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S2 E25 How AI Can Help Your Creative Business Grow with Lauren deVane

S2 E24 Life’s Initiations and Transitions and How They Help You Serve Your Clients

S2 E23 How to Create, Host, and Sell Out Impactful Retreats with Amber Hagberg

E34 How to Pursue Your Entrepreneurial Dream + Support Yourself Along the Way 💡💰

We all have this ideal picture of what being an entrepreneur looks like. To many, this is quitting your job, becoming your own boss, and immediately finding success through grit. But the reality is not always smooth-sailing. Having an "all or nothing" mindset can put an end to the dreams you’re pursuing. Sometimes, taking on work you don't want can get you closer to where you want to be.

In this episode of The Pollen Podcast, Diana talks about how to support your entrepreneurship dream realistically. Yes, alignment and energy are important, but you won't get there by waiting for things to work out. You have to work hard and work smart, even if it means taking on jobs you don't necessarily want. So don't quit your job just yet — it can be your stepping stone toward the career that really aligns with you. 🏃‍♀️

Listen to this episode to learn why pursuing your entrepreneurship doesn’t mean you have to quit your job!

Create your own creative entrepreneurship story of clarity, professional confidence, and profit. Join Diana’s 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. How to make genuine connections that don't feel solely transactional.

  2. Find out how to pursue a fully-aligned career without having to quit your job.

  3. Learn how taking on work you don’t necessarily want can support your entrepreneurship dream.


🎧Episode Highlights

[01:33] Connecting, Not Transacting

  • Diana is currently in Tamarama in Sydney, Australia.

  • By sharing where she's at and what she's doing in life, she’s been able to connect with so many people.

  • Going into situations with the intention of connection and not transaction is huge. Authenticity thrives in pure connection.

  • Tune in to the full episode to hear about the connections Diana made during her stay in Australia!

[07:36] Being Open on Social Media

  • Your followers are real people who most likely found you through something else.

  • Tag accounts and include the location when you’re sharing things that you’re doing on social media. It might get you a new connection or client.

  • Reaching out to your followers is a huge and easy thing to do. It's about putting yourself out there first, following through, and following up.

Diana Davis: “People don’t want to just follow you. They want to be connected with and not sold to.” - Click Here To Tweet This
  • Business is like dating — you have to keep the seed planted, the garden watered, and nurture the connection.

[10:59] Having a Day Job to Support Your Entrepreneurship Career

  • There is no shame in having another job while pursuing entrepreneurship.

  • Quit your job if you feel it is right, but be aware that there's no shame in working somewhere that isn't 100% aligned with you to make ends meet.

  • There is an in-between period where you want to do entrepreneurship full-time, but it's not quite working yet.

  • Think of your entrepreneurship career as a baby that's just learning how to walk. You can't ask it to run a marathon immediately.

[16:05] Knowing When to Say ‘No’

  • Being able to say 'no' to work that you still love to do is a privilege.

  • Sometimes, you have to be grateful for the job you have because it's paying the bills. The financial stress it relieves can then help you flourish in your aligned work.

  • Stay aligned with what you're doing, but analyze your situation.

Diana Davis: “Take the job at the brewery, take the job at the coffee shop, take the photography job that you don't necessarily love, but you're still able to use your skills, and you're still able to make new connections. And most likely, the universe is putting that thing in front of you as a stepping stone.” - Click Here To Tweet This
  • You don’t need to feel ashamed for having to get an ‘actual job’ to support your dream. It's part of the process.

  • You’ll get to your dream, but you won’t get there by just sitting and wishing for everything to align and work out. You have to co-collaborate with the universe.

[22:28] Being Smart about the Things Coming through Your Door

  • Success for many creatives is when people finally start hiring them for their style.

  • Getting your name out there may require doing stuff you don't necessarily want to do. But it could lead to various opportunities to finally take the work you truly desire.

Diana Davis: "Let's still work hard for what we want. Yes, alignment. Yes, energy. But you know, that's apparent too when we go and say, 'Hey, I'm willing to go work at a brewery part-time to make my dream happen.' That's energy and alignment too." - Click Here To Tweet This
  • It's about being smart and creative about the work you take on instead of always saying 'no.'

  • You have to get in tune with both your feminine and masculine sides to reach a place of alignment. You have to have riverbeds to support a river. Otherwise, you're a lake.

Enjoyed this Podcast on Supporting Your Entrepreneurship Dream?

Doing entrepreneurship full-time is THE dream for many of us. But unfortunately, the reality of getting there is not as easy as we'd like it to be. You can't just risk it all and go all in with no safety net to fall back on. Instead, you have to work smart. Sometimes, that means taking on work you don't necessarily want. So don't quit your job just yet — it might be just what you need to get where you dream of being.

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.


Diana Davis: If you are putting so much pressure on your entrepreneurship career to float your life and it's just not quite working, you have $20,000 worth of debt that you're trying to pay off. Clients aren't easily coming in. It's feeling like we're sort of pulling teeth to get things to really work for us. There is no shame in going to be a barista part time at a coffee shop.

Welcome to Pollen, the podcast for creative entrepreneurs. I'm your host, Diana Davis, multi-passionate creative, business coach, Gemini, manifesting generator, macho 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, welcome to another soapbox episode of Pollen. I am in Australia, in Sydney, in Bondi Beach, technically Tamarama. I think, it's Tamarama is how they actually say it. I'm learning all of the pronunciations including taking the R out of Melbourne, Melbourne, Melbourne, Melbourne. We'll get there. It's kind of like when I got in the taxi to literally go to my apartment for the first time in New York City from the airport, and the taxi driver was like, it's Houston. It's not Houston. I just need you to know that.

Don't call it Houston Street. It's Houston. So we're learning the ways. But I'm coming at you literally looking at the ocean from my window, which is so magical, and it is November 16 when I'm recording this. I'm looking at everyone on Instagram doing their Thanksgiving stuff, and I'm just not jealous. I just am not really missing the whole cold weather thing, holiday thing. My family's not really into the holidays.

If we're not there, it's not a big deal, and even I think my brother is traveling up to Montana to see my parents for Thanksgiving. I highly doubt they cook a turkey, like it's just not really a thing. So I actually am really grateful for that, because there's no pressure for me to be there, and I'm able to be literally around the world, which is, can we just talk about that. Right now, it's Wednesday, November 16, but technically, it's Tuesday for most people that I know in America, in even Europe.

It's crazy to be a full day ahead, and the way time works is just baffling to me. So I'm loving it over here. I am conking out everyday at 3pm, because of jetlag, but otherwise, loving it, meeting up with people, also want to talk about that for a second because I've already met someone in real life that followed me on Instagram, that was really fun, and just by sharing where I am at and what I'm doing in my life.

People are able to connect with me, and I wanted to say too going into these situations truly with the intention of connection and not transaction is huge. Parisian man who I was dating for three months, which is a whole other story and just a beautiful one and a sad one and a very healing one, he would ask me when I was meeting up with people, was it a prospect client? I'm like, I have no idea.

I'm just going in for purely connection, and that's where authenticity can thrive. Being genuine comes forward. If people want to work with you later or wanna refer you to someone, amazing, and if they just become your friend and connection across the world, also really, really cool, right? So I met up with someone yesterday, who I've been connected with on Instagram.

Literally yesterday, I went to this, it's called Bondi Vixen. It's a really amazing hard work out class, kind of Pilates hit style, and I had this gal next to me that was speaking with an American accent. So I said, “Are you from America?” She said, “Yeah, Montana.” If you know, you know, like, holy shit, what? You're from Montana. Okay, cool. Well, I went to college in Montana. My parents live in Montana.

I'm basically from Montana, if it's not Colorado. That's crazy. So I'm going over to her house tomorrow for lunch, which is so wild because I came here totally alone. This is another very, very solo trip for me. Nomadic isn't necessarily always solo, right? When I'm in New York, I have my people. When I'm back in Colorado, I have my people. Montana, I have my people. Even when I was in Paris, like I said, I was dating this guy for three months, so I was with him most of the time.

I wasn't alone. I was kind of living life, and then I broke that off, because I knew I just needed to be alone. I can't be in a relationship right now. I need to go explore and do my own thing. Traveling literally across the world, and knowing no one here is stretchy, but then just being open and not going around seeking connection or again, going in transactional, but just being open.

Like I'm gonna go to this class for me, and holy shit, someone from Montana is next to me on my mat. That's wild. The other connection I made that I'm having lunch with her today is this beautiful little shop called Commune, that I bought some amazing, very gorgeously packaged incense at. I was just talking to her and I said, “It's my first 24 hours in Sydney.“ So we started talking and she was asking how I live the life I live.

What do you do that you can be nomadic and travel full time? I was just telling her how I used to be a photographer and graphic designer, and that now, I'm a business coach for other creatives. She's like, “No way, I am a painter and a photographer. I'm totally a creative,” but she has this side hustle job, as a retail person at Commune as her support system, right, and that's what I want to talk about today.

So first of all, a lesson in connections and just being open to them, including on Instagram, right? If you have a follower that is new and you go to their profile and you see that they are not a fake account or crazy or about to sell to you, they're a real human and probably found you through something else. For example, someone at this other workout studio, I went to. God, my Gemini self loves to try 50 million different workout studios everywhere I go, my manifesting generator self too.

But I saw this gal followed me from this fitness studio, and I could just tell that she was from that fitness studio because I looked at her profile. She teaches there. They had probably reshard my story the other day, which is also a social media lesson in sharing the things you were doing, not only so your mom can see them and people can follow along, but that you can shout these people out, tag the freaking accounts y'all.

If you are in a restaurant, tag the account. If you're at a fitness studio, tag the account, also put the location and not necessarily the location of the restaurant, but maybe the location like Bondi Beach so that when people see and go to the Bondi Beach story, yours might show up. You might get a new connection, and you might get a new client, right? So this gal, I could tell was from that workout studio, so instead of just going, oh, she's from that workout studio, cool that she followed me.

I reached out to her, and I was like, “Hey, I enjoyed class the other day so much. I see you work at Leanbean Fitness. I hope that I can take a class and thanks for the follow.” So that's a huge and easy, easy thing to do. When people are like, how do you get so many people in your masterclasses? How do you get so many clients, etc. It's like connection first and actually putting yourself out there, first of all, and actually following through and following up.

People don't want to just follow you. They want to be connected with and not sold to, right? Maybe invited when the time is right, but I always say business is like dating in so, so many ways where you don't go down on one knee the minute you see someone in a coffee shop. You say hi. You wink. You buy their coffee. You do something like that, and then you feel it out, and they feel it out.

Then maybe it's a good fit. So keeping those seeds planted, keep watering the garden, right, and just nurturing your connections. Who have you connected with that is literally a warm lead. Can you hear the birds? I hope you can, because they're really fun. They're like a really fun sing song type of bird, and they copy each other. So if you can hear them in the background, Sydney, Australia says hello.

But just having those warm leads and following back up with those people, like have you looked through your follower list lately and just said, “Wow, I haven't heard or seen that person in a really long time. I'm going to re interact with their stuff, so they know I'm alive.” So that's a lesson in that. Moving on, going from kind of the commune story, and I don't know anything about this amazing person story, and I will probably more after lunch today.

But I've been talking to a lot of people even in Camp Clarity this round about having a job like a real job while you are supporting your entrepreneurship career, if that is wrong, if that is non-committal, if that is something where you're not really putting two feet in and if that's bad energy. What I want to say is that there is, first of all, no shame in having a job job. I know entrepreneurship is a job too, but you know what I mean.

For the sake of clarity, we're gonna call an actual job where you are not setting the rules, and you are getting paid by someone else, like a job job, right? Entrepreneurship is a totally separate thing that you're working for yourself. That might be the dream, and it might not. If you didn't go listen to Rolanda’s episode, a couple episodes back, she is a kick ass corporate maven, and she is not looking to quit her day job.

She has a side hustle of fashion blogging, and she is not looking to quit her day job. There is no shame in that. I am a coach that is here to help you make it work where you want to make it work and how you want to make it work, to make your life look like the way you want, not some dream or aspiration that someone else is putting on you, especially on social media. I am not here to put quitting your job on a pedestal.

Where I am here is to encourage people when they are miserable in their job, and they know that it is right to quit and go forth into their entrepreneurship career full time, that they do that from an empowered place. I give those people props. Remember, if you know my story, I had to be laid off to go forth on my journey. I didn't quit. When people actually make that empowered decision to quit when it is right, wow, that is fucking badass.

Also, when people decide to stay, that's also badass. So I want to talk about the in between there, because there is an in between where you do want entrepreneurship full time, but it's just not quite working yet. I use this analogy the other day in Camp Clarity that we have this baby, which is our entrepreneurship career, and it's just learning to walk. Call this entrepreneurship career, 1.25 years old, right, in baby terms, and it is just getting its legs underneath it.

It is just going from crawling to walking. We are just getting clients and we're just getting traction, and we're starting to be noticed more on Instagram. We're starting to build a network. We're starting to get income. Right? Then, we ask our entrepreneurship career to go run a marathon even though it just started walking, right, and sometimes that's possible. Sometimes it's more like the entrepreneurship career is maybe just like a little couch potato side hustle, and we need to train for the marathon.

Once we're up to running five miles at a time, we can quit the job and just go forth, like I said, into full time entrepreneurship, and really get those training legs trained. Versus this baby struggling, needing to be nurtured career that can't run a marathon. It just started walking. That's a lot of analogy. I hope you're following me there, and let me know if you're still with me.

But my point is, if you are putting so much pressure on your entrepreneurship career to float your life and it's just not quite working, you have $20,000 worth of debt that you're trying to pay off. Clients aren't easily coming in. It's feeling like we're sort of pulling teeth to get things to really work for us. There is no shame in going to be a barista part time at a coffee shop.

There is no shame in picking up some freelance gigs that don't quite align with you, right? I was talking the other day in Ascend the Mastermind, which by the way, we start second week of January. If you are interested in that, there's only a few spots left. This is for a high level entrepreneur who is already getting clients, already getting income and is just looking to expand.

But we were talking about how we say no and how we celebrate saying no to things that are not aligned with us. But I wanted to reflect to my people just like a little reality check that we are able and privileged enough to say no to work that we still love to do. For example, if you're a chef and you don't like doing catering events, and you're trying to make it in other ways, right, maybe you want to just do retreats.

You don't want to do catering events, but you just want to do retreats, but retreats aren't coming in the door like you want to because you still need to water that seed and grow that plant and be able to harvest it when it's actually ripe. To be able to say I said no to the catering event, even though that's still in the realm of the work you love to do, like you're still doing chef work, it's not like you're scrubbing floors or toilets, right, which there's nothing wrong with.

It just depends what your job is and what you're aligned with. Instead of doing that and saying no, we can kind of look at it and go, “Holy shit, I am privileged enough to be able to say no to those things, to work that I actually enjoy, and that is in line with my career.” Can we just take a second? My big example of this is when I shot a Bar Mitzvah. When I first started photography full time, I didn't want to be shooting Bar Mitzvahs.

I was gonna say baristas. I didn't want to be shooting Bar Mitzvahs. But I was like, I'm still able to do my job as a photographer, which what a privilege. I'm not having to go get a waitressing job or work at a corporate office and magazines, banging my head against the wall. I'm still able to use my camera and make my own money. So I'm still going to be really grateful for this job right now, because I need to pay rent and I need to have as much stress relieved as I can so that I can let my actual aligned work flourish.

Does that make sense? I do fully believe in coach that we should really try to stay aligned with what we're doing. If we're starting to feel anxious about a job or just have a bad feeling about a job or it just doesn't feel aligned or right, that we listen to that, and we're not afraid to say no. I don't want to saying yes to things like a full time job, a barista job, shooting a Bar Mitzvah job, a catering job.

I don't want us to say yes to those things out of scarcity, right, where we're just like, ah, I might not get something else and this is it. Then you're blocking the aligned things from coming in. You're not leaving space. You're just saying yes to everything. But if you're really analyzing your situation, and you can barely make rent this month, and you are so stressed and you're putting so much pressure on your entrepreneurship stuff going, “Why isn't this working?”

Then take the job, take the job at the brewery, take the job at the coffee shop, take the photography job that you don't necessarily love, but you're still able to use your skills, and you're still able to make new connections, and most likely the universe is putting that thing in front of you as a stepping stone. So instead of diverging around it and taking the longer way around, step on the stone and let yourself not be wrong for it and not have shame around the fact that you are not doing exactly your dream situation right now full time.

I hope this is making sense. I feel like I'm a little all over the place. It is like 6:30 AM here in Sydney. But I'm feeling really passionate about this. We don't need to feel ashamed for doing something that's not idyllic. We don't need to feel ashamed if we have to go get an actual job to support our dream right now. That's okay. That's part of the process. I promise you, if your dream is to be full time doing exactly what you love, you'll get there.

But you won't get there by just sitting there wishing and hoping for fairy dust to be sprinkled upon your gorgeous heads and for everything to just align and work out. We have to go searching a little bit. We have to co-collaborate with the universe on this stuff. Sometimes we go get that job to alleviate some of our stress and pressure around money, and we meet someone who is our next client.

We get a connection that totally changes the game. I have so many clients who have some sort of job job that they are working through, and maybe they don't want to be at, but they know exactly when it will be time to leave. Because right now, it's not so fruitful to just go two feet in and freak out your nervous system and tell yourself you must be doing something wrong when it's not working out, and you just don't have a six figure business at the snap of a finger.

So I hope this is a permission slip to you. I'm so inspired by so many people, especially artists, especially graphic designers and typographers and people like that, because I used to be in that realm as a graphic designer. I'd see a lot of those people speak on stage. I just remember success to a lot of them was when people would start hiring them finally for their style, like for exactly what they did that was absolutely unique to them.

For a while, to get portfolio work, to get well known, to get their name out there at all, they had to do some stuff they didn't want to do, right? That led to a lot of opportunity where they were finally able to be so picky about the work they took on and only do the stuff that was really in line with their style and their vibe and their brand. Let's not be the millennial slash Gen Z generation that is just spoiled.

Let's still work hard for what we want. Yes, alignment, yes, energy. But that's a parent too when we go and say, “Hey, I'm willing to go work at a brewery part time to make my dream happen.” That's energy and alignment too, so don't forget it. Let's not just be this generation that is like pamper me, serve me. I get what I want, and I only do what feels aligned at the time. It's like yes and masculine energy to y'all.

We have to have the riverbeds to support the river, or we're like an analogy I use all the time. That is not my analogy. I've heard it from other people. But man, so no shame in the side hustle, no shame in the full time job, no shame and taking gigs that aren't necessarily in line with you. Bar Mitzvahs, I used to shoot events that I didn't really want to shoot but they paid the bills. Yeah, I needed my bills paid y'all.

I was able to go from $30,000 worth of debt, a corporate job that was paying me not a lot, 60k a year, which was not a lot in New York City. It was $30 an hour, no paid vacation, no health insurance, nothing. Two full time on my own, but doing some freelance graphic design as a base that wasn't necessarily like filling my soul, but it was filling my bank account, which helped fill my soul.

Doing things like events and Bar Mitzvahs, until I was really aligned and only taking on things that I loved. But guess what, being smart about it, too, like having associate photographers that would take on these other projects, and I would get a cut of, right? So how can we be smart about the things that are coming through our door, instead of just always saying no. It's like, how can I be creative with this.

Two, getting totally out of debt, because I was smart about taking on projects that I needed to take on, becoming a business coach, getting really smart about my money, getting really smart about my intuition and what projects were aligned, delegating, hiring a team, working smarter. Now, five years later, I am able to travel full time, be remote, be talking to you on this microphone from Sydney fucking Australia, and did that happen just because I said I am in alignment, that I am in my feminine energy.

No, I'm sorry, but no, that's not how it happened. I was in both. I was doing the masculine side of things, the business side of things, the get down and dirty and work fucking hard, and do some things that I don't want to do, to the feminine intuition and the winging it, quote, unquote, right, of feeling like just in the flow and doing the thing that made sense and trusting the universe and collaborating with the universe.

Both of those, so no shame in the job job or doing a little work that you aren't totally aligned with as a baseline so that you can take the fucking anxiety out of entrepreneurship. So let me know if this resonated, it was a fiery one, y'all. So I hope you got some tidbits out of it. I'll talk to you next week.

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