The Fight To Become The Boss

The road to entrepreneurship is difficult. Following your dreams is difficult. Going against the grain is the most difficult and trying thing you will ever do in this life. But if there’s one thing that I hope me sharing my experiences with you communicates, is that it’s worth it. Difficulties are worth the growth you undergo while overcoming them. It is and will always be worth it, never question that.

Define Your Own Success

I am a certified international event and wedding professional, full-time entrepreneur, and owner of a start-up event planning company. As a first generation American in a West Indian (Trinidadian) household, these three things that I am overly proud of are not the things my parents aspired for me to be. When our parents migrated to America to provide a better life for us, there was a blueprint to achieving success. You go to school, you get a degree (preferably three) and then you become a doctor, lawyer, an engineer or something along those lines. They don’t understand any other process than that and if you don’t take those steps then you aren’t successful no matter what you do. It’s just the way they were programmed and it doesn’t matter how much you explain, they’ll probably never get it. Yes, it will make the journey more difficult but…refer back to the intro, always!

Fall down Three times, get up Four

It took three attempts for me to finally launch my business and trust me, I was ready to give up after the first. Here’s a quick outline of the year prior to me finally LEAPING:

  • 3 months before my first attempt – I was rear-ended and had to be in physical therapy for 3 MONTHS. 3 months that I couldn’t do the run around with venues, vendors, etc. and as my fellow entrepreneurs know, in the beginning it’s literally JUST US.
  • A couple of months before my 2nd attempt, my father unexpectedly passed away and I experienced the deepest depths of grief. At this point, I actually gave up. I lost all of my motivation and drive. It’s like the light within me went off.
  • I was offered a new job. I worked in management and I needed a less demanding job so that I could focus on my business and in this case, I’d be making more money to do less! BINGO.. or so I thought… Shortly after starting, a group of us at my new job noticed how differently we (of darker complexions) were being treated in the work place. In the month to come this treatment just got worse and worse. My mental health was hanging on by a THREAD. Not only was I grieving but I was being mistreated and targeted in the place that I spend the most of my time. I would cry all of the way to work every day and then have to TRY to fake a smile for 12 hours. But,

“When God wants you to grow, he makes you uncomfortable.”

Remember your purpose

Well, I don’t know if uncomfortable does it justice! Lmao (Thank God I can laugh about it now vs cry) Any who, long story short, I was very quickly reminded that that wasn’t my purpose. Being there, working in that place, with those people, was NOT MY PURPOSE.

The light turned back on within me. I thought “I can’t die with him. I have to keep living. I have to keep dreaming.” I set the date for my business launch and promised myself and God that it didn’t matter WHAT happened this time. I wouldn’t give up and I would see this through. I told myself “December 10th, 2017 will be the start of a completely new BOOK for me.”

Trust in God

Launching a business isn’t cheap so I also decided to continue working at that stressful job until I launched. This was the smartest move to make. I just had to stick it out. On November 5, 2017 – I got into a TERRIBLE, “Life flashed before my eyes”, “wow, this is it… this is how it’s going to happen.. this is the end” car accident. My car, totaled. My car that wasn’t even half way paid off, was totaled. To top that all off, the money I received for the car wasn’t even enough for a set of tires let alone get a new one.

My conversation with God went a little like this:

“GOD, I know I said ANYTHING buuuuut SERIOUSLY!? Where am I supposed to get this $9,000+ from? How am I supposed to pay off this car that I no longer even have AND get a new one? Oh! I can’t afford to get another one… so how am I supposed to get everything done for my business launch within this next month? How am I supposed to afford all of this with a startup business? Does this mean I can’t launch? Do I have to cancel? No… I promised I wouldn’t.” “God, I’ll trust you.”

Within the same week, the situation at my job reached its PEAK and mentally I just couldn’t take anymore. I felt like God was saying “I give toughest battles to my strongest soldiers.” But my thoughts were saying “I understand that God, but I’m human and I feel defeated and sad and angry and weak. I can’t do this. I don’t think I can do this. I can’t take this anymore. I’m breaking. I don’t want to be here but I need the money. I hate this.” Despite it all I decided to continue to trust that this was all happening for a reason

Take the Leap

One month before my business launch, I left my job. I started a new journal. Every day I would write prayer letters to God, being honest about exactly where I was. One day, I wrote that I didn’t have the money for table cloths. 2 days after, someone bought 5 tickets for my event and instead of purchasing them online as advertised, they gave me the money directly. That same day I was able to purchase them. The month literally went on like this up until December 10th, 2017.

I’ll be honest in saying that the event wasn’t 100% aesthetically what I wanted it to be. But every single thing I NEEDED – I had. Amazingly catered food, non-stop drinks, music, GREAT vibes, supportive friends and colleagues, LOVE, joy and happiness! It turned out to be everything I imagined and more.

Everything is working in your favor

There are little things I didn’t realize at the time. Being damn near forced into a corner to leave my job pushed me to pursue my dreams. Losing my car relieved me from a set of bills that reduced the stress of my startup business which helped me mentally/emotionally. I now had the time to put 100% of my time and effort into my business, my craft, my clients and myself. I was finally able to grieve and be honest about where I am in that process. Not being tied down gave me the freedom I always prayed for. Seeing and being mistreated by my previous employers has taught me everything about the leader I aspire to be for my team.

Fast forward to today, my business is a YEAR old. A year! I can’t believe I made it this far. No, the year wasn’t easy. No, I’m not rolling in money, but I am sufficient. I am happy. I am emotionally stable. Mentally stable. Flourishing, growing and learning every single day. This year was everything I needed and so much more. Being a woman that has suffered from long-term depression for the first time in my life  I have the time that I need to make sure I’m well. I visit home (Trinidad) often since I can work from anywhere which does SO MUCH for my overall well-being. Easiest way to put it is, “there’s no place like home.” I recently launched a blog as a side-hobby.

2019 is already off to a wonderful start and I know that I can make it through or bounce back from just about anything, with GOD.

What challenges have you overcome on your road to entrepreneurship?

Cherelle Jobe is a certified International Event and Wedding Professional  (IEWP), Founder and Lead Specialist of Cherelle J. Events and full-time entrepreneur. As a 24 year old, Trinidadian-American, she has and continues to fight against all odds that stand in the way of her and her dreams. 

Personal Instagram: @_CherelleJ  Business Instagram: @CherelleJEvents , Business Email:,Business Website:

Like this story? Follow Love, Daring Greatly on Instagram for daily tips and inspiration, check out our latest video on YouTube ,  and sign up for our email newsletter here.

Leave a Reply

Thank you for joining our Daring List.
Please enjoy this free 10 Things to Start Daring Greatly Flyer!

Take care!