The 5 Challenges of the Intermediate Entrepreneur

Wendy Piersall / Entrepreneur.com

I’d consider myself an intermediate entrepreneur. I have nearly eight years of self-employment under my belt. I know the pitfalls of entrepreneurship well enough to avoid them (relatively speaking), and I now am able to offer a considerable amout of help and guidance to newer business owners. I don’t have a million-dollar company or any full time employees, and I haven’t been on the cover of Entrepreneur magazine–yet.

I’d also have to say that in the past two years, I’ve had to overcome some of the biggest challenges of entrepreneurship. I made some whopping mistakes in my first years, but the challenges of the intermediate entrepreneur are a little different. I think the challenges we face are both harder to recognize and can be more difficult to overcome–mostly because we’ve been doing business for a while, and teaching an older dog newer tricks isn’t exactly a cakewalk.

The five following unofficial challenges are ones I have either had to face myself or see my peers struggling with on a regular basis. I’d love to hear what you would to add to the list.

I Bought Myself a Job

After about four years of being a solopreneur, I wanted to increase my income. But the way my business was set up, the only way to make more money was to put in more hours. I didn’t want more hours… and thus, I began the process of moving my business from a one-woman show to a semi-outsourced model. I had to go through the whole process all over again in my third business and, strangely, the second time was harder than the first.

Part of the differences can simply be attributed to the difference in business models. But I can also say that when I did it the first time, I knew I could always go back to my old way of doing everything myself if I had to. This time around, it was a much more permanent shift, and it was scary. It was a big risk; I was worried about quality control and ballooning project management. And if it didn’t work, I knew my business wouldn’t make it.

Thankfully, it was one of the best decisions I have ever made. I also didn’t sleep for about a month as I went through the toughest part of the transition. Billing out your hours is a great way to run a small business. But in the end, people and time have a finite amout of scalability. If you want your business (and income) to scale beyond what you are physically capable of, you need to stop being an employee and start being a manager.

Losing the Big Picture

When we first start a business, it is so incredibly easy to see the big picture–sometimes to a fault, as we can tend to gloss over the details. But after years of running the show, managing those details becomes our everyday life. And it becomes harder and harder to think outside of the box if your nose is constantly to the grindstone.

I know this happens if I have spent three to five months or so just focusing on to-do lists. Although there is a time and place to be focusing on the details of running a business, entrepreneurs are born and bred to be big thinkers. It’s not in our nature to be the detail person.

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