Blogging, Travel

That Day I Quit My Job to Become a Writer-Entrepreneur

For many bloggers, the “I quit my job” post is a rite of passage signifying to themselves and the world that they’ve made it in this new frontier of Internet business that nobody quite understands yet everyone wants a part of.

The writer begins the post by regaling a similar tale read in other “I quit my job” posts. After spending years of working both a fulltime job and 40 additional hours a week blogging, they finally looked at their bank statements and saw that they made more money in one month on their blog than they do in a year working their day job. I like those posts. I feel inspired by those posts.

This isn’t one of those posts.

My tale is much different. Some may call it ballsy. Some may call it risky. Some may call it foolish. All are probably true. I didn’t have a stream of income in one month equal to what I made in one year of working. In fact, I had made $300 in the past six months from my site prior to quitting my job. That’s not enough to pay for, well, anything significant. Nor did I have a grand journey in mind like bicycling around the world.

Why then did I quit my job?

First, I had a dream. Second, I was ready (sort of). Third, shit hit the fan.

I quit my job

This is not what I do all day as a Writer-Entrepreneur. Wouldn’t it be great though?

I had a dream.

I’ve always been a dreamer, imagining a life that defied norms. At the same time, I always did as I was supposed to instead of pursuing those dreams. For example, in college I was offered two dream jobs, two once in a lifetime opportunities, both of which required me to quit school. At the end of my sophomore internship in Nashville, Arista Records offered me a job in the mailroom with the promise of climbing within the ranks of the record label. At the end of my junior year, a friend selected me as his successor within a sports agency to manager Indy Car drivers. I said no to both of my passions at the time. Why? Because I had a full ride to college and finishing my degree is what I was supposed to do.

Art of Manliness calls this “shoulding,” and I was real good at “shoulding” all over myself. My “shoulding” didn’t stop after graduation. Instead of waiting tables in Nashville while a job opened up, I accepted a position my aunt secured for me with the federal government complete with the stability and benefits I “should” have. I became a bureaucratic cog caught up in suffocating red tape.

I hated every waking minute of my life and fell into a deep depression. I plunged into a downward spiral of underachievement as I listened to what others thought I “should” do to advance professionally over my heart’s desire. I pursued my MBA (racking up $50k in debt), worked for an unsuccessful startup, tried my hand as a consultant with a major bank (talk about soul sucking), and landed in a quasi-sales role. I watched my dreams come and go while I felt the passion, creativity, and energy drain from my soul. Finally, I turned to writing as a creative outlet, something that I had always longed to do.

Each morning I spent an hour working on a novel. After work, I would write this blog. It was during these hours that I felt most alive. My boss could tell when I skipped writing. I was irritable. Bitchy. This is what I wanted to do full-time. This was my real dream. But was it practical?

Ten years ago, I’d say no. However, technology has changed the barriers of entry to writing. The stodgy old men that run publishing houses are being pushed aside. Magazines and newspapers are falling away to blogs. Traditional book publishing is being replaced by independent eBooks. Writers and authors are finally getting paid what they deserve without the middleman sucking the profits from their talents.

All of that sounds great in practice, but…

I was sitting on a fledgling blog and a piece-mill novel about the mafia. Nothing felt developed or real. I wanted it to be real. I wanted to be a writer. I was miserable because I wasn’t. I remember house shopping for an “upgrade” with my wife. I found fault in each house. When I couldn’t find fault, I dragged my feet on an offer. Why? Because taking on a larger mortgage would further delay my writing dreams and probably punt them forever.

I thank God that Shannan is smarter than me. She caught on. I remember when she suggested that we delay the house search and instead take that savings to develop me, to develop my writing business. My first thought was, “What did I do to deserve such an amazing woman?” My second was, “Yes! Yes! Yes!”

Quitting my job

Foolishly optimistic as I graduated with my MBA and did as I was supposed to.

Together, we made a plan.

We’re financially conservative. We teach Financial Peace University and abide by its principals. Willy-nilly quitting a lucrative job wasn’t an option until we were ready. All debt (other than our affordable mortgage) had to be eliminated. Both of our cars were already paid for, and we’ve never had any credit card debt. Those student loans from my private graduate education were still looming though so we attacked them “gazelle” style. Once they were paid off, we still wanted a year’s worth of living expenses in case all hell broke loose and she lost her job while I was a struggling writer.

If you wish to follow I my footsteps, make sure that you’re financially ready. Crush your debt. Enroll in Financial Peace University. Read one of Dave Ramsey’s books. You’re not just eliminating shackles on your money; you’re also eliminating shackles to your life. Debt is a form of slavery. Your every waking hour is dedicated to the financial obligations that you created. So quit creating them.


We did.


Without the financial freedom that comes with living debt free, I would have never been able to quit my job and pursue our dreams. Without eliminating debt, I would have been a slave to someone else’s dreams. Please don’t be a slave to someone else’s dreams. Think right now what you want from life and create a plan. Do you want to be a yes-man BMW driver or millionaire free spirit?

Even with debt eliminated and our savings goals met, we still wanted the blog at a level that it was generating an income. I continued to burn the candle at both ends working my novel, job, and blog. I was working a plan.

And then that plan fell to shit.

My last business trip working for the man

Coming home from my last business trip working for the man

Shit hit the fan.

Sometimes things don’t go as planned. For the longest time, I held this next part out of my drafts to avoid sounding whiney. Alas, I decided to include it as it’s a story that needs told. I was abused financially, professionally, and emotionally by the Fortune 500 Company that I worked for. I know many others experience similar suffering, yet few are brave enough to fight for their rights out of fear. If you’re suffering in a similar situation, allow this story to inspire you.

After I was on the job for a little over a year, I realized that something was wrong with my commission statements. A bonus commission that I earned for exceeding targets was withheld. I asked my manager about it, but he would never give me a straight answer. Yes, he agreed that I met my goals, yet he couldn’t tell me why the company wasn’t paying me properly. He would look into it. Weekly I followed up with him, and the answer remained the same. Given that I can smell bullshit when I’m being fed it, I started to only inquire in writing to build my paper trail (always build a paper trail).

Then my manager quit to work for a competitor, and I had to pursue my pay grievances with a new boss. I received the same answer. More months went by. I complained to co-workers who had been around much longer than I had. Their answer? “That’s just how this company is. None of us knows how we get paid and they never honor pay discrepancies.”

I have more fight than that.

My new manager lasted six months before he, too, left for a competitor, and I had to take up my grievance with yet another manager. This time I had someone who was actually on my side. Sprinkles of back pay began to hit my bank account. Yet none amounted to the estimated $55k that they owed me. As much as I appreciated my new manager’s fight, progress wasn’t moving fast enough. After a year-and-a-half battle, I sought legal remedy.

I still remember that call with my manager. “Are you really threatening to sue your employer?” he asked.

“No, I’m not threatening anything. I’m going to sue if I’m not paid on Friday. The paperwork is already drawn up. It’s up to the company to do the right thing.”

They paid me in full that Friday, but I still didn’t feel that I won. Why should I have to beg for my paycheck from a Fortune 500 Company? This is also when the emotional abuse began.

One man is responsible for the missing pay. I’m guessing he received some sort of negative blowback because he made each day hell for me. The details are far too complicated to get into, but I once again had a long paper trail and found myself filing a retaliation complaint against him with Human Resources. That complaint went nowhere. I dreaded each phone call and email with him not knowing the verbal abuse and lies that awaited.

I wish I could say that this was the end of my pay issues. I was hit with two more. The first involved a violation of North Carolina labor laws and assistance from the North Carolina Department of Labor. I easily one this dispute. The second came from a new commission plan that was incomprehensible. Overnight, I saw my commissions cut to a quarter of the previous amount.

I eventually won that last pay battle six months after I quit. Over four years of employment, I had to beg my company for $80k in missing commissions. Robbing an employee of that much earned and promised pay is criminal.

At the same time, I was representing a product that had failed to innovate compared to the competition. Clients were leaving in droves. I saw no chance of my paycheck returning to its once prosperous level.

I was disheartened. I had a plan and was working that plan but found myself in a losing battle to keep clients whom I couldn’t blame for leaving. My choices were too find another job and clicking repeat, or pulling the trigger earlier on pursuing my dream.

Quote 03232015

And this is why it pays to marry up.

After a couple of months of watching my commission statement nose-dive, my wife came home from work to find me stressing in front of the computer. For over a month I hadn’t touched my novel or my blog because worked sucked every living minute from my life. My hours were increasing at the same portion that my pay was decreasing. I watched my dreams fade.

Then she suggested I quit.

We had more than enough savings. So what if the blog wasn’t generating money? If I continued in my job, it never would. If I took a chance, then there was a strong possibility it would. Over beers and BBQ (because that’s how we do it in NC, ya’ll), we decided that I would turn in my notice the next day.

I’d be lying if I said that I wasn’t nervous. I was shaking on the phone call with my boss. Yet, I was happy. I hung up the phone excited for my new journey. Then, when I met with a member of upper management on my last week and he told me, in front of a client, that I’d fail and be back in a year, I knew the decision was right.

Please don’t use this portion of the post as justification to up and quit your job. In most circumstances, that is not the right course of action. However, if your health, family relationships, and well-being are failing to the point of irreversible harm, then it may be okay to quit. Always balance that decision with your financial situation. I had savings and my wife’s income.


If you need any candid feedback on whether or not your situation warrants quitting your job, please email me at

So what’s next?

I hope that this post has inspired you to evaluate your own dreams. Are you living them or are they a distant memory like mine once were? If they are, what do you plan to do about it? Don’t be a BMW driving, bobble-head yes-man with a life is void of passion! With today’s technology, each of us can achieve our wildest dreams. All it takes is a plan and a little hard work. So create that plan, crush your debt, and achieve your dreams.

For continued inspiration, I plan to start documenting my journey by posting monthly financial reports along with lessons learned on my journey to become a Writer-Entrepreneur. Together, we can keep each other accountable!

Sign-up up for the journey by filling out the form below.