The Lack Of Collaboration, The Entrepreneurs Dilemma

Darren Matthews
4 min readJun 7, 2018


It was one of those knockout questions that you get in an interview that needed a quality answer. The question was;

“What had I learnt most about myself whilst being self-employed and why?”

It was a great, insightful question, and it forced me to pause and reflect on the six months I had spent setting up and running my own business.

What observations had come to light, and of those what could I offer as an answer that wouldn’t ruin my chances of getting the job.


I had decided to set up my business as I had identified there was a gap in the market for the service I was proposing to offer. I was happy and confident that I could make the business a success, but the role challenged me in ways I hadn’t expected.

I knew that I had the grit and focus to be self-starter. I was organised and able to create and stick to a plan.

I was a small business owner, an entrepreneur!

“A person checking stock market prices on their iPhone” by William Iven on Unsplash

It was slightly misleading statement really. I was self-employed, so everything was down to one person, me.
Don’t get me wrong, I enjoyed working for myself, I am an introvert and I value the time when I am able to work independently of others. Time to pause and think things through without interruption really invigorates me.

There is a drawback to this though, and I now believe it’s the biggest hurdle any self-employed person must overcome.

It’s not being able to collaborate.


Collaboration to me means working with others, sharing and analysing ideas. Talking through experiences and learning from those that you are collaborating with. It enables small businesses to grow into larger businesses.

If you have read Homo Sapiens then you will know that one of the critical success factors of our species over others on the planet is that we can collaborate.



Darren Matthews

I’m utterly curious about decision-making | Sharing lessons learned from the thousands of decisions I’ve studied and made | Founder