Pivoting Your Creative Business with Jasmine Star

Jasmine Star, photographer & blogger, on Profit. Power. Pursuit. with Tara Gentile

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Tara:  Hey, everyone, welcome to Profit. Power. Pursuit.  I’m your host, Tara Gentile, and together with CreativeLive, we explore the unique strategies that creative entrepreneurs use to take control of their lives, profit from their passion, and pursue what’s truly important to them.

Today’s guest is Jasmine Star, a world-famous photographer, educator, and law school dropout.  Jasmine is now building resources for other creative entrepreneurs on personal branding, making the best of social media, and achieving a business owner mindset with her methodology, The Path to Profitability.  Jasmine and I talked about being in the midst of her transition from wedding photographer to business mentor, how she listens to her audience to discover exactly what they need, and how she bridges the gap between inspiration and products that people are excited to buy.

Jasmine Star, welcome to Profit. Power. Pursuit.  Thank you so much for joining me.

Jasmine:  Well, thank you for having me.  I’m excited.

Tara:  Absolutely.  So let’s start with your origin story.  How did you go from law school to professional photographer?

Jasmine:  Well, it’s a rather long story, but the nutshell version was I was in law school, and it was my first year, and my mom had a relapse with brain cancer, and it kind of rocked my world.  It was like the first time that I kind of encountered a really difficult patch in my life, and I left law school because I wanted to be with my mom.  The doctors did not give her a very good prognosis.  In fact, they said that it was time to start planning her funeral, and the one thing I knew I wanted was my mom to see me marry my best friend.  I had been dating my high school sweetheart for about eight and a half years, and he proposed and we planned a wedding in three months.

Tara:  Wow.

Jasmine:  And against all odds, my mom and my dad walked me down the aisle at our wedding in Hawaii, and my life changed, because I saw that my wedding photographer did something more than just document my wedding.  He documented a miracle, because my mom is still with us today, and even though she wasn’t supposed to be, it was … I had this like coming to.  I was like, “My God, my mom is 50 years old and I’m 25.”  And I had like a mid-life crisis.  I said, “If I have 25 years left in my life, I don’t want to die a lawyer.”  And that was like this big wake up call for me, and when it came back time to go to law school, my husband asked me, you know, because he saw how sad and depressed I was, he’s like, “Well, if you could do one thing for the rest of your life, what would it be?”  And I said I want to become a photographer and I want to run a business.  And he said, “But you don’t even own a camera.”  And I was like, but if I did, I’m sure I can make it work.  And that’s the story.  That’s literally how it happened, and we had that conversation in November of 2005, and in December of 2005, that year, he surprised me with my first camera, it was a digital camera, and I started my business that year, and it exploded.

Tara:  That’s amazing, and what a story.  That’s absolutely incredible, and so I know we talked earlier that you’re kind of going through a bit of a transition right now, and I want to get to that, but let’s start, let’s pick up kind of right there where your business is exploding, you know, you’re learning photography, you’re experiencing photography, you’re getting it done, you’re generating revenue that way.  What misconceptions did you have when you started your photography business?

Jasmine Star, photographer & blogger, on Profit. Power. Pursuit. with Tara GentileJasmine:  Well, a major misconception was that I envisioned myself very close to like some forlorn hippie.  I was like it’s going to be me and my camera, we’re going to run through fields of wheat, and it’s going to be a very creative and amazing experience, and it’s just going to be all warm and fuzzy and butterflies everywhere, and it wasn’t that at all.  It was running a business.  I truly, then, only when I was in the thick of it, understood that, you know, I was a photographer 20% of the time, and an entrepreneur and business woman 80% of the time.  And so the largest misconception was that my creative life would dominate my daily activities, and that was completely the opposite.

Tara:  That is something that we have heard from a lot of people when I asked that question.  How did you feel about that?

Jasmine:  Well, I was intrigued, and I was passionate, and for better, for worse, I’m a scrappy hustler.  You know, I grew up in like a really rough neighborhood and my parents are immigrants and we lived super simply and we didn’t have much.  So what I did have was stuff that I was able to earn, find, hustle, keep.  Kind of that whole like beg, borrow, whatever I had to do to get what I wanted, and I think it kind of taught me how to navigate in a, in like a bootleg version, but in the business world.  It’s like I understood that I wasn’t afraid of hard work, and that I was willing to do what I needed to do in order to survive, and you know, to be able to do that with a camera was just like icing on top of the cake.  So while other people might shy away from it, I kind of dove head first into it, and I was like, “I’m ready.  I’m definitely ready for this.”

Tara:  Yeah, well, and it seems like that is really what makes the difference between people who succeed with their creative businesses and people who don’t.  If you’re only in love with the creative side of it, if you’re only ready to dive into the creative side of it, you’re just not going to be able to do what you need to do to make it work, and so for the people who can really fall in love with the business side, and you know, get down to business and really hustle exactly like you said, those are the people that really go on to succeed.  Do you see that, too?

Jasmine:  I absolutely see that, too, and I don’t want to … I actually read a phenomenal book a few months ago called Big Magic by Elizabeth Gilbert, and I couldn’t agree more when she said that as creatives, we cannot expect to put the pressure on what we find our art to be to be a source of sustaining us.  So for instance, just because I loved photography, if I wasn’t ready to have business acumen to run the business, then I should just be okay with it being a phenomenal hobby, something I love to do, and it satiated me creatively.  But in order for you to turn your passion or your art into a form of sustaining your livelihood, well, then you absolutely, positively need to kind of create a business structure around that.

Tara:  Amen to that.  So let’s talk about your business right now.  How’s your business currently generating revenue?

Jasmine:  It’s pretty diversified.  So we have an online store that sells products for photographers, and we started that about five years ago, and it’s been a great source for passive income.  This is the type, passive income is the type of income that when I wake up in the morning, I see that I have sold a few digital products, and that has been phenomenal, so that’s one part of it. 

I’m also a photographer, so I’m working heavily with about 20 clients this year.  We’re a boutique luxury photography studio based in Orange County, California, but we traveled the world for our work.  Another capacity is education.  So in-person and online education by way of woohoo, CreativeLive, and a myriad of other places.  That’s kind of been a big push for us. 

And then something new that we decided to start this year was to kind of pivot and launch, or kind of make a lateral change in our business.  I have spent years educating photographers the importance of building a personal brand and marketing your business, and over the past like two years, it’s been kind of like on the down low.  I was doing it for photographers, and then other people started seeing how I was helping entrepreneurs get off the ground and they started asking me questions to see if I would be interested in helping their business, even though they weren’t themselves photographers.  And so, of course, I was completely skeptical.  I was like, well, I know that it works for photographers, I’m just not sure if they would work for whatever, a graphic designer, a florist, a baker, a jewelry maker, and kind of started testing the waters and got into some phenomenal conversations, and what I decided to do was I realized that consulting creatives on a one-on-one basis just wasn’t scalable.  I only had a certain amount of hours in my day.  So the past like ten to twelve months, we’ve built a curriculum called The Path to Profitability, and it’s for creative entrepreneurs to market and brand their businesses.  So it’s applying the same principles, but like extracting the idea of photography, and really just applying it to creative entrepreneurs in general.

Tara:  Fantastic.  And so we talked earlier about this transition.  What was your thought process in … can you kind of walk us through step-by-step how did you realize that you wanted to make this transition?  How did you actually go about, you know, doing the work of kind of pivoting your brand, pivoting your message?  Can you walk us through that?

Jasmine:  Yeah, I mean, I’m going to be really honest.  It’s … these are the conversations and thoughts that I had two years ago.  I had just hit like a weird space in my kind of creative journey.  I loved being a photographer, and it was great, but I felt like something was missing, and I just didn’t give myself the permission to say … to pursue the thing I really enjoy doing.  I enjoy photography, but with equal proportion, I really love helping business people become stronger business people, and I always talked myself out of it.  Like I wasn’t enough, I wasn’t worthy, I wasn’t smart enough.  Like who am I to think that I could teach other people?  And this is the exact thing I preach against for all photographers.  It’s you are enough, you can pursue it, even though there are hundreds of thousands of people who have a camera and are pursuing it professionally, you offer something that nobody else offers, and I couldn’t take that advice for myself, which is ironic.  And it took me awhile, and once I started … once I gave myself the permission to believe that it was a possibility, and once I extracted all sort of expectations, because whenever you start a new venture, it’s just a new venture.  It’s not a new business.  It’s not a business until you’re actually profiting enough money to pay yourself an income, to pursue new ventures, and so I took out all kind of expectations.  I said I’m going to try this. 

I’m going to build this curriculum because this curriculum is in me, and it needs to get out of me, out into the universe.  Now, if it’s successful, phenomenal, and if it’s not successful, well, I know I’ll help people along the way, and then it’s just giving me more leverage to pursue something else.  But all I know is I have to get it outside of me, and that’s where we are right now.  I’m in this awkward phase of I’m about to launch this new thing, and I don’t know how it’s going to be received, but at the end of the day, I am just doing what I’m being called to do, and that’s to create and execute.

Tara:  Yeah.  And how has that affected the photography side of your business?  Are there changes that you’ve made there to open up space?  Have you taken on less clients?  Anything like that?

Jasmine:  Absolutely.  So it works in two ways.  We did take on less clients.  Last year, we shot 30 weddings, and it was phenomenal, we loved it.  This year, we’re going to shoot closer to 20 weddings, and we’re done booking for the year, so it’s nice to know our schedule in advance, and at the same time, wedding photography, which is specifically my niche, is very seasonal.  So I shot my last wedding in November of 2015, and I won’t be shooting my first wedding until March 2016, so we had this big break in months where a lot of creative photographers like to kind of just take a breath and hibernate, and instead, I just like to bring more stress into my life, so we kind of hit the ground running in last October and just didn’t stop.

Tara:  Nice.  Nice.  So I had mentioned that I had talked to Celeste, one of the content producers here, and she just went on and on about how motivating and inspirational you are, and clearly, that is your modus operandi, but you know, I know that a lot of motivational and inspirational people can build communities and build brands, but they don’t always go on to make sales or develop products that people want to buy.  Can you talk about how you personally bridge the gap between, you know, inspiring people and having that be a big part of your personal brand, and also creating products and, you know, promoting things that make people want to buy?

Jasmine:  That’s like a really great question.  Well, one, I’m flattered when people say I’m inspirational, but I don’t know if I necessarily see myself as inspirational.  What I think I am, and this is what I believe I am, is that I am a mirror to what people want to see in themselves.  Is that a girl who’s not qualified, who can work hard, who isn’t maybe the most technically savvy, or isn’t the most artistic photographer you’ve ever met, but she’s out there pursuing what she loves and being really successful at it.  I think that that is what inspires people, not me in and of myself, and so when it actually comes to selling things or creating products, it’s truly and wholly just based on what I’ve heard that people want.  People want more information on how to get busy.  People want information on how to build a brand, specifically, that always tends back to people want to make more money for the thing that they do, and/or they want to change the current structure of their clientele. 

So I hear this again and again and again, and so what I do is I just respond to pressure points.  What do people want help with and what am I good at?  And if once I bridge that gap, then the derivative is a product that I’m really proud of, and that’s exactly where we are with the path to profitability, is kind of I see pressure points, I know how to speak to the pressure points, and I really just want to create a phenomenal curriculum based on how to help people.

Tara:  Yeah, so I do the exact same thing.  I’m a big listener, I’m a big observer, I want to know exactly what particular pressure points, what pain points, what goals people have, and I want to create products to fill them, and I tell that to my clients as well, and they often say, well, how do you figure those things out?  How do you listen for that?  How do you see those things?  So can you give us sort of your process for paying attention, really?  Are you talking to people individually?  Are you talking to them in person?  Are you listening online?  What does that look like for you?

Jasmine:  I am a total hermit.  Like today, we had this conversation, Tara, it was just like are you sure that this Skype session, this interview, is going to be just audio?  It’s not going to be visual, right?  Like I am in yoga pants and an oversize sweatshirt, no makeup, so when it comes to listening to people, it’s by and large on the internet, where it is totally okay to look like a hot mess and not worry about it being a reflection of your business.  What I think people want to do is people want to hear, and they want to find the pressure points, but they themselves aren’t necessarily engaging in the type of conversations that would foster that, so I’m very active on social media, and I mean, everything from strategic business questions and answers type thing, but also, very much in tune with pop culture or the books that I’m reading, and it would be … it’s very crazy to kind of see a reoccurring pattern.  So I’m a big reader, this is an example, this is a recent example that just transpired two days ago.  On Instagram, I post the books that I’m reading.  Once I finish them, I give a little brief synopsis and what I thought about it, and I recently finished a book, and I openly admitted on social media that I have struggled with depression and I don’t think it’s ever in past tense. 

When somebody goes through like really hard moments, it’s I have to learn how to function in spite of how I feel, and it’s an active emotion and mindset that I have to put forward in order to not be overwhelmed when it comes to really dark places in my life, and putting that out on social media, and then just seeing this massive outpouring, and I know by and large my audience are … my audience is creative, and the thing that I saw immediately was that people kept on saying that they themselves just didn’t feel that they were good enough, worth it, talented enough, and that what manifests from that is an overwhelming sense of melancholy and depression, and that was just like a light bulb that went off, and I thought to myself, “This is a hot button topic that nobody wants to talk about.  It’s not okay to admit that you struggle with really hard things, and I’m open with it.  It is not … I don’t make it my story, but I include it in my story.  I still openly talk about how I see a phenomenal therapist who helps me navigate my business and personal life, and so I thought to myself, “This right here is going to be wonderful content for a blog post.”  So I plan on writing about what it means to be creative and also cite other, like, artists.  Specifically, like Hemingway and F. Scott Fitzgerald.  It’s very, very open that they struggled with, like, dark, dark moods and depression as a manifestation of their hard work in the creative realm, and so I think to myself, first I would listen, then I would write a blog post, I would see how that blog post worked, then I would kind of branch out from there.  Doing social media updates in regards, starting the conversation, and if I feel like there’s depth to that, then I can kind of create deeper content, maybe like a pdf or an eBook about what it means to be creative and balancing those sometimes like melancholic moments in your life.

Tara:  Oh, that’s perfect.  That’s my exact process, too.  So thanks for sharing that.  So that actually made me think about Imposter Complex, which is not the same thing, obviously, as suffering from depression or melancholy or, you know, any of those … those dark feelings like you were talking about, but I think it’s certainly related, and it’s something that many, many, many of us struggle with, and it’s certainly something that we’ve talked with a lot of guests about in the past as well.  Can you tell us what kind of role Imposter Complex has in the way you approach your work and how you deal with it?

Jasmine:  Absolutely.  So, ooh, this is … it’s weird.  I hate admitting it, but I am just, how do I say this, I suffer from the Imposter Complex every time I pick up a pen to write, every time I pick up a camera, every time I step on a stage, every time I step in front of a camera to teach.  It is always a litany of questions.  Like who are you to do this?  Imagine what people are going to say.  Think about all the negative, like, all the negative things that people are going to say as a result of what you’re saying, and for me, it’s really important to go through the full gamut.  What’s the worst that people can say about me?  What’s the worst possible thing that can happen?  And perhaps you aren’t in a position to be of authority to speak on this.  And then I say, “And then what?”  Like, okay, so … okay, let me take you on a detour, but I promise I’m going to bring it on back.

Tara:  Sounds good.

Jasmine:  So I grew up in a kind of like really rough neighborhood, and it was primarily Hispanic and black and my parents didn’t own a car, we used public transportation, and we washed our clothes at a laundry mat, and my dad got paid every two weeks, and on pay day, my mom would give us $5, and my sister and I would walk down to Little Caesars Pizza, and we would by a $5 pizza for family dinner night, and this was like a splurge for us.  So I have a twin sister, we walked down like three blocks from home, and I pick up … I pick up the pizza, and there is a chola, which is like a Mexican female gangster right outside the door, and she’s like, “Give me your pizza,” except she doesn’t say it like that.  It’s like, “Give me your pizza right now, okay,” and I was like, “Uh, okay.”  So I was like, my sister steps in, she’s like, “No, you can’t take our pizza.”  She’s like, “My mom would be upset.”  And then she says, “And then what?”  And then my sister goes back and says, “Well, then our family wouldn’t have dinner.”  And then she says, “And then what?”   And so she went through this like litany, and every single time we stated what would happen next, she just stated, “And then what?”  And that was the first time in my life where I realized that once I like outlined everything that could possibly happen and still be okay with the outcome, I gave myself the permission to always say that.  So although it wasn’t the best story when I was 8 years old to have my pizza stolen, now what I say to myself is, “And then what?”  You know, I have to have the little accent.  It was just like, you know what?  At the end of the day, if people say that I’m not in a position to teach or I don’t know what I’m talking about or I’m not worthy to stand on a stage, I say that, I internalize it, and then I squash it and move on.

Tara:  Oh, I love it.  That’s so good.  It also reminds me of the Five Whys from the Lean Methodology.  Are you familiar with that?

Jasmine:  I am not.

Tara:  Okay, so you’ve got … you’ve got a problem that you need to solve, and you ask the question, “Why?”, five times.  You start with a problem, and you say, “Well, why is that?”, and you get to the first reason.  And then you say, “Well, why is that?”  And then you get to the next reason.  And you get … say again, “Well, why is that?”  And so you dig down deeper and deeper and deeper until you actually get to the root of the problem, and I think that’s sometimes helpful with Imposter Complex as well, and that … that’s sort of a … not exactly the same thing, but it reminded me of it.

Jasmine:  No, Tara, it actually is the same thing, except yours is the smart and safe and educated way, and mine is like ghettofab.  It’s like, “And then what?”  It’s like, yeah, same ideology, different practice.

Tara:  Yeah, so everyone can choose which they prefer?

Jasmine:  Do you choose the five whys, or do you choose the chola decision?

Tara:  Exactly.  It is decision-making time.  Okay.  So let’s shift gears a little bit.  Well, maybe not too much.  Your blogs and your workshops and you know, the media that you put out, your blog posts, reach hundreds of thousands of people, and yet, you have a way of making individual people really feel seen and heard and understood.  What are you doing to make that happen?  Are there particular techniques that you’re using?  Is there something that you’re planning for that allows that to happen?  How do you make people feel so heard?

Jasmine:  Well … well, thank you for the kind words, and if I were … Okay, what … what you just described is probably the outermost shell of like an onion, but if you were to peel back all of those layers, the core of this, which is what I teach in my educational courses, both in photography and for creative entrepreneurs, and that is first and foremost, far before you actually think of how you’re going to brand your business or how you’re going to market your business, one of the very first courses of action you must do and create is an ideal client profile.  This is identifying and outlining who the person is that you want to attract, who you’re talking to, and who you serve.  And so for me, I have taken the time, as we navigate into this new business world for creative entrepreneurs, is I have taken the time to outline my ideal client profile.  I know her age.  I obviously know her gender.  I know that she’s married.  I know she has kids.  I know what kind of car she drives.  I know how she spends her weekends.  I know what TV show she watches.  I know what clothing store she shops at.  I know her most recent YouTube search.  I literally went through 40-50 questions that I asked and created for myself so that I completely knew who I was talking to.  I basically Frankensteined my ideal person, and so every time I sit down to write a social media update, a blog post, create content, I’m thinking and writing for her.  And because it’s such a honed idea and version of who that person is, every time I write to her, other people that would identify with my ideal client identifies with the thing that I’m writing. 

And it cuts both ways.  Because I am speaking so clearly to people and they identify and they embrace the things that I’m putting out online, there is an equal proportion of people who cannot stand it.  And I’ve completely subscribed to the ideology of attract or repel.  The more I put out online, I really only want to do one of two things.  I want to attract you into my orbit, or I want to repel you.  I don’t really want to deal with people who I’m repelling, because they are needy, they are negative, and they just don’t get me.  So if you don’t like what I’m putting out on the internet, simply turn and look the other way.  But the people who have drank the Kool-Aid, the people who get who I’m writing to become ardent supporters.  They build a tribe around this, and furthermore, they build communities.  So the core of it is knowing who you’re talking to, knowing what you’re saying, and know how to serve them.

Tara:  Yeah, I love that, and I think you also don’t want to even attract people who are kind of luke warm about what you’re doing either.

Jasmine:  Right.

Tara:  Yeah, because that can really … that can really derail your whole strategy, or strategies even not the right word, but just your response to the people that you want to be serving.

Jasmine:  Absolutely.

Tara:  Perfect.  So one of the other things that the folks here at CreativeLive have said about you is they go on and on about your people skills.

Jasmine:  Oh, God.

Tara:  So I was wondering what are some of the specific things you do to show your appreciation to clients and partners?

Jasmine:  Well, okay, so this is more of like a personal … a personal bent that I’m able to put into my business, but I love giving gifts, but I just don’t like to give gifts for the sake of giving gifts.  I like to give the gift that you know you want, but never really put words around it to put it out in the Universe that that is the gift that you want.  So I’m the kind of person like if we’re having a conversation and you said that like your first lunch pail was like My Little Pony and how you loved it and whatever the case may be, I would probably make a note in my phone that Tara likes My Little Pony lunchboxes, and I … either your birthday came around, if Christmas came around, I would look on my phone and realize, oh, I need to EBay a lunch pail.  And so that kind of gift giving, the kind of like listening in between the lines for what people are saying, to me, is like such … like such an asset for my business, because  when my clients mention that they went … oh, okay, so once, my clients had said that they met for their first date at an Italian restaurant on Melrose in Hollywood, and I just loved working with them, they were phenomenal, and as a thank you gift, I sent them a gift certificate to the place where they went on their first date.  So listening to those small details makes people really feel like seen and heard and personalizes the experience to such a rich degree.

Tara:  Oh, that’s excellent.  All right.  Let’s shift gears a lot now.  Can you tell us who’s …

Jasmine:  Well, actually …

Tara:  Oh, yeah.

Jasmine:  Tara, I have to back it up, sorry.

Tara:  Yeah, no problem.

Jasmine:  I should also mention that you had mentioned Celeste earlier in this interview, and Celeste was a content producer, and we worked together on many courses at CreativeLive, and she would wear a fanny pack, and for the life of me, for this girl from southern California, born and raised, like L.A., Orange County, my whole life, I would be like, “Celeste, a fanny pack, just no.  You cannot wear fanny packs.  I refuse.”  And she just rocked her fanny pack.  She was like, “I carry all my producer supplies in it,” and during our last course, we did some phenomenal things at CreativeLive, and so as a thank you gift, I bought her a designer fanny pack.  I said, “If you’re going to wear a fanny pack, then let me just approve of it,” and so to me, like, those kinds of gifts really kind of just define richer relationships with my friends.

Tara:  That’s so awesome.  Aren’t fanny packs back in style now?  I thought that was a thing.

Jasmine:  Well, actually, if you want to know, they’re not called fanny packs, they’re called like hip satchels or something.

Tara:  Oh, no.

Jasmine:  Yeah.

Tara:  That is awesome.  Okay.  Can you tell us who’s on your team right now?

Jasmine:  Well, my husband.

Tara:  Okay.

Jasmine:  He is like … he’s like the coach, he’s like the umpire, he’s like the sweep hitter.  I don’t even know if sweep hitter, clearly, I’m not into sports.  What is like a bit …

Tara:  Cleanup hitter.

Jasmine:  Cleanup, yes, cleanup.  Yes, he’s a cleanup hitter.  I mean, basically, he’s the whole infield and outfield, and the people in the stands, and somehow, I’m the one holding the bat, and so he’s … he’s everything.  He’s amazing.  Everyone, you know, people on the outside, the brand has become Jasmine Star, and I just referred to myself in third person, which is really annoying, but without him, it just doesn’t exist.  He is … he’s a secret.  He’s a secret sauce that makes everything amazing.  And just recently, as we started this new venture with the Path to Profitability, we brought on an assistant, and she’s been with us for five months, but prior to that, we did everything just myself and J.D.

Tara:  Wow.

Jasmine:  I know.

Tara:  That’s amazing.

Jasmine:  It’s kind of crazy.

Tara:  That is kind of crazy.  Okay, so then that leads me to my next question, which is how the heck do you manage your time?

Jasmine:  I think it’s … I think it’s hard.  When people are … at least it was hard for me.  When I was working, before being able to become a full-time photographer, I would listen to interviews or I’d read interviews and people would talk about their life and their business, and in my mind, I would imagine it to be a certain way, and I think on the outside, social media has a way to distort how things look and feel.  And so people might look at my social media and think like, wow, like she gets to go to yoga in the middle of the day, and while that’s true, what people don’t know is that I wake up like at 4:30 every morning, and I’m going to sleep like at 11:30, and I work all day long.  And I take breaks, you know.  I mean, just yesterday, it was my husband’s birthday, so I only worked a few hours on that day, and so because you work so much, you’re giving yourself the latitude as a business owner to take time where you need it, but how I get it all done is you work long hours and you’re extraordinarily organized.  So it’s ridiculous.  I have Post-It Notes, these large Post-It Notes, and I write down everything that I need to get done in that day, and then I assign a time schedule to my day, and I cannot veer from that time schedule, or else something will fall off my plate.  So when you’re juggling so many balls, everything has to be like with precision.  So this morning, I wrote that we had our podcast interview from this time to this time, and then I was going to take my lunch break, and then I was going to walk the dog, and you know, I even take time to schedule like when I’m going to update my social media.  I mean, it is really ridiculous, but that’s truly how I’m able to get everything done.

Tara:  Yeah.  Are there any other tools that you use in terms of just organization other than Post-It Notes?

Jasmine:  I mean, Tara, come on.  No.  It’s like honest to God, it’s ridiculous.  It’s silly that with technology being the way that it is, I’m still reverting to a ball point pen and multi-color Post-Its, but you know, if it ain’t broke, don’t fix it.

Tara:  Absolutely not.  I mean, I love Post-Its as much as the next girl, so I totally understand.  Okay, has there been any one decision that you’ve made that’s had a disproportionate influence on your success?

Jasmine:  I don’t know if it’s like a singular instance or particular event, but I think that when I decided to say yes, even if I wasn’t in the position to, it changed things dramatically.  The very first time I had a conversation with Chase Jarvis, the CEO of CreativeLive, he randomly called me on the phone and he asked if I wanted to partake in an online educational course, and I knew that I was not in the position, of all the other talented photographers who could have stepped in and did it, they were better and they were more qualified than me, and I still said yes, and I think that that was the first time, and that was in 2010, and since then I say yes.  I say yes to everything, as long as it does not compromise personal time or sanity.  So the decision to make yes has revolutionized my business.

Tara:  Yeah, that’s awesome, and it totally ties back to what we talked about in terms of the imposter complex.  Instead of listening to that nagging voice, you’ve chosen to really say yes.

Jasmine:  Absolutely.

Tara:  Awesome.  So one final question, and this is a … this is a question that I ask almost everybody, and that’s how do you balance the roles of creative and executive in your business?

Jasmine:  I think I’m going to answer this like an executive.  I have to build out time for creativity.  When it comes to being creative, it’s not something that you just turn on.  Like, it’s not like okay, now it’s time for me to be creative, but I build out certain hours of my day, and I know it sounds silly, but practicing yoga and walking my dog makes my mind turn off, and when my mind is turned off, it’s when I can hear and feel and be pushed in the direction that I know my soul is moving in, and so often, when you are just consumed with day in, day out, every single task to do, you don’t give yourself to be creative, so what I have to do is I just have to give myself the space and then the creativity will come.

Tara:  Got you.  And I lied, I have one more question.  What’s next for you?

Jasmine:  Oh, I hope sleep.  I hope sleep is next for me, Tara, I’m not going to lie.  We’ve just been … we’ve been burning the wick at both ends, and buy and large, I’m not one of those entrepreneurs who are like hustle at all costs.  It’s like hustle or die.  No.  There are times.  There are times to hustle, and then there’s times to revel in your hard work.  Right now, we’re in like the hustle mode, and it’s hard and it’s stressful and you feel, like, awkward, and I feel like people are looking and seeing whether or not this new venture of mine will succeed, and I … I don’t know, it’s just like a crazy … it’s a crazy point in time.  So what’s next will be to finish this, to sit in it, and to enjoy, and then kind of create things for creative entrepreneurs that feed back into the Path to Profitability, and the only way that I can create that content is how we started the conversation, is listening to the pressure points of people and then answering and fulfilling their desires.

Tara:  Absolutely.  Absolutely.  Well, Jasmine Star, thank you so much for joining me.

Jasmine:  Thank you so much.  I appreciate it.

Tara:  Jasmine’s CreativeLive boot camp, The Complete Wedding Photographer Experience, can be found by going to CreativeLive.com/photography.  You can find out more about her new venture by going to ThePathtoProfitability.com.

That’s it for this week’s episode of Profit. Power. Pursuit.  You can download other episodes of this podcast, and subscribe in the iTunes store.  If you enjoy what you heard, we appreciate your reviews and recommendations, because they help us reach as many emerging entrepreneurs as possible.  Our theme song was written by Daniel Peterson who also edited this episode.  Our audio engineer was Jaime Blake.  This episode was produced by Elizabeth Madariaga.  You can catch up on older episodes in the iTunes store, where new episodes are added every week, and you can learn more by going to CreativeLive.com.

Wait! Before You Start Your Next Big Project…

What follows might be the most apolitical thing ever written about American health insurance reform. What follows might also save you a lot of heart ache, time, and money on your next product launch.

To my mind, there is nothing worth building that should be built all at once.

That’s what really stunned me about the roll out of health insurance reform in the US. Politics aside, the company building the website–the primary interface for the reform–should have known better than to try to build something so complete all at once.

This was especially true here in Oregon where the state government went all in. Cover Oregon wanted to be the most complete, most comprehensive health exchange in the nation. They invested millions of dollars in a really great, you-know-you’re-in-Oregon-when marketing campaign.

The intention was great. (Sound familiar?)

As of January 1, they had not enrolled a single customer via the website.

Everything that serves, everything that has value, everything that has a message worth sharing has been built in pieces. Test upon test upon test. Ideas, features, details all carefully fashioned together one at a time.

Sculptures, transformational programs, jewelry collections, menus, books… all reach their fullest potential when they are reduced to a single this-is-what-really-works element. And especially when that element is not just what the creator wants to create but what is created to delight the customer.

Bottom line:

Don’t try to build something all at once.

Don’t let your ambition, your vision, or your perfectionism side-track the proper development of your idea.

Silicon Valley figured this out a long time ago, relatively speaking. It’s the essence of Lean Startup mentality. Build. Measure. Learn.

It’s why your new favorite app doesn’t actually do everything you’d like it to do (they’re working on it).

When you launch something all at once, you have to stop at “Build.” You have no time (or data) for measuring. You have no energy (or experience) for learning.

When Megan Auman sits down to design a new jewelry collection, she doesn’t try to create the whole thing at once. It starts with a single piece, even a singular idea. Maybe it’s a change in the way she designs the shapes, maybe it’s a shift in the way she composes the metals.

She plays. And then she completes… something.

What she does next is extremely important: she wears it.

She takes it for a test drive. She starts to understand how it feels, how it changes the way she dresses, how it attracts compliments and “gotta have its!” That’s solid data to measure.

Then she learns and adapts. Each piece that derives from the initial prototype is a new iteration on that single idea. She constructs each piece knowing that it’s built on a proven idea.

All to often I see people with brilliant ideas spending too long trying to realize the full brilliance of their idea. Businesses that bring truly valuable things into the world know when to stop and analyze.

It’s a leap of faith.

A big one.

But it’s one that pays off in the long run.

It’s a little light bulb that goes off and says “this is enough.” For now.

Before you embark on your next big project or idea, remind yourself to look for that first stopping point. Quiet your perfectionist’s brain enough to hear when a potential prototype is whispering to you. Challenge yourself to think beyond big and, instead, reach for small.

So before you being your next big project, figure out the small thing you’d like to accomplish first.

uncertainty, agility, failure, and the bets that will make you a success – or – how to have your art, analysis, & cake and eat it too.

I have often felt like a creative freak. I am not left-brained (metaphorical not physiological) enough to create detailed plans for ideation & exectuion. I am not right-brained enough to feel artsy fartsy and anything-goes-about creativity.

When it comes to my business, I am comfortable figuring out how things work, what you need from me, and when my strengths truly shine over time instead of all at once.

I am a Virgo but I’m not a traditional perfectionist.

I am analytical but not obsessive.

I am innovative but not overly imaginative.

Frankly, I’ve felt like I was doing everything wrong even when I was having great success.

Shhhhhh. Don’t tell. They’ll find out.

Which is why I’ve been stoked to find books on this very subject dropping in my lap over & over again recently. If you’ve been hiding a similar style because you thought it was “wrong” or it just didn’t fit with the paradigms on display, you’re in luck.

There are more of us than we thought, for sure!

I believe we all have a lot to learn from each others creative styles. But I also believe that this blend of art & analysis is an asset in the fast-paced, conceptual age we are currently navigating (and continuously designing).

Embrace uncertainty.

Settling on (or worse, waiting for) your “big” idea is a waste. Not even the venerable Mr. Jobs waited for his big idea. The big idea is a process – not an epiphany.

Which means that you need to get comfortable with “not knowing” more often than not. This is not about a lazy, post-modern denial of Truth. It’s about profound possibility. When you acknowledge that you don’t have the answers you’re more open to all the opportunities available to you.

Jonathan Fields just released the definitive book on this subject, aptly titled, Uncertainty:

The more you’re able to tolerate ambiguity and lean into the unknown, the more likely you’ll be to dance with it long enough to come up with better solutions, ideas, and creations.

Achieve failure.

I recently shared with an interviewer that everything I do is a mistake. On purpose. Positively.

When you realize that every service you offer, every product you create is likely to have something that you will learn & grow from, you start to become comfortable with putting great value into the world in the form of mistakes. You can do it better next time and still be happy with the “great” you are creating today.

When you’re focused on perfection instead of value, you lose sight of what is important to the recipient of your product or service. You lose sight of what’s truly important to you.

And “failure” is becomes discouraging if not paralyzing.

When you’re focused on value, on understanding what constitutes money well spent or energy best transferred, failure is a bridge to greatness.

Eric Ries discusses this at length in The Lean Startup as it applies to business:

Even when experiments produce a negative result, those failures prove instructive and can influence the strategy.

Place your bets.

At each part of your creative process, you’re testing assumptions and [dis]proving hypotheses. You do this for yourself constantly. Yet, you probably try to avoid this when bringing ideas to market, presenting them to your audience.

But it’s placing your bets – publicly – that will truly tell you what to do next.

It’s not enough to make a thousand private mistakes. You need to put your ideas to the test with others: a list, a network, a mastermind, a focus group.

Keep your larger goals – the higher stakes – in mind and smaller mistakes will remain in context.

In Little Bets, Peter Sims dissects this strategy:

Experimental innovators must be persistent and willing to accept failure and setbacks as they work toward their goals.

Or if betting on the product of your creativity is a little too Vegas for you, think of them as proposals.

Proposals are new, sometimes radical, most often completely unproven. Roberto Verganti outlines this in his book Design-Driven Innovation:

These companies are instead making proposals, putting forward a vision. That is why I call this strategy design-driven: like radical innovation of technologies, it is a push strategy.

These proposals, however, are not dreams without a foundation. They end up being what people were waiting for, once they see them. They often love them much more than products that companies have developed by scrutinizing users’ needs. These proposals are wellsprings for the creation of sustainable profit.


When I think about agility, the image that comes immediately to mind is jumping back & forth over mid-line of a basketball court. Back & forth, back & forth.

Strength. Quickness. Reaction. Response.

Muscle movement happens fast & furious. But not without a thousand tiny course corrections happening even faster. Lest you fall over.

Agility is one of the most important physical skills of an athlete. It’s the rigorous combination of physical and mental performance.

Agility in business is the same. It’s shifting priorities. It’s responding to true urgency and not reacting to perceived urgency.

Agility is empathizing with customers and analyzing your numbers – then doing something about it.

You can achieve an environment of agility when you get cozy with uncertainty, embrace failure, and place bets.

That’s an environment for not only financial & entrepreneurial success but creative success. It’s self-fulfilling.

How are you creating an environment of agility in your business right now?

there is no recipe: your great work is a process not an epiphany

I do business much like I cook.

I was reminded of that this weekend at The Creative Connection Event in St. Paul, Minnesota. I took a cooking class with Terry Walters, author of Clean Start. At the beginning of the class, she reminded everyone that, while measurements appear in her books, she never cooks by measuring. We shouldn’t either.

Oh, and the ingredients are just a guide. Don’t have something? Substitute something else.

Really, the whole recipe is just a template for your own creations. Get creative. Try new flavors. Mix it up.

Too many people are looking for a recipe for business success. They want to know exactly how much of this and exactly how much of that it takes to create a 3 course meal of profitability, sustainability, and life fulfillment.

I’m a business coach – not a consultant – because I know that’s not how it works.

Business is about using what you’ve got, trying new things, and seeing how it comes out at the end. That’s not to say that you don’t consult the recipe binder or make a trip to the farmer’s market. But you don’t let small hang-ups or unexpected events ruin your dinner.

You learn a framework that allows you to create success for yourself with as many different ingredients and in as many different environments as possible.

The three pillars of my business framework – my recipe – are passion, profit, and productivity.

Passion you get. That’s why you’re here. Even if you haven’t discovered what moves you to work at 3am or to forget about the passage of time, at all, you sense that “great work” is out there. That your heart is calling to you.

Profit you get, too. She may not be your best friend yet but you’re certainly her Facebook friend. You understand that being in business means making money above and beyond your output.

Productivity is often the missing link.

Productivity in cooking is making breakfast, lunch, and dinner 365 days per year. Maybe you don’t cook all of those meals – but you cook day in & day out. You feed yourself daily. You know what to do when you’re hungry.

My idea of productivity is not that kind that comes on a micro level. I believe the missing link between passion & profit is actually producing the things that you put on the shelf to sell.

Literally, the manner in which you make products.

Productivity in business is not about answering 5 hours worth of email in only 3 hours. Productivity in business is about producing – innovating – creating without end. It’s not once & done. There is no finish line to cross. It’s continuous and constant.

All too often, I hear about passionate people who long to become passionate entrepreneurs but they are too busy struggling with the hows and whats of producing a final product that they never produce anything at all. They wait for the illusive “great idea,” they pine away for the perfect process, they linger at each stage of development to make sure it’s “just right.”

But the final product isn’t an ending point. The final product is the jumping off point.

Once you’ve got a final product – something you can bring to market – created, it’s your job to discover what it’s missing, what is unnecessary, and what can be improved. Then you create the next final product, and the next, and the next.

You can’t get to the awesome thing until you produce the great thing and you can’t produce the great thing until you produce the good thing.

Productivity is not just making more stuff, but systematically figuring out the right things to build.
– Eric Ries, The Lean Startup

When you believe there’s a right way or a wrong way to make the dish, you get stuck in the recipe. You measure out the right ingredients and you ignore the opportunities to get creative or try something new. You fixate on making everything come out just so.

Just as in cooking there is no perfect dish, in business there is not perfect product or service. Stop waiting until you think you have all the ingredients necessary and start working on the recipe right now. Pay attention to opportunity, chance, and possibility. Allow them to inform your work.

Your great work is not an epiphany, it’s a process.

what’s your hypothesis? making the art business a science

You didn’t go to business school. You don’t have an MBA. You don’t run a tech startup. The only “C” in front of your title stands for “cook” or “cleaner.”

You’re an artist. You may not use paint or stone or metal. You may not sing or dance or write. But your work is an art and your passion changes people. And you, my friend, have taken this art and turned it into a business.

What could your business – one that’s based on soul stirring, passion inducing work – learn from the science of creating corporations? Turns out, a whole helluva lot.

Your business is here to prove something.


  • that great writing changes lives & leads to more sales.
  • that elegant jewelry boosts your self-confidence and takes the pain out of the morning routine.
  • that quality materials & craftsmanship really are worth the big bucks.
  • that creative expression saves lives.
  • that great design tells a story that words & pictures alone cannot.
  • that a well-decorated home keeps a marriage happy & healthy.
  • that a New Economy can be built around artist-business owners.

Yes, indeed. Your passion comes from your undying determination that part of your worldview is a Truth for many others. Your productivity comes from the resolve to share that with as many people as possible.

But, like any hypothesis, it’s not simply enough to state it. To deem it so.

Your business hypothesis must stand up to scrutiny, experimentation, analysis, and… dun dun dun… customer feedback.

Your hypothesis isn’t an excuse to put on your dreamer hat and sit in the corner while the MBAs play at profit. Your hypothesis is what gets you into the trenches and compels you to do business.

People don’t by WHAT you do, they buy WHY you do it.
— Simon Sinek, Start With Why

In starting businesses, we are most often concerned with what product we’re going to sell or what service we’re going to offer. It’s easier to understand the transaction when you know what’s changing hands. But it’s not the particular service or product that creates crowds of loyal fans. It’s not the product or service that spurs us to innovation & creative thinking.

It’s stepping outside the this-for-that exchange and stepping into something bigger & more powerful: our vision for the world.

Startups also have a true north, a destination in mind: creating a thriving and world-changing business. I call that a startup’s vision.
— Eric Ries, The Lean Startup

Business starts with a vision. The vision inspires a strategy. The strategy ends with the product or service being sold.

You can’t know what you’re selling until you know what you’re trying to prove.

To prove your hypothesis, you must experiment with a plan. Build, measure, learn.

Eric Ries, author of the brand-new book The Lean Startup, explains this process in depth. It’s a constant cycle of innovation & iteration that has at its goal creating a product/service that works to prove your hypothesis and achieve your vision while serving your customers.

This is true startup productivity: not just making more stuff, but systematically figuring out the right things to build.
— Eric Ries, The Lean Startup

How do you test the hypothesis? How do you figure out the right things to build?

Eric suggests the Build-Measure-Learn feedback loop. That’s a fancy (or not so!) way of saying: do it, discover what happens, and figure out what it means.


Sadly, the first step is where so many get stuck. Without a clear hypothesis, it’s hard to know what to build. Of course, “knowing what to build” is truly overrated.

The first few times through this loop, it’s not your job to know what to build. It’s your job to learn what to build. So we start somewhere.

Back when I started growing my business in earnest, the first product I created was 52 Weeks of Blogging Your Passion. It’s an ebook with 52 blogging prompts. Not fancy. Not overly sophisticated. Just a response to what I perceived as a need.

I didn’t stress about making the most comprehensive product or making the snazziest design. I built a product it and I shipped it. That’s when the real work started.

While you’re “building” consider:

  • Am I wasting time on details that don’t enhance the benefits of the final product?
  • Am I wasting energy on making the product more comprehensive than is necessary to test my hypothesis?
  • Am I wasting attention on tangential pain points that are unrelated to the product I’m currently building?


In the tech startup world where The Lean Startup was first developed, there are loads of customized metrics and formal experiments that can be run with the data from the first (and subsequent) product builds.

I would argue these sophisticated methods of measure are a distraction to the microbusiness owner.

Forget the percentages, click thrus, and dollars, and focus on what your customers actually tell you about the product. Consider not only the specific feedback but the tone of their words, the setting of their usage, and the community of users.

After releasing my 52 Weeks of Blogging, I got customer feedback. It was good. But it’s not enough to just revel in good feedback. Ask WHY? I probed deeper to find out how people were actually using the book and what questions remained for them. That process then lead to several other books and a course.

Measure the effectiveness of your product by considering:

  • How is the customer using my product?
  • What results is she achieving?
  • Is she closer to believing in my greater hypothesis?
  • What themes are emerging about the product I’ve built?


Learning is all about figuring out what you’ll do differently next time. If you thought building your product was the end of the production phase and the beginning of the promotion & PR phase, boy, were you wrong!

Production is constant. Learning helps you know what to produce next. What tweak to focus on. What features to improve. What about-face to make.

Each time I build a new product, I learn so much about the people who purchase it. I learn things from the metrics, of course, but I also learn from their reviews. Their frustrations. And their questions. I build those questions & frustrations into subsequent products, blog posts, and emails.

I engage buyers via social media and create conversation around these areas. I build a bigger & bigger picture from my learning so that I can act & produce based on what I’ve learned.

Learn about your product or service by taking the feedback you’ve gathered & measured, comparing it to your initial hypothesis. Contrast your actual customers’ reaction with the way you thought they would react. Compare their concerns with what you feel to be true.

And then build again.

While in the learning phase, consider:

  • What assumptions did I make that proved false?
  • What surprised me about the customer feedback?
  • What could be eliminated from the initial product?
  • What needs to be added to the product?

Just as scientific experimentation is informed by theory, startup experimentation is guided by the startup’s vision. The goal of every startup experiment is to discover how to build a sustainable business around that vision.
— Eric Ries, The Lean Startup

Bottom line: to effectively change and grow, your business needs to be plugged in to your vision for the world and the hypotheses you hold true.

Forget discovering what to sell and who to sell it to until you’ve got those details ironed out.