Updated: Apr 27
The first episode of Pollen is HERE!! Get ready, Creative Entrepreneurs. We are diving right in! In honor of launching this brand new show, Diana is giving away a FREE 90 min Biz Clarity Session with her if you enter her giveaway this week. You definitely don’t want to miss this. See below or press play for the full details on how to enter!
Being a Creative Entrepreneur and building the business of your dreams is quite the journey. But stay grounded! Recognize if you’re burnt out and overworked. Charge the rate that feels integrity to you — don’t just take any pay you can get. It’ll be a long road, but one worth walking.
In this pilot episode of the Pollen Podcast, Diana Davis talks about her journey from growing up on a ranch, to moving to New York without a job, to developing her creative brand, Diana Davis Creative. She imparts how she picked herself up after being laid off from a corporate job and earned her first six-figure income as a full-time creative entrepreneur. Lastly, Diana shares how to recover from burnout and other struggles of a creative entrepreneur.
If you’re interested in becoming a creative entrepreneur or are already building/growing your biz, this episode is for you!
Start your own creative entrepreneurship story and get on your path to clarity, taking action, and gaining professional confidence and profit in your creative pursuits. Join Diana’s 90-day group course Camp Clarity and learn everything you wished you knew: how to land dream clients, harness the power of social media, and make the money you deserve. Learn more here.
🔥Here are three reasons why you should listen to this episode:
Understand the power of networking in building your personal brand.
Learn how you can bounce back from burnout and have FUN building the creative business and life of your dreams!
Discover why YOU are your brand's biggest and safest asset.
In honor of launching this show, I am giving all of you a chance to win a totally free 90-minute Biz Clarity session with me ($750 value)! Here is how to enter:
1. Listen to an episode or two!
2. Subscribe/Follow the show on Apple Podcasts and Spotify.
3. Rate the show + write a review on Apple Podcasts.
4. Share a takeaway or a screenshot of the show on Instagram and tag @dianadaviscreative, then DM me the word “pollen”
If we break the top 100 this week by all of you following these steps I will be giving away TWO private coaching sessions. LET’S DO THIS!
Achieve the life, career, and clients you’ve always wanted (and fully deserve!). Sign up for Diana’s Camp Clarity Course
Access other courses from the Diana Davis Creative
[03:47] The Birth of the Pollen Podcast
The Pollen Podcast is Diana’s creative outlet.
Creativity does not have to make sense to be beneficial to businesses.
Diana had reservations about naming it “Pollen Podcast” because it may be unclear and unsearchable.
Diana: “We are [like] pollen floating in the wind. We are not on a linear journey. It’s something that takes a tiny little seed and blooms unexpectedly. That’s what creative entrepreneurship is to me.” - Click Here to Tweet This
Like this podcast's name, your outlets do not have to be logical all the time.
[09:07] Humble Beginnings
Diana grew up on a cattle ranch in a town of 500 people.
She was greatly inspired by her hardworking parents, from whom she learned good entrepreneurship values such as work ethic, appreciation for life, and hard labor.
[16:31] Diana’s Interest in Photography and Personal Life
Diana went to Montana State University and studied graphic design.
She was interested in photography but believed that there was no money in it. Despite this, she took a minor in photography.
Eventually, she got minor photography gigs and started making a profit.
Diana was married at age 20 and got divorced at age 24.
[18:51] The Move to New York
Diana relocated to New York without a job or a plan. She applied for a slew of jobs, all to no avail.
She went to LinkedIn upon her brother's advice and connected with people in companies she had a remote interest in, to which only 20% replied.
Diana invited those who responded to coffee dates and inquired how they got where they're at in their careers.
[22:28] Diana’s Experience at Time Inc.
Diana met with Mike from Time Inc., who eventually offered her a freelancer job, on one of her coffee dates.
She learned about print production while working as a graphic designer in Time Inc.'s native advertising department.
Diana was eventually promoted to art director after two years.
[26:30] Leaving the Corporate Life
Salary used to be kept “hush-hush,” and asking about it was considered inappropriate in the corporate world.
Diana asked for a raise when she became art director at Time Inc. However, there was a lot of “douchebaggery,” including empty promises and misogyny. This was her deciding factor in leaving the company.
Another company hired her for twice as much. After four months, she was laid off. This began her journey as a creative entrepreneur.
[31:12] The Start of a Creative Entrepreneur’s Journey
Diana was invited to a Six Degrees Society event, where she was encouraged to become a full-time entrepreneur.
She went all-in on photography and graphic design.
She started by networking with and photographing, women in wellness.
Her initial clients were mainly collaborations to build her portfolio and establish her name in the industry.
Diana: “I do not believe in free work. This was not free work; this was an energy exchange, just like money is an energy exchange. I was getting something out of it that was worth it to me.” - Click Here to Tweet This
[34:43] Diana’s First Six-Figure Income
In her first year as a full-time creative entrepreneur, she was already earning six figures.
Try out different jobs. Take on other jobs — even those you don’t want. This allows you to see what you like and don’t like.
After two years as a full-time creative entrepreneur, Diana was burnt out.
Many entrepreneurs don’t talk about burnout because they do not want their clients to see that they don’t have it all together and figured out.
[39:17] Seeking Coaches and Becoming One
Diana got herself a coach to deal with her struggles as a full-time entrepreneur.
She learned about other revenue streams like photography and mentoring in her coaching sessions.
Diana started providing mentorship to other entrepreneurs, and she was able to build her name as a coach.
As a result, people came to her even though she had yet to announce her programs.
[46:19] Creating Camp Clarity
She built her brand, Diana Davis Creative, where she created her first-course camp: Camp Clarity.
The camp is designed for entrepreneurs who have difficulty with entrepreneurship fundamentals like pricing their services, feeling guilty for charging for their services and presenting their brand confidently on social media.
Creative entrepreneurs have heart-centered gifts that they want to offer the world – and make money while doing so.
The camp was a $39,000 launch.
[48:32] Knowing Your Worth as an Entrepreneur
You have to know and believe in your work for your clients to believe in you.
Everything has to do with the calibration of self — your vibration, belief, and strategy.
Diana: “That is my winding road — from ranch kid to divorced, to Manhattan entrepreneur, to Colorado business coach nomad. I’m so excited to see where it goes from there. I'm so excited to see where this goes from here because I know we're not solidified… There's so much more for me, and I truly believe that, and I believe that for you too.” - Click Here to Tweet This
Enjoyed this Podcast on Creative Entrepreneurship?
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Thanks for listening! If you’re ready to land your dream clients, make money running a business that lights you up, and live a life that you love, you’re in the right place. Stay tuned to my website for more episode updates and other exciting programs and resources.
Get ready for the inspiration and motivation you’ve been looking for!
Diana Davis: I didn't get a job before I moved, I had to just take the leap, and I think that's a big lesson that you'll hear on this podcast for a lot of different entrepreneurs is that we don't always leave the job when we've replaced the job’s income with the side hustle. A lot of times, we have to actually take a really big leap off the cliff and just know that we can trust ourselves.
Welcome to Pollen, the podcast for creative entrepreneurs. I'm your host, Diana Davis — multi-passionate creative, business coach, Gemini, Manifesting Generator, matchadrinker, and travel junkie. I'm also the founder of Diana Davis Creative, where I went from a six-figure photography business to coaching creative entrepreneurs like you. If you want to have a career and a life you love, you're in the right place.
On this show, I'll be coaching on all things creative entrepreneurship, and you'll hear stories from fellow creative entrepreneurs that will show you it is possible to do life the way you want to. They'll share the nitty-gritty of their journeys — like the real shit — and how they are doing it differently. I'm stoked to have you along on this journey. Let's go!
Before we get into this episode, it would mean the world if you could take these four steps to help me in celebrating the launch of the Pollen podcast. By doing this, you're also entering to win a 90-minute business coaching session with me for free. I know — totally insane, such an amazing opportunity. Here are the four steps: number one, listen to an episode or two. Number two, subscribe or follow the show. Number three, leave a rating and a review. Number four, share your thoughts on the show on Instagram and tag me @dianadaviscreative. For everyone who completes all of these four steps and messages me the word “pollen”, you will be entered to win a private coaching session with me.
Now listen up. If we break into the top 100 in our category by all of you collaborating and lifting this up — by listening, subscribing, and reviewing, I will give away two private sessions with me. I cannot wait for you to listen and learn so much on the show. Join the party and help us in hitting some pretty big freaking milestones, by subscribing, reviewing, and sharing. What are you waiting for?
Holy frickin moly, this is happening! The first episode of my podcast — I have a podcast. You all, this has been a little tiny seed in my heart for literally over a year. Just goes to show you things don't happen overnight, and you can have something on your cosmic shopping list — if you don't know what a cosmic shopping list is yet, we'll be talking about that in further later episodes. But you can have something on your cosmic shopping list, and it doesn't have to happen tomorrow. Thank you for being here on The Pollen podcast. I hope you get so much out of this.
For me, why did I start this Pollen podcast in the first place? Well, honestly, a creative outlet, which all creatives need. Something that has no pressure, it's not a big deal, it's not to make any money, it's just to see what comes out of this beautiful microphone, out of the beautiful speakers on your end and see what the universe has in store for this. So thank you for being on this journey with me. As I say, let's see where the wind takes us. Okay, let's start with this name — Pollen.
I am one of those people that if I'm going to cut my hair, I'm going to ask 50 people their opinion — and usually go with my own opinion, the one I had from the very start, my gut, every time. But somehow, I need to source some external, not even validation, just like opinions which sometimes is really unhealthy. You get too many cooks in the kitchen, right? But maybe that's the Gemini in me, kind of pollinating all the flowers and meeting different opinions.
When I was going to name this podcast, first of all, I went to my amazing copywriter, Kirby Kelly — she's been with me forever, a good friend, she's epic. If you need her info, please DM me, I will set you up. She is incredible, and she is the one who came up with a bunch of names for me for this podcast. We had a lot of really logical things. We were going to call this Creative Revolution, we could have called this The Podcast for Creative Entrepreneurs.
But something felt so direct and generic about that. As a creative, I am all about doing something unexpected and doing something that doesn't really make sense. It's so fun to be a creative who is also a business coach because I do a lot of things that don't make sense, but it works for my business. That's what I really encourage other creatives to do.
When we came up with Pollen, it was like, “Ooh, that’s sexy.” But I had so many people saying, “I don't think it makes sense. I'm not sure what that would really make me think it was a podcast about. I have no idea it's about creativity or entrepreneurship. It doesn't even have those words in the name. It's not actually searchable. This is not a logical decision.”
Then, I called my mom who knows me really well, who knows that my heart of hearts wants to wear the bright orange pants and the iridescent jacket, that my favorite color is yellow, that I love bright pops in nature, and lemons, and all of this fun stuff — and my branding really reflects that if you go check it out on my website, Diana Davis Creative.
When I told her about Pollen, of course, she could also sense the excitement behind it — so that really mattered, so we can't say this was unbiased. But she was like, “Yes, I can picture that.” One of my favorite flowers is the little yellow Billy Balls, and that's kind of what I picture when I picture Pollen, and just the idea that we are Pollen — actually like floating in the wind. We are not on a linear journey, and it's something that takes a little tiny seed and blooms unexpectedly. That's what creative entrepreneurship, to me, is about.
Then, we can go into all the analogies of the hive, and the bees, and the team, and the community, and all of it. I just love the visuals, I love the vibe. I wanted to give you a little background behind the scenes of actually creating this name because it wasn't logical, and your story doesn't have to be logical either. Going with your gut, it's the vibe. So here we are, The Pollen Podcast. I'm so stoked.
The people who have really heard it so far are like, “Yes, I know exactly what that means. It's a vibe.” It's kind of like a, “If you know, you know”, type of thing. Thank you for being here, thank you for being an OG listener, thank you for being in the inner circle in this community. Community is a huge core value of mine. I am beyond honored for you to want to spend your time here because that is your most valuable asset. Alright, let's get into this first episode, shall we?
I am going to be talking about a lot of entrepreneurs and talking to a lot of entrepreneurs. But I figured you probably need to know my story first — being a creative entrepreneur myself so you have a little bit of background if you don't know me already. If you do know me — hello, come say “hi”, let me know if you listened, And maybe you'll learn something you didn't know. So who am I? I am Diana Davis. I grew up outside a town of 500 people on a ranch — a cattle ranch to be exact. Yes, my dad is a cowboy, my mom is a ranch hand — or was.
They are the hardest-working people I have ever met. Part of me has such an old soul, part of me has a very neon-millennial soul as well. But the old soul in me — it does hurt a little bit when I see how much we don't use our hands anymore, and how hard people like my parents had to work for what they earned. I think they took a lot of pride in that, and I think they really enjoyed getting their hands dirty. I hope you're on this journey with me for a long time because I really believe at some point, I will be getting my hands dirty again too in a very creative, messy, tangible way. We'll see what that looks like in the future.
But just giving a little background of my parents truly being entrepreneurs — that was modeled to me from a very early age. I saw my dad quit a very cushy job as a lineman for the city of Colorado Springs because he was burning out, and it wasn't healthy for him anymore. He was missing out on his family and missing out on a dream. He didn't have this ranch handed to him. My parents bought it — it wasn't a family-owned ranch, they created this thing from scratch. What an ecosystem a ranch is. I would love to hear from you if you're a ranch kid — like come say “hi” please because I get it.
There's so much to it, and I really believe I learned so much of my work ethic and my appreciation for life, and how things work in nature, and soil, and hard labor, and also following your heart. My parents are very spiritual people — call them even woo-woo. If you're familiar with the Farmers’ Almanac, they actually do things on their ranch, which we don't have anymore. But they do things for their animals and for crops, and for anything really, according to the moon, and the phases, and the stars. It's actually pretty scientific, but a lot of people think that's really woo-woo.
Even things like — I'm just going to spout a few woo-woo things from the ranching world — well witching, which is literally going over the ground with a willow stick and it telling you where water is in the earth just by it kind of bending, and only certain people have this gift. They're like cowboys, like rough and tumble old dudes who are witching these wells. It's so cool.
As I am getting older — I am 31, I'm realizing how much we all have in common because I kind of went from this very Christian upbringing world to refinding my own spirituality, getting into oracle cards and spirituality, and crystals, and the Earth, and the moon, and the stars, and back to the basics versus this man made stuff, and realizing my parents had that all along — I just wasn't paying attention.
That's kind of my upbringing — a town of 500 people, and not even in that town, outside of it. Then, I moved when I was 15, but to another town — very small, a metropolis of 750 people this time, in Northwestern Colorado into the mountains. We lived at a place that was 8500 feet in elevation — the winters were wild. Again, if I had seen my parents work hard before, then I had never seen them work harder.
I think a huge part of my story also — and this is where a lot of you won't know this if you already know me — is that I've kind of developed this really hard shell because of ranching life. There's a lot of death, there's a lot of life, there's a lot of hardship, and there was also a lot of injury. Actually, literally in my family, I would get calls more often than I'd like to admit, saying like, “Hi, your mom's being Flight for Lifed to Fort Collins. She's okay, but she's going to be in the hospital for a while or whatever.” I'd be like, “Cool. Should I still go to school? Should I go to work tonight? What's the plan?”, where most people would freak out.
That was just pretty normal for us because ranching can be very volatile. You're dealing with live animals, and they're pretty unpredictable sometimes, and crazy weather, and all of that. That kind of made me have a little bit of a hardcore shell, which I've really had to come out of in the last few years — really start to get vulnerable and let people in again, and let myself feel emotions, and feel hurt, and feel loss, and celebration, and all of the above — and it's this beautiful evolution. I think our evolutions mimic nature so much.
My good, good friend who will absolutely be a guest on this podcast, Nicole Wild, who is a yogi and a meditation teacher, always talks about how the leaves fall off the trees and how the trees don't try to keep them. Can you imagine seasons, and seasons, and seasons of dead leaves on the trees always while the new ones are trying to come in? No, they shed and they regrow. They shed everything and allow themselves to detox, and then grow something new, which I think is so beautiful, and we all do this.
We didn't even know this conversation was going to go there, but you can get a taste of that. There's going to be some “woo” in this podcast, there's going to be some spirituality, and there's going to be a lot of strategy, and a lot of just really raw real stories. Let's fast-track this story a little bit. I went to school in Montana — Bozeman, Montana. Shout out! I know a lot of you are listening.
I went to school for graphic design and photography. When I was 16 in Colorado, I actually started professionally photographing weddings with my cousin who was a professional photographer and a bit older than me — she mentored me in that. So I had been photographing professionally and making money on that since I was 16. So I decided to go to school at MSU (Montana State University) for graphic design actually, at first. I thought photography wasn't feasible. I was like, “Good luck to all of you trying to get into galleries.” Besides wedding photography, what do people pay photographers for? Instagram was not a thing at this point.
I went to school for graphic design. True Gemini, true Sagittarius Moon — I transferred twice, both for men, I'm not even going to lie to you. I'm not necessarily proud of that. I was very easily swayed in a lot of ways, which I have worked on for a lot of my life. Now, I feel very solid and coming from my own power. So here's to your 30s, it's an amazing time. But I actually finished school there.
I actually got married when I was 20. This is also something I'm just starting to talk about. I was divorced by the time I was 24. I would not trade that experience — I learned so much, and it feels like I've lived 50 different lives. But that was a big part of my story. That's also a big part of this shell that I've been breaking out of in the last few years as well. Here to talk about that and normalize that as well. After I got divorced, and I graduated college, I decided in college — so back up for a second — to get a minor in photography, just for kicks, because I was a year behind because of the transfers, decided, “Let's just get that photography minor just for kicks.” Hilarious because I then became a professional photographer several years later, full-time.
After I graduated, after I got divorced, I moved to New York — New York City, that's my soul city, probably always will be, it really has my heart. It is kind of an abusive relationship — I won't lie to you. It's no joke — if you know, you know. Shout out to my New Yorkers, right? I moved to New York, with literally no job, no plan. Before I had moved to New York, I had been applying for jobs, trying to get a graphic design gig or work for an agency, or something. You know the deal, it goes out into the abyss — your application — especially with big corporations in New York City.
My brother who is and was a recruiter, he actually told me to get on LinkedIn. This is technically my first social media success. He told me to connect with anybody at any of the companies that I might even be remotely interested in. I got on LinkedIn, and I said, “Connect, connect, connect, connect”, and maybe 20% of those people actually connected back with me, and to those people, I messaged them and just said, “Hey, here's my situation. I'm coming in from Bozeman, Montana. I'm a graphic designer. I'm trying to move there with a job, but this is hard. I'm putting my application out into the abyss.”
I didn't ask them for anything, I just asked them their story. So I said, “I love your resume, your story sounds really intriguing, and you're working for companies that I'm really interested in. I would love to just connect and hear how you got where you got.” Basically, this podcast is a lot about that. I'm going to be interviewing people about that specifically — so full circle. Maybe 20% of those people responded.
But the people who did — shout out, Mike Churcher — were amazing, and just really there to help. I didn't get a job before I moved, I had to just take the leap. I think that's a big lesson that you'll hear on this podcast for a lot of different entrepreneurs is that we don't always leave the job when we've replaced the job's income with the side hustle. A lot of times, we have to actually take a really big leap off the cliff, and just know that we can trust ourselves and that we are our own best asset, our own best bet. That's what I did.
I moved to New York City, I had never met my roommate, I had never seen my apartment, I had never been to the Upper East Side. I got a taxi from the airport with my three suitcases and showed up on the doorstep. That began my journey. Then, I started reaching out to everyone I had connected intimately with on LinkedIn and said, “Hey, I'm here. I'm in Manhattan. Can we get coffee?” I went on a coffee shop dating spree.
Long story short — long story also long — I met so many amazing people, so many amazing people to just give me their advice, and like really take the time to help me out like a mentor. Eventually, I met Mike Churcher of Time Inc. If you're not familiar with Time Inc., it is unfortunately no longer — it still exists, but it's just been bought out and acquired by several different companies. But at the time — no pun intended — it is the company that created Time Magazine, Real Simple, Fortune, People, Sports Illustrated, Travel and Leisure, Food and Wine — and I met Mike Churcher in the Time & Life building in Midtown.
If you've seen the Secret Life of Walter Schmidty, that's the building he works in — I'm pretty sure. We just had a conversation. It wasn't like an interview, and I think that's what was so beautiful about it. Take all of these as little notes of like, “Oh, yeah, I can just have conversations with possible clients or people I'm going to hire — and just be a human instead of having this really stagnant, structured thing where we have to intimidate each other.” We can just have a conversation, and it can be a two-way street.
We had an amazing conversation. He said, “I love that you have photography and graphic design experience. I think we can find a place for you as a freelancer, and let me get back to you.” I'm here to talk about numbers, I'm here to talk about money, I'm here to be as transparent with you as possible. If I'm ever not, just call me out — for real. I'm here for it.
I remember getting an offer from him. He had talked to his boss, and I believe it was $20 an hour — it might have been $25, but I think it was $20, and I literally cried. This was very low, by the way, especially to live in New York City, and for only three days a week of working. I cried and I was very upset because I had high expectations. But I really sucked it up and put my shoulders back, and came back to him and said, “That's not going to work for me. I need $45”, or whatever.
Eventually, we settled on $30 an hour, which was fine. It wasn't great, but it was fine at the time being. I became a graphic designer within the native advertising part of Time Inc. At the time, it was called Time Inc. Content Solutions, and then it later became The Foundry. Pretty soon after that, we actually moved the office to Brooklyn, which was really cool. It was an open office, it was very Google-esque, we had a full-time barista — and way too many Americanos during the day. By the way, I do not drink coffee anymore. I realized it gave me so much anxiety.
We had lunch delivered on Fridays, and all that jazz, but we're in the middle of nowhere — Industry City, Brooklyn, and I just moved to New York. I fricking wanted to be in Manhattan — I wanted the shine, and the stardust, and the craziness. That was a little bit of a bummer to me, but I was here to learn — and boy, did I learn a lot there. I was there for I think two-and-a-half years, I quickly moved up.
The thing that I needed to learn was really print production and all of that. A lot of logistics, as far as actual print and politics honestly of a corporate office like that. After quickly moving up and becoming an art director, I started asking for a raise. One of the reasons I talk so much about money is because of this instance. When I was asking for a raise, I had no idea what was even feasible, what would be laughable, what was fair — because no one, even my closest office mates, no one would tell me what they made. It was so hush-hush. There was no camaraderie and no help in that regard. I think people just looked at it as inappropriate because that's corporate life.
As I was negotiating, there was a lot of issues — and maybe we'll talk about that on further episodes, but a lot of just kind of douchebaggery, if you will, from some people controlling that effort of my raise. A lot of empty promises, a lot of misogyny — it was a mess, and I knew I needed to leave, and stop being manipulated and promised things that weren't going to happen. One of my co-workers actually had been poached over to Hearst, actually a couple of them.
Hearst is another magazine publishing house — they do a lot of stuff. But the magazines that they have are more like Esquire, Cosmopolitan, Seventeen, Harper's Bazaar — more fashion-forward. I hated it there. But backing up, I got poached over to Hearst for twice of what I was making as an art director, which was amazing and sounded amazing. The office was in Manhattan, a few blocks away from Central Park. It was a beautiful entry to the office, even though once you actually got in it, it was cubicles.
But I got poached there for twice what I was making — so $60 an hour which would have been $120k If I didn't take many days off. Because reminder — these were permalance positions. If you've heard of freelance, you're not actually employed by that company. Permalance just means that you're guaranteed 40 hours a week, it's not so volatile, but you still don't have health insurance, or benefits, or paid time off. You could accrue sick days or sick hours — but that was it.
So fast-forwarding this, I was only there for like four months, and it was a catty four months. There was so much drama, and so much just like wounded sisterhood stuff. Everyone in the office was a woman except maybe two people. This one person literally moved my stuff around the corner — totally away from the team and had her assistant sit at my desk instead, just some bullshit things where I was like, “You know what? I cannot wait for this contract to end. I'm just going to put my head down. I'm not a dramatic person — I don't like drama at all. I'm not even going to be entertaining any of this. You can do whatever you want. I'll sit over here in the corner and do my work, which only takes me like three hours, and I'll get other freelance gigs and do my thing.” So that's what I did.
Four months later, the colleague that had hired me and poached me, came up to me and was like, “I am so sorry, but they are eliminating your job. They had a misunderstanding. I was told I could hire you, and the budget’s not there.” I was like, “Wow, I'm okay with this.” I almost had to console him. I was stoked. When I told my mom, when I told my partner, I had to preface it with like, “Hey, I have some news. It's typically bad news. But I'm actually really excited about it, so I need you to hear me out here. I just got laid off, and I think this is going to be great.”
A few months later, he got laid off, and then the boss that laid him off got laid off — it was just a shitshow, publishing still is. It's a really crazy, crazy place. I just want to remind everyone, when you think of these big-name brands, shiny New York City jobs, they look great from the outside, but it's not always the case — actually, pretty rarely — because the hustle in New York is very, very real.
That night, I had actually been invited to a Six Degrees Society event. I had no idea what it was — someone just invited me. My friend, now really good friend, Emily Merrell is the owner and founder of Six Degrees Society. When I had been laid off, I was like, “Well, I guess I need to go network. Let's go.” I went to my first Six Degree Society event, which was beautiful and full of so many female entrepreneurs, also corporate women as well. But I met some of my key people there that night, including Emily.
We went to coffee a few weeks later, and she was really encouraging me to go full-time entrepreneur, and I was here for it. We kind of made the pact together that I was going to really go for it, not dip my toes in submitting applications, and then trying entrepreneurship, but really going for it like a no-brainer, “This is 100%. I'm all in. If I'm broke and miserable by December — this was September at the time — then I will go get a real job, but I'm going to give this my best shot.”
I started picking up my camera again for the first time in years, actually. There's a whole career for another day in Montana where I was a food photographer and shot a cookbook and did all the things. I hadn't picked up my camera in several years of being in New York because the corporate life was just draining my creativity. I didn't even want to pick it up. I picked it up again and started really networking and photographing women in wellness. When I got divorced, I realized I wasn't being myself — I didn't even really know who I was. How are you supposed to know who you were at 20?
I got to refind myself and reinvent myself — and part of that was wellness. I'm obsessed with it. I'm obsessed with talking to people about it, especially obsessed with the people who are in it, who have the info — the Reiki people, the nutrition people, the yogis, the fitness instructors. I just want to soak up everything they know. I find it so fascinating and so fun, and such a cool community. I started photographing these women.
At first, I was really doing some that were collaboration shoots, which just meant building portfolio and asking them to post about me in exchange for photos. Believe me, we'll talk about this — but I do not believe in free work. This was not free work, this was an energy exchange — just like money is an energy exchange. I was getting something out of it that was worth it to me. That's really important to note.
I was doing some discounted shoots, reaching out to people specifically that I knew saying like, “Hey, I'm going for this full time, and I'm offering these shoots. Would you be interested? I would love to work with you.” That was the beginning. Fast forward within the first year, I was making six figures, which to give you perspective, blew my “Colorado, Montana western” mind.
First of all, I was making more than my corporate shiny job? How is that even possible? Also, if you would have told 22-year-old Diana who was maybe making $34k a year, and thought that was phenomenal, that she would someday make $100k — that would have blown my mind. $100k, that number was for rich people — like truly rich people, that just wasn't an option for me. When I was making six figures on my own, it was really a big milestone — something that it was like being able to prove to myself again that I was my biggest asset and I could do this.
I did a little bit of graphic design freelancing on the side, which kind of helped float the boat and curb a little bit of anxiety, and I was photographing my little heart out. There's so many stories within this story that I could tell, and will tell on later episodes, but it was a big deal. I was photographing and graphic designing full-time, and I was, quote-unquote, “successful”. I had started sharing this journey on Instagram the moment I got laid off . That was the beginning of my Instagram journey.
I just really started sharing everything with the life of a, quote-unquote, “freelancer” looked like, which we'll talk about the difference between freelancing and entrepreneurship at some point. I was busting my butt — I was hustling, I was taking on literally everything, saying “yes” to everything and “no” to nothing. I had shot a Bar Mitzvah — like I don't shoot Bar Mitzvahs, but it was like, “Okay, $1,500. I'll do that”, and quickly realized how much I was doing that I didn't want to do, which I think is really important in the baby stages of entrepreneurship, really playing in that sandbox and seeing what you like and what you don't like.
But everyone who saw and was following me on Instagram, and then would see me in person would say, “You're really busy”, and I started to take that as a red flag because I didn't want to be busy. I didn't want to seem like I was hustling, and I was. I was hustling so hard. That really kind of planted a seed in my mind pretty early on that I do love to be all over the place, and do all the things, and have a packed schedule — but running around New York City, walking 13 miles a day with a heavy photo equipment backpack and a changing tent, maybe wasn't the most sustainable thing to do.
Maybe, I was charging too little, but I didn't know what I could charge. Maybe, I was saying “yes” to a lot of things that I shouldn't be saying “yes” to. However, I continued to hustle. I would shoot 11 shots in a week, and go home to Montana to visit my family and be editing photos the entire time — the entire time, even in the shotgun seat of my dad's pickup on a family drive. It just wasn't good. I quickly burnt out. About, I would say two years in, I started sharing about that.
The first post that I made that went really — not viral, but viral to my community — was about burnout. A lot of people are really scared to talk about that kind of stuff because they don't want their clients to see that they don't have it all together. But what we forget is that our clients buy from people. They want to hear you as a human and what you have going on, and not in like a venting way, not in like, “Oh my God! This sucks, and I'm so busy, and I'm so tired all the time.” Just a genuine way to really relate to you as a human. People buy from people — that's another episode in the future for sure.
I was burning out. I was getting really passionate about helping other creatives do it better than I did. I had a lot of people coming to me who are quitting their full-time jobs, and asking me out for coffee and just picking my brain about how I'm doing what I'm doing, how do I find an accountant, what kind of systems do I use, how are you showing up on Instagram in this way, how did you get the guts to quit. Guess what? I didn't, I got laid off. That was kind of the beginning of coaching for me, but I had no idea it was.
I was also doing some mentorship sessions a little bit, teaching bloggers food photography and things like that. February of 2020 came around, I had no idea the pandemic was a thing. My partner, Bobby, and I were planning on going to travel the world abroad full-time, literally in June of 2020. Our first stop was going to be Italy. It's February of 2020, those plans are still in motion, we're going to travel abroad, but I am having the most anxious month of my life — like probably at my lowest low.
My money wasn't coming in, projects weren't coming in — I had no idea how to make this sustainable. I was three years into entrepreneurship and still on a crazy, crazy roller coaster. So I, out of desperation, hired my first business coach — which shout out was Emily Merrell of Six Degrees Society, the person that I met the first day I got laid off. I put it on a 0% APR credit card. I just needed help — it was time.
We started, and she talked about revenue streams. At this time, we still didn't know about the pandemic — didn't think it was a big deal, this Coronavirus thing, and I was still going to be photographing. Of course, right? Wrong. We are talking about different streams of revenue, and I said, “Maybe I could do mentorship sessions officially and charge for those.” She was like, “Great, let's price that out.” I was like, “I don't really want to do that right now. Let's not worry about it. I'm going to photograph — I don't even have time. I'm going to the Brooklyn Bridge at 7 am, and then Central Park by 7 pm, and doing all these shoots. I don't have time for that.”
She's like, “You know what? Let's just price it out anyway, just in case.” I can see her smug face right now, literally right after I priced out what would be like a mentorship session. I had one person in my DMs — shout out to Sydney, who was one of my first coaching clients ever, saying, “Hey, can you look over my client workflow?” I was like, “Wait, I don't even know you. This isn't a DM question.” I was like, “Wait, mentorship sessions. Okay, let me practice this”, “Hey, I'm actually doing these mentorship sessions. Would you be interested in trying one?” And she said yes, and she was my first one.
Then, I got a random email — funny how the universe works — from a gal in New York who was an actress, a fit pro, and a writer, which is so New York of her, and Gemini, to be honest. She messaged me, emailed me and said, “Hey, I would love to do a strategy session with you.” Mind you, I had not announced any of this. I kind of responded and said, “A brand photoshoot, you mean?” I don't even know where she's getting this from — the strategy sessions. She's like, “No, I would like to pay you for your time to ask you questions and pick your brain.” I was like, “Oh my God, this is coming out of nowhere. Hello, universe, hello.” I also gave her my mentorship session package — kind of the beta version and realized, “Okay, this is a thing.”
I randomly decided — if you listened to the intro, you know I'm a manifesting generator — randomly decided that inspiration sparked it struck to announce this finally on Instagram. I did it in the most authentic way I knew how. I just got on and said, “You know what? I am so stoked when I promote all of you. I'm so happy to promote all of you and help you out. But it is really fucking hard to promote myself — really hard. Anybody else? Anybody else feel that way?”
I said, “But I'm going to do it right now because I know that's what we have to do. As creative entrepreneurs, we have to put ourselves out there.” I said, “I'm announcing these strategy sessions, and I am so excited about it. Here's the link to sign up. They are free, they're 20 minutes, and let's just see how it goes.” The response was unreal.
So many people that I thought — which is so unfair of me — but I thought it would be like, “Who the hell do you think you are? You're not even the best photographer out there, you're not even the best business owner out there. Who do you think you are doing this?” They were actually the ones to say, “I cannot believe you didn't do this sooner.” I was just baffled. I still have the story in my archives of just being so grateful for everyone's support — so amazing.
I started these strategy sessions, it turned into paid sessions, which turned into three-month containers. Then, my friend, Jess Glazer, came along, and I was seeing her stories, and people, her clients going — she's a coach, by the way, as you'll see — her clients saying, “They were having $100k launches”, which if we go back to the $100k conversation, it’s asinine, right? Let alone to make $100k in a year. $100k in a couple of weeks?
I asked her, “Hey, I'm all about money mindset. I love you are a badass at making money — all of these books, and I get the vibe, and the spirituality, and the manifestation — but I'm baffled at how this is possible.” She was like, “You know what? We should talk.” I had a conversation with Jess, who became my coach for many, many months after this, and she's like, “What's your resistance to a group course?” I said, “I guess nothing because I just launched these strategy sessions. They're off the hook, and people are stoked about them, and I feel really aligned with it.”
I joined her course, E+mpower, to create my first course, Camp Clarity, for creative entrepreneurs who are having a hard time pricing themselves, having a hard time not feeling guilty for taking money for their services, having a really hard time showing up confidently on social media, having a hard time knowing what kind of client workflow to have, having a hard time with taxes, with legal, with all the entrepreneurship foundations that you deal with as a creative.
That's my definition of a creative entrepreneur — that you have a heart-centered gift that you want to put out into the world and make money off of. But that's really hard when it's heart-centered, and we put our hearts on the table and ask money in exchange. Camp Clarity was born, and I had my biggest month ever when I launched it in July of 2020. I had a $39,000 launch, and I didn't know one could hold that much money at a time. It was baffling to me.
Backing up a little, a few months before — several months before, I had started going from $350 photoshoots to $4k photoshoots, which were huge for me. Then, at this time of shifting my vibration and receiving higher income, and wealth, and energy exchange from people, I was still photographing — just on the side and inside because it was COVID — doing some product stuff, and I started doing $30,000 photoshoots.
I guess my point here is it wasn't just coaching that made me money, it was the actual calibration of knowing I could charge that much, and what that looked like and felt like — because anyone can go out and say, “I'm going to charge $30,000 for this photoshoot.” But if you don't believe it and your cells aren't aligned, they're not going to say “yes”, they're going to know that you don't believe in it either.
I want to be very clear — making $30k had nothing to do with just coaching because I was also making $30k in photography. It had everything to do with my calibration of self, my vibration, my belief, the strategy behind it, the coaching, the help — all of it put together. That's when things really started to change for me. I never had been to a restaurant and not freaked out about the bill, I had never gone on a trip without worrying about the money, I had never been able to donate without fear that I wasn't going to have enough — that I was going to be able to pay my rent. This was a huge money change for me in my world in my beliefs.
Eventually, holding coaching, and holding photography still, and holding graphic design was too much. I had a nervous breakdown on a call with Jess Glazer in front of 50 people, and she told me, “You need to drop a ball. Just let it fall and don't pick it up, and don't let anyone else pick it up. You don't even need to do anything with it. Just let it drop.” The first thing I did was quit my graphic design freelancing job, and then in August of 2020, I did the last photoshoot that I know of, paid — I don't know if I will do another one, maybe someday. But I basically quit my photography career and never picked it back up.
That's when my partner, Bobby, and I were looking at moving to Colorado and out of New York because of the pandemic, and he loves the mountains and all of that, which I had no idea I was going to move back to my home state — that was never the plan. Obviously, we didn't go abroad in June of 2020, and we made it happen. All of a sudden, I had this very nomadic business that I always wanted — to be able to be literally anywhere and to also lead other creative entrepreneurs through this journey. That's where it all started for me as a coach.
Now, we're here on March 25 — I'm recording this episode of 2022. Wow, two years later from that pandemic, starting from me hiring my business coach, from me totally expanding — I like the word expanding versus pivoting — expanding my offerings and myself, and who I was as a person in my capacity to lead. And here we are on the Pollen podcast.
I never thought I would be here. That is my winding road — from ranch kid, to divorced, to Manhattan entrepreneur, to Colorado business coach nomad. I'm so excited to see where this goes from here because I know we're not solidified. This is not it — there's so much more for me, and I truly believe that, and I believe that for you too.
So that is my story. Thank you for listening. I would love to hear what resonated. Please rate and review this podcast — it would mean the world to me truly. Let's collaborate, let's support each other, share this episode on your Instagram stories and tag me — I would love to hear from you, and let me know what resonated, what really struck you today, and also maybe what you want to hear in future episodes.
They won't all be this long. I'll have a lot of little short snippets for you — some tangible action steps, some mindset work, some amazing guests. I'm so excited to have you along on this ride. I am truly honored. If you got to this minute of this podcast, you are my people. I appreciate you.