100 - From Broke Depressed Writer to 6-Figure Entrepreneur

100 - From Broke Depressed Writer to 6-Figure Entrepreneur

Author: Michael Leonard: Copywriter & Freelance Writing Coach June 17, 2020 Duration: 23:19

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.

Why I Decided to Quit My Six Figure Job​

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
On one of my business trips with Yelp.com, I started talking to my director about everything I learned about personal finance, and she advised me to start a blog about it and that's when the seed got planted.
 
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
I made a lot of mistakes, and I went through a lot  in 2015, 2016, 2017, 2018 or 2019, and even this year. So I just want to help you out and give you some support. If you're feeling down, just email or DM me on Instagram. Let me know what you're going through and let me give you a one on one call.
Thank you so much for being with me throughout these 100 episodes and I wish you all the luck in the world!

 

 

Watch the RISE of the Digital CEO by James Wedmore (100% FREE Video Series): https://www.jameswedmoretraining.com/a/28723/4y9XF7wK


Michael Leonard was a professional copywriter earning a solid salary before he walked away from that career in 2017. With no safety net, he built a thriving online writing business from the ground up. In his Inspire Your Success podcast, he gets into the real work behind that transition, moving beyond simple inspiration to offer a practical roadmap. Each conversation is grounded in his experience as a freelance writing coach, focusing on the actionable steps needed to build a sustainable independent career. You’ll hear honest discussions about the mental shifts required to leave a traditional job, the systems that actually generate income, and how to navigate the common pitfalls of entrepreneurship. This isn't about vague motivational talk; it's a detailed look at creating a business that affords more freedom, whether that means paying off debt, traveling, or simply designing a life with more flexibility. Tune in for a blend of strategic business advice and personal development insights, all drawn from Michael’s own journey from a structured 9-5 to successful self-employment. The podcast serves as a direct mentorship for anyone feeling stuck, providing the tangible tools and mindset needed to turn professional aspirations into a working reality.
Author: Language: English Episodes: 100

Inspire Your Success
Podcast Episodes
67: All Successful Freelancers Do THIS [not-audio_url] [/not-audio_url]

Duration: 14:57
In today's Monday with Michael episode today's episode, I talk about the importance of investing in yourself, how I invested over $35,000 in my own freelance writing business and personal development and then provide som…
65: 7 Most Common Freelance Writing Questions Answered [not-audio_url] [/not-audio_url]

Duration: 21:27
In this Writing Wednesday episode, I cover the seven most commonly asked questions about freelance writing, so I can help you take action and start making money as a writer. Freelance Writing FAQ's Answers to the most fr…
64: The Mindset of a Wealthy Freelancer [not-audio_url] [/not-audio_url]

Duration: 18:56
In this episode of Monday's with Michael, I talk about how you can have the mindset of a successful freelance writer. This episode is full of tips to jumpstart your Monday motivation. Why You Need to Master Your Mindset…
63: From $0 to $125K in One Year on Upwork (Lisa Cumes Interview) [not-audio_url] [/not-audio_url]

Duration: 46:15
In today's guest interview, I had the opportunity to interview Lisa Cumes. She went from $0 to $125K in her first year freelancing on Upwork and has rapidly scaled her business since leaving the 9-5. Lisa's secret weapon…
62: 5 Best Strategies to Price Yourself (Freelance Writing Rates) [not-audio_url] [/not-audio_url]

Duration: 23:01
In today's episode of writing, Wednesday, we cover exactly how you should price your freelance writing rates even if you're a beginner. Once you get freelance writing clients, you need to learn how to actually charge the…
61: How to Beat Overwhelm as a Freelancer [not-audio_url] [/not-audio_url]

Duration: 22:22
In this Monday with Michael episode, we talk about overwhelm versus busyness and go over five tangible action steps to keep your freelance business moving forward. The Difference Between Being Overwhelmed and Being Busy…
60: 7 Reasons You Aren't Landing Freelance Writing Clients [not-audio_url] [/not-audio_url]

Duration: 25:00
In this Writing Wednesday episode, I go over 7 reasons no one is hiring you as a freelance writer. I recently published an article on Medium with this same topic and it really resonated with my writing audience, because…
59: How to Battle Loneliness Working at Home [not-audio_url] [/not-audio_url]

Duration: 11:21
In this Monday with Michael, I talk about how I overcame loneliness as a freelancer and provide some actionable steps for you to not feel the same way. One of our basic desires as humans is connection. When I worked my 9…
58. Why You Need a Writing Website in 2020 [not-audio_url] [/not-audio_url]

Duration: 19:57
In this Writing Wednesday episode, we are talking about why as a writer you need a website. This is the first thing I tell my writing coaching clients that they need to do, because it is very important to have a home bas…