How do you know when it is time to take a risk?

The regular visitors to the site will have noticed a bit of a refresh on the design as well as an updated ‘About Dave’ section and the new ‘Work with Dave’ section.  This is not just a coincidence but part of a decision which I have taken to pursue a career ‘working for myself’ as an E-commerce Consultant.  I have been able to consult for a number of businesses on a part-time basis before whilst having a full-time job based in an office.  So this led me to think about, how do you know when it is time to take a risk? 

I wrote a post about risk about 18 months ago which you can see here.  At the time of writing that I had no idea that a year and a half later I would be self-employed having just taken the biggest risk of my life so far.

Background – The Feeling

It’s hard to explain it but when you experience it you will know instantly what I am talking about.  It’s a strange feeling of unfulfillment even if you’re doing everything right in your job. For me I have had this feeling for perhaps the past two years.  The problem was I didn’t know what to do about it.  I had the stereotypical 9-5 job, I was good at what I did and the team I was a part of had taken the e-commerce side of the business from strength to strength.  For me though the challenge had gone.

“Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do. If you haven’t found it yet, keep looking. Don’t settle.” – Steve Jobs, 2005, Stanford University

I then jumped ship to a new company who wanted a whole e-commerce set-up implementing and the director gave me quite a lot of free reign to go about this how I wanted.  For about 4 months ‘The Feeling’ had gone away.  I had implemented eSellerPro, Amazon, Play and set up a lot of automated processes to streamline the sales order process through to dispatch.  Guess what happened.  After all of this had been put in place, the feeling came back.  But this time it was easy for me to spot the problem.  What I loved doing was helping businesses grow online, and I knew I was good at it, but what I didn’t enjoy was the office environment, the stagnant 9-5 routine and the feeling that I had not that much in common with others in the office.  I had been called it before but this was when I realised deep down there was an Entrepreneur wanting to get out.  I had a lot of exciting ideas that I wanted to run with but didn’t have time.  I had the decision to make, did I turn my back on a good job with a guaranteed income stream to follow my dream or did I suck it up, push the thoughts to the back of my head and carry on existing in the office.

Crazy or Entrepreneur

For me it was a simple choice, I turned to those closest to me, told them what I wanted to do and because they were my family and friends they told me exactly what I wanted to hear.  “Follow your dreams”  “You can make it work” and other things to this effect.  I guess this is the beauty of asking those closest to you…they are the ones who will never hold you back.  Since then I have spoken to others and they have questioned my sanity turning my back on a good job in a recession to take a massive risk in working for myself.  I smiled to myself one particular time when someone said I was crazy.  One of my favourite quotes is one that is attributed to Steve Jobs and it goes like this:

“Here’s to the crazy ones. The rebels. The troublemakers. The ones who see things differently. While some may see them as the crazy ones, we see genius. Because the people who are crazy enough to think they can change the world, are the ones who do.” – Steve Jobs

Totally by accident I had been inspired even further that I had made the right choice.

So am I crazy or am I some form of entrepreneur?  To be honest I’m not sure, but I do know that I am crazy enough to believe I can change how things work and I know I have the ability to make things happen.  Last year a good friend of mine Matt Ogborne wrote the following article on “The Problem with being an Entrepreneur”.  The general message is that entrepreneurs see the world differently.  Largely people associate being an entrepreneur as a positive thing.  However as Matt points out there are a couple of downsides too.

An example of this is when I was just 16 in sixth form I had a weekend job at Sainsburys and with no offence meant to Sainsburys it was the worst job I have ever had.  I worked on the tills for 8 hours every Saturday.  This experience is the most mind numbing task I have ever come across.  Some colleagues tried to make games of it by seeing how fast they could put items through the scanner.  I on the other hand could see past their little games that this was it.  Nothing changed about the job, this was it, the beep….beep…beep endlessly for 8 hours every Saturday.  My only motivation at 16 was the money I got paid as it was my first job, but as soon as I could leave I was going to be out of that door.  I knew I wanted more from a job or career than that.

However there was one lady there who was in her 70’s, who had worked for that same Supermarket, on those same checkouts for more than 40 years.  She was a nice old lady who always had time to talk and was always smiling.  She was happy in her job, she enjoyed the security it gave her, that the bills would get paid every month and she would be able to live her life how she had become accustomed to it.  The job that she enjoyed and had been doing for 40 years (She had a gold watch to prove it) was my definition of a living hell.  Not everyone is ready or willing to take a risk which can totally change the direction they were heading in.  I believe those that do however, are the entrepreneurs.  They are willing to turn their back on the ‘easy’ route and turn their hand to create something that doesn’t exist or to make something that does exist better

So how do you know when it is time to take a risk?  I believe this is down to the person you are, your situation and your self belief.  Are you crazy enough to believe that you can change the world?  I have just seen someone define the term Entrepreneur on LinkedIn on a post by Richard Branson.  If this sounds like you and you’re not happy in what you do, then maybe it’s time to change.

Entrepreneur – “A person who is tired of following the status quo or some hired boss and wants to take the reins of his or her life by creating something that inspires them to show up and create everyday in the market and nurture their business to success their way”

Thanks for reading


2 replies
  1. Lace
    Lace says:

    Hi Dave,

    Enjoyed reading this, especially on a good morning! Many of our community members ask the same question and many of them have also taken the plunge and achieved the walk from their regular jobs.

    Surprisingly, one of the usual regrets they had is not leaving their job earlier 🙂


    • DaveF
      DaveF says:

      Hi Lace

      Thanks for leaving the comment. It’s true this is my first proper week outside of full time employment and I can believe the opportunities that have presented themselves now I am open to them. It is early days yet but this is something I have been toying with doing for a long time and fingers crossed I too will question why I didn’t do it sooner.

      Great work as always on the wholesale forums there is some fantastic info and opinions on there.

      Thanks for the comment



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