Rai Cornell 0:02
Welcome to Season Two of the SOAR podcast, the place for creative entrepreneurs who want to build healthier, happier, more profitable, self employed businesses. I’m your host Ray Hyde Cornell, business mentor at Chiron consulting and CEO and senior copywriter at Cornell content marketing, get ready to soar.

All right, well, today on the SOAR podcast, we have Anna MacDonald, who I am so excited to have here because I have the pleasure of working on her brand copy. And she is just such a shining example of entrepreneurship and what it really means to live your dreams. So Anna, can you introduce yourself and tell us about what your business is?

Anna MacDonald 0:52
Yes, thank you so much for having me. I’m honored to be here. So as you said in the onset, my name is Anna MacDonald. I live in Maine with my three daughters. I have two cats and a Golden Retriever who will never be forgotten, of course. So yeah, let’s jump into what Stella’s Desk even is. So I started Stella’s Desk last year 2021 initially as an office supply subscription box and quickly realized that growing a brand for no one, or for everyone was a brand for no one, right? So I kind of scratched that idea. But knew I had something with Stella’s Desk, right? I just really needed to refine it. So it developed and I’m sure we’ll get into this deeper, but it developed into a subscription box for female entrepreneurs and a way for me to follow my passion, which is really empowering other women to live their life to the fullest, to be unapologetic, to be decisive and go for what they really want. And form that beautifully with branded copy from you, of course, and somehow contain that in a quarterly subscription box. So that is what Stella’s Desk is. Eventually I plan to develop workshops and really grow it into a community based lifestyle brand, really, but you know, I have big dreams, of course. So for now we’re sticking with the quarterly subscription box and then we’ll see where it goes from there.

Rai Cornell 2:37
Yeah, and your journey was, like so many of ours. And I want to kind of normalize this and tell people it’s okay, that your journey was not linear. When you had experience in the corporate America world, you started out in the virtual world as an OBM and a VA. And now you have a product base subscription business. So tell us about that journey, like how did you get to this point? And what was kind of the tipping point for you that made you realize, okay, actually, I want to go out on my own and do my own thing?

Anna MacDonald 3:08
Yeah, that’s a great question. So I had initially decided that I wanted to start my own business in early 2020, shortly after the pandemic hit right. And we were all working from home and online business really blew up. And I had a good friend who was working on a membership for parents at the time, and she really opened my eyes to the possibilities of having a business online. And I had no idea what I wanted to do. I had no idea what my purpose was. I just knew that that was the lifestyle I wanted. So I kind of hemmed and hawed on what I was admired for or what people asked me about a lot, which at the time, I was an executive support in commercial banking. So in the corporate space, I had been in corporate America for 13 years at that point. And I thought, okay, so I’ll start coaching other executive assistants, right, and other executive support and see where that takes me because I get asked a lot about how I provide a superior level of support. So I started there. And then, of course, all of the creative juices started flowing. And why stick to just one thing when you’re multi passionate. So shortly thereafter Stella’s Desk in its original form was born.

And that was, as I mentioned before, an office supplies subscription box, that was just for other office supply lovers like me, right? And unfortunately, that’s not a super lucrative niche, when you don’t know how to market it correctly. And of course being pulled in those two different directions, right, so trying to split my energy, really three ways, my corporate job, I guess, four ways, my family, Stella’s Desk and my coaching membership for administrative support in the corporate space. So for a while, I felt that split but I didn’t want to give any of it up. And I think that that happens with a lot of us, right? We’re multi passionate, and we’re told over and over stick to that one thing you want to be known for. But I liked different things. And I wanted to be able to do it all. And I genuinely believe that women can do whatever they want, right. And so we just have to figure out how to make that happen. So I went along that way for months and months and months.

Fast forward to 2021, people were starting to get called back to the office. And I was already like, knee deep in this online business space. And it’s really where my gut was pulling me. And I think everybody, including my husband, at the time, thought I was crazy, because I had a great job, a stable job at a fortune 100 company, great benefits. I would have stayed there my entire career until it was time to retire. But I just felt pulled in this direction and felt like the world was my oyster. If I could figure it out. If I could just figure out how to run a business online. I could do anything I wanted, travel, live the life I wanted to live. So I quit my job, I quit my corporate job with kind of just a dream and a prayer and some hope. And luckily, we had some savings that could kind of hold us over. And yeah, so off I went. And I think everybody at my job thought I was crazy, but super supportive. At least in my face, they are super supportive. And so fast forward about two or three months into being fully self employed, I started to feel a lessening of my passion for the coaching of people in the corporate space because the further and further removed from it I got, the less in touch with it I was.

Rai Cornell 7:39
It’s like those weren’t really your people anymore. Almost

Anna MacDonald 7:41
Exactly, I no longer could resonate with them in the same way because I wasn’t living that day in and day out. And it is a completely different lifestyle than being self employed. I also started to realize that I much preferred the actual doing of the work and being behind the scenes than being really the coach and the face of it. I much preferred helping the executives at the time run their business. So I started to do a little research about how I could do that, while also self employed instead of going back into working for someone else. And I learned about the role of an online business manager and it was like the gates of heaven had opened. It was everything I wanted, it was systems, it was Excel spreadsheets, it was operations, it was team management, all of those great things that as high level executive support you love about your role, only doing it while self employed and sort of on my own terms for who I wanted to work with, right, which was female entrepreneurs who are building an empire, who are in the active role of building their dream.

So I shut down my membership. I felt like I was disappointing the members, right. I feel like they had trusted me, they had invested in me. But I really had to follow, continue to follow that gut feeling and that calling that I felt. So I transitioned to online business management. That business quickly grew as word of mouth grew, referrals grew. And I was loving it until I really realized how hard it is to scale a completely service based business when it’s just you. I felt like I was dropping the ball with clients which I hate and people who are VAs or OBMs who are listening know that feeling, we are servants at heart And we don’t want to let people who we are supporting down. So that started to really bother me. And I knew I didn’t want to grow an agency. So I was kind of like, you know, where am I going to go with this, this is great while I’m doing it, and I’m blessed that I’m able to be making money doing it. But I really need to take a hard look at scaling and the future of being self employed.

And in comes, Stella’s desk rearing its head again, you know, I really want to pick that back up, I really think there’s something there. I just need to get it right. And I don’t know what right is, but I want to find out. So that’s when we met. And I said, you know, this is the direction I want to take it. Throughout that sort of year and a half time of working online, I had been working with female entrepreneurs exclusively. And that’s, you know, to watch women build an empire and live their dreams and live a lifestyle that is completely unique to a female entrepreneur, it was like lit me up. And that I could still work with them just in a different way that I could scale differently, and pull on all the strengths that I have still offering digital products that are more of a DIY instead of DFY. But even broader than that, beyond just the systems and operations, as well as the empowerment, the mindset around what it takes to run a successful business. So we work together really, really banged out some strong copy and verbiage about how to talk about what this is because it’s more than just a subscription box. Right? It is an entire lifestyle. It is an entire movement. And that’s my vision for Stella’s Desk is that, you know, an author takes a picture with the box and says, Oh, my gosh, I was included in Stella’s Desk this month. Like, that’s just like I’m manifesting that right? Just by saying it

Rai Cornell 12:26
Yes, you are

Anna MacDonald 12:29
I felt like it was all working together. All of this time of being in business online was coming together so that I could understand female entrepreneurs in a different way. And now serve them using all of those skills and all of that knowledge that I had accumulated through corporate and being self employed to make this a really powerful brand. So completely nonlinear, completely a challenge. And I’m still not where I envisioned myself to be almost a year out from quitting my corporate job. But I know that it’s there, right. And so you just keep going.

Rai Cornell 13:16
Exactly. And it keeps going in the direction that your gut is pulling you. And one of the things that I love about your story is that you had so many opportunities to do the things that everyone says you should, quote unquote, should do. Or that, you know, Instagram is saying it’s the next level, this is the next step in your professional achievement. Like, you could have stayed with that fortune 100 company, you could have taken the you know, quote, unquote, smart route, the predictable route. But that wasn’t what was lighting you up, something was pulling you in a different direction. And then when you went into the coaching arena, I feel like nowadays, that is like the thing. Like, if you’re in online business, the goal is to get to a point where you are coaching other people to do what you do. And that’s great for some people. Personally I love coaching. I love being a mentor. I love teaching, I’m constantly coming up with workshop ideas and freebies, and like handouts, checklists and systems and tools and things that I just want to give away. I want to teach people how to make their life so much simpler and easier.

But for you, you’re like No, the coaching thing, like that’s just not my route I want to do the doing. And then there’s this other myth in online business of you have to build an agency. Well, once you figured it out on your own, then you of course, like of course, you have to hire people, you have to build a team and you have to grow and grow and grow and scale. But that didn’t feel right for you either. And throughout all of this, even though it was very nonlinear, you were really chasing that one golden thread of what is my gut telling me and it took you back to Stella’s Desk which I want to talk more about Stella’s Desk and just the powerful connections that you make with female entrepreneurs, we’re gonna take a really quick 30 second break to drop some resources for our listeners. We’ll be right back.

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All right, and we’re back. And I want to get into talking about what Stella’s Desk really is because I feel like not only do you talk the talk, but you walk the walk, you’ve been there, you’ve been in that corporate environment, you’ve done the online OBM work, you’ve immersed yourself in the world of female entrepreneurship. And you seem to have this profound insight into what it is actually like to live this lifestyle. And even though Stella’s Desk started out as an office supplies subscription box, that’s kind of like the cool, neat thing that we get as subscribers. And yes, I am a subscriber of Stella’s Desk, I am absolutely obsessed with what you’ve created. But that’s like the side benefit, right? The office supplies are kind of like the side goodies. Because for those of us who can’t walk into a Target or an Office Depot without leaving with a shiny pen or a nice new notebook that we just can’t wait to break open. It’s that kind of like material satisfaction. But it’s so much more than that. Right? Like tell us about the culture and the mindset that you are trying to spread with Stella’s Desk as a physical tangible box.

Anna MacDonald 17:46
Yeah, so I think sometimes people wonder why it’s called Stella’s Desk and my name is Anna. Some are like wait, why isn’t it Anna’s desk? So really the inspiration and the the walking the talk comes from the boxes and the business’s namesake and that was my mom. So and again, we’re gonna get really confusing because my mom’s name was Kristen. But she

Rai Cornell 18:17
Makes sense. Don’t worry.

Anna MacDonald 18:18
I know. I know. We’ll get there. She was a force and she was a trailblazer for goals that she wanted to go after. Whether it was socially acceptable or the aka right next step. If she had a goal or had a vision she would go after it and Stella comes from her alter ego. So Stella when she would have a couple cocktails or even just feel super empowered that day, Stella would come out and Stella was like my mom on, you know, a couple margaritas just completely take no prisoners, unapologetic, brave, fearless, dancing on tables, jumping in the lake with her full garb on, like she just was a force. And that is the passion that I want to bring to other women who want to be trailblazers, who have a vision, it’s not conventional. It’s not what everyone just assumes is going to be the next thing that they do, right? Women entrepreneurs experience entrepreneurship differently because we have all of the societal pressures that we get, the pressure from our family that maybe our brother who’s an entrepreneur might not receive or an uncle who started a business right? Like we experience it differently and that should be completely supported, embraced and empowered. And that is what I was taught from my mom. And I want everybody to have a Stella I want every woman out there who wants to have a business or is running a business and struggles with mindset and doesn’t have that support system. Or that person, they can call, that Stella they can call and say, you know, like, I’m having limiting beliefs, or this person asked for a return, or I don’t feel like I’m pretty enough to be on Instagram, right? Like, I want them to have a Stella that’s saying, You know what, screw that. You can have everything you want and more and you’re going to do it. So that’s really where the name comes from. The passion that is behind Stella and seeing that growing up and seeing that sort of attitude towards life that the world truly is our oyster. And we can have anything we want. We just have to keep going. Yeah.

And I see it here when we talk about you know, Stella is your mom with a few margaritas, we’re not talking about getting drunk and rowdy going and swimming in a fountain which admittedly, I’ve done before, but what we’re really talking about is that kind of like zero shits given like, absolutely no fucks left, I don’t care, I’m just gonna live and I’m gonna just be joyful and just be exciting and just do whatever I want to do and taking action from within. What do I feel like doing, what is life calling me to do, not the shoulds. And I love that you pointed out this kind of like societal role, that women who have a family, women who have a household are put into and especially for those of us who have lived a very quote unquote, responsible life where for you, you did have the corporate career you had made it as they say, you had a family to look after, a house to pay for. And when you have always been that responsible person. And I’m the same way, I’m like an Uber Capricorn. I am just super organized, I got the degrees, I did the things, I got the good grades, you know, all the certifications and accolades, whatever, but it didn’t matter. Because even if you are that super responsible person that everyone sees you as you can still have that other side of you. And I feel like that other side is what Stella’s desk honor so well. It’s that rambunctious joy for life, and just the sake of being you authentically 100% you that the box really encourages you and kind of reminds you every quarter, you’re still her, even while you are running your business, you’re still that other person too

Rai Cornell 21:23
Exactly. Take the chance, what would you do if fear was not a factor? And that’s not to say, like, always burn the whole thing down and just start over. Like I have a couple times

Me too, we’ve been there. But you sometimes need to do that. Sometimes you need to light the thing on fire. And that’s ok

Anna MacDonald 23:14
That’s right. If it’s not lighting you up, and it’s not, you know, I really feel like when you can align your passion and your purpose with how you can make an impact. I mean, that’s gold. That’s what we’re here to do. And so if what you’re doing isn’t feeling that way, even though it’s what seems to be accepted. Screw it, screw that, like I just, I just feel like life is too short. And that’s really what my mom had instilled in me, and then by her passing when I was in my early 20s, again, instilling that tomorrow isn’t promised. And she lived every last moment, as big as she could. And I want that for every woman, especially if they don’t have someone in their corner like that.

Rai Cornell 24:11
So what advice would you give someone who’s listening to this, and maybe she’s done the corporate thing, maybe she’s done the online business thing. And none of it is quite feeling right. And she’s hearing all of these messages that, oh, when you’re an online business, you can be a VA, you can be an OBM you can be a writer, you can be a designer, you can do all these things. And she’s just looking at this and she’s like, Yeah, but nothing’s really clicking. I know I have those worlds of possibilities, but nothing quite feels right. You took that leap and went into product based business subscription business, which is a wildly different environment to plan your business, make a profit, pricing, client acquisition, everything is different when you have a product based business. How did you make that leap

Anna MacDonald 25:01
Knowing that I could, knowing that I could, I didn’t know. And I’m still learning, right? I’m still, as much as I love spreadsheets, pricing out things every month. And you know, that just it doesn’t light me up. But I learn how to do it right, I’ll learn how to do it until I can pay a bookkeeper to do. But I think the biggest advice I would give is, if fear was not a thing, what would you do? And you can do it, even if it seems wildly different than what you’re doing. There are no rules, there are no rules. And if it aligns to your passion and your purpose and your impact, you can’t go wrong. And you’ll learn from it. And it will take you to the next level, the next step, right. And whether that’s up down sideways, backwards, it doesn’t matter, because it’s all learning and no matter how uncomfortable it feels, you can do it. Yeah.

Rai Cornell 26:03
And one of the things that also I feel like was like a common theme throughout your story was doing things even when you didn’t feel ready. And what advice would you give to those people who are putting off their dreams, they’re like, Oh, I’ll start the subscription box, once I get this business or once I reached this monetary goal, or once, you know, my kids are off at college, or once they’re in elementary school, or we feel like we’re always putting off the big thing that we want to do for good reasons. But really, maybe it’s just because we’re not ready inside. What advice would you give to someone who’s feeling like that right now?

Anna MacDonald 26:43
The best advice I ever got when I first got into online business was just do it scared, you’re gonna be scared. I mean, there’s not many days where I don’t have to do something that makes me kind of tense up like about something right? What are they going to think? Is it going to sell? What if the product doesn’t come in on time, right? Like, there are literally fears about everything. But just do it scared, do it anyway. Work through the fear, because it’s all in your head. And once you get to the other side. Now you’ve learned that and now you can battle the next Goliath, climb the next mountain. All these euphemisms I’m using but it’s true that once you get past those first few challenges and you gain that confidence, there’s nothing that can stand in your way if you truly believe in what you’re doing. So that’s what I would say is do it scared, and get out of your own way.

Rai Cornell 27:44
And newness comes with the territory, right? I mean, this is one of the things that we talk about in my how to beat impostor syndrome workshop, it’s if you’re going to be an entrepreneur, the definition of being an entrepreneur is literally taking on the risk to do new things and explore new avenues. New, newness, all the time, you are constantly going to be doing new things. And part of that is looking back at your history and going how many times have I done something that I didn’t think I could do, and it was totally new to me. I had no experience in doing this thing. But I did it. And if you know that you can do new things, and hard things, then you can really do anything. So Anna, where can people check you and Stella’s Desk out?

Anna MacDonald 28:27
Yeah, so you can find me on Instagram at Stella’s desk or visit our website which is Stellas-desk.com. And, yeah, reach out to me too in the DMs. I’m always in the DMs. I’d love to hear that you listened to this episode and connect over there for sure.

Rai Cornell 28:43
Yes and you have a gift for our listeners as well. People who are struggling to sell their offers. Tell us about that.

Anna MacDonald 28:49
Yes, so we do have a guide to creating reels to confidently sell your offer. So I like to tell people that you are capable of more than doing lip synching on reels. So let’s put your face out there. Get creative, get silly, get fun. And people can find that at reels.stellas-desk.com

Rai Cornell 29:10
Fabulous. It’s absolutely perfect and something that especially as introverts really need help. Thank you so much for being here, Anna.

Anna MacDonald 29:18
Thanks so much for having me.

Rai Cornell 29:32
Hey, Rai here again, thanks for listening. If you liked this episode, please subscribe and rate us in your favorite podcasting platform. Want to be a guest on the show or know someone who has an amazing story of entrepreneurship? Apply on our website at chironconsulting.us/podcast.