen: Yes and I would have never expected what happened next. My father had been in the entrepreneurial space as an owner of a franchise. He said very nonchalantly to me, a couple of weeks to months into doing this, why don’t you start your own tutoring business?

Doria: And that hadn’t occurred to you?

Jen: It hadn’t, but it sort of [had]. I was aware that I could do this on my own after working with these couple of students. 

The thing that struck me was that before I left the school, we had [a] small reading group with students. I recognized the connection I’d have with small groups of students when I was left on my own with the students without anyone telling me how I had to do things, what I had to say, and how I could and couldn’t teach. I saw the effect I had on these students and their growth. When he said that to me, I realized I have this unique ability with kids and I thought maybe I should do that. 

From December to March, I started my first business called, “Teacher on the Go.” I ended up working one-on-one with students. I had no idea how to market a business. I’d go to Starbucks with my laptop and I’d go through my cell phone, and go through teacher and parent contacts, and anyone I knew that had kids I started telling them the services that I was providing.

Doria: That’s excellent! That’s what I’ve learned to call relational sales, right? These were relationships that you had, and you just let them know what you were doing and you built it from the other thing? 

I’ve interviewed a lot of tech entrepreneurs and they talk about proof of concept. What’s interesting about what you describe with those three students is that that was your proof of concept — to know that what you could do, if you could scale it up, was sustainable and something you enjoyed.

Jen: I’ve never thought of that as proof of concept. I had no idea. I think it also speaks to a kind of “Marketing 101.” Where do you start? You start with what you know. I know people, relationships, and connections. All I need to do is open my mouth and say the words that this is what I’m doing and this is what I’m looking for. Do you know of anyone? Are you anyone? 

This is exactly what I teach my clients. It is the easiest first step you can take. One of my clients just started dipping her toe into her business, and I said to her, “Okay, we’re going to create an announcement that you’re going to make.” She came up with a price and created an introductory offer. That way she felt comfortable enough with the pricing that she could get behind and talk to people. Within a week, she not only got her first client, but the client said to her, “Your introductory rate is too low. I want to pay you double.” I’m not making this up.

Doria: No, I believe you. I believe you. Because as women, I think that we tend to undervalue ourselves all the time. We feel like we shouldn’t ask for too much. That is amazing. I’m an introvert, and the idea of approaching people in any kind of way makes me uncomfortable. 

Marketing for Introverts and HSPs

Doria: Do you have tips for someone who’s a little bit more introverted?

Jen: Yeah, so I’m not an introvert. I’m an HSP —  a highly sensitive person. I have introverted tendencies. Many of the women that I work with are introverted and/or are also HSP, highly sensitive people. As an introverted person, you have a unique ability to make deep connections within intimate relationships and connections. In general, introverted people are better at one-on-one or small groups of people because they get to connect at a deeper level, which is more fulfilling to them. Because of that, they are naturally poised to be able to serve and support people at a high level.

Doria: I really like that. The other thing that it made me think about is listening. I enjoy listening to people. I think that that’s also a part of sales that is often overlooked — hearing what it is that people need.

Jen: Yes, I agree 100 percent. That is also a skill. A highly sensitive person is an introverted person who has the willingness to listen deeply and get what someone is sharing versus talking constantly or being aggressive. I’m not saying that an extroverted person is naturally aggressive, but when you are willing to listen, that leaves someone feeling seen and heard. That leaves someone feeling more connected to you and feeling like I’ve gotten. This person gets me. I want to work with them. I want to invest in their service or product.

The “Aha” Moment of Non-Nine-to-Five

Doria: Exactly, I love that. You built your teaching business, and at some point, you had an epiphany about The Non-Nine-to-Five, which is your current business. Walk us through how you got there.

Jen: While I was doing Teacher on the Go, I’d thrown myself rigorously into personal growth and development for, at this point, probably 20-plus years. I was taking a workshop where we had a coach. It was a workshop for a small group of women. The workshop was all about turning your passion into profits.

I’m doing Teacher on the Go, and something is gnawing at me saying, “This is not it for the long term. You’re good at this. You’ve been able to make connections with students and parents, but this is not for the long term.” 

What I became excited about was the idea of me coaching like this woman was in this workshop and teaching adults. I was feeling the energy of that and it took me a bit of time, but I recognized I’ve been doing this now for almost two and a half years. I’ve been able to stand on my own two feet, pursue this work, not go back to a nine-to-five job and do this on my own. If I’ve been able to do this on my own, there are others that want to do this, and I can teach, support, coach, guide, and train them how to do this as well. That became my journey into creating this. It took me about another 1 to 1.5 years to birth Non-Nine-to-Five.

I ended up going through another depression and bout of anxiety because I couldn’t figure out how to get this together. I went to see a woman speak, who was doing a couple-day event. She was a business mentor, and what she was speaking about resonated with me. I’m the type of person who if I’m investing in a workshop, I’m going to talk, participate, and ask questions; I’m going to get my money’s worth, so to speak. 

I ended up going through another depression and bout of anxiety because I couldn’t figure out how to get this together. I went to see a woman speak, who was doing a couple-day event. She was a business mentor, and what she was speaking about resonated with me. I’m the type of person who if I’m investing in a workshop, I’m going to talk, participate, and ask questions; I’m going to get my money’s worth, so to speak. 

We went on a break for coffee or something, and I walked to the back of the room and I started conversing with a woman who was working with the woman who was speaking. I don’t remember what I was saying, but she said something to me that was very clear and I remember everything from that point forward. She stopped me mid-sentence and said, “Jen, we see a lot of potential in you.” The moment she said that and I’ll never forget this, I put my hand over my heart and I felt a sharp pain in my chest. I had this really visceral reaction and I looked her in the eyes, and I gritted my teeth, and I said, “That is the worst thing that anyone has ever said to me. I will be damned if I live a life full of potential.” 

Doria: Wow. What was that about?

Jen: What that was about was that woman was 100 percent right. I was living with this potential, but I wasn’t owning it and going to the next level. I was someone who would get an idea and freak out like I had the idea of starting this business. I would tell myself I was a loser. I’d say I couldn’t do it and flounder. It’s all okay, like I’m a human being, but there was something that was going on for me. The best part about this is that I had the opportunity to invest in the support of the woman who was leading this event. At that time, I was doing Teacher on the Go while working another part-time job. I was just getting by at that time. I was over $100,000 in debt.

I don’t have any regrets about going to that school because I’m an experienced person and that experience was wonderful. The people I met and the teachers I worked with were fantastic. Could I have gone to a different school and saved a lot of money? Yes, so maybe that would have been better. It’s the choice that I made at that point and that’s the [best] decision that I made.

Doria: I get that. Yes, I did the same thing. I also went to NYU for graduate school, so I understand.

The Decision That Changed My Life

Jen: I was over $100,000 in debt and I had this opportunity to make this investment and having support in place is really important to me. There was also this feeling that I should be able to do this on my own.

I made a bold decision by taking a very radical action to take the only credit card that I had and put the deposit on my card, but it was the best decision I could have ever made. I think it’s really valuable to share that this woman is still my mentor. It is nine-plus years later. I still invest. I make very high levels of financial and time. I put a lot into it, but because I’ve been willing to go beyond my fears of making the financial investment, I have been able to create what I have. It’s been amazing and beyond my wildest dreams. The biggest thing is the woman that I become, the confidence that I have, how I see myself, and how I handle situations — be it personal or professional —  is worth all the money in the world. 

I really value support. I talk to prospective clients and my [current] clients about how their investment in becoming a member of the Non-Nine-to-Five is not just about successful self-employment, it’s about so much more. It’s about becoming the woman that you say you want to be, and the woman you’ve always wanted to become, and transforming, which is so important.

The Non-Nine-to-Five Process

Doria: It sounds amazing. It took you about a year to get it up and running based on what you were saying before, and you went to another coaching event and that personal coaching has helped you as well. There are so many coaches in general right now. How can someone determine if a coach is the right fit for her?

Jen: When I connect with a prospective client, I will offer up an hour of my time, which is important that I do. I’m answering your question in two ways. I’m sharing it from my perspective, and then I want to share it from a prospective client’s perspective. 

In my perspective, first and foremost, you’re filling out an application because I need to first see if there is an alignment. If there is an alignment from the information you’re sharing with me, then I want to invite you to a gifted call to connect with me. On that call, we’re going to go really deep because I need to hear what’s going on for you. What’s not working? Where are you struggling? My aim is that you feel seen and heard because if you don’t feel seen and heard by another person or someone that you are prospectively going to work with, then what are you doing? It doesn’t make any sense.

Doria: How do you handle the ones that aren’t a fit?

Jen: I’ll read through the application and if there’s something that’s glaring like “this isn’t really a match,” I’ll get in touch with them directly. I’ll say “This is why I see that we’re not a match,” and I’ll refer them if I have a recommendation for another coach or a resource. 

The fact that you filled out an application says so much because you took the time to sit down and answer these questions. I want to be able to give you some support moving forward, and I know tons of amazing people. If there’s someone else, I want to connect with them, or [say] “Here’s a book that I’d like you to start with,” or “Here’s a podcast I want you to listen to.”

Doria: Excellent. I was curious about that. Once you’ve gone through, you’ve gifted a call, and you really want to get into the deep part —that must be hard to do in one conversation. I know for myself, I’m pretty guarded. I don’t know if I would be able to but maybe I would. How does that work?

Jen: It’s interesting you say that because the people that I connect best with are willing to go deep, and because I’ve been doing this for so long, we can accomplish a lot in an hour, but sometimes we go over by five to 10 minutes. There’s so much that I want to cover and I share my personal story because it’s important to make that connection. 

Let me start with when someone is looking for a coach. First, you want to know that you are open and willing to receive support and that you don’t have a belief that you can do it all on your own. If you do have a belief you can do it on your own, you recognize the need for help, and I’m willing to seek help because not everyone is willing. 

Then, it’s “does this person’s energy resonate with me? Do I feel seen and heard connecting with them? Does their story resonate with me?” That’s first and foremost. It’s so important. 

From there, it’s within you [to have] the willingness to trust where your heart and intuition are guiding you. I’ve had clients who have felt a connection to me where I absolutely feel a connection to them, but they are afraid to take those steps, which makes so much sense because they’re afraid to make a financial and time investment. 

All these reasons come up, and I have no attachment whether someone steps into work with me, but I’m going to support them to see those resistances and to ask themselves to trust what they’re feeling in here. Because whatever is in our heart, whatever we’re intuitively feeling, there is nothing more powerful than that. 

We have a logical brain that will say, “I can’t afford that. I can’t put the time into that. My partner, spouse, husband, whoever won’t agree that I do this.” That’s all coming from the mind, the logical brain, the reasoning. 

If you drop down into your heart, into your intuition, what’s really there? I really want support where I feel seen and heard by this person. I believe this could make a difference and that’s where you want to make a decision from.

Doria: That is so well said. I love that.

Jen: I love your questions. I’ve done so many podcast interviews. I love the depth and uniqueness of your questions. It allows me to say so much more than I have ever before in a podcast interview. Thank you.

Doria: Thank you. You’re very open to sharing. When you bring someone on, do you work with them personally or in a group setting? How does that work?

Jen: Members of The Non-Nine-to-Five both work with me privately one-on-one and within our community. All of our programs have a private aspect with me where we have private coaching calls, and we have a beautiful, safe, sacred, very intentionally curated online forum. We have a private online form and I am e-coaching. Clients are posting specific plans, asking specific questions, and they have real-time support from me. I’m on the forum almost every day checking in on them. 

Once a month, we do community-wide teaching and support calls, where we all join on Zoom, and I am teaching a specific concept or some sort of teaching or training that I’m bringing forward. There is participation and sometimes group work that we’re doing. I also do community-wide training where we come together for a full day, where we’re going in-depth into a training. 

The approach that I take with the work that we do is a dual approach. We have an inner and outer approach. The outer is the practical and actionable steps. When I started my first business, the actionable steps I was taking were calling people, sending emails to people, and marketing my services in that way, so I’m teaching women how to network intentionally, how to enjoy it, and how to do it when you’re more introverted. 

A number of the women I work with are very introverted to the point where it can feel almost paralyzing to connect with someone, and I work with them on that. What happens is that their confidence rises and they make deep connections, so we’re talking about practicality on one hand. Then, the inner work is the ability to go, follow, listen to your intuition, work through the fears, doubts, worries, and learn how to rewire. 

We’re rewiring your brain to stop walking down this same path. If you have a pathway in your brain that says, “I am not good enough, I am not good enough, I am not good enough,” [then] we can’t create any type of growth or success from that place. I share very specific tools to rewire that. One of the biggest inner components that women hands down tell me all the time is that they have confidence that they’ve never had before. If you have confidence that you never had before, you can do anything. If you feel confident, you can create just about anything.