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  • Writer's pictureLibby Jackson

Going from employee to entrepreneur.

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?

  1. I made myself accountable to doing good work.

  2. I never overestimated my value.

  3. I never tooted my own horn.

  4. 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.

  1. Do you still have viable business model? Yes

  2. What would you do differently next time?

    1. Have a business attorney review any contract presented.

    2. Be clear about fees for the project term & provide invoices to track completed work

    3. Use my legal name for compensation and tax purposes. I didn't need to be a business entity to do this work.

  3. Have you designed a customer relationship model that clearly defines roles and expectations?

  4. Are you ready to believe in yourself? I'm still on the fence on that.

  5. 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.

  1. Be accountable

  2. Know your value

  3. Toot your own horn

  4. Know and negotiate your worth

  5. Believe in yourself

  6. Be okay with uncertainty







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