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It’s Time to Overcome the 5 Common Obstacles Keeping You From Full-Time Entrepreneurship

After spending years helping people realize their professional dreams, I've identified key obstacles to entrepreneurial success, as well as ways of overcoming them

By | Simon Lovell |

At the age of 21, I decided that it was time for me to break free from employment. I’d been working for a video game publishing company and was not being rewarded for my efforts, no matter how much I put in. Over the course of a year, I became increasingly demoralized, to the point where I started to look for freelance opportunities. 

Then, up popped a role where I could work from home. It paid double what I was making and I was able to build my own team and leverage my time producing content. It was the best decision I’d made to that point, because it put me into a place where I was forced to make things work on my own.

I was born to be an . When I finally outgrew video games, I became a self-employed personal trainer working out of gyms — paying monthly rent and having to attract my own clients. This was never a struggle because I was so passionate about what I was doing. I would take new signups on a tour of the equipment, give them a free session and then they would end up signing up with me.

Over the years, I’ve helped many people quit their jobs and go full time as entrepreneurs, and in the process have discovered a few different elements/dynamics that keep people stuck in their existing positions.

1. The money issue

One question I ask everyone contemplating a professional pivot is, “What specifically needs to happen for you to quit your job?” Most people respond with something like, “I need to replace my current income,” which is a fair but broad answer. The word “specifically” is important here. So, for example, if someone is taking home $5,000 per month, then I would ask, “Do you need to make $5,000 for three months from your side hustle to quit, or does it need to be six months?” When you drill down to the actual turning point, it creates a mental shift. Then the follow-up question is, “What specifically needs to happen for that to happen?” Again, we go into details here, so we can drill down to any milestones that will lead to the resignation, because if there is no  that a change is possible, it just won’t happen.

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