How I Quit My Job and Became My Own Boss- Part 1 of 3


Seeds can wait for years for the right conditions to grow up.”  Tinka Plese, conservational scientist and sloth savior.

There are seeds that are planted in us early on in life. For some people they bloom immediately.  I think of professional athletes that have devoted their lives from a young age to their craft. For others, it’s more of a process.  It takes more experimentation or simply trial and error.  I fall more into the second group.  As I approached the end of my 30’s, I realized that I had suppressed my true calling for fear that I wouldn’t be able to make a living from it. I didn’t know exactly what my true calling was, but I knew it wasn’t a director of marketing for a billion-dollar company.  I also knew very clearly that I wouldn’t figure out my next step while working in my current position.  So, I decided to quit.


The Money

I am a planner (literally that was my job title for the first seven years of my career).  I am averse to being financially unstable. You may feel the same way. In order for me to muster up the guts to take the leap, I had to prepare.

I knew for a long time that I wanted to leave Corporate America.  I never felt it was a great fit for me and I yearned to take a break. I was having this conversation with the Finance Director in my office and he asked me the question that started me down the road of preparing to leave: “How much do you need each month to live?”  It’s a basic question, but I didn’t have an answer. I shrugged and gave him a blank stare.  He said, “Figure that out then multiply it by how many months you want to take off and then start saving. When you hit your goal, quit”.  He made it sound so simple and it really was.  Sometimes is just takes an outside voice to simplify what we think is so complicated.

I immediately went back to my desk and opened a spreadsheet and started to list all of my monthly expenses. I also made sure to include a healthy budget for entertainment and travel because I didn’t want to drastically change my current lifestyle. I got to a number pretty quickly, and it seemed huge.  However, my motivation to take a break from work was more powerful than the largeness of that number.  I already had an online savings account for my emergency fund. I started another automatic savings fund with CapitalOne 360 Savings . I read that if you name your savings goal, you’re more likely to achieve it. Personalizing it makes it more real.  Try it!  I named mine “Freedom Fund.” The name alone kept me motivated and made me smile every time I checked my progress.

I started to reduce my spending on ancillary things like clothing and shoes and random beauty products from the drugstore (my weakness). I started to only buy things when I needed them vs. stock piling. You would be amazed at how much money we waste by buying in excess. I also started to cook more during the week and use leftovers for lunch. I enjoy going out to restaurants, so I reserved that for the weekends.  It was important for me to continue to do the things that made me happy.  I didn’t want to be unhappy at work and disgruntled in my personal life because I was saving for later. I was still living in the now.

Set A Date

Another important part of the process is having a target date to take the leap.  Sure, it can change as life happens, but it’s important to have a pre-identified end to the chapter.   There’s something about putting it out into the world that makes it more real.  We are more likely to stick to goals if we write them down.

Identifying a date helps to drive accountability with saving.  I started to align my life around that end date. I was less likely to remove money from my Freedom Fund because it would change my end date (and with increasing stress on my job, not an option!).  My quit date also aligned nicely with receiving my year-end bonus, hitting my savings goal, and my lease ending on my apartment. I was not only liberated from my job and career, but also from a city that I was ready to leave. 

Trial Runs

In the time that you’re waiting to quit, it’s a great time to experiment and try different things.  I was still performing well on my job, but I was energized to figure out what else I could be good at.  I always wanted to work for myself, so I started to network with people that worked for themselves.  I was able to address my concerns around sourcing clients, taxes, health insurance and the starting out process. 

Being around like-minded people allows you to expand your mind to what’s possible.  The good thing is that people love to talk about work they are passionate about. Throughout my conversations, I thought, if they can do it, why not me?  We put people on pedestals without knowing the back story.  Getting the back story helped me to see that I was just as capable. We may not know step 10, but we do know step 1. Take it.

“No matter how clueless you may feel right now, pay attention to suggestions and opportunties that suddenly present themselves… Take the first step in the direction toward something that feels right and see where it leads you. And do it NOW.” Jen Sincero, You’re A BadAss.

I also put myself into new environments, which started to get the gears going in my head of what I could do next.  While still earning income, I invested in this process. For $180.00, I attended a local start-up/entrepreneur conference.  I gained more information on entrepreneurship and was able to be around people that were in a different space than I was accustomed to.  Seeing the many types of different careers and businesses started my wheels cranking on what I could do next. I also learned that investor money and accelerator programs were available for startup companies all over the country, not only Silicon Valley.

I had always considered being a marketing consultant.  I had done marketing and branding for over 15 years, but I was unsure if I could apply those same skills to any business.  I got the opportunity to help out someone with a marketing plan for his fitness equipment business.  I did it pro-bono.  It was a great opportunity to test out my skills, get feedback and see where I may have gaps.  Most of all, I was able to see if it was a line of work that I would be interested in doing on a more full-time basis. I found that free trial runs were a low to no risk way for me to gain experience and refine my next steps. 

To recap, before you take the leap, look!  There are practical ways to plan and get comfortable with what’s next.

1.     Figure out a budget. Determine how much you need to live per month and start saving!

2.     Give yourself a time limit. Plan a quit date and stick to it. Writing it down makes it real and creates accountability.

3.     Change your perspective.  Put yourself in circles with people doing the things you aspire to do.

4.     Take a trial run. Try out projects for free to gain insight and experience.

Every day, I take new steps as I figure this entrepreneurial life out and walk in my purpose. Stay tuned for more helpful tips in part 2 and 3!

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