If you’re thinking, planning or just curious about what it takes to leave a corporate job and become your own boss, this podcast episode is for you.

My guest, Ellen Yin of EllenYin.com and host of The Cubicle to CEO Podcast, shares some of the most amazing advice and strategies I’ve heard when it comes to helping people successfully transition from a corporate position to going full time and becoming their own boss.

While there are loads of practical and tactical concepts we cover in this interview, perhaps the most valuable aspects are related to mindset and how to break free from a salary “job like” mindset when becoming your own boss. We also dive into topics like how to go full time when you have more risk like a mortgage, supporting a family, etc for those of you who don’t have a lot of time to waste in building a 6-figure web design business.

Ellen was an amazing guest who was super engaged, very transparent and who is clearly very passionate about what she does as a business coach which is why this episode is one of my favorites to date. I think you’ll agree 🙂

In this episode:

01:45 – Some co-opetition
05:12 – Greeting to Ellen
08:15 – The best students
10:56 – Why now is good
12:06 – Stable and secure??
14:20 – Thoughts of “times”
17:42 – Is entrepreneur for all
19:00 – It’s a journey
23:22 – Entrepreneurial traits
24:51 – Undertaking risk
27:12 – Able to fail forward
29:51 – Do or do not
30:38 – Pivot and persist
32:04 – Wisdom to quit
34:28 – Knowing to pivot
38:59 – Theme of reality
40:51 – Afraid of investment
44:49 – No success shortcut
46:17 – Value of peers
47:50 – Those with risk
51:56 – Push of family
53:40 – Where to find Ellen
55:36 – Tell past self

Ellen’s FREE TRAINING on How to Create your First 10k Month

Connect with Ellen:

Featured links mentioned:

Episode #114 Full Transcription

Josh 0:15
Hey, everybody, welcome into the podcast. This is Episode 114. And before we dive into this episode, I want to say something I have so enjoyed every interview I’ve done on the podcast. So far, I’ve been so fortunate to talk with some amazing guests from all over the world in all different walks of life. But I do have to say the interview that you’re about to hear is one of my favorites. I think it’s one of my favorites for a couple different reasons. Number one, because of the topic that we’re about to dive into, we are going to get into how to go from cubicle to CEO and to become your own boss. And this is obviously something I’m so passionate about. Because I’ve been so fortunate to help a lot of people do this over the last couple years to leave their corporate job and become a full time web designer and build their own freelance web design business.

Josh 1:01
And I think the second reason why this is one of my favorite episodes today is because of the guests I’m bringing on my guest in this episode, Ellen Yin, is also a business coach. Now she doesn’t coach just web designer, she coaches people from all different entrepreneurial industries and freelance industries, to help them become their own boss and to go from cubicle to CEO. And she was just an incredible guest. And she really dishes out some of the most amazing actionable information and strategies and ideas for going from cubicle to CEO. She actually is also the host of a really great podcast called the Cubicle to CEO podcast which I recommend checking out. But it was such an honor and a pleasure to talk with Ellen.

Josh 1:45
It’s funny because we actually have a mutual student. And that’s how we got connected. And as I got to know, Ellen, I wanted it to bring her on and to pick her brain about this because there are so many people going full time and there’s no better opportunity than right now, to become your own boss and to start your own freelance web design business. And again, Ellen was just an open book with not only her journey, but what she’s learned from working with hundreds of people all over the world with becoming their own bosses and leaving that cubicle in that corporate job. So I cannot wait for you to hear this episode and to hear how it impacts you. Because Ellen was she was just so great. She has a wealth of information.

Josh 2:24
And it’s, it’s interesting. You know, you can tell in an interview, when somebody is really into the conversation, Ellen was just that she was engaged, she was fired up. And she really dishes out some just incredible stuff that I can’t wait to hear how it affects you and helps you go full time. Because this could be a conversation that is a turning point for you in your journey, particularly for those of you who are about to make that leap to go full time. So I can’t wait for you to hear this one.

Josh 2:50
Now, before we dive in. If you are, if you’re if you’re going full time, and you are somebody who might not have the amount of time that I did take six to seven years to build a full time six figure business, I want to help you expedite your journey. And if you didn’t already know, I have all of my web design courses wrapped up into my web design course bundle, it is going to be the quickest way for you to follow a proven path. So you can level up your services, get to know all the systems and processes that I use to build my business. And you can apply immediately to help expedite your journey. And it’s interesting because I always send a welcome video to all my students. And I got a video back from a recent student who joined my bundle Heather, and I wanted to play this short clip from what she sent back because I thought it was really interesting.

Josh 3:37
“I recently got handed a project it was so over my head I was like having nightmares like I couldn’t sleep at night, I was like crying. Because I could not figure out how to do the work that I needed to do for this client things that should have been easy. were impossible. And so that was kind of my push that it was like, if I want to be able to actually offer like higher priced like quality services to my clients, then I need to actually continue my own education.”

Josh 4:04
So you heard right there from Heather, that she was at a place where she just didn’t know what to do. She was just almost at a breaking point. A lot of people I think get to that point. And that’s it. That’s it for them. They never move forward. Well, as you heard, Heather realized that she was in a place where she needed to invest in herself in order to make that happen. And I want to do the same for you if you’re in that position like Heather was or maybe you are right now, I want to help guide you in your journey. And you can do that by joining my web design course bundle. I’ll be there with you every step of the way. You can go to the show notes for this episode at Josh hall.co/114. There’ll be a link there you can join and Heather a quick note to you. I know you’re a podcast listener I’m super excited to be alongside you in your journey. And without further ado, guys, here is Ellen Yin get ready to get inspired and get pumped up because this was such an incredible interview. We’re going to talk about going from cubicle to CEO. Apologies for the long winded intro but there was just a lot I wanted to say to get you ready because this was so much fun. Let’s dive in.

Josh 5:08
Ellen, welcome onto the show. It’s so great to have you on.

Ellen 5:12
Hey, I’m so excited to be here, Josh, thank you for having me.

Josh 5:15
Pretty interesting because we have a mutual student. And I wanted to start this podcast off with that, because I think it’s extremely valuable to have a couple of different business coaches or mentors in your web design journey for anybody. It was funny because our mutual student, April Ray, who is an awesome web design, entrepreneur, solopreneur, she told me that she was featured on your podcast, and the seat in a cubicle to CEO podcast. And it was so funny because she was so nervous about sharing that and she told me, she’s like, hey, Josh, I just want to let you know, I also have kind of another business coach. And I was like, April, I was like, that’s awesome. I encourage that there’s something so valuable, about getting to different perspectives. And as you now know, Ellen, I’m specifically coaching web designers, whereas I know you’re coaching freelancers in all different industries. So there are some things that I teach April that are very web design specific. But when it comes to like sales, that’s very broad. And that’s very general. So I’m sure you’ve gotten some incredible tactics that, you know, maybe I do differently, or I don’t know about. So I just wanted to start off by saying, it’s pretty cool to talk with somebody who we have a similar student, and she’s gleaned a lot from both of our experiences. So I’m really excited to dive into this and to ask you more about that approach, going from cubicle one, a corporate job to CEO, before we dive in, do you want to let everybody know where you’re based out of and I guess if you could summarize kind of what you do.

Ellen 6:44
So as Josh mentioned, Hi, my name is Ellen Yin, I’m the host of the cubicle to CEO podcast. And I’m based in Salem, Oregon, a little about me, if I could sum it up in one sentence is I help service space entrepreneurs make their first $10,000 month without a large following or posting every day, which if you’re in the freelance world, or you’re trying to make that jump from your corporate job into entrepreneurship, I’m sure those are two, two big things that plague a lot of people, right? Like, Oh, I feel like I don’t have an audience or following or there’s constant pressure to post every day. So we tried to remove that from your journey to 10k.

Josh 7:19
Well, I love that it’s one reason I wanted to have you on because I love your approach. And I love that style. I think in the age of hustling and grinding, there’s also an up and coming set of folks who are fairly anti that way. Not that we don’t work hard. But we just realized we don’t want to work 90 hour weeks. And I don’t know what your situation looks like Ellen, but I have a family, I have two little girls, I don’t want to be gone all the time in these years. So that’s one reason I love your approach. It’s a very organic and balanced way to go about it, which is super cool. So I know you deal with a lot of people coming from the corporate world. I guess my first question is for you. I’m just curious, do you work with people who are about to make the jump or thinking about it? Or do you work with people who have already done it? And they’re early in their journey? Or mix of all? What does that look like with who you coach,

Ellen 8:13
We work with a mix. I would actually say some of our best our best students are people who are early in their journey, but maybe they’ve had like one or two clients. So they’ve gotten that first taste of Oh, this is what it would look like to work with clients and and they’re committed to making their business work. So it’s not so much like they’re in the stage of like, do I start a business at all? Or do I stay with my job that they’re committed to, to making their business work, but they are early in their journey. So they don’t have necessarily a system yet for generating leads? Or they don’t know exactly, you know, how to close competently on a sales call? Or how to structure their services in a way that’s most profitable. So somewhere in that early to mid stage.

Josh 8:58
Gotcha. And do you have folks who are running a business on the side while working a full time job?

Ellen 9:05
We do have a few. Yeah. It’s interesting, actually, one of our members, I will always remember this because I was doing a live webinar. And I remember seeing in the chat section I no idea who she was at the time, but she was like, I am about to walk into my boss’s office and put in my two week notice right now I was like, Oh, right, like right this second. And she was like, Yeah, like right now. I was like, oh my gosh. So it was kind of cool to see her journey, you know, completely from day one of being in business. But we do certainly have others who, like you mentioned are still full time and their corporate job or whatever business they work from, and they also have some clients on the side and are trying to grow that in order to replace their current income.

Josh 9:48
Yeah, and that’s interesting, because there’s kind of three subsets there and that’s what I’ve found as well. That’s generally who I coach. I have folks who are early in the journey they’ve committed. I’ve a lot of folks who do as a side hustle meaning web design, and then they’re like thinking about taking it full time or they’re really close to doing that, which takes a whole nother approach than somebody who’s already, you know, going in, there are the people who are, you know, considering it as a as a job change or life changing. For me personally, I don’t know, if you’ve seen this, I’d be curious to see what you found in the spring of 2020. But once the COVID stuff went wild, that’s when a lot of people came through my courses. It was like a flux of people who got laid off from their jobs and who had quote, quote, unquote, a stable job, and found out that actually, it’s not that stable, and more and more people are turning to web design and other freelance industries. And I found it was really fascinating because a lot of people had started something on the side, and they were forced to take it full time, or some people did web design, in my case, years ago, and then we came back to it. And I guess that’s kind of one of the biggest first questions I have for you, Ellen is, why is now the time to do this.

Ellen 11:01
So I love your question about or maybe it wasn’t so much a question, but your your observation, I should say, of, of security and stability, and what happened when COVID, you know, and everything changed for a lot of people losing their jobs or being furloughed, I did notice a similar trend, Josh, that there was just an increased demand for online learning for seeking a different path. And I think now is such a great time to start your own business, or to monetize your existing skills and turn that into something that you can make money from, even if it’s not going to be your full time source of income. Because there Okay, this, I can’t take credit for this. But there was someone I can’t remember who right now. But there was someone who came on my podcast, who offered such an interesting perspective of security and stability that I hadn’t heard her frame this way before. So I just want to share it with you guys.

Security actually comes from having options and having choice having full control at any time over what you can do. – Ellen

Ellen 11:55
She was saying how, you know, we tend to grow up in this view of having a nine to five job with a steady paycheck every two weeks or every month as as what is stable or secure, because we can depend on it. However, she was saying, as we saw with COVID, things can change in a second in a blink of an eye. And to her stability. And security actually comes from having options and having choice having full control at any time over what you can do. And I think that is what entrepreneurship entrepreneurship is because when you’re in a job, if your boss tells you like, Hey, we’re gonna, you know, dissolve your role or change something dramatic about it. Or, hey, we’re not going to give you the raise, or we’re not going to do this or that you have very little control or choice over those parameters. But when you’re an entrepreneur, even if something doesn’t go the way you wanted it to you have the ability and the choice at any time to pivot to change your mind to say yes or no to the opportunities that come your way. And I think there is a level of security and stability that comes from that choice.

Josh 13:02
What a great answer. That’s such a unique approach to that question. Because Yeah, I totally agree. And I think that’s for any entrepreneur who’s who sees and and who’s done it for a while you realize there are, typically you’re not going to lock yourself into one product or one exact path or service, there’s going to be numerous ways to go about it. And I know, just my path, I wasn’t a web design solopreneur I scaled my business. And then I started teaching and then I eventually sold my business. So for me, I actually have I think, last I think I’ve got like nine or 10 main funnels of income at this point between sale of the business courses, some coaching, consulting, affiliate sales, there’s there’s quite a few different pathways, which is incredible, meaning I can I have some which are much more profitable than others. But if God forbid, something happened, there’s other options to be able to capitalize on and work towards. That is so valuable. I think that’s probably one of the best answers to why is now the time because not only is the idea of stability, different now, there’s also more options. And with technology, there really isn’t too many barriers or too many limitations at this point. Do you have any thoughts on that with just what you’ve seen from a technology standpoint over the past couple years and why now in 2021, there’s even more of an option to do what you love to do and get it online and work when and where you want?

Ellen 14:33
Absolutely. Well. I mean, I think this is a growing trend over the last number of years. So it’s not unique to 2021. But if you really think about it, because we are so lucky to live in the digital age, we don’t have to depend on a network or something outside of ourselves in order to have a platform anyone can have a platform these days for good or for or for bad, right? I mean anyone can can have their voice be heard on something that they want to Talk about and so I think that unique ability to reach anyone in the world and be able to turn something that you are already naturally good at, or that you get asked a lot of questions about I say this to people all the time, like who are you the go to person for in your existing circle of friends are your professional network already. Chances are whether you’re aware of it or not people see you as the the best person to ask about fill in the blank, right. And it could be something like the best person asked about training your dog, the best person to go to advice for when you’re choosing what what to wear for date night. I mean, there’s there’s unique gifts and talents that you have. And I think being able to turn that into a service that helps someone who is not naturally good at what you are naturally good at and being able to reach anyone you want on on your own platform without having to have media credibility firsthand or to have a direct connection to, I don’t know, CNN or Fox or whatever. I think that’s so powerful, and it’s an opportunity that should not be wasted.

Josh 16:02
Do you think this was a question I was gonna ask later, but I think now’s a good time. While it’s watching before I forget it. Do you think everybody could be an entrepreneur? Or do you feel like entrepreneurship is something where it’s, it’s, it’s suited for certain people or personality types?

Ellen 16:19
This is such a good question. I love these questions. By the way, Josh, I, you know, I go on so many shows, and it’s always refreshing to have a conversation about just kind of these, like, more, I don’t know, theoretical things, then like, how exactly do you need to do X, Y, Z?

Josh 16:33
I was thinking this too, because, you know, like, we could talk about getting clients and stuff. I’ve covered a lot of that in the show so far. And I just feel like it’s worthwhile diving into some of these deeper subjects. Because this I mean, reality is what we’re talking about going from a secure job to freelance is completely and 100% mindset. So we kind of need to unlock the barriers. But yeah, I’ve been really, and I say this, because I just had this conversation with my dad, this weekend, who is a salary guy he even said, he said, I love a paycheck. My family is not entrepreneurial. I’m a very black sheep, family, it really was a mental hurdle to get to where I am. Because I don’t come from this background, I was told that I should chase security. And, you know, my parents were terrified that I was going to end up on the streets, basically, just with that stable type of bake back on, and I’m maybe exaggerating that. But they were a little bit worried when I did this, because there doesn’t seem to be any quote unquote, security. But he said that, he said, I love a paycheck. So I kind of wonder, I don’t know if entrepreneurship would be for him. What are your thoughts on that?

Ellen 17:38
Yeah. So I, my answer is two part. Do I think anyone can make money online? from from from an existing skill? Or, you know, whatever it is? Yes. Yes. I do think everyone is capable of doing that. Do I think everyone should be an entrepreneur? No. And I really think that, like you mentioned, Josh, entrepreneurship takes a very unique I don’t even mindset, yes, but it takes this desire to truly forge your own path and create something in spite of every bad thing that could be thrown at you because it’s tough. It’s people love to glamorize, like, Oh, you work for yourself, and you get to be in your PJs, and you can make an unlimited income. And you know, they, they shout all these things from the rooftops. And while those things may be true, for some people, I, I think people don’t often talk about like, there’s a lot of hard stuff that comes your way when you’re an entrepreneur and you have to want the the journey bad enough that you’re willing to go through it. Because people often just see the end vision. They’re like, Oh, well, if I could just, you know, make a six figure income or seven figure income as an entrepreneur, then that’d be amazing. But the thing is, like 99% of your time is not spent at the end post, right? It’s the journey. So if you don’t actually love the journey, I don’t think you’re going to love being an entrepreneur. And what I will say to that as well is I think the world needs both. I don’t think everyone’s minds and spirits in hopes and dreams are desired to be on to be like business owners. And I think that we as entrepreneurs could not be successful without great teams, if you choose to have a team. And so I think some people like your dad, they they thrive in being part of a mission that’s bigger than themselves and working together with their peers and using their skills for good and making an impact through their jobs and receiving that paycheck. And for them, the reward is, is there. It’s fulfilling for them. And I think that sometimes too, maybe you’ve noticed this in the entrepreneur entrepreneurship world, people tend to shame the nine to five world as if like it’s something that’s bad and should be avoided. But I think that’s only true if it doesn’t fulfill you because it does fulfill some people. And so I think, yeah, to answer your question, in short, no, I don’t think everyone should be an entrepreneur.

Josh 20:06
Well, that’s a great answer, Ellen, that was a really well rounded way to look at that. Because I totally agree, I it’s not for everybody. And I do want to ask you about how you identify that if you have filters for people who maybe shouldn’t leave a cubicle. But it’s really interesting, because, like, I knew from an early age, that was not me, the cubicle lifestyle, I just even in high school, I’ll never forget my guidance counselor. Basically, made made me feel terrible. Because I didn’t want to go to college, I had no idea what I wanted to do. I didn’t want to go hundreds of 1000s of dollars of debt. I didn’t want to be an accountant working nine to five somewhere in a cubicle, and I knew I would be miserable Now, are there people who are happy doing that? Yes. And maybe they would have felt differently. There are people who love that paycheck, like my dad said, and my whole family is like that they even my brother as a software engineer, he just wants a job. And that’s cool. Like, he’s really good at that he wants to clock He even told me one time I want to clock in and clock out, I want to go home and I don’t want to worry about it.

Josh 21:03
I am not wired like that, from the very early age, I could tell I was much more want to do my own thing, think outside the box. And I could tell I didn’t really realize this until later on. But this is for me. And I think a lot of designers and a lot of freelancers find out that if you if you get into the entrepreneurial path, and you do love the journey, and you love that idea of just enjoying progress, which is the name of the game, I totally back up on that. It’s It’s gratifying in a different way than it would be for a salary person. And I think it all goes back to delayed gratification. Because an entrepreneur is not going to see a paycheck immediately. Well, you might see it, you might land some jobs, but you’re not going to get a stable income like you would do if you just land a job quick, right?

Josh 21:48
You know, like, it’s gonna take time to build something. And I think that journey you hit you hit it, that is the name of the game, it kind of makes me think about like, when I do a course, I tend to like the process of creating the course and content more than launching it because I have a bit of a depressive drop. And I don’t know if you’ve experienced this, but when you launch something for a lot of creatives, you wonder like, Why do I feel down? There’s like, there’s this high, when you launch something, then immediately, it seems like you’re just down for a little bit. And that took me off guard in the early days, because I was like, Why do I feel like this, I’ve been working so hard, I should be excited. But reality is I feel kind of weird, and not like, you know, seriously depressed, but there’s always a drop. And I think it comes from that entrepreneurial journey as you’re creating that’s where the excitement is. And you know, the payoff is great. But sometimes the journey is more exciting than the actual payoff. So I couldn’t agree more. I do want to talk about those filters to know whether this is for you. So for people listening to this, they might be wondering, okay, I’m considering doing this. I’m sure we’ll talk more about what to prepare for. But yeah, do you have any filters or any type of screening for people who decide, okay, this is for me, or, you know, maybe I am more more, you know, prone to this. Or maybe you can have a hybrid approach. I know some people who do like the freelance job type roles, but they are more free and entrepreneurial in some areas of the business, which is kind of interesting.

Ellen 23:15
Absolutely. And, to your point, Josh, I do want to add that you can have entrepreneurial traits in a job. Like if you have a leadership role, where you have that creative control, or that ability to bring new ideas into life, you can absolutely have some of those same experiences in a traditional job setting if you work in a great company culture that that allows for it, right? So that’s, that’s another thought to have. But as far as filters, I don’t have specific defined filters, but some things that I’ve noticed over the years of people who tend to stick it out with entrepreneurship, or who thrive in entrepreneurship versus those who don’t. I think one of the common themes is an extreme amount of accountability to self, meaning, the people who tend to not do well in entrepreneurship are ones who, who rely on other people to create their success.

Ellen 24:16
Meaning like they’ll, for example, they’ll buy a program. And if it doesn’t immediately work out, they’ll go, Oh, it’s the program’s fault. Like I you know, they’re, they’re the refund seekers. They’re the ones who were, you know, going on online forums and being like, Oh, this sucked in blah, blah, blah, blah, blah. They’re also ones who they kind of look at coaches almost as their saviors like, Oh, my business isn’t doing well. So if I just hired this coach, like, they’ll fix it for me, they depend on other people to solve their problems. Whereas if you think about it, even in the definition of the word entrepreneur, it comes from a French word that literally means to undertake risk.

Ellen 24:53
So, as an entrepreneur, you need to have a high tolerance for risk and more importantly, you need to understand stands that you and you alone are responsible for creating the results that you have. So yes, while coaches and programs and mentorship and community may help and and support you in that journey, it’s ultimately on you whether or not something happens or doesn’t happen. And so I think if that scares you, and you don’t like thinking like that, then that may be, you know, something to consider about whether or not entrepreneurship is right for you. I think another big trait of successful entrepreneurs is that they are willing to start things before they feel ready. They don’t, they don’t wait for things to happen to them, they create their own circumstances, they create their own opportunities. And again, they create their own solutions, right? They’re always problem solvers. And they’re very, very willing to, to fail. And, and they actually embrace it. And I think that is a really hard thing, especially when you’re moving from the nine to five world into entrepreneurship. Because in the nine to five world, I think failure is often penalized. Because, you know, usually points to you getting written up, or you’re not doing your job correctly, or you being at risk of being fired, right. So

Josh 26:12
Or failing a test, which was my I hated test, which is probably the first indicator that I was born an entrepreneur, because I was a solid C student.

Ellen 26:24
Many great entrepreneurs are, right. So I agree with I think, if you have a an extreme fear of failure, and you’re not willing, like if you’re if you’re going to be someone who’s like, I will not take any action, until I have a meticulous, detailed plan that ensures that I will be successful and try one, that’s going to be half. That’s the reason that you have to overcome, I truly, as an entrepreneur, I really believe that everything is just an opportunity to gather data, I literally think of myself as a little data miner, and I’m like, okay, everything I do, whether it’s good or bad, whatever the outcome is, it’s an opportunity because I collect data, and I let that inform my decisions. And I do better next time. And I just go forward with that. So I think failing fast and failing forward has to be something that you embrace as an entrepreneur.

Ellen 27:17
And ultimately, it comes back to that previous sentiment about is everyone designed, or is everyone meant to be an entrepreneur. And I really think that in this world, we have people who thrive in the doing, and then we have people who thrive in the designing in the in the vision. And so if you don’t, if you don’t really like to create things out of nothing, and forge forth a vision that isn’t pre planned for you, you may not be an entrepreneur, because there are some people who, who truly, they just want to be given parameters and said, like, this is your role, this is what you do. And then you you’re given the solution, and then you execute the solution. If you like to execute things, then you’re a great doers, and your great team member and the world needs, needs people like you. But if you’re like, no, I like to create the solution, then you’re the entrepreneur.

Josh 28:07
And a lot of times an entrepreneur needs somebody like that to be alongside them. There’s a great book called Rocket Fuel where there’s the visionary, and what’s the

Ellen 28:18

Josh 28:19
Integrator yeah. And that’s a perfect example of somebody who like has the ideas, but somebody’s got to reel them in and actually do them. Because there there’s a couple questions I have on what you just talked about. But there is a problem with entrepreneurs who just jump to new thing to new thing to new thing and will either not get something done, or it’s just all kind of half assed. And there are a lot of cases where some some people just personality types work together. Well, my wife is just like that she is not an entrepreneur, she always says I don’t have a creative bone in my body, although she can plan a party and do amazing stuff here in the house, with her creativity. But she doesn’t want to start a business and worked for herself. Now. She loves a checklist. If I like she loves completing a checklist and being done.

Josh 29:01
I don’t like that. I’m great at creating checklists in the never looking at it again. Like that’s not my style. I much rather create something than follow a checklist because it just doesn’t fill me up like it does her. So there there’s there’s, it’s there’s something to be said to where? Yeah, I agree. I don’t think entrepreneurship is absolutely for everybody. Although I agree. I do think everyone can make money on the side and have a hybrid approach. But there there’s you know, there’s a lot to that I was kind of curious when it comes to like committing to something. And I say this because one of my students who is killing it with his business, and he’s got a lot of risk. He’s got three kids now. He just recently went full time with his business, there’s a lot more risk, but he told me something that was fascinating. And I saw a little fire in his eyes and shout out to Leo who I’m talking about. But he said, I’m doing this I’m committed.

Josh 29:51
There’s a big difference between somebody who says that and somebody who says yeah, I think I’ll maybe try to do my own business and just kind of hope hopes on a wing and a prayer that I have There’s also I think one topic worthwhile diving into, I’d love to hear your approach on this is being committed to something. And then also knowing if it’s time to pivot or like, because failure is kind of interesting, you’re, you’re gonna fail a lot on micro levels, you might fail and not get a proposal or fail and not land a course sale. And you also might get to a point where this business model is not working, I’ve got to change something. What are your thoughts on that between like committing to something, but then also thinking about failure as like, potentially an opportunity to pivot from something if need be?

My whole theme in life is pivot and persist. – Ellen

Ellen 30:34
Absolutely. Well, I think so my whole theme in life is pivot and persist, like you can persist toward the same and outcome and goal, while changing paths on how you get there. Right. And, again, I feel like failure is an opportunity to gather information to collect new data that you didn’t have before and then to look at the data and say, okay, objectively, what is this telling me? And how do I how do I make changes in order to do better the next time. So I think commitment is important. And one thing that an early mentor of mine shared with me that has always stuck with me, as she told me your word is your bond, whatever you say, whatever you tell people, whatever you commit to whether it’s a commitment to someone else, or a commitment to yourself, it’s important that you follow through, because that’s, that’s your, that’s your reputation, that’s trust on whether or not people can believe what actually comes out of your mouth.

Ellen 31:34
However, just because just because maybe you set out with an intention to do XYZ, and halfway through, you realize this is really out of alignment with what I actually want out of life, you know, my family situation, the, there’s so many other circumstantial things that may change. I also think that this old adage of like, you know, quitters are losers or whatever, I don’t think that’s true, either. I think sometimes, it’s actually it takes a wise person to know when to quit on something. And quitting on something, quitting on a goal does not necessarily mean that you’re quitting on yourself, if, if the decision is not made out of fear.

Ellen 32:17
That’s the big caveat. If you’re quitting, because you’re scared that you’re not good enough, or that you you’re not capable of doing something that is a decision rooted out of like a scarcity, mindset and fear. And I think that’s when maybe quitting is not the right decision, but you’re doing it because you’re scared of failure. versus if you actually gather all the information you’re like, based on the facts. And based on what I actually want, this is not the right choice or not the right path for me, and then you pivot from there. Because you’re actually excited to seek something else that’s better aligned for you. That’s a totally different story. And that I think, should be encouraged. And you shouldn’t be afraid that you may change change your way, once you get started.

Josh 33:03
That’s great. It makes me think about one of my other students and members, Adela, who I think her episode will either be right before yours, or maybe shortly after yours. But she lost her web design business, and was very committed, but found out she didn’t necessarily like a lot of the aspects of web design. But what she did was she kind of analyzed the data like you’re talking about, and realize that she really enjoyed marketing and sales and strategy behind web stuff. She didn’t like design and development quite as much. She didn’t like coding and some of the other things that came along with it. So she pivoted.

Josh 33:39
She actually has now morphed from a web designer to a web strategist, and partners with other people who do the development and coding and design. And she strictly is more strategy, which most web designers get into much later. Most web designers Don’t think about strategy and website journey and stuff like that, which is really crucial. So that’s kind of her zone of genius. So I think that’s, as you were talking, and it just reminded me of her because I’ve seen her journey girl. And I saw her get to a point where, you know, when she looked at that pivot, I guess she could have quit completely and said, I don’t like web design. I’m done. But what he did was he didn’t take that approach. She actually said, Okay, here’s what I do like about it. What have I just honed in on this? And I think that’s a great example of pivoting. Whereas somebody may have just call it quits in that case.

Ellen 34:28
Absolutely. And I think that’s really admirable because it’s scary sometimes when you envisioned your business or your life a certain way. And then all of a sudden you you get there maybe you’ve been create the success that you always dreamed of. And you go, Oh, wait a second, like this is not at all what I wanted. And it can feel scary to tell people actually, I’m changing my mind and this is the new path I’m going but I think it’s so so necessary. And I’ve pivoted my business. So many times, Josh, I mean, it It started out like When I first started my business, when was that three years ago, a little over three years ago, I was a social media manager and I was a freelancer and I worked with brands on managing their accounts.

Ellen 35:12
And then and then I pivoted into only doing Instagram marketing and more as like a boutique agency. And then I pivoted into primarily being a course creator. And, and having digital products be our main stream of revenue. And now we’re entering that next stage of pivot where five to 10 years, the big picture vision is we want to be a digital media company. And, and so that’s a whole other ballgame. And we’ve brought in, you know, the revenue stream of brand partnerships, because that’s, that’s huge for for a media company. And that’s something that’s new, and that we’re not necessarily pros at yet. But I think it’s so important that you give yourself the grace and the freedom, the flexibility that as you change as you grow and evolve in your business grows and evolves and your life grows and evolves, that it’s okay to to make those pivots.

Josh 36:02
I think that’s a great approach for any entrepreneur because things are going to change. And in the case of my students in web design, stuff changes so fast, there’s really not. And I think this is why a lot of colleges and academic programs fail for their students, because there’s these books, these textbooks that are so out of date, by the time they get printed, the need is different. I know that like I can’t tell you how many people have come to my courses and said, Oh my god, I went through like four years of college and I learned more in like your your courses than I did in that entire program. But I spent $150,000 on like, it’s crazy. Like, there’s some value in academic higher ed, and I’m not a college guy. So of course, I’m not a big proponent of that. But again, it wasn’t for me, it is it for some people in certain industries.

Josh 36:51
Yeah, but in the case of most entrepreneurial ship and online world, your there is no exact proven path, like you can take a lot of the things that I’ve done, and you’ve done, I’m sure in your journey, but it is going to depend on what you want to do and what you want to go into. Now the trick is, I don’t want that sound daunting. I think that’s actually incredibly, incredibly freeing, because you can pivot and decide what you want to focus on. And I think my journey is a good example of that. Because I started off as a solopreneur. Like I said, a designer, I built my business. And I had every intention on being an agency owner and having a website design and graphic design business. And once I figured out that you know what I really love teaching. And I’m really, I’m good at teaching, it doesn’t feel like I’m working when I’m teaching. And I also realize I’m really good at connecting people, I love connecting my clients together. And I love being in a networking group and connecting people. And at the core of it, I loved helping people I just loved helping people, you know, do something and see their dreams come true.

Josh 37:51
So when I started doing courses, I realized pretty quickly, this is this is what I want to do. Like I enjoy building websites, and I love working with clients. And I never felt burned out by that. But I did realize I loved this so much more that the pivot came a little easier for me now it was still really hard. I cried when I sold my web design agency and I like I did I legit like it. I was it was emotional things. I have clients for years. And I part of me felt like I was letting them down. And I was kind of nervous at how it was gonna go, how are they all going to respond. But the feelings of what I do now just outweighed all that so that all that to say, I think you and I probably have a good example of how pivoting is is going to be the case when you’re an entrepreneur, it doesn’t mean that you’re going to build a business and sell at once a year. But it does mean that you’re going to add services and pivot and do things differently. And and I think I love that. I love that idea. And how do you feel about that? Do you find that daunting or freeing when it comes to the unknown of entrepreneurship?

Ellen 38:50
I actually find it freeing because you get to create your own reality. It all comes back to that theme of choice, right? And an understanding that at any moment, if you don’t like what’s happening, you can change it like you’re in control of changing it. It’s not. It’s not happening to you. You’re choosing what happens. And so I think I find it really freeing and I find it really exciting to think about Oh, what could be I’m you know, we’re big dreamers. Right. That’s why we’re entrepreneurs. And so I really love that. And to back up for a second Josh, I think you you threw in kind of an interesting point that I just wanted to kind of elaborate on you mentioned how you have some students who come through your courses, and they’re like, Oh, my gosh, what I learned in here is is far more valuable than what I got in a college degree $150,000.

Ellen 39:44
I totally understand exactly what you’re saying. Even I remember I mean I didn’t study marketing in college, but my friends who even recently graduated in marketing, I mean, it’s so behind the curriculum there in terms of what is actually moving and happening in the world. But in Interesting thing that I did want to point out is, oftentimes new entrepreneurs are very hesitant to invest in their education, outside of college, like they’re very afraid to invest in programs, investing coaches. And I think it is so, so so important to understand the value of investing in your network, your mindset, and your skill sets in that order.

Ellen 40:27
But most many of those things come through investing in programs being part of communities investing in mentorship and coaching. And an interesting thing that I’ve noticed, again, when we’re talking about filters between who is successful in entrepreneurship versus who is not, is I’ve noticed, if we’re bringing it back to that idea of accountability, people who tend to be afraid of investing, I have noticed, I don’t know, maybe you can relate they the last questions like, if I buy this, I don’t know, 997 program? What can you guarantee? Like, what’s your guarantee? Right? And I always find it so fascinating, because many of these people are college educated and you know, pursue to higher education. And I often think like, did you march into the admissions office on day one and go, this college degree is going to cost me $100,000? What can you guarantee? Right?

Josh 41:24
My guarantee. Maybe that was the case in 1960, but it’s a little different now.

Ellen 41:29
Exactly. And no one ever thinks to ask that question in higher education. But yet they, they will debate that over like a $27 product. And so I just think that it’s really interesting to notice those behaviors in yourself. And to ask yourself, like, Why? Why am I asking those types of questions, because I really think that the quality of your questions will determine your success. And so I really challenged those of you who are listening, if you’re newer in your journey, and maybe you have found yourself hesitant before around those types of things to really think about, like, how am I showing up as a leader in my business rather than then someone that things just happen to?

Josh 42:12
Well, and I think if you take a proactive approach on educating yourself, no matter what that looks like, whether it’s a free webinar, or whether it’s a paid course, whether it’s a community. And going back to the idea of you and I having a similar student in April, one thing that I found really valuable is your mindset is completely expanded, in reality, like you said, is changed when you have a few different minds kind of all working together. And that was a really confusing way of saying, Let’s take like sales, for example. When I started selling, I can’t believe I made enough money. Luckily, I was very low risk. I didn’t have any bills. I lived in my dad’s basement when I started my business that there wasn’t too much risk.

Ellen 42:55
Classic entrepreneur story,

Josh 42:57
Classic entrepreneur. Yeah, yeah. But my idea of sales was just what I knew, and what I experienced, I was very late to investing in courses in training. And I did some night school at my community college, which helped from a technical perspective. But if I asked one of my professors how to get clients or sell Good luck, yeah, no help there. So you know, like, he’s working at the community college. And so you know, there’s there’s a catch 22 there. But I say that to say, I went a very long time learning things the hard way by myself. If somebody invest in a program, or course, or in our case, two different coaches and communities, not only do you have your experience in sales with what you’re finding out and maybe hear firsthand by people you’re like, personally in touch with, but you also get to hear sales, from my perspective, my perspective and see what has worked for me and how I do things.

Josh 43:52
And then in the case of April, she got to see your experience with sales and what has worked for you in different industries. And I can’t tell you how valuable that is. Because immediately, you go from having one mindset to basically three mindsets all on one subject, which that bypasses the the amount of time it would take to to learn all these different methods with sales in this example. So I think when it comes to educating yourself, that’s the mindset that I learned to have is, yeah, I realize, not only is my experience factored in here, but I now get to learn from people who have either already done it or just have a fresh perspective, and it makes you think it makes you It makes the world literally look different. And I just wanted to back you up on that because I think that’s such a solid thought when it comes to education and training, in particular.

Ellen 44:43
It does. And you know, I’m sure you can agree with this, Josh, but I really don’t think there is a shortcut to success, right? Like if you if anyone’s out there looking for a quick fix a magic solution. It doesn’t exist, but you can absolutely shortcut mistakes. That’s a different thing. And if you don’t have to go the suffering way, then I encourage you not to. Because what I’ve noticed too on my journey is, you don’t know what you don’t know. And so when you’re, I always use analogies. And so like, if you’re thinking about like a, like a high rise, right, like in a city, if you are starting your journey on ground zero, and let’s say someone who’s been in the game for a long time, like you, Josh, maybe you’re on the 10th floor. If you’re on the first floor, and you are just working your way through the problems, sometimes you don’t even know what to ask because your view of the world from the ground floor is so different than someone from the 10th floor or the 100th floor.

Ellen 45:45
And so you may not even know the right questions to be searching for to be Googling to, to ask. And so I think it’s really important. I really can’t understate the importance of community and like you said, the more perspectives that you have, the better. And I have found I even did an entire podcast episode on this once about how I think the true value in programs is not even necessarily the tactical skills that you’ll learn like how to sell or like how to design a website, but it’s actually from the peers that you meet in your group, the network that you gain the access to a teacher, like yourself, Josh, who, you know, whatever, wherever that leads, I think that many people undervalue the people aspect of programs and they overvalue the the information aspect of courses.

Josh 46:38
It’s just yeah, that’s an interesting perspective. I totally agree with that. There’s something so valuable, valuable about having that network and community behind you, because suddenly, you’re not alone. And I talk about this often, but entrepreneurship is very lonely, unless you have a community you’re a part of. So I I agree with that completely. Yeah, I love those those thoughts on that Ellen, I actually wanted to ask you a more specific question that’s a little more tactile. And that is because a lot of people are probably listening to this. And they’re inspired, they might be in a cubicle working a full time job, or maybe close to going full time. But they have a family, and they have risk.

Josh 47:14
And like you just mentioned, I had the typical entrepreneurial path where I you know, I was, I was in a band, and then I started my business, I did t shirts, and then I started it was just that it was just a progression. And I didn’t really have too much risk. Back then I had I have my family now. And I would go full time, I would have a completely different approach, I would be very business minded. So my question to you is for those folks who do have risk, and have a mortgage and have a lot more writing on it, what I know this, this is a whole other episode in itself. But what do you what are some of the most important things to think about in your mind for those people who do have a lot of risk? But are, you know, have a calling to be an entrepreneur?

I do think that opportunities present themselves when you make yourself available for opportunities. – Ellen

Ellen 47:55
That’s a great question. And I will, I will put a disclaimer here that I am not currently married, I’m in a long term relationship, I have a mortgage, right? I have a house that I bought, actually this past summer. So I understand some of those, some of those risks, but I don’t have all of them like I don’t have children. So I know that completely changes the game when you’re thinking and caring for someone outside of yourself. And I think that this is so unique to every person, I think this is why I don’t necessarily love some of the advice out there where it’s like, oh, you know, just just do whatever, like, who cares, just like cut the cord and like jump in. I do think that opportunities present themselves when you make yourself available for opportunities.

Ellen 48:39
So don’t get me wrong there. I do. I do love like that saying like jump and then the net will appear. But I think you also need to look before you jump, like know where you’re jumping to. And if you have more risk, like you have family members that you’re caring for you have a mortgage, you have bills that won’t go away, you know, just because you decide to be an entrepreneur, you as a family unit need to decide what your risk tolerance is, and what you’re willing to do to make this work. I think the most important thing is clear communication, and a cohesive unit. I think if you’re trying to do something, and let’s say you’re married and your spouse is not on board, and you’re you know your kids. Well, not that your kids necessarily weigh in on the financial decisions.

Ellen 49:25
But if you’re not really making it clear to your whole family, like this is what I’m doing. And this is how we as a team, as a unit are going to make this vision come to life. I think that’s that’s where most people may go wrong is they kind of live in this isolated like, Oh, this is just my decision, and I’m not really sure. And they take all the responsibility on themselves. Instead of realizing Wait a second, I have a network that cares about me that wants me to succeed. How do I bring them into this decision making process and help me figure out a solution if it doesn’t go perfectly? Right off Right off the bat, and for me personally, like, I was young when I started my business, um, well, I still am young I, I was 23. Right. And I didn’t have a lot of risk. And I had actually,

Josh 50:10
I was 23 too.

Ellen 50:12
Really? Oh, that’s awesome. Yeah. And, you know, I was lucky I that I had paid off all my college loans before I graduated. University, that’s a whole other, whole other story in of itself. And so I didn’t have a lot of like looming bills. And at the time, I had moved back in with my parents to save on some money while I was working my corporate job in my hometown. And so for me leaving my job was not it was not a do or die, it was not like, if I can’t immediately make money, I’m going to be out on the streets. I understand that for some people, that could be your reality. And so understanding your own tolerance for risk and what your solutions are, is extremely important.

Josh 50:57
You Well said, I, yeah, everything you said was was great, I would have, I would have thought you went through that yourself and had a family the way you very, very eloquently put all that together, because that was very well said it kind of? Well, I think one thing to think about too, is a lot of people, when you think about this topic of cubicle to CEO, it’s like you stop your job, you get two weeks severance, or whatever. And then you’ve got to start getting clients immediately. And you got to start making money immediately. Well, the fact is, and I pulled this from one of my mentors, Pat Flynn, who I had on my podcast recently, and he said the same thing. He said, You can slow roll your way into it, you can absolutely build some stuff up on the side, doesn’t necessarily mean you’re gonna match your income right away. But you can absolutely get stuff going that way.

Josh 51:40
When you do make that jump, like you said, You’re not necessarily trying to think of a good analogy, I’m not the best of analogies. You’re not necessarily just jumping blindly. But you actually kind of have something going and started you know. So I, I love that because that is really important risk is it is very different for people who have families. I will say though, for anyone listening, who maybe does have a family, or maybe is about to have kids, that makes you very different in a good way, I have actually find some of the best entrepreneurs are parents because they had like, there’s the push, they’ve got mouths to feed.

Josh 52:13
That’s a whole different ballgame than somebody like myself early on, who took six or seven years to get to a place where I’m helping some of my students get there in a year or two, which is like the most gratifying thing ever. Like a lot of my students are aware I was six or seven years in the journey. I’m like, man, to your point. There’s no exact proven path. And I can share everything that I’ve learned. But at the end of the day, everyone’s journey is different. And somebody that goes down the personality types, some people might be comfortable going to a networking group and some not so much.

Josh 52:43
So there’s a lot of those little intricacies. But I love that idea. I think everything you said there as far as dealing with that risk, making sure everybody is involved. And it’s not just a personal thing. And there’s care, there’s planning, there’s doing things on the side to get ready for that. I love that. But at the same time, I also don’t want people lingering on a nine to five, if they have an opportunity to do this. That’s another big thing too. I’ve got a couple students who are about ready to make the jump and trying to be as encouraging as I can like, just realize you can make so much more money than you’re making right now. If you do go for it. So there’s a little bit of everything there. I know there’s no right or wrong so well. And this has been awesome. And I think I could go for about three hours with you. But I know you got it.

Ellen 53:25
I know this is so interesting.

Josh 53:28
Actually, before I have one final question for you, but I do want to see where would you like my audience to go? I know you’ve got a lot of different resources. Is there a certain website or resource or podcast or anything you want people to check out?

Ellen 53:40
Absolutely. Well, two things. If you’re a podcast listener already, I’d love for you to come join us on Mondays over on my show, the Cubicle to CEO podcast if you just search that it should be wherever you listen to your podcast. And then as far as resources if you are someone who has not yet made your first $10,000 month and you want to know how to do that without needing a large following or without relying on you posting every day, you can check out my free masterclass over at Ellen Yin.com/get clients. And it comes with my 10k month workbook. And I hope that helps set you on your path to 10k. So those are those are my two resources. And of course as always, if you want to say hi on Instagram, let me know that Josh sent you here. My Instagram is at Miss Ellen Yin. And I’m a very open book. So anything you know that maybe came to mind after this podcast episode that you want to ask, I’d love to chat with you my DM.

Josh 54:34
Awesome. We’ll have all that linked in the show notes. I didn’t even get I had written down to talk about quality versus quantity. But I know we didn’t get a chance to dive into that because I love that approach as well, particularly when it comes to social media. I would love to know since you’re pretty far along in your entrepreneurial journey, what would be one thing you would do differently or if you had to go back to when you started at 23 like I did what would maybe be something that you would tell yourself to do a little differently?

Ellen 55:01
I love that question. Um, I would say, definitely to, to narrow my focus to one single offer that I could scale. I think when I was starting, and I think this is common, right and and maybe it is a necessary phase where when you’re starting out, you kind of just like take on almost like any project any client, you’re like,

Josh 55:25
Oh, you you’re a beating heart, you have money to give me.

Ellen 55:28

Josh 55:29
I don’t care what I do.

Ellen 55:30
Yeah, exactly. So you’re in the exploration phase, and you’re trying to do everything and be everything to everyone. But if I could go back and tell myself, look, if you can be really, really, really good at one specific service to one specific ideal client dream client, instead of having to produce 50 solutions for 50 different types of people, you’re producing one solution for one very specific type of person, you are going to get better at that so much faster, the results are going to speak for themselves. And you’ll actually, like you attract so much more referrals, word of mouth. And ironically, when you niche down on something, I often find that you actually become more of a go to expert on all things like people just come out of the woodwork and ask you all sorts of things have nothing to do with what you’re actually, you know, really, really the expert in. And so that would be my advice is to is to get clear and get focused.

Josh 56:21
Oh, love it. All right, Ellen. Well, I know I got let you go. We could like I said, we’ve got about three other podcast topics Now we could go off there on this one. Thank you so much for your time. And for everything you do. I’m really excited to make this connection with you and they keep in touch.

Ellen 56:35
Thank you so much, Josh.


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