I’m so excited to share my episode number 100 with you! That’s right. We just hit triple digits of the show. And in this special episode I want to show you how I went from broke, depressed, blogger to a full time thriving, six figure freelance writer and coach, and how you can do it too. Coming up.
I was a corporate, uh, hostage at YELP, living with the golden handcuffs. And I always knew I wanted more, but I didn’t know what that was.
I wasn’t ready to quit my job yet, So I started exploring. I did a lot of different stuff, with some of them being:
- Enrolled into acting classes
- Engaged in eCommerce
- Dove deep into personal finance
How I Started Out as a Blogger
Early 2016, I’ve decided to start supermillennial.com. My first blog was born and that was really the start of it all for me. I didn’t know that 15 months later I would quit my six figure job and go out on my own. In 2019 I was about two years into my journey and I hit rock bottom. I was going through absolute depression – I could barely get off the couch. And I was just suffering in silence.
It was the time when a coach Jim Forton came into my life when everything changed for me. And so 2019, I was able to crawl out of this whole pay off credit card debt, and double my income over 2018 and had an extremely successful year. I started to grow this brand after I joined James Wedmore’s program Business by Design – it was like finally all came together.
Now in 2020, I have the freelance writing, the online courses,online coaching program, the podcast, a team of four people and I’m just grateful.I just want you guys to know that five years is how long this all took. And it’s not like I’m all done now.
The Mistakes I Made Along The Way
Although I’m very grateful for the entire process, there are some things which I didn’t do, which I want you to start doing NOW:
- Slow down and look back at what you had done
- Celebrate Your Wins
- Take care of your mental health
- Don’t ever compare yourself to me or anyone else
- Don’t give up
Are You Ready to Start Your Freelance Writing Career?
If you are ready to take the next step and launch your freelance writing career, I would love to help you build momentum!
I still have a few spots left in my coaching program, fill out an application to learn more 1/1 coaching.
Speaker 1 (00:00):
You are listening to inspire your success podcast. Episode number 100. That’s right. We just hit triple digits of the show. And today I want to show you how I went from broke, depressed, blogger to a full time thriving, six figure freelance writer and coach, and how you can do it too. Coming up.
Speaker 2 (00:25):
Hi, I’m Michael Leonard and I built a full time online writing business that offers me the freedom to never go back to a cubicle in a nine to five. If you’re like most people you want to make more money to pay off debt, have more freedom travel, and actually -enjoy your life. Whether you want to earn $500 per month as a side hustle or scale writing business to five figures per month and quit your job. Making money as a writer has never been easier in this podcast. I want to inspire your success as a freelancer and show you how I 10 X my income in one year and made $20,000 in one month as a freelance writer. If I can do it, I know you can too. Thanks so much for being here.
Speaker 1 (01:10):
All right, welcome back to inspire your success podcasts. Again, this is your host Michael Leonard. And if I sound a little bit giddy, I’m not gonna lie guys. I am. It is episode number 100, gotta celebrate this win. Never thought I’d have a podcast that reached people around the world and never thought I’d have a hundred episodes. And so, uh, just wanted to say a huge thank you to everyone that’s following. Uh, anyone that’s left me review shared it with family, friends, coworkers. Uh, again, just wanted to say thank you so much. Uh, I am just so, so excited. I started this show, uh, just because I wanted to help others and I wanted to have a voice to give people some inspiration. And so I’m really grateful for all the opportunities that have came from this. And, uh, every single person has listened to even five minutes of the show.
Speaker 1 (02:02):
I just want to say thank you. So, uh, this episode, uh, you know, if you’ve listened for a while, I tend to share a random fact and then get into some writing advice or freelancing or entrepreneurship, maybe a little bit of mindset stuff in there. And today we’re going to do a little different because it is number 100 and I want to celebrate it. And I want to really take you through my journey because I know everyone listening right now is in a different spot. Everyone starts kind of in their own journey and it has to go through their own trials and tribulations, whether freelancing is a side hustle, it’s a full time gig. Maybe you’ve never written a thing in your life, but you want to get on medium or you want to help people like whatever it is. I just want to show you how I was able to go from where I was to where I am now.
Speaker 1 (02:46):
And again, it’s not to say I have it all figured out and everything is just perfect all the time, quite the opposite. Uh, but again, I’ve, I’ve had a lot of wins and I’ve had a lot of losses. And so I want to share all that with you because I want to be fully transparent. I’m not someone that wants to say only an entrepreneurship is for everyone. And it’s really easy. You just gotta start a website and it’ll be, it’ll be simple because it’s really not the case. And so I want to just again, share my journey and give you some inspiration, because that is the exact reason that I started this brand. Um, and I was in a meditation. I think it was in January of 2017. I believe that I, or 2018, excuse me, that I switched from my old blog, super millennial to inspire your success.
Speaker 1 (03:28):
So I just want to share this. So maybe you can get some inspiration. Maybe you’re not feeling really good about where you’re at right now, or you want to make more progress or you just want to learn a little bit more to figure out how I kind of went from where I was to where I am. And maybe you can learn some tips and tricks to speed up your success. Because again, that is the name of the game. So let’s take it back. Uh, it all started for me, uh, in 2015. So at the time I had just bought the house that I am recording this in, um, which by the time this gets released will be up for sale. Uh, so about five years I own this house. Um, for me it was, it was a thing where I was really going through the motions, right.
Speaker 1 (04:10):
I was a corporate, uh, [email protected] I was living with the golden handcuffs. Uh, and I, I knew I wanted more, but I didn’t know what, and when you’re 27 years old and you’re Googling how to retire early, there’s probably something wrong with that right there. There’s a lot more to life than just figuring out how to get out of your job. And so that, for me, it was like, okay, well I want to quit my job. That was like the first thing I realized. Um, and I got to that point because I had bought this house thinking that if I bought more stuff, I’d just be happier. Um, but that wasn’t true and, uh, quite the opposite. And so for me, I was always going with what society told me to do. I was doing getting the corporate job and buying the house and buying the BMW and doing all the things that the world wants you to do.
Speaker 1 (04:59):
And you know, that that could work for you. And if you’re happy, great. Uh, but for me, I was miserable. I was drinking a lot. I was, uh, you know, just going through the motions really. I was kind of like a zombie, to be honest with you, that was a corporate zombie. I, uh, made it through work every day and live for the weekends, partied my face off. Um, and I, you know, it was, it worked for 27 years and I got to the point where I was like, there’s gotta be more to life than this. And, uh, so for me, 2015 was the first time I realized that I wanted more from life. And, uh, I didn’t know what, but I, I wasn’t ready to quit my job yet. Uh, but I knew I wanted more. So I actually started exploring, I kind of call 2015, 2016, this, these years of where I just discovered who I was and what I wanted.
Speaker 1 (05:42):
Uh, I did all kinds of things, guys. I literally went to an acting class. I I’m a huge movie guy. Uh, I got a wicked good Boston accent coming through right there. Um, and I love movies. I love Netflix. I mean, not just like veg out, like I love thinking about, um, working in the business and promotions. I created movie trailers. I mean, I’m a geek, uh, with this stuff. So this first two years, uh, really of when I discovered, Hey, I gotta do something more with my life. I didn’t want to quit again. So I just tried everything. So I went to acting class, which was a hilarious experience. People thought I was a very out of place as I was. And there was a lot of people that have been doing it for years and years, but you know what I said, screw it.
Speaker 1 (06:24):
I’m going to have fun. Maybe I’m going to be the best actor. Maybe I’ll win an Academy award. Well, we’re still waiting on the statute, but, uh, I had a lot of fun. I got to practice a monologue of bed Aflac, which was amazing. I still don’t know where that footage is. So it’s probably floating around on the internet somewhere, but maybe I’ll see it one day. Uh, but again, I tried everything. So I started, uh, I tried, I didn’t really go all the way through with it, but I tried to do, uh, some different, um, online eCommerce stuff. I was buying items from China. I was thinking about reselling them on Amazon. I never actually pulled the trigger there. Uh, I did the movies. I started getting into doing like movie trailers. I was thinking about a YouTube channel. Um, I, I did everything guys.
Speaker 1 (07:06):
I, and that’s when I really, when I got back into golf and I really discovered how much I missed it and I loved it, but those first two years I was just trying to do everything. And I was also, like I said, obsessed with personal finance. I was Googling how to retire early. And so pretty quickly I became a personal finance geek. Uh, I really wanted to just get out of there. I was like, how can I retire ASAP? And so that led me to learning about stock options, investing, uh, 401ks, Roth, IRAs savings, you know, all this stuff that I felt like college, uh, never really taught. And so it was on a worked, uh, vacation that was a president’s club trip. Uh, it was in the fall of 2015 and, uh, I was a top sales rep and I got to go on this cool trip with Yelp, those couple hundred people that flew us all down to, I believe this first one was canned Coon, which was amazing.
Speaker 1 (08:00):
I mean, four days, um, you know, unlimited drinks food. It was a great time. And, uh, I was really, uh, after about, you know, five or five or 10 drinks, uh, talking to my manager or actually my director and I was talking about personal finances. I just wouldn’t shut up. I was talking to her about everything I’d been learning. And she mentioned that her cousin actually was a personal finance writer, and she’s like, you’re really knowledgeable about this stuff. You should start a blog. And so the seed got planted late 2015, so 2016, I decided, you know, what, new year new me, I’m gonna figure this thing out. And so I started a blog, so it was a January of 2016, super millennial.com. My first blog was born and that was really the start of it all for me. I didn’t know that 15 months later I would quit my six figure job and go out on my own.
Speaker 1 (08:52):
And so, you know, if you’ve been following me or the show for awhile, you know, that’s, that’s kinda my Mo I started blogging in 2016, but I didn’t really take it too serious. I was kind of doing that. I started playing golf more. Like I said, I was just trying to mix up my life and figure out what made me happy. And it wasn’t work. I’ll tell you that. So I was doing a lot of stuff outside of work. And, um, for me, like the first thing is that I realized I really loved writing, but I really love just helping people, like when someone would comment on my blog, that the, my content helped them out that made, that just meant the world to me, even though I had like 10 visitors a day on my blog, no one read it, except my mom, most days it was still so cool.
Speaker 1 (09:28):
And, uh, I had a semi viral article. Uh, it was, I think it was may of 2016 on rockstar finance. And, uh, it was just so cool to me. I remember driving to the dentist office and I saw like my Google analytics. I like 3000 people on my page, which is like 3000, 300,000 more percent than normal. And I kind of felt like, Whoa, I made it. And I remember that feeling I honestly can say, I was literally driving to the dentist. I have this most surreal moment. And I just remember like crying. I had this like tear of happiness, even though I didn’t make any money from the post, but it was like, wait a second. This is working. And I felt that feeling that I want everyone listening to this to feel, which is that feeling of ultimate fulfillment and impacting others with your work.
Speaker 1 (10:14):
That was a, that was addictive to me. And so I really decided, Hey, I’m going to figure this out. So I saved up money. And, uh, when you came around to May 11th, 2017, I quit, I was done. I was officially no longer a corporate hostage and, uh, went out on my own and I did not have a successful blog. I wasn’t making money. I did save a bunch, but I’d only made $200 from my blog ever. So, uh, for me, that was kind of the first year was like, what am I doing? Am I trying to be at digital marketer? Am I a golfer? Or am I a blogger? Uh, I didn’t know what I was doing guys. I was flea market flipping. I was, uh, doing a lot of blogging, but it wasn’t making much money, so I really didn’t have much success. And so it kind of all changed for me, uh, in 2018 when I pivoted from freelance, uh, from blogging to freelance writing.
Speaker 1 (11:03):
And that’s really when I started to make some consistent money online, I wasn’t making six figures a month or anything, but, you know, when you’re making nothing do, uh, making a couple thousand a month, it feels like you’re a millionaire. And so, you know, for me, 2018 was a really cool year. Uh, I went from $650 in freelance writing income in January of 2018, uh, to $6,500 in January of 2019. So in 2018 I realized, Hey, I have a skill. I can make money. I did a lot of personal finance writing. I got into some personal development writing. Um, and then I really did that in, uh, 2018. Um, but I still really wanted more. I always wanted to be a coach in a, in a, someone like this. I had a podcast, but I didn’t know what to do. So, you know, I was investing in all these programs and trying to be a digital marketer.
Speaker 1 (11:51):
And again, I was just hustling all the time. And so if you listen to episode number 99, you know, that hustling is not the answer. Um, and you know, it really get to 2019. Uh, and I was about two years into my journey and I hit rock bottom. I mean, I was, I was going through absolute depression. Um, there was about six weeks where I barely got off the couch. Uh, I didn’t tell anyone I suffered in silence. And, um, you know, I was just, I was making money as a freelance writer, but the rest of my business was failing. I think I had five businesses. I was trying, I was trying to YouTube show. I was trying, um, an eCommerce store. I was trying to do copywriting. I was trying to do, uh, courses. I mean, I was trying to do way too much and I hit a really, really dark point in my life.
Speaker 1 (12:36):
But, um, I learned later looking back, of course, hindsight is always 2020, um, that the universe was really just trying to teach me a lesson. And, uh, and so it was at that time when a coach came into my life by the name of Jim Forton and, um, it’ll really change everything for me. And it helped me go from that depressed, uh, solo preneur to learning about things like hypnotherapy and mindfulness and just so many things about the subconscious mind and why I was feeling the way I was feeling and just so much life changing content. And so 2019, I was kinda able to crawl out of this whole pay off credit card debt, double my income over 2018. And really like, I always like to say from Jim and James Wedmore’s to really change my life, uh, from the inside out. And so I really scaled a, had a, a very successful 2019.
Speaker 1 (13:30):
I started to grow this brand after I joined, uh, James Wedmore’s program business by design. Um, and then 2020, it’s finally all came together. So it’s like, you know, I have the freelance writing. I have the online courses, the online coaching, the podcast, we have all these amazing. I have a team now of four people. Um, and I’m just grateful. I’m so grateful. I have a following on medium. Um, so many cool things have happened. I don’t mean it in a bragging way. I just want you guys to know that five years is how long this all took. And again, it’s not like I’m done. I mean, I want to get to a million downloads. I want to reach millions of people around the world, but I know that I’m on the right track. And so if you’re listening to this and you’re feeling stuck, or you’re S you’re struggling, and you don’t know what to do, look backwards and realize how far you’ve came.
Speaker 1 (14:22):
One of the biggest mistakes I made is that I didn’t slow down and I didn’t look back at what I had done. And I constantly was always chasing this new shiny object, new amount of money I needed to make new thing. I wanted to do new business. I wanted to start. And that’s just a losing formula because the goals always move. If you’re like most people, you always want to make more, be more, do more, which is great. But if you don’t celebrate your wins and you don’t look back and you don’t congratulate yourself and be so proud of who you became and what you’ve done, you’re never going to find fulfillment. And, you know, that’s why I really want to talk more about mental health and just being open and honest with yourself, because life is what you make it. And if you know, for awhile, a lot of people didn’t know I was struggling cause I, I kept it all inside and I didn’t tell anyone.
Speaker 1 (15:19):
Uh, I thought, Hey, I got myself in this all. I have to get myself out and you know, it was noble, but it didn’t help me. It wasn’t actually helping me help more people. It wasn’t helping me make more money as a writer. It wasn’t helping me impact the world. Um, so again, I really want you wherever you’re at right now to just be proud of yourself, uh, and look back and you know who you are a week ago, a month ago, a year ago, that that, that version is gone. You’re under this next thing. And so congratulate yourself, celebrate your wins. Be excited. You know, maybe you got your first follower on medium. Maybe you got your 1000 follower on media. Maybe you got your first email subscriber. Maybe you made your first dollar as a freelance writer. Maybe you got published in a big publication.
Speaker 1 (16:02):
Um, you know, it’s so easy to compare ourselves to other people. And so if you’re listening to this and you really enjoy this show just never compare yourself to me or anyone else, because I did that for years and it robbed me of my happiness. It left me as a shell of my former self because I was constantly comparing myself to other people. And no two people have the same karma, no two people have the same skills or the same goals or the same, anything. So why compare yourself to anyone but your former self. And so, you know, that’s just one of those things, guys that I just can’t stress it enough. Um, you know, if you’re listening to this and you’re just kinda down and out, I just want you to know that you can do it. I want you to know that you’re worth it.
Speaker 1 (16:41):
And I want you to know this quote that I just love from Jack Canfield. I want you to write this down is that you are not given a dream without the capacity to fulfill it. So if you have a dream of being a world-class writer and making $10,000 a month, you can do it. If you have a dream of starting an online business, that lets you work at home. So you can spend more time with your family and pay off debt and travel and do whatever you want. You can do it. We get these dreams. And a lot of times they feel so unattainable because they’re so far from where our current situation is. But hopefully my story goes to show you that, you know, each year you can make a lot of progress. And in five years you can’t even believe how much progress you can make.
Speaker 1 (17:26):
But the sad thing is that most people give up too quick. You know, a lot of people I started blogging with in 2016, they don’t blog anymore. They never even kept going. And again, I’m not saying it’s going to be easy. I’m not saying that’s guaranteed success. There’s no guarantees as an entrepreneur, as a freelancer or as a writer, but I’ll tell you what, there is one guarantee. If you quit, you’re not going to hit your goal. And that to me is worst thing that you can do. And it really bums me out when people give up, just when they’re on the one yard line, they’re so close, but they give up too quick. So I just wanted to share my story to show what can happen when you get an idea, when someone tells you, Hey, maybe you should try this out. You know, life is short.
Speaker 1 (18:09):
Uh, don’t make this your entire existence go to your job. If it makes you miserable, go out there and figure out what makes you happy and chase that dream as if your life depends on it. Because honestly it does. If there’s anything I can do, please let me know. And in fact, I actually want to give you an opportunity because if you listen to this far, it’s a long episode, right? And I know not everyone’s going to make it through it. Maybe some people that want it, maybe this one is tactical advice. That’s fine. But if you’re someone that’s listening to this show and you’ve got a lot of inspiration, maybe you started writing on medium or freelancing or Upwork, or you just wanted some inspiration. So you started listening to the show. I’m excited, and I want to share some stuff with you. So this, this is a hundred a hundredth episode, and I want to celebrate.
Speaker 1 (18:55):
So I am going to take some free, no strings attached coaching calls. I want to just help you because I’ve been doing this with some subscribers lately. And some people on Instagram and people are getting massive results. And it’s made just, just been the coolest feeling to me and has made a huge difference. And so many of my listeners and followers. So please, if you want a free coaching call on zoom with me, we’ll record it. I’ll send it to you afterwards for anything about your online business or your writing business, or figuring out how to build a brand online or whatever it is I want to help. So again, to do this, to become eligible, shoot me an email at support at inspire your success and use the subject line episode 100. And let me know your story. Let me know where you started, where you’re at, where what you’re going through.
Speaker 1 (19:49):
Inspire. Give me some, uh, some inspiration because you know, I love inspiring you guys, but man, I get so inspired by learning about you and figuring out how I can help you out. So again, I want to reward anyone that’s listening to the show. I want to, again, just give my time as much value as I can to you and just help you overcome some of those hurdles that we all go through. Maybe I went through it in 2015, 2016, 2017, 2018 or 2019, or maybe even this year. So I just want to help you out again. If you listen to this far, I want you to do that. Go email me support and inspire your success. Subject line, episode, number 100, let me know your story. Let me know what you’re going through. And let me give you that one on one call together.
Speaker 1 (20:32):
Let’s make some magic and I want to help you out. So again, if you have any questions, shoot me an email, uh, DME on Instagram at I am Michael Leonard. Um, and as always, you know, guys just want to say thank you so much. Um, and letting me get to episode number 100 and finally guys again, just a quick reminder that business by design James Wedmore signature program that I’ve went through and thousands of other entrepreneurs have went through is available next week. It’s not going to be around long. It’s a four day launch. He runs it once a year. It is the best program I’ve ever taken. Um, it’s helped me again, make, uh, an entire new segment of my business and start this podcast and, and grow the podcast and start coaching and impacting more people. So again, if you’re someone that has a, has a skill and you want to make a business out of it in any niche, not just writing, it could be literally you’re good at helping people lose weight.
Speaker 1 (21:32):
You’re good at helping people grow a garden on their apartment, a patio. Literally, I have a friend that does that and he has an amazing business. It could be that you can help people teach sports or play an instrument or get organized, or, um, anything literally, if you have a skill and you want to turn it into an online business, you have to check out James’s program. I would never suggest anything that I haven’t personally went through or thoroughly investigated and went through on my own. But again, um, James, his number one fan, he’s impacted my life in business so many ways. So again, just want to just share that with you. You can click the link in the bio to learn more, get on the wait list and watch his free video series a, which they can is so, so powerful. So take a look at the show notes. Let me know if you have any questions, submit that inspirational story. And thank you so much again for helping me get to 100 and I cannot wait for the next hundred. Thanks again for listening. And as always, I hope you have an Epic day.
Speaker 2 (22:32):
Thanks for listening to this episode of inspire your success podcast. If you’re the kind of person who likes to help others, please leave a positive review on iTunes. So more people can learn about the show. Also, if you have any questions about freelancing, I’m here to assist. Please email [email protected] And I may even use your question for a future episode topic. And if you want more inspiration and freelance writing tips to build your business, follow me on Instagram. My username is at, I am Michael Leonard. Finally, if you’re ready to learn how to make your first thousand dollars as a freelance writer, check out my free seven day [email protected] forward slash one. Kay, thanks again for listening.
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