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Transition from Employee to Entrepreneur: Part 1

Anthony | December 27, 2020


How I Transitioned From Entrepreneur to Employee back to an Entrepreneur

Firstly, I’m scared and excited to share this story with you.


Because, back in Mid 2010 I experienced some of the bleakest, saddest, most despair-filled moments of my life.

It’s hard to relive those moments and it makes me feel pretty vulnerable to share publicly after there was no choice but to apply for a role as an employee after the not so surprising collapse of my business.

My Rise in Entrepreneurship

I always dreamed of being a full-time entrepreneur. I bought into the message that you’re not a true entrepreneur if you’re side hustling and have a full-time job. I was mesmerized by the freedom, the excitement, and the unique challenges of being your own “boss”.

I had been working as a public servant for several years and felt my talents would be more suited to running my own business.

I remember being offered a contract role within the Australian Taxation Office (ATO) in February of the year 2000.

The Year 2000 problem, Y2K as it was known, (check it out here if you’re not familiar with Y2K) had just happened and the ATO was on a deadline to deliver the GST by July 1 2000 for the then government.

I was excited and keen to deliver value only to realize I was surrounded by people who did not share the same enthusiasm to get work done.

Within three months of starting the contract I had left the role and found myself packing all my belongings into a storage shed and traveling to Port Macquarie where my mum is located (and still si to this day. It was a day I will never forget as a wave of freedom swept over me along with a wave of “oh crap what am I going to do”.

I landed in Port Macquarie with no job, no idea of what I was going to do, and no clear direction. If you’re not familiar with Port Macquarie, then the following may help you better understand what it was like.

It was a small town of approximately 35k to 40k residents, at that time, spread across various areas including Wauchope, (to the West), Lake Cathie, and Laurieton to the South with a large number of single parents living the sea life on a minimal wage.

I struggled to say the least and began to throw myself into finishing my Masters Degree in IT.

After successfully completing the study over a couple of years there I was in 2003 wondering what next and thankfully found myself a training role teaching unemployed people how to use Microsoft Word, Excel and PowerPoint so that they could get a job.

I loved that job and gave 100%, I was meeting people, traveling North to Coffs Harbour most weeks, traveling south to Newcastle and essentially making good money delivering value to people who needed my services.

I soon found myself in attending seminars with well-known speakers, such as Chris Howard, on Neurolinguistic Programming (NLP) and this began to fuel my desire to deliver new course material on “How to trade stocks and options for Profit”.

At first, it was tough, I had no marketing skills, no idea how to attract prospects let alone convert them into paying clients which is when a lady, let’s call her Lisa, stepped into my life who bought into my vision.

My Fall in Entrepreneurship:

We started with a simple website and began attracting prospects, little by little converting these prospects into paying customers through delivering events. However, it was happening too slowly, and the business outgoings were far exceeding the incomings which left me in a dilemma to either go bankrupt or get a job.

It was June 2010 by this time and I was worried about money way too much. I had been living a limiting belief of ‘not enough’ for the first 6 months of that year. Even when I had more than enough, my brain defaulted to ‘not enough.’ This was so very distracting and painful.

Painfully I pulled out my resume, dusted it off, and began to update it with the past 10 years of my life. I drew a blank at first because I had no idea of my skills.

As an entrepreneur, I had the ability to fulfill my goals and aspirations as an individual. I didn’t have a boss to interfere with or make decisions for me. My life was my own and the amount and size of the risks that I had taken up to that point were my choices.

Here I was facing a blank page with which I had to somehow summarise my skills acquired from being an entrepreneur so that someone could employ me so I would not go bankrupt.

The fear of having to follow a potential employer’s instructions and fall into the trap of becoming dependent on a monthly income which I knew would lead me to debt was making me weak at the knees. My life had taken a turn for the worse and I had no choice but to apply for every and any role that was available.

I became totally confused by the barrage of rejections I was receiving and it did not occur to me that many of these companies often had some valid concerns.

Most of those concerns involved questions about my ability to transition from entrepreneur to employee. I was often asked how I was going to adapt to the company’s culture after running my own company and doing things my way.

The questions at many of the interviews went along the lines of, Can you take orders without question? Will you be able to work with a team when you’re not in charge?

I was focussed on getting hired

The single most important thing I was focused on was getting hired. There was a problem with that, I was not committed and never fully set my mind on being someone else’s employee.

I soon realized the challenge I was facing which was how can I transition from entrepreneur to employee if part of me is still holding out hope that I could continue to be my own boss.

I was so focused on thinking of ways to revitalize my failed company? Mulling over new business ventures? and was totally resistant to the idea of taking orders from someone else?

After 80 something applications submitted and only 5 interviews, I was eventually offered a full-time role in a different state at a Bank as a Business Analyst on a salary that was not in alignment with my skill set.

Click here to read Part 2


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About the Author


How would you like to attract more leads, convert these leads into paying clients and deliver more value to these clients? Join a team of like-minded entrepreneurs who are generating more money, delivering meaning and have more freedom to live the lifestyle they choose