The Lack Of Collaboration, The Entrepreneurs Dilemma

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!

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“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.

When you are isolated you are at risk of being incorrectly influenced by confirmation bias.

Collaboration offers the opportunity to discuss, assess, review and put heads together to open new ideas. What collaboration brings is a collective stop, it’s like second order thinking in a sense that a discussion offers the opportunity to consider potential outcomes.

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Photo by rawpixel on Unsplash

During that period, I had frequently questioned what I was doing (as you should), was it working, what could I change to make it better?

I assumed that as customers weren’t kicking my door down that something wasn’t right with the website. So, I would look at other websites, compare and make changes. Looking back that had happened several times.

The Interview Answer

I had learnt that although I was an introvert, I was more effective in an environment where I could collaborate with others. That would help improve my decision making and subsequently the outcomes of the tasks I was faced with. Collaboration was something that I would have as part of my employed role.

The lesson for any want to be entrepreneur

What I don’t have an answer for is exactly is how you overcome this when you are self-employed.
Certainly, having a mentor can help, depending on the access you have to the mentor. Given the self-doubt I have suffered with having potential access daily would have been required!

All jokes aside though, a mentor needs to be with you from the start of your journey as a small business owner.

If you don’t have a mentor, what other options are there?

Yes, you can discuss your business with family members etc, but they maybe don’t have the experience that a mentor has or the position to question you. If you are part of local networking group you could try them, but I think the challenge is that you will have to admit to your perceived weaknesses and that isn’t something most people want to do a group environment.

As you can see I don’t have the answer, if you do, please feel free to comment.

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I’m curious about decisions, strategy, and how to live my best life. Follow me as I write to figure it out and share some wisdom along the way.

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