Going from employee to entrepreneur.
- Libby Jackson
- May 27, 2022
- 3 min read
Updated: Jun 5, 2022
In 2018, I took a bold step to leave a the organization that I work with for 15 years. I was confident that I could create a business of my own, doing what I had spent the last 15 years doing.
What made me a good employee?
I made myself accountable to doing good work.
I never overestimated my value.
I never tooted my own horn.
I was okay with my compensation and never tried to negotiate for more.
After years of being a "good employee" complacency set it. As long as I good do my "good work" and receive the customary annual increases.
After seeing my fellow colleagues move through the ranks because of their personal ambitions, I believed that my "good works" would make way for me. What I didn't realize was that my focused efforts on being a good worker could be perceived as one lacking in ambition.
Many of my colleague that had started alongside me on my journey were all the way in the game, when I decided that I play. I would find it almost impossible to get in, because knew players had been introduced and they were being fast-tracked through the line of succession while I was still waiting my turn. I believed that I had no choice but to bow out gracefully, so I quit. This is when I came to the conclusion that I had what it took to start my own business. That is how Transition Training Works Inc. was born.
The concept: Create a training business that would act as the training resource for software companies looking to role out a product to organizations of all types. However, my market share would be broadcast companies, healthcare institutions, and educational institutions.
The big idea: I would reach out to vendors, who software I was familiar with, to let them know that my company will offer a training resources to design, develop and deliver Instructor-lead training to their clients.
Getting it done: Project Managers at their organization would include me in all product design, development and plan for delivery strategic meetings, so that I can design a training plan for rollout of the product to stakeholders and end-users. Being involved from the beginning will help strengthen or enhance my understanding of the product and their client's business so that as user-stories and workflow information was shared by the organization, I could build effective training material.
The Middle Man: Without going into the details about the software developer or the organization were he product was rolling out, I will say that I knew the the Owner of company and his software, so that was the easy part. The difficult part was developing a relationship with the stakeholders in the organization striving to implement the product. As I began to meet with the stakeholders, they began to express their concerns about the product.
I found myself in an awkward position, because I knew that the software developer wouldn't be able to meet the needs of the stakeholders. To make matters worse, the Software Owner, who was paying me as a self-employed contractor, was treating me like his employee and required that I share no information with the stake-holder that would potentially create any red flags. As his "employee" I gave away the autonomy that should've existed as a 3rd party entity.
Shook!- This experience shook me and my confidence was broken. I began to second guess my business model and decided that maybe my idea was half-baked. When my contract ended and I successfully provide him with training documentation to accompany any upcoming instructor-led courses, I ended the contract with myself and went a found a job. Maybe I wasn't cutout for entrepreneurship.
Revisiting entrepreneurship- Here are the questions that I needed to ask myself.
Do you still have viable business model? Yes
What would you do differently next time?
Have a business attorney review any contract presented.
Be clear about fees for the project term & provide invoices to track completed work
Use my legal name for compensation and tax purposes. I didn't need to be a business entity to do this work.
Have you designed a customer relationship model that clearly defines roles and expectations?
Are you ready to believe in yourself? I'm still on the fence on that.
Are you okay with uncertainty? Yes
Now, I must state here that entrepreneurship is a mindset. I don't know where I'll end up, but I do know that for the rest of my professional life, I will operate as an entrepreneur even if I become someone's employee again. As an entrepreneur/employee all of the lessons learn still apply.
Be accountable
Know your value
Toot your own horn
Know and negotiate your worth
Believe in yourself
Be okay with uncertainty

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