Why Being A Service Based Solo Entrepreneur Is the Hardest Career Path

James Boileau
The Startup
Published in
3 min readDec 3, 2016

You have an inspiring vision and a “thing” that helped shape and change your life for the better. Now all you can think about is sharing this amazing gift with others to help better their lives. The notion of working a soul-sucking 9–5 job makes you nauseous. Besides even finding a good job where you’re valued and able to fully contribute is challenging. You see many of your friends and strangers taking the entrepreneur route and it looks enticing. So you decide to leap and join the freedom, flexibility and fulfillment of being an entrepreneur.

But not just any entrepreneur — you choose to be a service based solo entrepreneur. Perhaps a social media manager, personal trainer, nutritionist, life coach, PR consultant, reiki practitioner, interior decorator, massage therapist or photographer. All these jobs and many others provide wonderful services, but many people who go this route struggle with one key area — business.

What got you starting your business were passion and a skill or service you want to share. In order to do that you need customers — which requires business skills — especially sales and marketing. For most of you those are not your strong points. Yet, only when you have done those well do you get the reward of providing the wonderful service you offer.

Everything is so personal because you are your business.

Building a brand and service offering to a specific audience takes time, research and lots of trial and error when you’re selling a product. When you are your product it’s exponentially harder. Separating you from your business so you can objectively create the messaging and delivery the service is the task required. Knowing what questions to ask, how to build a strategy and measuring feedback all the while finding clients, following up with client leads, networking, servicing clients, billing, marketing and so on. Being pulled in all these directions is hard, but figuring out what directions are important and which are wasteful is one of your top priorities once you’re going. You are the only person in your business and you have a finite amount of time, energy and money before shit hits the fan and you’re losing your mind.

Being a service based solo entrepreneur is one of the hardest things to do. Not just because you’re wearing so many hats and needing to be proficient in many skills, but everything is so personal because you are your business. When a client doesn’t buy, or doesn’t return it’s hard not to take it personal and wonder if it was you. When you don’t feel at your best you still have to preform or you don’t get paid.

Don’t fool yourself in thinking this is an easier route than a corporate job.

For those of you who are service based solo entrepreneur or thinking of becoming one I say go for it. But have your eyes open; be honest about the enormous task at hand. Don’t fool yourself in thinking this is an easier route than a corporate job. And please, PLEASE get business help. Take courses; ask friends or experts, get a side job in someone’s else business to learn from them or anything that will help you be better at the business part of your company. Having a “thing” you want to share with the world to make peoples lives better is wonderful, but trying to build a sustainable business around it is not the only way to share this gift. If this is the path you choose, be patient, be practical and don’t take everything personal. Good luck.

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James Boileau
The Startup

Author. Coach. Designer. Helping 20 and 30something navigate the intersection of business + personal. www.jamesboileau.com www.instagram.com/own_your_shit