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30 Months After Leaving My Job - (The Risk & Rewards of Entrepreneurship)

“Hey, Lyndon are you sure you want to make this move. You know things are a bit tough out there right?”
Those were words mentioned to me in 2018 when I felt it was time to call it quits from the corporate space to pursue my dream of starting a business.
It was a decision many could not really understand and to avoid the naysayers or anyone telling me to wait, hold your hand, now is not a good time, etc. I didn't let anyone know that I submitted my resignation letter. I just closed my eyes, asked GOD for that guidance, connected the attachment to the email, and hit send.
Honestly, there were many mixed emotions night because it was the riskiest move I would have ever made. Just think about it - ten (10) years in a very secure job where you're very successful, there is growth in your career within the organization and while things were not perfect within the company, there's no real reason to leave.
Especially when you're coming from a background where there were prior financial challengesand then was able to comfortably overcome them and be in very little debt. My daughter was 3 years away from leaving secondary school and higher education is on the horizon for her, plus the discussion of settling down and starting a family.
Sounds pretty crazy right?

So Why Leave?

I left because of an overwhelming “desire to make a bigger impact on more people“ and as noble and sometimes silly as that may sound to some, I literally started to feel overwhelmed and afraid of doing the same thing over and over for the next 10 years. I became bored with sharing or trying to share new strategies with my team or management. Tired of delivering a shiny new piece of equipment to a customer. Even the aspect of promotion was not very appealing to me. Not because it wasn't lucrative or the company was bad or anything like that.
  • I want to help more sales managers, like myself, experience the same level of success I had.
  • I want salespeople to start believing in themselves and their abilities.
  • I want people to be better at their jobs so that they can grow.
  • I want to help those looking at starting a business to use the things I learned so that they can be successful.
  • I want to develop a tech-based company that helps other companies in the Caribbean region GROW!
All in all, the main goal was to make an impact on people and companies that I felt was not possible while holding down an 8 - to - 4.

Did I Achieve It?

All of it? No, but approximately 20 customer engagements, two (2) regional sales conferences and interactions with at least 500+ people later (not factoring in social media), I believe I'm well on my way.
Not to mention, securing a major international partnership with HubSpot to become the first in Trinidad & Tobago and possibly the English-speaking Caribbean, says a lot. Also, securing a major international speaking opportunity at INBOUND 2020 (another first for me), and a great opportunity to showcase talent and expertise within the Caribbean region.
Let's not forget the people, because I would not have been able to achieve some of those things without the support of friends, family, and most importantly my customers. Remember I spoke about making an impact on others? As much as the accolades are great, I believe they wouldn't be worth anything if they were not fostering change in some way.
Here is some feedback that lets me know I on the right track.

Was it worth it?

The short answer? Yes, but like everything else, it comes with its costs. While you may be impressed with the achievements stated earlier, I would let you know that those things did not come easy. It's a sacrifice and with that sacrifice sometimes comes serious losses, self-doubt, relationship challenges, feeling embarrassed to ask for help, losing the value of self because you get desperate, etc.
Are you willing to get up early enough to provide taxi services just to make sure you have money to send your daughter to school? I was! And it was something I had to do for some time until business started coming in consistently enough to stop.
That's something I've never really shared with anyone, not even my daughter, but I'm sharing with you guys reading this because I want you to know that success does not come without sacrifice, risk, many losses and determination.
While I have no regrets, looking back I would do a few things differently if I had to do it over.
Entrepreneurship like everything else requires work and in many instances more work than your traditional eight-to-four. It requires you to be ready to put yourself out there for what you believe in. You are no longer representing that company with the nice big established name you worked for you are now representing you, your company and your brand.
While I expected it to be hard work, I would admit that I thought I would have had a lot more wins a lot earlier. One key learning that came with this journey was learning how to manage my own expectation. Also, when people ask me if I have any regrets of leaving I say this: It has been a hard journey, but if I did not make that decision and acted on it, I would not be where I am today.
If I had to do it again, would leave the job? Yes and knowing what I know now, there are a few things I would do differently.
Founder | Lead Consultant | Father