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Should I Quit My Job and Start My Own Business?

Updated: Jan 7, 2022

Are you feeling like you're ready to take on full entrepreneurship? If the answer is "yes" it's important to make sure you are taking the steps necessary to plan for success.

Should I Quit My Job?

Would you believe me if I told you that I am writing on this particular topic while down the street from the place of employment I resigned from when I decided to quit my job and finish writing Go for Yours? I know that can be hard to believe because I no longer live in Chicago. However, as I write this, I am waiting on my sister, who is down the street at the salon. How crazy is that?


When I decided to walk away from my full-time job in 2010, I had just reached my second work anniversary. I initially had no plans to leave and was simply “writing a book on the side.” I didn’t know the culture of entrepreneurship well enough to take such a giant leap of faith. While writing about some courageous people who were brave enough to follow their dreams, I could only wish that I would be able to do the same one day.


If it weren’t for the stress of being micromanaged, I could potentially still be at that desk or somewhere similar. Before resigning, I daydreamed about the day I would chuck the deuces to my supervisor and the entire department. There were days I would sit at my desk and imagine my last day at the gig. I would let my supervisor know how I truly felt about her and everyone else that irritated my soul. But not before glancing at my favorite colleague and saying, “but you’re cool,” as I so modestly walk out of the door.


I thought about all of the benefits that came from working for myself. I knew that the idea I had for Go for Yours was unique, and it could stand on its own. But only when the time was right. However, on a frigid day in December of 2010, my supervisor requested to see me in her office. I just couldn’t take it anymore. I handed in my letter of resignation I had written months prior.


Maybe writing my letter of resignation and saving it in my desk drawer helped manifest what was indeed in my heart. Months later, I couldn’t help but think, had I made this decision too soon? Although I can’t turn back the hands of time, there are some things I would have done differently. If you’re sitting at your work desk reading this, here are some tips to help you quit your job and start your business when the time is right.


Gain knowledge about your industry of choice.

Before diving in headfirst, think about what it is you want to pursue. Most people who have successful businesses did research about their industry of choice. In Go for Yours, I talk about Jerome Boykin, who became a millionaire after starting his parking lot cleaning business. Jerome started his business after learning about the industry and its success rate. On the other hand, all I knew was that I wanted to be an author. Instead of creating a successful plan to transition from a full-time job to entrepreneurship, I led out of passion and curiosity. If I had done further research, I might not have struggled as much as I did at the beginning of my journey.


Talk to people that have been successful in transitioning from a full-time job to entrepreneurship.

The keyword here is "successful." When getting advice, you want to talk to the right people. Make sure you speak to someone who has transitioned successfully and has overcome any obstacle in their way. Just like a full-time job, there are cons to entrepreneurship. Talking to the wrong person who is doubting their choice of entrepreneurship may steer you away from your decision. I would recommend talking to someone who could navigate through the hard times.


Start your business while you are employed.

This is one of the best decisions I could have ever made. Although I didn't know every aspect of the field I was entering, I started saving money and taking care of expenses while still employed. I looked at it as my employer being my investor. I used money from my bi-weekly paychecks to invest in my business. I didn't have to worry about these expenses when I was no longer employed.


Have enough money saved for 6-12 months of expenses.

Starting a business with bills hanging over your head is never a good feeling. Trust me. It's hard to visualize your success with minimal funds in your bank account. You don't want to worry about how you will pay your rent or even your phone bill when you are trying to build a successful business.


Create an exit strategy.

There's never a perfect time to quit your job and dive into entrepreneurship. However, there is the "right" time. An exit strategy will help you map out goals that will help you in your transition. An exit strategy is normally a method used by venture capitalists or business owners use when they want to get out of an investment they are involved in. You can use this same method to transition from a full-time job to entrepreneurship.


Hopefully, these tips have helped you identify whether or not you are ready to transition into full-time entrepreneurship. If you'd like some guidance, feel free to book a one-on-one consultation to discuss your goals.


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