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.
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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 entrepreneur. 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 belief that a change is possible, it just won't happen.
2. Flipping around fear
Of course, particularly when you've spent a lot of time working for other people, there is safety in that paycheck, but it's important to address any associated fear and start to think differently if there's any chance of making a power move. Common anxieties include the possibility of not attracting clients, fear of both failing and succeeding and the fear of simply looking foolish. While looking at the worst-case scenario can sometimes be helpful in preparing for upcoming challenges, in most cases it's just clever self-sabotage that protects us from living our true potential. So, we have to become conscious of fear, then flip it to positivity. If you keep thinking, "I won't get clients," turn that around to, "I will attract plenty of clients" and come up with evidence to support that expectation, as opposed to shutting down ambition because of a thought that simply isn't true.
3. The energy shift
Big decisions create a change in energy. Just like thinking about breaking up with someone, there often comes relief when you actually find the courage to make the move that your soul has been screaming for. It's the same dynamic when it comes to thinking about letting go of a job that doesn't support you. Every day, week and year that goes by and you keep putting off a decision, you will lose vital energy. The moment the decision is made, however, energy shifts because you've moved into alignment with what's best for you.
4. Uncomfortable emotions
Some people don't quit because they are afraid of the reaction of someone else, any difficult conversations that need to happen or because they can't handle the feelings that might surface — and so years get spent avoiding the life we want. When I recently helped a high-achiever in her job finally quit and go into real estate full time, I had her text her boss while we were on Zoom. She had the conversation that same day, and it was done. She'd been putting off this decision for years, but when she was on the other side said, "This is the best decision I've ever made."
5. Setting an intention date
It's part of human nature to keep on putting things off… to keep on protecting ourselves. So, if you're 100% serious about quitting your job, it's important not just to solidify that intention, but to also pick a date when it will happen — to make a decision, because decisions have power. Then ask yourself whether there any reasons why it can't happen in half that time. You will be surprised by the number of people who end up making big decisions faster after considering that simple question.
Having the courage to go full time as an entrepreneur is a bold move. It takes digging deep, self-awareness and a mindset devoted to breaking free. It's also a big part of being a full-time entrepreneur, because quitting is the first test: If you have the courage to quit, you have the courage to face the bigger challenges coming your way.