How I Prepared to Leave My Job for this Site

How I Prepared to Leave My Job for this Site

leap of faith

Over the past six months, I’ve had a lot of questions asked by readers. Everyone wants to know how I make money. Newer bloggers want to know what works best for social media strategy and monetizing a site. Some readers just want student loan tips or to say hi.

I don’t get to all of them – but I promise I try as hard as I can (typing this as I shudder thinking about the 15 pages of emails I haven’t opened yet). A reader had a question the other day that was very direct, and made me realize that I usually skim over probably the most important part of my “story”.

“How did you prepare to take the leap of faith?”

Well…that isn’t verbatim what they asked, but this is basically what they wanted to know. It’s so interesting to me, because quitting my teaching job feels like it happened 10 years ago! In reality, I haven’t even crossed the 2 year mark of being self-employed.

Before I get to how I handled the process – I do want to make an important note. You can prepare for a leap of faith or big decision like leaving your job all you want, but it’s scary as hell. That’s just the reality of the situation.

I never felt comfortable as an employee

To be honest, I was a crap employee at almost every job that I’ve ever had. It wasn’t that I didn’t do the work well, but I always questioned everything and thought I had a better or smarter way of doing things. I know it annoyed my bosses.

When you have an entrepreneur mindset, you feel suffocated in a day job. I wanted to have more control over my life, and working for myself just seemed like the best way to make that happen.

That’s one of the reasons I love blogging so much. There are countless opportunities to make money IF you put the time in and learn the trade. I have more control over what happens on a day to day basis than I ever thought possible.

Read also: November 2016 Online Income Report: $11,173.63

The first step was to get rid of my debt!

One of the biggest reasons I paid off my student loans so aggressively ($40,000 in a year and a half) was that I didn’t want to be trapped in my teaching job. I was surrounded by so many 40-somethings that were clearly burnt out, but their various debts kept them in their career.

Being debt free was the biggest key to having the confidence to walk away from my teaching career. 

If you are thinking about working for yourself someday or switching careers, I HIGHLY suggest that you pay down as much debt as possible. The less money you need to make to survive…the better.

I started researching businesses I could start

If I had to pick the hardest aspect of preparing for a leap of faith – this is it. A lot of would-be entrepreneurs want to do something cool, but they have no idea what business they want to pursue.

My two biggest ideas were a real estate investing company and a pool business. Weird, right? I was *this* close to attempting my first house flip while I was still teaching. However, I realized that I would be stuck at my job because I needed the W-2 income to get traditional financing.

A good friend of mine owns a pool company and let me try it out during the summer before I quit my teaching job. It only took about three weeks of turning wrenches in the Houston summer heat before I realized I wasn’t about that life.

I wanted to make money with my mind (and my money). Not with physical labor.

Blogging was just one of the various things I tried out, and I didn’t have a clue it would end up being my full-time gig six months later. If you want to be an entrepreneur – try at a lot of things and don’t be afraid to fail or pass on things you don’t like. You’ll figure out your path.

My wife and I saved a year of my salary in cash

I haven’t been shy about telling people that my wife and I rented a room from her parents while I was paying off my student loans. After my loans were gone, we stayed in what was a pretty uncomfortable situation and started hoarding as much money as we could.

Once we had around $50,000 in cash, I put in my notice at the end of the year. After multiple awkward conversations with my co-workers and administration, I was finally free and haven’t looked back since. I want to say that my teaching certificate expired, but at this point there’s not much reason to even find out. 🙂

Don’t. Do. What. I. Did.

If there’s anything I can stress, it’s this: leaps of faith are dangerous. If you want to leave your job – start planning now. Build your side hustle until it matches your income, get rid of your debt, save cash, and THEN jump.

Related: 8 Side Hustles You Can Start This Weekend

Don’t be crazy like me and quit when you aren’t making any money. Even with our low cost of living and my wife’s teaching salary as a safety net, things could have been rough. I had no idea this would turn into a viable business so quickly. It could have taken years or completely failed!

Just…be smart, OK?

Question for you:

Does the leap of faith sound awesome or scary?


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


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13 comments… add one
  • Jon @ Be Net Worthy Dec 23, 2016, 7:27 am

    Hey Bobby, this is great advice and I’m glad to see you are recommending people build up their side hustle FIRST and then quit. The leap of faith is exciting and it’s awesome that you made it work, but it could have ended badly as well. Plus, you had your wife’s income as an extra cushion which I’m sure gave you some peace of mind.

    Good advice and thanks for sharing – have a great holiday!

    • Millennial Money Man Dec 23, 2016, 8:06 am

      Yeah I have a big fear of people reading my site and then quitting their job before they are ready. It worked for me, but I’m sure the success rate is ridiculously low (especially for blogging). Having my wife’s salary and keeping our expenses low definitely helped! Still – by far the scariest thing I’ve ever done in my life. Scrapping a career and half of our income for a dinky little website was definitely an experience haha.

  • MannyJMaldo Dec 23, 2016, 8:29 am

    Hey! Great article. I do think it’s really important what you stress about building up that side hustle. It’s a good indicator if you can work for yourself. If you can’t get your side-hustle off the ground in several years, then you have no business working for yourself. Most people, unfortunately, don’t have the self-discipline to make this happen. They would rather get off of work and go drink beers and watch the game.

    • Millennial Money Man Dec 23, 2016, 9:04 am

      Thanks Manny! I agree – M$M was a side-hustle (that didn’t make any money) that I built after work. If you aren’t willing to put in the time while you have a job, you definitely will have a hard time if you work for yourself.

  • Mrs. COD Dec 23, 2016, 8:34 am

    I’m glad you are honest about the challenges of what you’re doing. My story is similar to yours in that I quit my teaching job after paying off student debt, and made sure to have the security of my husband’s income. We did it so I could be home with our kids, but definitely couldn’t have done it if I had still carried student loan balances. Getting rid of debt was the biggest factor in my freedom to quit! Now, I’m hoping to build up side income through blogging and other freelance work, but know I may head back into the classroom in a few years. Keep preaching the pay-off-debt message! People need to hear it!

    • Millennial Money Man Dec 23, 2016, 9:06 am

      I’m sure I could sell more websites if I pretended that blogging or any business was super easy, but it’s just not true. It IS awesome once you have everything rolling, but it’s a slow process to get to that point. Lots of work with little reward.

  • Mrs. Picky Pincher Dec 23, 2016, 9:06 am

    I think leaps of faith are called “leaps of faith” when they work out. Otherwise they’re called “bad ideas.” 😉 I’m a little envious of your gumption, though! I’m an anxious planner, so I don’t know if I could quit cold turkey–although it sounds like you were more prepared than you let on!

    I’d looooove to leave my full-time gig to do blogging full time. For me, I don’t think it makes sense until I start replacing my income with the blogging income first. Of course, that’s easier said than done, since profitable blogging is a full-time job by itself. Sigh.

    • Millennial Money Man Dec 23, 2016, 9:22 am

      I’ve mentioned how much money we had set aside and where we lived in previous posts and news features, but I’m not sure if I ever put it all together in one post before. I can just tell you from experience, even a year’s salary in the bank doesn’t make you feel a whole lot better when you are quitting something you’re good at for something you have no idea will work out or not.

      I STILL get nervous at the beginning of the month now that I’m making good money. Just part of the game.

  • Ricard Torres @ Escaping to Freedom Dec 23, 2016, 1:40 pm

    Great advice Bobby – spot on. I was in a very similar situation: I felt that my job was not making me happy, and I was feeling the entrepreneurial itch. But I planned the exit for over a year – got debt free and then saved up $20k before taking the leap. I’m working way harder now than I ever did at my job, but I’m SO MUCH HAPPIER!! 😀

    I also think that, while it’s vital to plan this right and have ample amounts of cash saved up, it’s also important to actually do it and “jump”. I’ve met people who are in a position to quit their careers and try something different, but they never do it out of fear. I always say that, if everything goes badly, they can always go back to their old career – it’s not like the professional skills they have would become irrelevant if they left!

    • Millennial Money Man Dec 23, 2016, 5:02 pm

      Oh that’s awesome, I didn’t realize you had saved up $20k! Great work!!!! Having extra cash saved up makes it easier, but even at $50k I was too scared to take the leap. I was going to wait until I had $100k (which could have been several years), but a friend/mentor of mine convinced me jump sooner. I’m SO happy that I did!!!!

    • Derek Hopper Dec 28, 2016, 9:56 pm

      Ricard, I totally agree with you. At some point, you have to go for it. I always remember the saying, “Jump off the cliff and build your parachute on the way down.”

      Plus, I’m a big believer in that failure makes us stronger. Like you say, you can always go back as long as you don’t burn bridges.

      I’ll always give a ton of credit to people who take a risk and pursue something scary. If you fail and have to go back to your old career, your experiences will give you a huge advantage on everyone else.

  • Sarah Dec 27, 2016, 4:39 pm

    Sounds scary as hell. But then, you can’t let yourself be controlled by fear.

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