How to Overcome Challenges of Solopreneurship

How to Overcome Challenges of Solopreneurship

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Cheryl Henry writes articles to Passionistas website For the Modern Female Entrepreneur

In 2010, I decided to take the biggest risk of my career to date. After 20 years working as a Career Counsellor for a variety of companies and organizations, I found myself standing on the other side of the spectrum. I had been laid off due to the massive shift and downsizing in my industry. The “counselor” had now become the “client”, and the question on the table for me was “is this the time to take the leap and move into self-employment”? I had never even considered it as an option until the possibility was right in front of me. Questions that occupied my mind for weeks were, “can I really do this”? “And have I got what it takes to work for myself”? I’m sure many of you can relate to standing at the crossroads of this decision as I did five years ago.

Fast-forward to the year 2015 and I’m proud to say that I’m still here working my career coaching business as a “Solopreneur” without regrets. Was it an easy transition? No, it wasn’t, and I’m sure many of you ladies also walking the entrepreneurship walk know that it’s one of the most difficult, yet rewarding journey’s you’ll ever take. Although there are days that are truly hard and test your commitment to the journey, if you are anything like me, you know deep down in your gut that you’ll never look back. However, I learned very quickly that I was the Employee and the CEO all in one, and if I was going to have a successful business, I needed to know how to do this effectively. Not many of us can wear more than one hat at a time. It’s a must to keep a business growing in the right direction. I realized very quickly that having the right skill sets and knowing how to apply them was going to be the key to my success. If you are a solopreneur like me, then you’ve probably encountered some of the same roadblocks so here are a few tips to get through the challenges of doing it solo.

The first challenge I had to overcome was marketing the business vs. harvesting (actually doing the work that gets you paid). I found myself confused about how much time to allot to each and quickly realized that although I could do both, I was much better at doing the work than marketing the business to find the right clients. If I had opportunities coming at me, it was great! I loved preparing and delivering training, working with my clients and, of course, getting paid for it. But when the wave died down I became anxious because I had no new clients on the horizon. Quickly, I learned that I was much better at doing the work and needed someone to help me with marketing my business. As a start-up business, money was tight, so I utilized business resources within my community and found that internships are a great way to get the help you need without having to pay someone to do it. Opportunities were available through non-profit organizations and community colleges to place marketing students within my company who needed practical hands on experience. What a relief! I didn’t have to focus on marketing my business, and I could give the task to someone who had the theoretical knowledge and now would apply that “know how” to helping me build my business. The return for them was the concrete experience that they could now add to their list of skill sets and resume.

The second challenge I encountered was collaboration. I needed someone else to bounce ideas around with, or just to get feedback. I’m sure many of you would agree that having someone to share ideas and goals with adds great value to any business. But the question was with whom should I collaborate? Family and friends are great, but not always objective. They love you and want the best for you, but sometimes objectivity is a problem, right? Again, I reached out to business resources and found a wealth of information about networking groups of all kinds. The best resource that came to me was a website called What an amazing resource this was! I now had options to connect with other like-minded businesswomen all over the city through various networking groups. This international site allowed me to connect to local groups on a monthly basis for collaboration, marketing and most importantly empowerment. Meeting women who were veterans of business ownership or new to the world of self-employment opened doors for productive collaboration that continues to help me grow my business. It’s important to choose the ones that fit best with your business objectives and let them help guide you with objective insights and feedback.

Lastly, I learned that it’s important to pay attention to who you are and from where you draw your energy. If you’re an extravert like me, then the environment around you energizes you. It became necessary for me to take my home office outside. So, from time to time I’ll work in a library, coffee shop or a business resource center. Having the stimulation of others buzzing around me allows me to feel connected to a larger world other than me, myself, and I while working my business. If you lean more toward the introverted side of the scale, then working in an alone space is energizing within itself since your energy comes from internal reflections. If this is you, then it’s a necessity to have a space that doesn’t allow for distractions by others during your working hours.

The journey of entrepreneurship is not an easy one. The vision is to have business partners eventually to achieve my long-term goals, however, I’m currently learning way more about myself and the tools I need to keep my business growing and thriving than anything else.

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