How To Create The Life That Will Make You Happy – with Scott Dinsmore

Episode 100

Why do you want to make money online? This is something that you really need to sit back and think about. Scott Dinsmore is all about finding the things that truly make you happy.

Watch the show below: Duration: 26:07
[leadplayer_vid id=”511C1CD031697″]Stuff mentioned in the show – Scott’s website

Raw transcript

How to Create the Life that Will Make You Happy – with Scott Dinsmore

Mike: Hi there everyone! Welcome to Episode 100 of the Mike from Maine Show, the place where we do daily interviews with successful online entrepreneurs. This is your host, Mike Thomas. And today on the show, I’ve got Scott Dinsmore on from Live Your Legend and we’re gonna talk about doing things that make you happy and really address the fact of why you’re doing what you do. A lot of the times, we look at this thing, like we wanna make money on the internet, wanna make money online. But, why, why are we doing that? Why do we want that? The reason for me, anyways, is that I want to be able to have freedom in my life, to be able to live where I want to live and do what I want to do. It doesn’t mean that necessarily this whole like passive income thing, it’s not necessarily that I’m not working, but I’m able to choose when I wanna work and to choose more what I want to do. I think that’s for me, anyways. That’s what makes it really important for me. So, you know, we’re gonna talk to Scott a lot about today and I just want you to, while you’re listening to the interview, just really think about why you’re doing what you’re doing and I’m sure that Scott will resonate with you. Without further ado, Scott Dinsmore.

Mike: We are here today with Scott Dinsmore. Scott, welcome to the show.
Scott: It’s great to be here Mike, thanks a lot.
Mike: Let’s start right off by having you tell us a little about yourself and what you do. Scott: Yeah, it’s a, it’s a big question.
Mike: I know, I know.

Scott: The first answer is I love to explore, I see a map in the background, you can probably see mine in the background here. That’s why I got pins in mine for where I’ve been and where wanna go but try to like treat life as an experiment and exploration and, and so that, it leads me to like, really the business part of things, I have a website called Live Your Legend and our goal, our mission is to help people find and do work that they really love and found their passion about and build a career around work that excites them. And I think, if we get enough people doing that, we can start to make traumatic changes in just, really like the course of the world. I mean, think of what is the statistics, it’s like 80% of people don’t like the work they do. I mean, that makes me cringe and think about, like on the average the people you see everyday are unhappy with how they spend most their time and yeah —

Mike: I was just gonna say, there’s a quote that I love, ah by Henry David Thoreau and he wrote the book for those of you that didn’t study English very well in high school, ah he wrote a book called Walden and the quote is, “The massive men lead lives of quiet desperation.” I don’t know if you’ve ever heard that.

Scott: Yeah. I, I have, I’ve heard that. I know there’s second part to it, right? It’s something about going to the graves with their song unsung, or something.

Mike: You know more than I do. I thought I could make myself a little smart here. And then, you go and, and recite the whole — you probably know the page number and —

Scott: We play on each other but, no, but that’s a sad thing. And Mike, I’m sure we’re getting this in a quote but if people around you aren’t inspired by the work they do, like just, by just like, human nature, we’re gonna not think we deserve it and we’re not gonna operate on that level and then we treat people differently, and then you’ll treat your wife, or your girlfriend, your kids, whatever on different ways if you love your work or if you hate, it just, it ripples. So, that’s our goal here. There’s all kinds of ways that we do it with our community.But that’s the basic idea.

Mike: How did you — give us a little bit of background here because for anyone that goes to your website, they’re gonna look and see, okay, this guy’s got it all together. He’s — you’re making all these money, you’re able to support yourself doing what you love. How were you able to even create the life that will make you, make you happy? How were you able to do that?

Scott: Yeah, I think, you gotta kinda bank into it. Like, there’s a lot of people, especially today, that look at the internet, and hear people making money and doing really well. I think, yeah, great, there’s a lot of people doing well online but the internet is just like a tool. Okay, it’s like a very cool tool that allows us to help a lot more people with something that we care about, something that we’re good at, to connect with people. And so, you, if you start with ah — okay, I wanna make much money online. I think, that’s the total reverse way to approach. It’s how can I really help people? And then, how can I use the internet to help them? And if you do that, then you’re gonna find a way to make plenty of money doing that and using whatever tools, making courses or doing coaching, there’s all these kinds of ways and it started for me, I am — I had a terrible job out of University. I live in Spain for a year, which was

fantastic. I came back planned to like, do something big and great and then all my adult mentors said, ok, get a real job. And I did. And it was at this big international corporation, like 4500 company, it was awful. I pat my head against the keyboard. So, I quit and said I wanna find something that I can’t screw up. And that’s how I put it and I just wanted to have an impact. And, so I went on to search and I ended up finding a great business some friends were running, we’ve got a health card company. And I don’t just find, for the first time, I found like work I was passionate about, I really cared about, like the way we were helping people it was — Health and Fitness was a really big part of my life and that was just the very cool thing and then, bit by bit, I went through a ton of work on my own, like figure how do I find a work that makes me happy and that I’m good at and all that. And then, I read all kinds of books and worked with coaches everything and I started making my — these own discoveries for myself. One more friend started to ask for help though, a case I got, like you um, you found something you’re excited about, it seems like you’re really into this whole career thing, could you sit down with me for lunch. And I say, sure but at that point, my quit rate was 80%: 80% of the people that I had lunch with would quit their jobs in like two months of meeting with me and it wasn’t anything like magic, that I was doing. I would pretty much just ask one question, like why are you doing what you’re doing. And almost always it would be, well coz I’m supposed to. I’m trying to get here, this is to fill this resume line out or whatever and it reminds of the Warren Buffet quote that um, “Taking a job just to build a resume is like saving up sex for old age”.

Mike: Yeah, it pretty much is.

Scott: So why, I mean here. If you think about it, it’s like why would you ever like waste your time doing something you didn’t like. So that maybe eventually or something you did, like everyone’s better off if you start right now doing something you’re good at and something that, that people — that you enjoy coz other people will, will benefit. So, —

Mike: I think — sorry to interrupt you, but I think objection would be that I think a lot of people do things that they, that they hate because they feel like you said they feel like they’re supposed to but it’s because people have bills to pay and responsibilities and you think, ok, maybe I don’t like doing this but what else, how else am I gonna pay the mortgage? How else am I gonna put food in my kid’s mouths like that. l think that is an issue as well.

Scott: Well, yeah. And so, I hear that objection, I think you’re making the assumption that there’s like inherent risk in doing work that you love and I don’t believe there is. I think the biggest risk is, is not, is not even trying coz then like you know you’re gonna be miserable for the rest of your life. Like that’s, that’s a terrible thing but thing is like it’s not just about being an entrepreneur. I happen to love that and I know you do too and there’s a lot of great ways to do that but it start with just being intentional about the stuff that you do, like understand yourself. Know what you’re best at, what are your strengths? What are your weaknesses? What do you love? What do you absolutely hate? And, and do that stuff that unfortunately you never learned in school, no one really walked you through it, it’s on you to do it. And I mean, you spend more time in University picking out your dorm room TV set that you do picking your major and it’ just crazy but, so but if you do that, then at first it’s not just about like quitting it all and starting fresh. Not everyone can do that right away, that’s totally fine. But it maybe it’s making a 5 or 10% tweak in the work that you do at your current job, that all of a sudden leverages those strengths that make you come alive because, I think, what really creates fulfillment in what you do more than anything is day-to-day, using your natural talents and strengths and the thing — and doing things aligned with be your values. And that doesn’t have to be risky. In fact, I think it’s the opposite. If you start just making decisions based on that.

Mike: So, ok. I, I wanna do something like what do you tell people, like I’m one who you sit down these people for lunch and you said they have an 80% quit rate. Like okay, you ask them you said you ask some why do they do it. Is that what you said, what was it?

Scott: A number of things but generally it’s why are you doing what you’re doing and just get to the heart of it. If you ask why enough times, you’re gonna get pretty, you’re gonna get some pretty serious clarity on either how silly something is or how much it means to you.

Mike: And, ok. What I wanna know from, from what you’re doing coz you seem pretty happy with your life and, and everything. And how, how were you able to really construct the life that you have now. How were you able to do it in less, in less abstract terms but more like physical ones, like how did you make it so that you’re, you are making money on the internet. How are you able to do that?

Scott: Yeah, definitely. So, to piece it together coz I think a lot of people again will see people doing well in life and think, oh they just, they’re just doing that, like it’s no problem. Like, they’re doing well, like my buddy Leo, I love giving his example in Zen Habits. It was one of my biggest personality site in the planet. An um, he — he’s a very chill lifestyle and family of 8, supports them all with his blog. And that guy, he ‘s also a good friend. He was in San Francisco and people look at him and say, oh Leo, you’re so chill and he travels around, he works for little and again, fine but five years ago he had a full-time job that he didn’t like. He was supporting his family of 8. He has, he was 70 pounds overweight. And while doing all of that, he started Zen Habits and he wrote 20 articles a week.

10 for his own site, 10 for other sites. Coz he just — he saw, he wanted, he knew he needed a change. It mattered that much to him. And that’s how he created Zen Habits. He didn’t create Zen Habits by doing what he’s doing today. So, that’s the first thing to realize, obviously takes work and you and it comes back to like the idea of modeling people which is I — one of the biggest acts in the world is you wanna do something that you know you wanna — let’s say you have a goal, let’s say run a marathon, start a business, whatever. Find someone who is successful at it, who’s much of the kinda person lifestyle you want as possible and deconstruct how they did it. Ideally become friends with them but you don’t have to. You know, like, for one in Buffalo, we have an investment fund. We deconstructed out, he managed money for families when he was 30 years old and what, did all just research like crazy. You don’t have to know them personally. Anyways, so I first started helping people just over lunch and I noticed a lot of people have this issue. And then I started to write. I remember I picked up a book when I quit my job and it said that you could — it’s called Internet Riches by Scott Fox who has now become a good friend and I was a little taken off by the title and so as he I guess, his publisher kind of acquired the title but — anyway, it said you could start a website without knowing code and I don’t know anything about code or any of that technical stuff and so I said sure let’s try it. So I created this site, it was book reviews called Reading for Your Success. It was book reviews about personal development products. I was like, it’s just, it was personal development book and things like so I was writing just different ideas and book reviews but what’s my ideas about the world and ending career and stuff and I just, for four years I did that kinda that on the side and developed my voice and be honest, like it got frustrating. No one was paying attention, it grew by 0% for four years. And it was only my wife and my parents really following it, a few you know, friends, out of courtesy but it was 110 subscribers or 112 for four years and I was gonna shut it down but then as when I moved to San Francisco and at that same time, I started to meet a few people in private, a dozen or two that had these incredible lifestyles online. and they used the internet as a tool to help people in unique ways and also give them these great lifestyle. And so, Leo, has a family of 8 , he has a blog he writes on 2 or 3 times a week and supports them like, that was so far outside of my realm of what I thought was possible. It was, I never even thought about that, but when you see it, it totally — it reframes everything and, and also on the internet, I start to learn about more and more people doing this stuff so it gave me this new found confidence and so it gave me something to work on and then instead of shutting it down, I rebranded it to Live Your Legend and said, I’m gonna really focus on this specific way of helping people, I learned, I studied like crazy about how you write online, how you build an audience, I wrote for sites all over the place. And I remember within 6 months in meeting these people, the site grew by 10x. And within 18 months in meeting them, it grew by 160x and turning to like a real business. And really what happened was I went from having known nobody online, I didn’t even know you could have a web business, to being around it every day and my thinking went from how could I possible do this, to how could you — how could I possibly not? And then you, coz your standards go to a new level. Coz when you change your surroundings, everything else in your mind, in your world starts to change even if you don’t change your goals. It’s crazy. It’s like that Jim Rohn quote, “You’re the average of the five people you spend most time with.”

Mike: Yeah.

Scott: I think that is the ultimate life fact, like no matter what you wanna do, change your surroundings, change is a result. So, that was it, that was like the nuts and bolts was, you know, working hard, writing from different places, developing my voice, understanding the audience enough to really know what they really needed help with, starting with face to face lunch meetings. And then I went on to build Live Off Your Passion which is our first main course about how to go from I don’t have a clue what to do or what I’m good at, to knowing your passion and building a career around it and that came from coaching people. I coached them, you know, for a year or two. I don’t really coach anymore but I coached them and I got to learn more and more. What are those main points, turns out, there’s like 5 or 7 main things that everyone hits as a road block. You know, the biggest one is: I have a mortgage, I can’t change. You know, so you address all that stuff and I’ve built that with them, so over the course of 6 months, I — you know, created based on exactly what they said their main problems, I wanted to solve those. So then, when I launched it, it — I had a pretty good idea that people are gonna want it and it did really well. It sold a lot. And, um, and then I did the same thing with our newest connect — How to Connect with Anyone Course but it’s, that’s a much more in depth course where we create mastermind groups for everyone. It’s, it’s real time and all kinds of things we get into but the main point is I guess to go from making no money to making money, doing anything but especially online or creating a product, built exactly what people asked for and, and do not assume you know what they want but build what they asked for because if you — if you, in your office, you just kind of start creating a product you think they’ll want, odds are you’re gonna be totally wrong. I certainly am every time I assume. So, that’s what I feel is a risk of launching something. You know, you should never, I don’t think today, launch any product with anything. Any industry that doesn’t do well, you should have been able to do your research, know enough about the market to decide this is all worth my time. Or else, you’re just gonna go and see.

Mike: How were you, okay, so you got your, your newest product, How to Connect with Anyone. And okay, how were you able to know that this is gonna do well before you launched it. What were the steps that you took?

Scott: And actually I can give you a link coz I have a, a whole product launch checklist. It’s like 7 pages. It starts about 6 months out, in terms of getting to move your audience and it’s — it’s free in Live Your Legend, so it’s, um, I’m welcome to share it with you guys but the Connect with Anyone, for instance. The first time I noticed that I should maybe think about a course like this is people

started writing me non-stop, like how did you become friends with Leo Babauta? How did you meet these people that inspired you to change, you know, your belief about things and how did you, just all these things, how did you meet these folks and so I’m like, wait, I can’t take it granted. I love giving people. I love being around folks, I love helping them out. There’s all these stuff, it’s fun and I decided, okay I heard this enough I gotta sort this out and then I realized that Connect with Anyone or Live Off Your Passion is like the nuts and bolts of finding your passion, building a career around it. But if you don’t have inspiring surroundings, your odds of executing on that are almost zero. Like if your family is — if your family is telling you like “Hey Scott, you’re an idiot. Like, why are you telling them that. You can’t do that. No one can do that.” You’re gonna give up most likely. So, no thankfully, I have a very supportive family and friends and colleagues but part of that, um you work to kind of embrace and create but so I noticed that and then I started to ask people. I’ve run a survey, maybe 6 months before or even a year before, I said I’m thinking about doing this, would you be interested? And I said, what — what are the main things you want me to cover and people mentioned a number of different things that turns out one main thing was being an introvert. A lot of them said, “I am an introvert, I’m shy, how do I address that”. So, we brought on — I made sure to get Chris Guillebeau who, you know, on The Art of Non-Conformity, very well known guy, one of the biggest guys in the space, a massive introvert apparently. He came on as one of our guests experts and explained kind of how he goes about leading a thousand person live event when he’s an introvert. And Jonathan Fields, another guy whose an introvert and um, and then I you know covered the different main things and we just built that way. And then, over time, I’m you know I’m — and then, I launched the product and to be honest, I created 10% of the product when I launched it and sold it. And I told them —

Mike: Wow.

Scott: I said it. I said, listen I’m launching this before we finish it because it’s gonna be much better if I build it along with you coz it’s gonna be way more relevant and you’re gonna get to help me, you’re gonna get your fingerprints on it to help create it and so I would just how I like to launch anything and so I call it — I learned it from a good friend of mine that a mentor friend Frank Robinson in Santa Barbara in California. He, um, he’s nearly 65 and created this process where he called — he called it, because it’s synchronized development, developing a product in synch with your customers and instead of designing something and then building it and then selling it, you sell it first then he designed it and then he build it. So, people bought Connect with Anyone and I already knew a lot of those stuff that would be in it based on the interviews and all that. And then, over time I — I built it out with them over a course of a couple of months and it um, it ended up being from what I could tell, way more useful than I would have taken just their first feedback and said okay. Now, I’m gonna lock myself in a room for two months and start well, try killing myself, trying to write all these stuff, that alone I can’t do it. It gets to be a lot of stuff, so you wanna, you know, break it down.

Mike: I think, I think it’s super smart though when you’re, when you’re gonna release a product to definitely feel out your audience I mean you’ve got that amazing tool already and what I’m doing is I’m gonna create an interview product and what I did first was I sent, I mentioned it in a post that I wrote and I was like here if you’re interested in, in learning about this, let me know and let me know what the things that you wanna learn about and why, why, I asked. Why are you doing this? What are your goals in, in doing this. Do you wanna, do you wanna get brand awareness? do you wanna get more subscribers, make money or sell a product that you have? So, it was really good for me to kind of find out what the desires were and the fears in my audience, so that I can make that product even better and make sure that I cover everything that they’re wanting to learn about coz you know, you might think that — you might think that they want something completely different than from what they really want.

Scott: Yes. And that’s, you almost, you can almost be assured of that just coz —

Mike: No.

Scott: It’s much like to think, oh I’m my own customer, I know my customer like, it’s total BS. Like, the only way to know your customer is to get real with them and and learn from them and then I’m sure you probably knows interviews and things, and the survey, like learned a lot of things you may wouldn’t have thought like, I didn’t realize introverts was such a huge thing coz I personally am not an introvert. But it’s a massive, you know challenge for me, so great we covered so much on that and I learned a ton it was great but, that’s um, it’s just — it’s also a very risk-free way to build something. You know, I mean to think that it’s just, just arrogant to think you can, that you’ re — I know enough that we can build it and totally have it figure out before showing anyone. And for me, it’s just a waste.

Mike: Well Scott, really thank you so much for taking time out today and coming on the show. Is there anything else that you wanted to mention before we wrap it up today?

Scott: I mean, I think, It’s a lot of stuff. I’m trying to think of just, for me, the most powerful thing is to think back on, I mean the people who are probably watching this are you know wanna build something using the internet, wanted to have an online income, probably want to maybe travel up to freedom. Just one, make sure not to get the — the car too far ahead of the horse, in terms of, like it’s not about making money online, it’s about helping people in a way that you’re uniquely good at, that you care about and

then using these incredible scale of online tools to instead of work with ten people, work with ten thousand. And, and yeah you get ten thousand customers, but you also get to help ten thousand people and think of what happened like, what if they interacted with ten people, I mean you can start having these crazy, crazy impacts. So, you start with that and then, if you — it’s also gonna be daunting just looking at the big gap between like, let’s say where — you know, let’s say where you or I am, with what we’re doing or the people way above us compared to people that are just getting started. First off, I was — I had a 111 or 112 followers two years ago and I was gonna shut things down. Like no one had ever heard of anything related to Live Your Legend, that was only two years ago. So, you know, things can happen. It won’t happen overnight but they can happen faster than you think and you have to create that surrounding, like do not do this stuff on our own, like it’s — it’s gonna be next to impossible and your outcome is gonna be a tenth of what could be. And I mean, find those people who inspire you, who do the things that — who live the lifestyle or have the business you want to and the impact that you wanna have and make sure that they’re not just really financially successful. Make sure they actually, they treat people well like they have good morals and they have a good family. I mean, it’s, it’s — it’s a little challenge, even like, let’s say the investment banker, you know, wants to be the general banker of the firm and he’s so you know, so envious of that person’s success, except for their, you know, divorce, they’re stranger to their kids and um, 50 pounds overweight. I mean, perceive the whole picture coz at least for me the money is an important part but certainly not anywhere close to the the biggest part, so get all of those in mind and think about that quote, “You’re the five per — you’re the average of the five people you spend most time with”. And just take it deadly seriously coz I mean, it’s a hundred percent in your control. Like, no one can tell you who you can hang around or even so, more so like no one can tell you — or you can say, “I can’t hang around anymore coz they pull me down”, like get away from those people, get around the people who inspire you and it seems like I’m going around and stuff. And, so you people, do it and when they do like, everything changes. So, um that’s part of why I love doing these interviews too is coz you get to like get some of that out there and also they get to see a little more about the people who are doing the things maybe they would be kind of inspired to do and so I’m — it’s an honor. It’s a fun stuff to do, I mean, if you have anything else that’s at the top of your mind.

Mike: No, I think that’s — that’s it. Um, yeah Thanks for getting on. I appreciate it. Scott: It’s an honor and thanks for doing what you’re doing enjoy it out there in Turkey. Mike: Thanks, man.

Mike: I hope you enjoyed the interview today with Scott. Make sure you go to and also you can check out his How to Connect with Anyone Course if you go to And right now, it’s not currently open but it’s gonna be. You can sign up for that and get a notification on the 19th at 7AM. It will be opening up but there’s a place right here where you can put in your name and email address. Thanks for watching and I’ll see you all tomorrow.

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