The Biggest Challenges Facing Solopreneurs


1. The Collaboration Crisis

Leveraging your skills and talents when you are a one-(wo)man-band is the toughest challenge for any solopreneur. So, why don’t more of us collaborate? It would enhance the value proposition to clients, spread the daily duties around, and increase the potential to get new and different kinds of work. And yet, “I do it all by myself,” is the battle cry I hear from most singleton shops. Let that go—and find good partners. It’s the only way to fly in 2012 and beyond.

Thanks to: Hope Gibbs of Inkandescent Public Relations.

2. Not Every Hat Fits

Solopreneurs may find themselves trying to wear all of the company hats: marketing, accounting, web designer and service provider. But creatives aren’t always good at keeping books and financial advisors might not be very good at marketing. Hats can become a major challenge! Bartering or trades can work, especially for start-ups. Outsourcing should be considered later on. Just don’t let a “hat” hold you back…because it can…and will. Find a way to hand off that hat to someone who wears it well.

Thanks to: Shelley Ellis of Remarketing Weekly.

3. Talking to Yourself

When you work alone, day fades into night and before you know it; your work is your life. Without social interaction, you start to talk to yourself, to your computer, to the plants, and to the printer. It’s a hard habit to break. Even when surrounded by others, you sound like the Howard Cosell of daily living!Thanks to: Deborah Laurel of Laurel and Associates, Ltd.

4. Get Stuff Done!!

The biggest challenge or issue I see small business owners make is in the area of implementation and execution. There simply isn’t enough getting done and they are so easily distracted by the new, shiny object or idea that comes along. Time blocking is a great way to focus and almost force yourself to get more done. Block your time to do certain things & then do that one thing and nothing else during that time. No phone, email or other distractions will help you Get Stuff Done!

Thanks to: Diane Conklin of Complete Marketing Systems.

5. Think Like a Business

After years of freelancing, working in corporate jobs and starting businesses, I’ve learned the importance of thinking like a business and not as a freelancer or solopreneur. For example, you need to calculate all expenses, time and overhead, and then set prices and present them to the client. Don’t just take a job because someone offers to pay you something.

Thanks to: Kendra Bonnett of Women’s Memoirs.

6. Selling vs. Doing

Doing limits time for selling, and selling limits time for doing. Reaching the correct balance between the two is the solopreneur’s never ending challenge.

Thanks to: Leonard Scott of Leonard Scott & Company.

7. Doing Your Non-Favorite Task

As a solopreneur, the toughest challenge is doing those tasks that are your least favorite to do. For some, that is bookkeeping. For others (believe it or not), it is sales and marketing. Some jobs can be farmed out – lots of accountants out there. But for those who are truly “solo”, then it is simply buckle down and do it. There is a wonderful sense of accomplishment in completing an “unfavorite” task.

Thanks to: Heidi McCarthy of Toughest Customer.

8. Know Your Target Market

I see marketing and understanding one’s target market as being the biggest hurdle. If you know your market and customers and provide what they need AND want, the money will come. Many solopreneurs only see marketing as “advertising” and that’s inaccurate. Instead of spreading the word to everyone with mass advertising, focus on the customers you really want and give them lots of attention. Good products and offerings that provide value to customers trump mass advertising.

Thanks to: Chad Walters of Lean Blitz Consulting.

9. Technology!

Entrepreneurs need to know technology and they feel overwhelmed by it. I’ve witnessed the incredible transformations that only technology can trigger — wild product launches that uplevel your tax bracket, unstoppable buzz + media opportunities, and the rock-steady confidence that comes when you truly understand the how-tos and how-comes of building + marketing your business online.

Thanks to: Ali Rittenhouse of Ali Rittenhouse, International.