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
118: 5 Ways to Land Writing Clients in 2022 [not-audio_url] [/not-audio_url]

Duration: 21:29
​All you need is one person to say yes and give you a chance as a freelance writer. Today, I want to share you with the five most common ways to land your first freelance writing client so that you can find success as we…
117: The #1 Tip to Start Writing in 2022 [not-audio_url] [/not-audio_url]

Duration: 20:06
Quit dabbling and start taking action. This is your time to start landing clients and making money as a freelance writer. To learn more about working with Michael, check out: inspireyoursuccess.com/coaching
115: How I Got My First Freelance Writing Client [not-audio_url] [/not-audio_url]

Duration: 14:53
On this Writer's Wednesday podcast, I take a trip down memory lane to tell you how I landed my first freelance writing client. Landing that client was a game-changer as it gave me the confidence to go pitch more clients…
114: 9 Lessons from Leaving My $100K 9-5 [not-audio_url] [/not-audio_url]

Duration: 29:47
Do you want to quit your job and learn how to make money online? Before you give your notice at work, make sure you listen to this episode a few times. Because in 2017, I did just that. I left my corporate job and 6-figu…
113: How Kathrine Became a Top Writer & Quit Her 9-5 [not-audio_url] [/not-audio_url]

Duration: 34:44
Learn how one of my Freelance to 5K students became a top writer on Medium.com and quit her 9-5 (in only 5 months)! Kathrine is a writer and mindset coach. She helps people with insecure attachment, in life and relations…
112: 7 Lessons From My Failed Blog [not-audio_url] [/not-audio_url]

Duration: 18:46
I quit my $120,000 career after making $200 in affiliate sales from my blog. Most people thought I was crazy. But I was determined to prove everyone wrong and show that you could make money blogging. After reading endles…
111: How to Beat Overwhelm As a Freelancer [not-audio_url] [/not-audio_url]

Duration: 21:33
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…
109: 5 Ways to Upgrade Your Life During This Pandemic [not-audio_url] [/not-audio_url]

Duration: 22:33
When the world nearly ended 12 years ago, I was an immature 20-year old drifting through life. As I had nothing invested (as I had pretty much no money) and my job was delivering pizzas, the recession didn't affect me mu…