Hey everyone! We are going to kick things off this year with a guest post from my man over at the Millennial Money Man blog about his transition from a band director to blogger – or, as he calls it, “online entrepreneur”. Take it away, Bobby!

I’ve spent a lot of time reflecting lately. At 28 years old, I’ve basically retired from one career and started thriving in another. A lot of people change jobs throughout their lifetime, but it seems pretty rare that young people take a complete 180 in lifestyle and career in such a short time like I have.

I’m a professional blogger

I really struggled (and still do) with explaining what I actually do. When you have a normal job, you never realize how many people use the question “So what do you do?” as an ice breaker! I always pause for a second or two, because I’m not sure what would make the most sense to the person that is asking.

I try to answer based on how computer savvy I think they may be, which rarely works and still leaves the person that asked confused 99% of the time.

If you were wondering, the conversation ALWAYS goes to “So…how do you make money?”, and then “So…you don’t really work. Must be nice.” A lot of my friends legitimately think I don’t work at all, and that somehow I got lucky and stumbled into an online career.

Don’t get me wrong – I understand that everything above is a serious “first world” complaint. But it is one of the many weird things that happens when you transition from a normal job like band directing to working online full-time.

The transition from band director to full-time online entrepreneur is NOT how you think it is.

In every blog coaching session I do or email I answer from someone who wants to quit their job to work online, I always try to stress that it’s not simple and that the vast majority of people that attempt it will fail.

Anybody that has taken a swing at blogging knows that just making your first dollar seems like a mountain to climb. Making $10,000+ per month seems almost impossible, and making $1,000,000 per year is just a stupid fantasy (which is one of my many goals for the coming years).

The truth is, working online for a living is a slow process.

I started MillennialMoneyMan.com about two years ago when my wife and I were still renting a room from her parents. I had just finished paying off my $40,000 of student loan debt, and I was starting to become really passionate about personal finance.

My band directing job was something that I always thought I wanted to do, but after getting into the profession I realized that it wasn’t really for me. I felt suffocated by the job, which is a common symptom of being an entrepreneur trapped in an employee’s body.

As far as technical skills like website building or writing, I had none. The night I decided to start writing about personal finance, I opened up a word doc and basically poured everything I thought about money out onto my computer.

After a quick Google search, I decided that Medium was the best option for posting what I had written. I slapped the post on Facebook, and then watched my life change the next morning as the post was shared over and over by my friends.

That post started the slow, painful death of my teaching career.

Once I realized that I had something to say about personal finance (and that people might actually listen), work became WAY harder. I stayed up late every night after teaching all day and researched the crap out of blogging and how to run a website.

Somehow all these random internet nerds were making multiple times what I was making at my teaching job! I thought it was crazy and absolutely fascinating at the same time.

Work from wherever you want, whenever you want. Wow.

So, I started writing a post on the site every week. At the same time, I dreaded going to work more and more every day. Every month that I saw the website traffic climb a few thousand views, the harder it was to focus on the job I had that was actually making money.

My wife and I started ramping up our savings even more, but she really had no idea I was planning to make a leap of faith into running M$M full-time.

I quit my teaching job 6 months after I started my site.

* This is where I need to put a disclaimer. Please please please don’t read what I’m about to write and then quit your job. One of my biggest fears is that a reader quits their job without being completely prepared first!

With our super-aggressive saving, my wife and I managed to put away about a year’s worth of my salary. I was still planning on teaching for another year, but an older, wealthy friend of my wife’s family convinced me to take the leap…so I did.

I put in my resignation the next day and haven’t looked back since. M$M on its own had made about $3 in Google adsense revenue, so you wouldn’t be wrong to call me crazy for quitting the way I did.

Blogging income doesn’t come directly from your own site in the beginning!

This is the biggest misconception that I see from readers about blogging. The majority of your income won’t come from ads on your site or affiliate income in the beginning. The key to making money with your blog alone is to have traffic, and new sites just flat-out don’t have enough to sustain an income.

One of my blog’s readers had been following me from the beginning and really liked how I wrote. He owned a jewelry company that needed someone to write content for their blog, and he asked me if I would be willing to do it. I wasn’t making any money with my own site, so I jumped at the opportunity.

That partnership evolved and I eventually started managing his SEO (Search Engine Optimization), email marketing, website, etc. I was barely able to make a sustainable income with that gig, but it gave me a platform to survive on while I continued to add content to M$M.

Making money blogging is more about monetizing your skills than anything else. In today’s online environment, understanding how to produce content for companies is a service that a lot of small business owners need, but can’t afford a big marketing company or to hire someone full-time to run a website.

After almost a year, M$M started making money too.

While I was hustling and trying to get more clients for my marketing business, I kept writing content for Millennial Money Man even though it wasn’t doing much. I would get a $100-200 sponsored post offer here and there, but it obviously wasn’t enough to live on.
I’ve always read that most bloggers quit too early, so I kept going even though it was frustrating.

Then one random day I was mentioned on Marketwatch. Then Lifehacker. Then International Business Times. Then Reuters…US News….Forbes….CNBC…Business Insider…and on and on. All of the sudden I was a “personal finance expert”, and things have legitimately been incredible for me since then.

I’ve been flown out to places like Boston and New York to speak to large banks and brokerages about reaching Millennials. I’ve done radio shows, podcasts, and even TV appearances in the last few months. It feels crazy honestly, but the key was that I put in the work without reward and found creative ways to make money through the skills I already had by running my blog.

If you want to make money blogging – it IS possible. But I would highly recommend that you continue to work your blog as a side-hustle until it consistently matches your existing income.

Don’t be crazy like me and leave your job…yet!

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