“You Google, you freak out, you panic, you hesitate, you don’t do it, you get tired of not doing it, you sleep, you YouTube…and then you do it [Laughs]. And so there comes a point in time where you get so sick of yourself that you do it!” – Ishita Gupta
Please enjoy the transcript of Episode 033 with Ishita Gupta, lifestyle design and business consultant.
Dan: Episode 033 of Prologue Profiles, bringing you inspiring interviews with passionate people pursuing their career dreams. I’m your host Dan Feld, my guest today is Ishita Gupta.
After college, Ishita got accepted into med school but becoming a doctor didn’t feel right.
She decided to embark on a journey of self-experimentation which lead her to working side by side with marketing expert Seth Godin.
Ishita has since launched her own online magazine called fear.less and is now a lifestyle design and business consultant building her own line of personal development products.
You’ll hear Ishita discuss how she worked through her confusion and fear to create a path with potential, the joy of unexpected inspiration, and that with a strong belief in yourself there’s no stopping you
Ishita: Hi this is Ishita Gupta, I am a publisher and a coach and you’re listening to Prologue Profiles.
Ishita: I loved animals, I’d bring every single animal in our subdivision to our house. I’d know all the dog’s names before I’d know the owner’s names.
Dan: Were you a threat to the neighborhood?
Ishita: [Laughs] No I wasn’t a threat to my neighborhood! I was a threat to my family and my parents. They were like “What are you doing?!”
Dan: So let’s talk about what you are doing, so you founded Fear.less Magazine?
Ishita: I founded Fear.less Magazine which is all about overcoming fear. I was in a great deal of fear at the time when I started it and so I wanted resources for myself.
Dan: And on top of that you are coaching and teaching?
Ishita: Yes so I have a coaching business which is like private clients that I see face to face. But what I mean is over Skype or over the phone. So it’s just like a private coaching. But then I am building an information product business. It’s a big way of saying digital e-books or products or courses that you run and people can take online.
Dan: You’re doing a lot of things on your own, it sounds like. So Ishita talk to me about the path you took to get to this point?
Ishita: The path that I took to get to the point that I’m at right now is very circuitous. So I did not know ever ever that I would be in publishing or in the online world at all. In high school and college I was gunning towards medical school simply because that’s what my parents were telling me to do and really I didn’t know what else was out there. So I was like okay and I took the entrance exam 3 times and finally after 2 years of trying got into medical school and sat on my acceptance for like a full year. Because I was so confused as to what to do. Here was this path that of course at the end of it you make a ton of cash and you help a lot of people and what have you. I just didn’t know. Like I was just confused.
Dan: You didn’t know what?
Ishita: I didn’t know if I should take it. I mean it’s a serious commitment of time, of money, of heart.
Dan: So you were gonna go to medical school. You applied, you got in but something was kind of…
Ishita: I think my heart was like just take a minute to relax. And so I took a year off right after school and my aunt, my dad’s sister is physically and mentally challenged. She lived with us for 25 years. So I just I took care of her for a year. And it just took me down to a place where I was like “What am I doing? What am I doing in life?” And I was in my parent’s house, I was taking care of my aunt and I’d go out into the woods and I’d take walks. And it was just kind of all of these big questions were looming and were in my face. What do you want to do? What are you here for?
I remember being consumed as a kid by this question of like, I know that I’m here for something big but I do not know what that is.
Dan: So where did that questioning lead you to?
Ishita: I started focusing on myself. So I started not necessarily worrying about what everyone else thought and I just started to make decisions for me. So I stopped taking care of my aunt because it was very very difficult for me to do. And forever as a kid I’ve been consumed with like photo albums. I thought god I have this fascination with photography and I went to photography school.
Ishita: 2 years. I worked enormously hard, but I found that I didn’t like it. I found that the camera was kind of more of a barrier to what I felt like I wanted to be like with people. Which is like what you and I are doing we’re looking at each other right now and digging into like deep things.
Dan: So what did you do?
Ishita: I started reading blogs and reading about personal development. And I started reading a man named Seth Godin’s blog. Who we all know now is a great entrepreneur and big blogger. And at the time I didn’t quite understand why I liked it.
Dan: What year was this?
Ishita: This is like, I’m so terrible with dates that’s why I have a twin sister [Laughs].
Dan: She keeps the books?
Ishita: Yes exactly she really does. I think it was like 2006, 2007. So I started reading his marketing business blog. And I actually really enjoyed it and resonated with it a lot.
And one time when I was in Boston I heard he was giving a lecture in New York City and so I went there and I heard him speak and was like weeping through his whole lecture like a hysterical woman. And I left there and I just had this thought it said “You’re going to work with him or you will work with him.” And I thought okay whatever what does that mean? In the moment it doesn’t mean anything right? It is what it is. And so I took the bus back to Boston, went to photo school graduated a few months later, and then I moved to New York City and I thought I’m going to rock this city somehow.
And my idol in photography at the time was Steve McCurry. He does National Geographic; he’s the one who did the Afghan girl with those eyes. And then he found her 30 years later.
Dan: Time Magazine right?
Ishita: It was National Geographic actually yea. They may have put it on Time Magazine.
Dan: They bit off that I’m sure.
Ishita: Yea sure. I emailed him and said “Look, hire me. Hire me as an intern; hire me as your studio manager.”
Dan: Just out of the blue like that?
Ishita: The best jobs are not gonna be the ones that are hiring.
Ishita: So I started working with him and a couple of months into it I saw a ceiling. I don’t mean glass ceiling, I just mean ceiling of like when you’re working with someone big there’s not enough room for more people to get big. And I feel big inside. And I don’t mean that “Oh my god I want to be like Steve McCurry” but I’m here for something and like there’s a purpose and so I want to be big in that sense and I didn’t feel that there.
And like low performing at work is what I like to call it. Like I was browsing blogs and just like reading stuff online. And all of a sudden I’m reading and Seth’s blog has this title that says, “If you could change your life would you?” He was having a 6-month program that he was running to learn about entrepreneurship, business, publishing, marketing. And it was free. It was his way of kind of giving back because he had amazing mentors when he was growing up. And I just felt like this was made for me.
I just in that moment I gasped. I instantly knew that I was going to quit my job. I quit that night and I started applying to this thing where the application process was very honest. He asked you some really honest questions about mistakes you’ve made, about where you want to go. I just wrote for 3 days straight I swear to God I barely ate, I barely slept. I’d wake up at 2 in the morning like, zing. I just moved to my computer and had to write. And I hit send after 3 days and I just prayed. I prayed a lot like crazily.
And I kind of believed that it was really for me.
Dan: So you made it to the first round and what was the interview process like.
Ishita: It was like 25 of us and then we had a 2 minute interview with Seth each of us. Upon which where I blibbered and blubbered like an idiot I don’t even remember what I said. And then he said write down who you think should be in the program and why and how many people you think should be in it. And so everyone who got in was a person who was on everyone else’s list if that makes sense. So you chose each other essentially, does that make sense?
Dan: You got Godin’ed. [Laughter]
Ishita: So Seth one day walks in and says start a business or a project. And I was like “What the hell does start a business mean? Like what on earth, how does one do that?” So I started a project and lo and behold what I started was a magazine that specifically dealt with fear because that’s all I was feeling, that’s all I was doing, that’s all that I was dealing with.
Dan: You had no previous magazine experience…
Ishita: I had zero magazine experience. People think, they email me all the time and ask me “How did you do it?” Literally I emailed my idols, writers, authors, artists and I wanted to know how they dealt with fear.
So that was 2 months into the program. Then you’re in the program and I’m running Fear.less while I’m in the program and then you end the program. And Seth comes to me and says, “Well why don’t you stay on with me and I have this book that I want to launch and I have these events coming up and stuff and you can kind of help me run all this stuff.”
And then for the next 2 years I worked with Seth! He started a publishing company called the The Domino Project. We published 12 bestselling books. I did media at the Domino Project when he was running it. He had these things called road trips where we went all across the States in different cities. We did 8-10 different cities or something like that and I ran those events.
Dan: And how’do you feel while you were doing all this?
Ishita: Um scared, terrified. I mean here’s the thing about fear is that you keep doing bigger and bigger things, your fear also gets bigger and bigger. It’s not like this stuff goes away.
Dan: And back to your other work experience. You felt like there was a ceiling that was capping your potential. Was that still a factor here? What was happening around that?
Ishita: You know what? That’s a really good insight that you have because I think that was the one thing that was missing, in a good way. To have a mentor like that believe and guide you. I felt like, “Okay Ishita this is not a joke you know you’re here for something like now is the time.” And that ceiling wasn’t there, all I could see was constant increasing potential. And I felt…momentum.
Dan: So where’d you go with that momentum?
Ishita: So I stopped working with Seth in January 2012 and I wanted to run with momentum, but what actually happened was I got really scared to go on my own and start a business and start all this stuff. And I flailed around for a couple of months asking everyone else in my life what to do. I emailed every smart person I know. I talked to my parents, I talked to my sister and I didn’t know.
Dan: In terms of what to do next or?
Ishita: Yes like what to do next because even though I knew that I had all this good marketing and publishing experience and I knew that I wanted to practice coaching and run a business but I didn’t know how to start. I didn’t know how to start on my own.
Dan: So how did you overcome that? Where to start, how to start?
Ishita: It was tough. I emailed everyone I knew. And what was so insightful there was that the best people in the world like literally people who are changing the world doing big things, really what came back was, essentially Ishita like you’re gonna have to figure this out yourself.
And see the thing is is that I think that we want answers right away. And one of my other mentors Parker Palmer told me “We’re not looking for answers, we’re just looking for the courage to live with hard questions.” Because vocation and career and what you’re going to do for the rest of your life, those are really hard questions and so I wanted answers and I wasn’t getting any even from the best people in the world. So what do you do then? You have to go back to yourself.
And then what I did was I just started. I sent out that email that said, “I’m a coach! I have this service!” to 15,000 people on my fear.less list! How did I start? Literally, I started. Right? You Google, you freak out, you panic, you hesitate. you don’t do it, you get tired of not doing it, you sleep, you YouTube and then you do it! And so there comes a point in time where you get so sick of yourself that you do it!
Dan: So how did you decide to become a coach?
Ishita: Because I couldn’t not do it. Like I was constantly telling people. Everybody in my life, family, friends whomever I’m constantly giving them love, relationship, personal development, productivity. Here’s how I got through my fear, here’s what’s working for me. People are like, “Get out of my face.” But more than that, I resonate with people which I didn’t know before.
Dan: And what’s the example of a typical coaching project for you?
Ishita: I met Katrina she’s this ballerina, she’s lovely. She wanted to start her business and she had no idea how to start. And I saw that she was really talented and in a span of a few weeks we created her packages. We put up her website.
Dan: You get your hands dirty here?
Ishita: Yeah. I would only want to work with someone who got their hands dirty with my life so that’s exactly what I do. Like we’ll get in there like swimwear with anything that you want to work on. And we’ll work on it.
Dan: And you’re also creating a business around your own products.
Ishita: Essentially it’s a piggyback off of my coaching practice. Like the Confidence Course I had 4 calls with people but I had content for each of those 4 calls. And so we talked about confidence every week for a month. And we took questions and everything and now I’m gonna turn that into a digital product.
Dan: So let’s talk now about your day to day. Ishita, what’s a typical day like for you?
Ishita: A typical day for me, I wake up in the morning.
Dan: What time?
Ishita: I say 6 but really it’s like 8 and I’ll do my morning routine which is I drink a couple of glasses of water with lemon and then I’ll sit down and do my affirmations. You see how my…
Dan: …I’m witnessing them, they’re pumping me up and they’re not even directed to me!
Ishita: I’m glad they are, no I say like 4 particular affirmations and then I visualize myself in the future. And like a year from now I visualize like my book launch party. And what I’m going to wear and how I am going to feel. And what products I’m going to have out and…
Dan: Yea there’s a little drawing of Ishita with a little sun dress here. [Laughter]
Ishita: And Mondays and Fridays are like writing and errand and whatever else days. But Tuesday, Wednesday, Thursday in the afternoons I’ll see clients over Skype or over the phone. And I do like a chunk of hours, like 1-5pm on those particular days. So I save the mornings for me because when I fill myself up first I’m also far better for other people.
Dan: And what would you say you love about what you do?
Ishita: I love that when I work with someone else and I get like this feeling of a new lease on life. You know when someone tells you something that you’re just like, “I’m going to start over and I’m going to do it!” Or you get some kind of encouragement that really helps you get started or make a move. That for me is everything that feeling that when I get it myself. So that’s what I like to give to other people so love when I feel like I’ve done that. Don’t get me wrong I mean coaching is people say it’s selfless. No like it’s selfish. I get so much from coaching.
I love being able to see like real solutions to problems and not conventional wisdom. Like I think conventional wisdom is stupid. And my peers are actually some of the most generous people. Like I had a friend Peter Shallard his company is The Shrink For Enterpreneurs. He’s amazing. He just literally sent me an email today that was like this is the copy that I use from my clients and this is the email that I send them. And who does that? Who reveals their secrets? I mean he’s just incredibly generous and people online I’ve found have been very helpful.
Dan: So what do you dislike about what you do?
Ishita: It takes a lot of effort so like I used to have 7 clients a day. And I just would be nackered. I just would be burnt out.
Dan: So how do you manage that?
Ishita: Only by trial and error I mean I used schedule 7 now I only schedule 4. I used to always go over my hour to like 20 minutes over. Now I stick to my hour and stop at 45 and say let’s go over questions now. Just little things like that but make such a difference.
Dan: So you’ve had a circuitous path as you said and that meant taking risks, trying new things, sometimes they worked sometimes they didn’t, but you moved forward nonetheless. What character trait would you say has helped you get to this point?
Ishita: Resilience and a high tolerance for not caring about what other people think. Resilience in the sense that I’ve failed at what could be considered of 2, 3 or 4 professional ventures. And that matters not at all to me. It doesn’t feel like, “Oh my god now this thing I’m really going to do now I’ve failed and no, it’s just like let’s do it next time. And not caring about others is that I love my family and friends and peers enormously, but not one of them knows why I’m here. I rarely, rarely ever take advice. I trust myself enormously even when I’m confused within myself. Does that make sense?
Dan: Hell yeah.
Ishita: I mean we’re confused about life 90%of the time. But to have a sound understanding that what you want and knowing that that’s right for you. Knowing that what you want is right for you, that is everything. That is everything and you have to keep coming back to that belief over and over and over. I must tell myself that every single day and that’s in fact one of my affirmations. If the thing you wish to do is right and you believe in it go ahead and do it.
Dan: And what would you say inspires you?
Ishita: I live in a building where we have a stoop and there’s constantly like drunk people on my stoop every night. And late at night men trying to tell women their pickup lines and things. And I’m on the first floor so my window is right next to the stoop and often times I’ve stuck my head out and said, “It’s 3 in the morning she doesn’t like you, leave my stoop.”
Dan: I could use you, actually.
Ishita: [Laughs] In your area?
Dan: It’s crazy in Jersey City.
Ishita: [Laughs] I charge for those services
Dan: That’s fine [Laughs], it’s worth it.
Ishita: But so yeah yesterday night at 11pm I left my house and I saw this big guy outside with this like overcoat and his hair was all wild and messy and was about to launch into like, “Why are you on my stoop. It’s 11pm. The bar is over there.” So I stopped before I said anything. And all of a sudden I see what he is doing. He is putting tinsel and silver sparkling stars on our railing and on our stoop for Christmas. And he’s lived here, George, has lived here for 40 years.
Dan: Look at George he just wants to…
Ishita: Look at George! And I’ve lived here for 2 going on 3 years. And he was so sweet. He’s like I do it every year I do it every year, I’ve been here for 40 years. And it’s those moments that immediately, because I had been stressed out yesterday. I had to do this media contact list. I have to do things for my business.
Dan: But it’s nice that you have a contact list!
Ishita: [Laughs] And so that’s what, after George, I was thankful that I had a contact list. I said, “Ishita rewind, rewind for a minute.” Instead of launching into our default habits and our default character traits that override, I said to myself, “This was an amazing moment.” It was an inspiring moment that really took me out of that state that I was in and put me in a state that Parker Palmer calls it life giving, more life giving. What that means is it’s allowing you to continue living. So anything that gets me out of a moment like that and just reminds me of what’s here and what’s good and George putting tinsel on my stoop, that is inspiring to me.
Dan: And what fears do you have?
Ishita: My fear, here’s my fear: That I will not be responsible enough to what I have created and what I want to create and I will fall into a paralytic state of mind. So my biggest fear is not oh my god I’m going to have to get another job. It’s the apathy that comes before that. I’m scared of the feeling of indifference and not caring whether my business succeeds or not.
Ishita: Because I don’t want to die with the music inside of me. I don’t want to die with unfulfilled potential. My goal in life is to use myself up so that I’m like a withered prune. Or I guess a prune, that’s redundant, a prune is already withered.
Dan: [Laughs] Extra withered.
Ishita: So that I use myself up totally. Like not one drip, not one drop, not one ounce of unused potential.
Dan: So where would you say you are in your career right now?
Ishita: I would say I’m at the beginning of my career. I don’t feel like I’ve made it, I don’t feel like I’m anywhere near where I need or want to be. I’ve accomplished an enormous amount that I never thought that I would. But man my road is long and there’s a fortune cookie fortune that I love and I keep it with me it says that from error to error we uncover the entire truth. And that’s I think my path is that I need to move faster now. I just called Seth 2 weeks ago and I was like, “Oh my god I’m so scared. Nothing’s really happening I need to move faster.” And he’s like, “Then you need to move faster.”
Dan: Do you have a vision for where you want to take things?
Ishita: Yes I do. I mean my [Laughs]. I always laugh when I talk about this because it’s such…they say that when you talk about your dreams you always end up feeling a little bit vulnerable. But I always wanted to create a little multi-media personal development empire. I want to create the best resources in the world, make them accessible to massive amounts of people to help people solve their problems. Whether it’s confidence or whether it’s fear or whether it’s relationships. I want to leave like a legacy of constantly relying on yourself.
Dan: And how confident are you that you can get there?
Ishita: I am 10 out of 10 confident that I will get there. I am 10 out of 10 that that path will not be easy and free of challenges and fear and obstacles [Laughter].
Dan: Is there any feeling of self-doubt that those obstacles might…
Ishita: There’s always self-doubt whether or not I’ll be able to do it. Whether or not but inherently that self-trust that I was talking about, there’s no way that I won’t do it. So like whatever obstacle, I mean when you’ve made a commitment I feel like the universe is on my team obviously I’m not doing it alone, they’re my serious partner. He, She, It is my serious partner. There’s no way. I have the right intention. I have the intention to help. I have the intention to serve and it’ll happen.
Dan: So Ishita what advice would you give to someone who sees what you’re doing and is wondering if it’s possible for them?
Ishita: So everyone should listen to my advice and only take what fits and totally throw out the rest. The first thing I would say is that without a strong belief in yourself which is different than self-confidence. A strong belief that what you are doing is necessary and good and that you want to do it, you won’t be able to do it. So you have to have that kind of self-belief first.
Dan: And what’s the difference between belief and confidence?
Ishita: Because I feel that confidence is something that you can fake it ’til you make it. Confidence is something you can learn, confidence is something that you can build, it is totally attainable. But that is very different from the strong belief that I am here for a reason. Because the path you are about to embark on is going to test that every minute of every day, that has to be your crux, that has to be the foundation.
Dan: And what if they are not sure what they believe in?
Ishita: You have to experiment, you have to explore, I wasn’t sure. I had a belief in myself I guess that I could do something. I had no idea what that would manifest as. And so I just explored. Self-experimentation is something we never think about. We think that we’re all supposed to pop out of the womb and know. We’re not taught life skills, really. And so self-experimentation is huge. Ghandi wrote a book “My Experiments With Truth” where he like ate meat for a few months and then he didn’t eat meat. It’s like you have to experiment with yourself.
And don’t be afraid to have a few years, yes years, where you’re just straight up experimenting. I had years of experimentation and that was exactly what I needed. I’m saying this in hindsight I get it at the time it felt totally horrible and crazy and confusing. And it will always feel like that when you’re exploring because you just don’t have answers.
Dan: But it’s possible to find what you believe in
Ishita: It’s totally possible to find it. I believe that people who think they don’t have a passion just aren’t looking hard enough. We all have things, whether it’s…I mean come on I went to photography school from the idea that I looked at albums as a kid and maybe that’s where my passion came from.
Dan: I was with you.
Ishita: You were with me? I was with myself for a time too until I realized, “Oh, this isn’t working out.” But it’s that kind of gutsy way of saying I have this inkling about myself and what I’m interested in. I need to go and explore that with no plan B.
Ishita: Because what’s the alternative? My alternative was going into a system that didn’t feel right for me. Or staying and taking care of my aunt or remaining confused. Remaining confused is like a fate worse than death to me. Confusion is the worst, confusion and overwhelm are almost worse than fear. Remaining in a state of confusion is not an option for me.
So yes it’s totally possible to have self-belief. It’s totally possible to cultivate self-confidence. It’s totally possible to do what you were put here for. And that does not mean that you will be free and clear of really tough stuff in the process. But that just means start early so that you can get through some tough things and then keep learning and navigating that as you go on.
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