The 5 Challenges of the Intermediate Entrepreneur

The 5 Challenges of the Intermediate Entrepreneur

Wendy Piersall /

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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