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S2 E22 How Treating Your Brand Like a Magazine Will Help Your People Connect More to You and Your Offers

S2 E21 Everything You Need to Know Before Hiring a VA or OBM for Your Business with Alexandra Smith

S2 E20 The Truth About Building a Community of Over 100 Creatives

E4 Betting on Yourself as a Creative Entrepreneur ✨💥

When was the last time you took a big leap of faith? And I don’t mean the physical kind! I’m referring to bold moves like relocating to a new state or quitting your corporate job to pursue a side hustle.

If you’re a creative entrepreneur, you have probably made a couple of bold moves already. But it shouldn’t stop there. Moving towards success requires taking leaps — even and especially the ones that seem big or scary.

In this short but sweet episode of the Pollen Podcast, I talk about the importance of making big leaps of faith — especially in creative entrepreneurship. Listen as I share my experiences, taking one leap to another, and how each move has contributed to my journey as a creative entrepreneur.

Tune in to learn more about the importance of taking a bet on yourself and taking a leap of faith in your journey as a creative entrepreneur.

Create your own creative entrepreneurship story of clarity, professional confidence, and profit. Join Diana Davis' 90-day group course Camp Clarity and learn everything you wish you already knew, like 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:

  1. Taking big leaps is the key to success in entrepreneurship. Learn from my leaps, and even from my stumbles, and how each experience contributed to my success as a creative entrepreneur.

  2. Understand the importance of self-trust and self-love in making big, bold moves.

  3. Recognize the importance of having a solid support system, may it be a partner, a coach, or a community of entrepreneurs.


🎧Episode Highlights

[01:25] The Importance of Taking Big Leaps

  • Taking big leaps, in Diana’s opinion, is the number one key to successful entrepreneurship.

  • It pays to not overthink everything. Make big leaps for yourself and your business.

  • These leaps can be as simple as confidently showing up for a client or hiring more people despite constraints.

  • If you’re still hesitant, you can always take inspiration from other people.

Diana: “It’s so empowering to hear what other people are doing. And when we're around people who are taking big leaps, we're more apt to take our own big leaps.” - Click Here to Tweet This

[03:54] Learning Risk Tolerance from Diana’s Father

  • Diana was raised in a family of entrepreneurs who took big risks — including those that were less smart and more heartfelt.

  • Diana built her risk tolerance seeing her father work in a high-paying corporate position, but decide to leave to be an entrepreneur.

  • Diana believes in the value of prioritizing “living” over security and wealth.

[06:47] Learning from Healthy and Unhealthy Leaps

  • Not all leaps are the same. Some are super healthy and some aren’t.

  • Our relationships play into who we are as a people and how we show up as brands.

  • We should learn to appreciate both our successful and failed moves because they teach us valuable lessons.

[07:31] Self-Trust, Self-Love, and Betting on Yourself

  • After her divorce, Diana lived alone and started to journey within herself. She learned to stop seeking validation from other people.

  • Self-trust and self-love are big themes in taking leaps. You have to have both to succeed.

Diana: “When you get to the place where you are your favorite person to hang with, where you actually love yourself more than anyone else and honor your energy, boundaries, and life before anyone else… When that happens, it is magical.” - Click Here to Tweet This

[9:02] Diana’s Bold Move to New York

  • Diana moved to New York without a job or a plan.

  • This is where Diana learned to trust herself. She knew that she had the skills and hard work ethic to succeed.

  • Know that you have navigated yourself to where you are today and that you can move forward and navigate yourself onto the coming path.

Diana: “You have to take the leap, and not just monkey bar [leap]. You have to have some hang time without anyone to catch you or anything to hold on to. And guess what? You’re going to reach the other side or there will be a net beneath you.” - Click Here to Tweet This

[11:48] The Value of Full Commitment

  • Diana got laid off from her job in the magazine industry and decided to take her biggest leap yet: pursuing entrepreneurship.

  • Diana gave herself an ultimatum: if she hadn’t progressed after 4 months, she was going to get a corporate job again.

  • Diana knows that it is relatively easier to get a job nowadays. That is her net.

  • Commit fully and you’re going to make it. Stutter step and you’re going to fall short.

[13:44] The Importance of Having a Solid Support System

  • Get yourself people who can cheer you on as you make the big leap. Believe that they will guide you down the best paths in life.

  • Your support can be your friends, a coach, or a community of other entrepreneurs.

[14:06] Diana’s Latest Leap: Moving Back to Colorado

  • In terms of making big moves, Diana didn’t realize she could go backwards.

  • It was a big leap for her to commit to someone and choose another person over herself.

  • Make conscious decisions based on self-trust.

Enjoyed this Episode about Betting on Yourself?

Now’s the best time to start betting on yourself! Take that leap and believe that no matter the outcome, it will move you further on your journey to success.

Pollen is a podcast for Creative Entrepreneurs — just like you! If you enjoyed this episode of Pollen Podcast, subscribe and help us spread the word by sharing it!

Leave a review and share it! ⭐⭐⭐⭐⭐If you enjoyed tuning in to this podcast, we'd appreciate it if you wrote us a review. You can also share it to help other creative entrepreneurs.

Have any questions or want to leave a suggestion? Come say hi on the 'gram @dianadaviscreative. You can also subscribe to my newsletter for travel updates, learn about special projects, and get tips and tricks for the creative entrepreneur life!

Connect with me on Linkedin: Diana Davis Creative.

Thanks for listening! Stay tuned to my website for more episode updates and other exciting programs and resources.


I was raised by a family of entrepreneurs. My family owned a ranch in eastern Colorado and they took a lot of big leaps. Some of them, probably to the public, maybe even in their eyes now, maybe weren't even smart big leaps, but they were heartfelt big leaps.

Diana Davis: Welcome to Pollen, the podcast for creative entrepreneurs. I'm your host, Diana Davis, multi-passionate creative business coach, Gemini, manifesting generator, matcha drinker, 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.

Hello, and welcome to episode four of the Pollen Podcast. Today, we are talking about, in my opinion, the number one key — not second, not third, not fiftieth — number one key to successful entrepreneurship. Are you ready? We're talking about taking big leaps. And this was actually a request from my partner, Bobby. Just a minute ago, I was like, “I'm about to record a podcast episode.” Joy of entrepreneurship or real-life version, I have to kick him out of the house because even if he's two levels down, I can hear him slamming cupboards and stuff. So I have to kick him out of the house.

I'm like, “Hey, Bobby, I'm going to record a podcast episode, you’ve got to get out. What should I talk about?” And I had a plan, but I wanted to see what he said. And he said, “Taking big leaps.” And honestly, I was like, “Yeah, that's really good, and something that my life really has revolved around and my success can absolutely be attributed to.” That's the number one key — spoiler. The number one key is taking big leaps in yourself, in your business, and in life. It's not the strategy. And it's not necessarily the mindset.

The mindset does play into these big leaps, of course, but there's so many things that we could say. Hiring was the biggest key or showing up confidently. And honestly, all of those kinds are big leaps. If we decide to hire a team, that's a big leap. If we start really showing up on Instagram in a confident, courageous way, that's a big leap, too. I want to talk about some of the big leaps that I have made in my life. Maybe these will resonate. And I would love — oh my god, I would love for you to share this episode on Instagram on your stories and let me know which big leaps you have taken. Because it's so empowering.

Rising tide lifts all ships, right, it's so empowering to hear what other people are doing. And when we're around people who are taking big leaps, we're more apt to take our own big leaps. As you know from episode one — if you haven't listened to that, please go listen to my story so you know a little bit more about me — I was raised by a family of entrepreneurs. My family owned a ranch in eastern Colorado and they took a lot of big leaps. Some of them, probably to the public, maybe even in their eyes now, maybe weren't even smart big leaps, but they were heartfelt big leaps. For example, my father ended up quitting his corporate job. He was actually really high up, climbing the ladder, doing the thing — no pun intended, he was a lineman. He actually did climb poles at one point. But he started being kind of in the office more and in administrative stuff more, as you do when you go up the corporate ladder. And he was also about an hour commute away from our home and had finally decided that wasn't what he wanted anymore.

He wanted to be near his family, he wanted to pursue this dream of ranching full-time, and he quit. He didn't take retirement, he didn't do a lot of things. He just led with his heart and went for it. I got to see that from an early age and I really attribute that to my risk tolerance. We were definitely a family where life, and happiness, and fulfillment, and hard work, and just like getting your hands dirty and living, like really living, meant more than money to us. Therefore comes a lot of limiting beliefs also, which is a whole other episode, as I always say, but I really think my family expanded me in a way that a lot of kids don't get, where instead of honoring safety, prioritizing safety and wealth, we prioritized living, which is really special to me.

The first big leap I would say I took was moving to Montana. After high school, I went to college in Montana and that was a big leap because no one else was doing that. And that's kind of why I did it. I'm kind of a little flighty. Like we've said, I'm Gemini. I want to pollinate all the flowers. I have learned to embrace this versus looking at this as a flaw. I never really know where I want to be, but I like to kind of pack up and leave — for lack of a better phrase, which sounds a little toxic and scary, and it probably has been in the past. And it can also be really great and healthy. But I moved to Montana for college because no one else in my massive class of 22 was going to Montana. They were all going to CU or CSU, or California or Denver, whatever. So that was a big leap for me.

Honestly, I, again, promise to be talking about this more because I think there's a lot of stigma around marriage and divorce, and, “What does this have to do with entrepreneurship?” But I think it all plays into who we are as people and who we show up as brands. But getting married was a big leap and I just didn't really even think twice. At the time — and I got married so young — at the time, I just was ready to take the leap, like, “Of course, yeah. You say jump, I jump,” which again, some leaps are super healthy and some maybe aren't. But I learned so much from being in that relationship and also navigating my way out of it.

I would never trade the title of being divorced for my experience that I had because I learned so much and started to develop the self-trust, which is another big, big theme in this taking big leaps topic — where self-trust is required to take these big leaps, where betting on ourselves is the best option, and self-love and all of that comes into play here too. And when I got divorced, that was the first time I really started to trust myself. And I lived on my own for the first time, and I was alone with my own thoughts, and I started to journey with myself instead of always getting validation from other people.

I can tell you — and not in a conceited way, just in a really confident way — when you get to a place where you are your favorite person to hang out with, like you actually love yourself more than anyone else, and honor your own energy, and your boundaries, and your life more than anyone else, oxygen mask on yourself first, when that happens, it is magical, and it's a place a lot of people don't get to, and it's a place a lot of people don't even think of striving to get to.

Once you start to trust yourself, these big leaps become not really a big deal. And so the next big leap was moving to New York City with no job, no plan, all by myself. I literally knew no one there. It was wild. And as I said in episode one, I showed up on my doorstep with my suitcases at an apartment that I had never been to, on a street I've never even walked, roommate I've never even met. That was a big leap and I had to trust myself. And a big part of that was trying to do it the societal way, and get a job before I went, and apply, and be the responsible person, and trying to save up enough money to get by for a while.

I didn't find a job before I left and I could have so easily just said, “You know what? I can't go until I find a job. That's just not smart,” but I trusted myself. I knew that if I just went, I would figure it out. And I have a lot of skills and a lot of hard work ethic, and I knew I could get three waitressing jobs if I needed to, to pay my knees New York City rent — I can't remember exactly how much it was at the time. It was expensive, let's just say that, especially for a dark apartment looking at a brick wall out the window. If you're a New Yorker, shout out, you know. So these big leaps, they are self-trust. It is one and the same.

Moving to New York City with no job or no plan is kind of like quitting the job to start entrepreneurship or taking a bet on yourself and pivoting into something new, just knowing that no matter what happens, you're going to be okay because you've got yourself, you have your best interest in mind, you have navigated yourself to this point, and you can move forward and navigate yourself on the future path. And I knew if I moved to New York City with no job and no plan, I'd frickin find a job. My ass had a fire underneath it, and that's what I tell a lot of my clients is, “Honestly, if you're waiting for the moment where your side hustle is replacing your full-time salary, which usually isn't even possible — it is possible, but if you're doing time for money, and you're not getting support, and not really knowing the capabilities, having your side hustle replace your full-time job, that's like having two full-time jobs, which, you're going to burn out, baby.”

Usually, you have to take the leap and not just monkey bar from one monkey bar to the next. You actually have to have some hang time, like in the air, without anything to catch you, without anything to hold on to. And guess what? You're going to reach the other side, or there will be a net below you. And what I did — going into my next big leap of entrepreneurship — when I got laid off from the magazine industry, I decided and gave myself a deadline, “You know what, I'm going to leap as far, and as long, and as hard as I can go. I'm going to take the biggest leap I can. And if I'm broke and miserable in four months, then I'll get a job.”

We have so many opportunities at our fingertips, especially in the day and age, we're living in, especially in this millennial world or whatever generation you're a part of. We can get a job any time, even if we have a limiting belief that we can't. That can always be the net. But giving yourself this deadline of, “Hey, I got laid off today. I'm going to give myself the weekend, I'm going to go to Prague, take my first international trip ever at 27, and then I'm going to come back and decide if I'm going to get another job or if I'm going to 100% fucking go for this entrepreneurship thing.” And that's what I did. And I think it's so important, right?

If we picture actually even running up — so close your eyes — running up full speed on the cliff, and we leap to make it to the other side, if we commit fully, most likely we're going to make it. But if we even stutter step, we're going to fall short. A huge part of it is really that self-trust and going for it. Instead of kind of applying for jobs, and kind of applying over here and asking around, and then sort of trying the entrepreneurship thing, like, “Maybe a few photoshoots here and there,” I just committed. So I'm asking you to commit as well in whatever big leap you are currently kind of looking at.

You're looking at that canyon going, “Oh, shit,” but guess what, the biggest thing, get yourself some support. Get yourself some people who can cheer you on as you're making that big leap, who can tell you the best route to go for your big leap. Whether that's friends or coaches or a community of other entrepreneurs, so important. My last big leap, I think, as of late was moving back to Colorado and, honestly, I never thought I would. I never thought I'd “go backwards”. What? But I knew that was right for my partnership, because Bobby, my partner, loves it here. And mind you, if I hated it here, I would not be here.

Even after the divorce, and then being so independent and having my armor on — oh man, I had some walls, I still do, a little bit — to choose a person who may be over myself was a really big leap too. And again, so that might sound counterintuitive when I'm talking about self-trust, and yourself being your favorite person to hang out with, and like putting yourself first — yes, for sure. But deciding to also commit to someone — I don't know about you — that was a really big leap for me. That was a bigger leap than the marriage that I naively kind of just was like, “Yeah, let's do it.” This was a conscious self-trust moment of like, “I'm going back to Colorado and I don't know what's there for me. But I know this feels right for us right now.”

This is going to be a quickie, little short episode. I hope that this has inspired you to take some big leaps. That cliff you're kind of waiting on the outskirt of, take the leap, baby. You can do it and trust yourself.

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