I’ve had plenty of people tell me that I’m “lucky” to work for myself. One friend of mine regularly tells me how much he “hates” me for the freedom I have because I’m my own boss. I always respond in one of two ways: “you could do it too, but you probably won’t” or “I’ve worked damn hard to get where I’m at today.”

A lot of people tell me that they wish they could work for themselves. In the back of my mind, I’m thinking… “Do they REALLY want it bad enough to do what it takes to get there?”

The Decision

Going into business for myself required a drastic lifestyle change. When my ex-husband and I still worked as employees, we lived in a sweet apartment in downtown San Diego that had a beautiful pool on the roof overlooking the bay and the downtown skyline. I was winning awards at work, making an incredible impact on the company and felt great about loved I was doing.

But funds were tight, I was addicted to my Crackberry, and my family life was falling apart. The husband was never home either, hated his job, and the kids were in daycare for 10 hours a day. Is this what making 6 figures required? If so, it wasn’t good.

In order to be “free” we felt we needed more income but were just about capped at our current salaries. In our minds, the only way to do that was by starting our own businesses.

Drastic Lifestyle Changes

With no savings whatsoever and no plan for how to actually make money we depended only on the belief that if we threw ourselves into a situation without a life preserver that we could make it. With only that, we took the plunge and quit our jobs. We knew we could never afford the $2000 per month rent payment in San Diego and would have to dramatically reduce costs until we started making an income.

So I drove out on the 78 freeway eastbound through the vacant desert and into a middle of nowhere California agricultural valley, stopped at the first town (which consisted mainly of a gas station and a taco shop) found a house to rent for $850 a month, rented it and we moved in a few weeks later.

To cut costs we eliminated all extras including television. There was no time to relax and watch TV anyway, we had to bust a** to make this work.


I was terrified every single month that we would not be able to come up with the rent. Though my ex-husband was a high level programmer and I was a had just left a position as an operations manager, we had no idea about what it really took to work for ourselves.

For months, I didn’t hang up the pictures in the house because I was afraid that we’d be out of there at any moment with no place to go. Within the first 3 months, one of our cars was repossessed. There was no washing machine and dryer in the house so I had to do laundry whenever we happened to make some money. During one particularly difficult month when I didn’t even have enough to wash the clothes, every single item of clothing was piled up in a mountain in the walk in closet. I sat on the pile and cried.

I finally became so desperate that I wrote a passionate post on Craigslist detailing all of my skills and stating my availability to help with any project that matched. The next day, someone responded, stating that the passion is what caught his attention, and I landed a $5,000 web project.

That money came and went quickly to back pay for many things and prepay the rent. There were a few other sporadic projects, but nothing regular. When we did get money, we never knew when it would come again. I would buy enough groceries to last for months – cheap, non-spoilable things like Bisquick and Ramen Noodles.


During this process, I learned that I absolutely hated working with my husband and he hated working with me. This did not lead to a very productive or profitable business. For the first 6 months, I was wrongly mistaken that his skill set was more profitable than mine so spent my time attempting to find jobs for him that were not working out as planned.

My degree was in Writing and my employment history in sales and management. His profession was programming. He never missed an opportunity to let me know that he was more valuable than I was. Slowly and surely, my own confidence began to wane until I truly felt like a worthless failure.

Breaking Free

After growing sick and tired of trying to manage projects for an unmanageable person, I tapped into my own buried confidence. I flooded myself with old college stories that I had written that had received rave reviews, dug through a box of awards from previous jobs and decided that if I was going to make it, I would have to do it completely alone.

It was around that time when I send the email that landed me $100,000 over the following year and half, gave me the financial stability and courage go out on my own, move back into civilization, and live an enjoyable life.

Lessons Learned

It is absolutely essential to create a system that provides regular, steady income. If you’re always wondering where your next meal will come from your mind is not clear or relaxed enough to see the big picture in order to generate big-picture ideas. Always have a base amount of work that will bring you the money you need to get by, but that doesn’t completely fill your time. You need this extra time to be developing bigger ideas that will move you beyond “paycheck to paycheck” mode.

Depend on yourself. Even if you have a business partner, you’ve got to depend on you. Period. If you have a business partner that is dragging you down, get out now.

Trust that everything is going to work out. It was extremely difficult to switch from panic mode to a sense that everything would fall into place. At first, I was panicked that there wouldn’t be enough work for me from week to week, but the moment that I let go and began to trust that it would be, new work began to flow in effortlessly to fill the void.

Hang in there: If you’ve worked for someone else your whole adult life, your mind must go through the process of ‘unlearning’ everything you’ve been taught about making money. It will take time, but the world on the other side is incredible and something not to be missed.

photo credit: Winding Road Ahead via photopin (license)

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