The Reason I Quit My Job for Blogging

The Reason I Quit My Job for Blogging

I have a ton of posts I’ve been meaning to write lately. “100 Ways to Make Extra Money“. “How to Grow your Twitter Following Quickly“. “What Does it Feel Like to Be A Millionaire?”. This one is absolutely more important, so those can wait. I have to share this message with you.

Don’t worry, I’ll get to them eventually. Just so you all know a little bit of my methodology for coming up with posts, it’s not all about SEO (search engine optimization) or what I think would be popular/controversial.

I write stuff that I think would have the most impact on people’s lives. Making/saving money and all that stuff is cool, but I want to help people. That’s why I do this.

I know a lot of you out there right now want to take the leap to something else, or you aren’t happy with your situation in life. I get your emails and messages on Twitter about the bad@$$ things you are about to try or want to achieve. It’s awesome, and thank you for letting me be a part of it.

Now let me share a story with you.

A year ago, I quit my job to do this. I had a totally different life before as a band director, and it’s important that you know why I changed directions so drastically.

I started drumming in Jr. High. I was slightly more talented than my friends that were in band, but I didn’t think much of it.

Then I got to high school. I pretty easily passed up everyone else that was around me when it came to drumming. As a sophomore, I could literally play circles around any human that could pick up sticks at my school.

After that in college I took it to a whole new level. I moved up to an activity (Drum Corps) that is literally the top 1% of the top 1% of drummers in the world competing across the country every summer. Here’s a little sample. I’m the fourth guy from the left:


I graduated college and landed my first job teaching band at a high school. For a lot of reasons, I wasn’t happy with my choice. But ultimately, I had a conversation with my boss that changed everything for me. It went something like this:

Me – “Man, the raise we get every year is less than the rate of inflation. You literally lose money every year by teaching…that’s so jacked up”.

Boss – “Let me give you some really important advice. You can’t think about stuff like that in this profession. If you focus on that you’ll never be happy teaching”.

And that was that. My teaching career was f****d from that point forward. It was like someone told me not to imagine an elephant. It’s all I could see.


I was already in the process of paying off my student loans, but I decided I would switch focus after that and start saving up for a leap of faith to something…I didn’t know what though.

I was still about two years away from quitting my job, but it was my main goal in life. I was going to work for myself. Period. Then I started this website. It changed everything for me.

After 3 years of teaching, my student loans were gone and my wife and I had roughly $50,000 in cash after sacrificing and living like we were massively poor. For some reason one day I pulled into the parking lot at the school and texted one of my best friends (and also financial mentor). I told him I had $50k in the bank, and I would quit my job after the next school year.

Even with about a year’s salary in cash, I was too freaking scared to quit my job, I desperately wanted to be an entrepreneur but I couldn’t bring myself to do it. I was going to wait another year!

My friend’s response? “In the grande scheme, what’s the difference between $50,000 and $100,000? You need to quit this year”.

That was it. Two weeks later, I told my boss I was going to leave so I could run M$M. It was insane, stupid, foolish, whatever. I sat in an exit interview with my principal at the time, and he basically stared at me like I was crazy for a while and then said: “Well, I wish I could do what you are doing. You’re chasing your dreams.”

dream big

And that’s the point.

Your dreams are valid. If there is something you want to do in life, you need to do it. The reality is that we all will die eventually (sorry). If you sit around watching opportunities pass you by like I was going to, you’ll waste something that could be incredibly fulfilling. Or it could be an absolute failure, but thats ok. We’re young and have time to recover.

Even if you aren’t young and you’re reading this, you still have time to recover.

My life is awesome right now, and I’m not ashamed to say that. I wake up and do something I love every day. This site and the digital marketing that I do are my absolute passion, and I would have never found that if I didn’t chase that one thing that I wanted. I want that for every person that reads this site. I really really do.

So, I’m not saying go quit your job today. But I am telling you to pursue what you want in this life. Just…be smart about it. Live below your means, get your money right, make a plan, and jump to whatever it is you’ve always wanted to jump to.

The pursuit is worth it.

Questions for you:

  1. What is your dream?

  2. Why haven’t you started chasing it?

Live differently, your bank accounts will thank me later. ~M$M

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44 comments… add one
  • Colin @ rebelwithaplan Jul 25, 2016, 6:51 am

    Never lose sight of the goal! I read another story about this entrepreneur who started her own information product business. One of the points she mentioned in her story is how people get super caught up in having the typical $x amount of money saved up before taking the leap. She felt discouraged not having the typical 6-9 months of income saved up but she assessed her work ethic and decided to take the leap with not much money saved up. That was a few years back and she’s still going strong! Working for herself and has grown her monthly income to an impressive level.

    It boiled back down to resourcefulness and being in tune with your unique work ethic. She never lost sight of her goal. Her story motivates me a lot.

    • Millennial Money Man Jul 25, 2016, 6:58 am

      Yeah it’s not really about a certain number or anything like that. I would just recommend a STRONG emergency fund though. I barely made any money for a few months after I bailed.

      It’s also not about becoming an instant multi-millionaire, which is one of the stories you see a lot about startup owners. It’s just not like that working for yourself. After about a year, I make roughly $6,000 a month doing this stuff, although it does grow consistently right now. I think I’m on the high end for first year business owners honestly.

      The thing about what I did is that I’m HAPPY. That’s why I’m able to wake up at 6:00 am and start working on this site or other marketing projects I have.

  • Viral Trivedi Jul 25, 2016, 7:31 am

    Wake up call for me in this article. I have my own blog but since I’ve been laid off for a few months Im thinking of creating a website instead of keeping the free blog. It’s getting to the point where weekends feel the same as weekdays. Do you blog everyday or a few posts per day?

    • Millennial Money Man Jul 25, 2016, 8:28 am

      I probably write about 5-6 posts a week on average. I manage blogs for companies and do Facebook advertising/email marketing as a service. I’m thinking that I’ll start income reports at the beginning of 2017 so people can keep track!

      I’m biased of course, but if you are serious about making money doing this then I would switch over to a website. You can use that as a portfolio for potential clients!

  • Mike @ Super Millennial Jul 25, 2016, 7:43 am

    Nice article, can’t imagine how awesome/terrifying it was to quit your job…well done! Whats been the hardest part about doing the blog full time? income? Accountability? Buying your own insurance? What about the best?

    • Millennial Money Man Jul 25, 2016, 8:32 am

      Terrifying is pretty accurate haha.

      The hardest part has just been learning how to monetize correctly. I used to only make money from sponsored posts, but now I’m working hard to build up my affiliate income and then eventually will work up to selling my own products. I have a long way to go, but between this blog and my marketing company it looks like I’ll bring in ~$70,000 this year. Couldn’t have I would be there just one year in.

      Accountability is built in for me. I want to be successful, and I want my wife and future kids to have a kick@$$ life. So, I do my best to make money haha.

      The best is the flexibility. I have great clients that don’t mind me working from wherever I want. In my mind I’m happy doing what I’m doing so it allows me to hustle more and bend over backwards to push products.

  • Matt @ Distilled Dollar Jul 25, 2016, 8:49 am

    Thanks for rehashing some of those painful memories and conversations. You’re right, it is a painful transition, but that’s what it takes to make that transition happen. If we are too comfortable then it is nearly impossible to change it up.

    I’m glad to see your blog has been such a success and I’m even more excited to see what’s in store for the future.

    And what a crazy response by that other teacher. It goes to show some people prefer to conform to their surroundings while others will do what it takes to change them.

    • Millennial Money Man Jul 25, 2016, 9:23 am

      Oh no problem Matt, they aren’t too painful – I really appreciate the time I spent doing music and teaching.

      It is an uncomfortable transition. Working for yourself is weird at first – the income isn’t steady, the insurance and that kind of stuff you never think about with a salaried position is scary too. Totally worth it though!

      That’s a pretty common response by teachers honestly. They aren’t paid the way they should be. It sucks for the people that are mega passionate about teaching, because a lot of the time their salary increases are like ours where you actually take a pay cut every year.

      Not everyone wants to work for themselves, which I totally understand!

  • Stefan @ The Millennial Budget Jul 25, 2016, 10:13 am

    Thanks for the great Monday motivation Bobby! Many people struggle to take the leap of faith due to fear of failing but you have shown all of us, including the guys now getting out of college like myself, that you do not have to go the path others want for you. Sure it can be terrifying not knowing if you will receive a decent pay at first or live without many benefits provided by companies but with enough grit many can succeed.

    I want to work in the corporate world for a while (If America lets me stay here!) and hopefully go into teaching one day as helping others is the ultimate goal. My mom is a teacher and I know she does not get paid enough for her crucial role in society but she helps so many people which is the driving force.

    • Millennial Money Man Jul 25, 2016, 10:17 am

      No problem Stefan – I hope they let you stay too!!! 🙂

      A lot of people do struggle with it, and they should. It’s not a choice that should be taken lightly. I’ve incurred a ton of risk by doing what I have, but I think I’m crafty enough to figure out how to make this work over the long term. And if I don’t, I’ll be trying something else again. Maybe some people are just programmed to be entrepreneurs?

      Teaching is a great profession, and I never want to drive people away from it with my story. It just wasn’t for me. We NEED dedicated teachers that are serious about their role. I was always in awe of people that could do the job for years and ignore some of the BS that goes along with it. It’s very fulfilling…but have a side-hustle too!

      • Marcia Jul 25, 2016, 10:40 am

        Bobby, you are right. Some people are able to be an entrepreneur, and some people cannot do it. They are not self starters, and they are not organized. I have suggested many times over the years to many people to start a business, and only one person has done it. The others say they don’t know where to start, or they can’t imagine working from home, they wouldn’t stick to it. Many excuses. It takes a strong willed person that is a self starter and self thinker. It takes patience to learn the right things to do; legal items to business sense. It takes organization to put what you need to do in order, and do it. And it helps to be able to have good spelling and good grammar, not to mention communication skills and ability to work with others.

        Here’s another thing I have seen over and over…..someone gains a little success in something, then they lose it. The thing is, it takes gumption to get there, but the real hard part is MAINTAINING it once you get there. Anyone can score a touchdown once, but to do it over and over again every day is the real challenge!

        • Millennial Money Man Jul 25, 2016, 1:12 pm

          I’m glad I have my wife around, because she knows all the little grammar rules that I have no clue about. She actually proofreads MOST of my posts (not the comments though haha).

          Working from home is ok. I actually prefer working from my office, but since she’s off for the summer I’m trying to make it work! Not sure if I’ll be able to do it next year though if the site is bigger. We’ll see!

  • Marcia Jul 25, 2016, 10:34 am

    When we started our business I was working for an architectural firm and doing what I could during bathroom breaks and lunch breaks. They were told I was starting our business and they were very supportive. We were just about where we needed to be for me to quit when the owner took me into his office and said they really needed me to put 100% back to them, and could I hire someone to run our business? Really???? Hire someone so they could have me? I said no, I wanted to run my business, and if they didn’t want me to leave at lunch time to do my business then I needed to put in my resignation. It was scary, but we persevered, and here we are! 14 years later and would not want to work for someone again.

    The important thing people need to remember running their own business is; you MUST be dedicated, you MUST be organized, you MUST do things by the law, no cutting corners or you risk losing everything one day in the future. You MUST commit to time to work and time to play. It looks glamorous, but it takes hard work, just like everything else in this life. You must work for it to appreciate it!

    • Millennial Money Man Jul 25, 2016, 1:11 pm

      Ha that’s pretty wild, hire someone to run your business? He must have really needed you!!!!

      You’re right, especially on the organization and legal side of things (read IRS for me). Getting everything set up so far has been a little complicated, but once you’re settled in it gets easier. My company is a LLC with an S-Corp designation, so it took a while for me to get my salary set up and make sure I was cool with Uncle Sam.

      There’s a lot of work on the weekends, after normal work hours, etc. I enjoy it though, so I don’t feel like I need the time off that a salaried job gives. Thanks for sharing as always Marcia!

  • Vicki@Make Smarter Decisions Jul 25, 2016, 12:15 pm

    Fellow educator here too! (Hey – you are still a teacher – just a different kind of teaching now – and in a different format!) I am at the other end of the spectrum but did make the break about 6 years before I am eligible to collect a pension (and almost no one leaves before that!) I am still hanging on to a few online/part-time gigs related to teaching – but most days are mine. Just started a blog too – and loving it! I’m not sure it was my dream – but after reading them for years – I decided that I had a lot to share. Thanks for your push here – other educators can do it too!

    • Millennial Money Man Jul 25, 2016, 1:08 pm

      That’s true, it is still teaching! Glad you started a blog, they are a ton of fun. There are a ton of teachers out there with blogs and cool Instagram/Facebook groups, definitely a unique perspective to speak from!

  • Nancy Hoyt Jul 25, 2016, 5:16 pm

    Glad you are happy doing what you are doing now. Being your Mom, I totally enjoyed the drum corps video and all the great memories it brought. Just shows that you have been talented at everything that you have been passionate about in your life.

  • Kelan Kline Jul 25, 2016, 6:38 pm

    M$M what an awesome article! I loved reading it and you did a great job of writing it. You got me jacked up right now ready to make a move. I have been an entrepreneur since my parents told me to “get a job” when I was 14. I have owned my own e-commerce business since then and I love selling products on all kinds of different platforms. Recently my wife and I have started building a blog. We would love to get your personal email to talk to you more about making the leap, my wife is a teacher as well!

    Once again thanks for the great message I will certainly be sharing it! Keep up the good work we got your back!

  • FinanceSuperhero Jul 26, 2016, 10:38 am

    It’s awesome to read more of your story, Bobby. I’m aspiring to do exactly what you’ve done and walk away from education. This past year, I served as an elementary assistant principal and developed a classic case of burnout. I’m going back to a general music (K-5) teaching position for this coming year with no commitment to stay beyond that. In the meantime, I’m going to chase my dream and build my website into what will hopefully be an empire. I’ll also be working a side hustle as a real estate agent. Thanks for the inspiration!

    Also, I can’t quite tell by the uniforms, but were you a member of the Cavaliers? I’m a huge DCI fan and could talk for hours on end about drum corps and marching band in general. What years were you involved?

    • Millennial Money Man Jul 26, 2016, 11:11 am

      Wow small world! I will tell you this – when you do leap the real estate agent gig is going to be your money source. Expect a few years for the blog to really start making money! I still couldn’t live off of M$M right now (makes about $1,500-2,000/month depending on the month, although it’s getting closer. I would have been screwed if I didn’t start doing digital marketing!

      I marched Arizona Academy 2007 and 08, the Cavs 09 and 10 all on snare. I also taught the Cavs snareline in 2012 and 13. I keep finding readers that are into drum corps, so cool!

  • Kelan Kline Jul 26, 2016, 1:36 pm

    What digital marketing do you do?

    • Millennial Money Man Jul 26, 2016, 2:11 pm

      FB ads, Email campaigns, SEO, Social Media, etc.

      • Kelan Kline Jul 27, 2016, 4:58 am

        This is for your own website or you do it for other people as well?

        • Millennial Money Man Jul 27, 2016, 6:57 am

          Other companies, my main clientele is jewelers surprisingly.

          • Kelan Jul 27, 2016, 5:09 pm

            How did you start/learn to do digital marketing after being a teacher?

            • Millennial Money Man Jul 27, 2016, 10:08 pm

              Trial by fire 🙂 I wrote freelance articles while I was still teaching and learned the game of SEO. Then, I put it into practice with this site, and I was lucky to have clients in the beginning that were willing to let me learn and grow with marketing.

  • Financial Samurai Jul 27, 2016, 11:38 am

    Bobby, I LOVE people like you who have the guts to chase your dreams! I didn’t have the guts, so I hung on until I found the catalyst 13 years later at the age of 34.

    There’s only one thing I hope everybody can consider before chasing their dreams: to negotiate a severance get laid off instead of quit. If you negotiate a severance, you’ll have health care, WARN act pay, and your severance. It will provide folks a nice financial runway to not sweat bullets figuring out how to make ends meet.

    If you’d like a copy of the book I wrote, pls shoot me an e-mail. I think it is a no brainer for folks looking to transition into entrepreneurship!



    • Millennial Money Man Jul 27, 2016, 10:13 pm

      🙂 Thanks Sam. I don’t know if I could have negotiated a severance with teaching, but I’d imagine that most people in regular jobs could do it!

      • Mystery Money Man Sep 11, 2016, 7:05 pm

        Great article, Bobby! A severance would be ideal, and may work in a number of industries. I plan to make the leap in the next few years as well, although I’m just starting down the path. One option for people to consider is to “wean” themselves out of their full time gig, so to speak, by first taking a part time job that will provide the flexibility to put more time and energy into the side hustle!

        • Millennial Money Man Sep 11, 2016, 9:58 pm

          Thanks! My advice would be to NOT quit your job before you are matching your salary with your side hustle income.

  • Bo Amusa Jul 27, 2016, 1:51 pm

    This is great. Even if you’re working a 9 to 5 you can still chase your dreams on the side one day at a time.

  • Millennial Moola Jul 27, 2016, 8:26 pm

    My favorite is when bosses have to justify these lower than inflation level raises to their working class peons when the bosses also receive very little themselves. Got so tired of it I quit my job as well and started Millennial Moola. You’re probably way better off than me in the website income dept M$M

    • Millennial Money Man Jul 27, 2016, 10:14 pm

      Ha maybe for now but who knows down the line?? I just couldn’t shake it man, it killed me.

  • Ricard Torres Aug 1, 2016, 2:56 am

    You definitely did the right thing in quitting your job! It’s a super scary thing to do, but you’re proof that it’s a pain worth bearing just to see the results.

    I had a similar plan to you, in that I was going to quit my job to run my site – something that I love doing. Annoyingly, I was laid off a few months before I could quit… It just accelerated the next step in my life, and I have a nice emergency fund in place to keep me going. Yay for savings!

    • Millennial Money Man Aug 1, 2016, 4:06 pm

      Wow that’s awesome Ricard, so you are doing the site full time now?? If so, congrats! I didn’t have any income from the website so to speak when I quit…makes it a little more scary but still doable with a great emergency fund!

  • Xyz from Financial Path. Aug 18, 2016, 4:29 pm

    I wish I had your gut!

  • Gail @The_KnittyKitty Aug 30, 2016, 9:32 pm

    From one drummer to another, you have some MAD skills. Do you still play (Even if its just for fun?)

    • Millennial Money Man Aug 30, 2016, 10:10 pm

      I play literally once a year now on St. Paddy’s with a bagpipe band! It’s SO much fun (and random haha)

  • Brenda - greenspunky Jan 5, 2017, 12:01 pm

    When you quit your job were you already making some sort of side income from you blog? I am planning on quitting my job this summer. I should have a year’s worth of expenses saved up by then but it’s still scary to think I will not have any income coming in every two weeks.

    • Millennial Money Man Jan 5, 2017, 1:33 pm

      No I really didn’t, although I was trying to work out the details of a freelancing gig after I knew I was going to quit. I’d start now by trying to find small businesses that need help with their blogs or content for their site. All it takes sometimes is an email letting them know what your skill set is and how you can help them reach more people.

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