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  • Writer's pictureWill O'Brien

A journey into self employment

Updated: Jun 3, 2020

I wrote this short article pre the pandemic and it might give some insight for those considering self-employment or those sales executives in furlough positions….

A journey into self-employment

So after 1 ½ years of being self-employed, I think more clearly now than I have ever done in my 33 years in the Technology sector. Following 68 quarters in the hot seat as a sales VP I have the time and space to look back and remember the people, the places, and the situations that I encountered. At the time it was a blur but hindsight gives you the perspective to reflect and question would you done things differently?

My simple answer is “no”. Despite relentless pressure to over perform I would never have done the job any differently. I always felt it’s important to never fundamentally change the way you deal with people, be they customers or the teams you worked with. I always believed you should be able to look in the mirror after the working week and never feel you compromised yourself, your company, or the people you rely on. I maintain these values into my role as the founder of Day Five Consulting.

A great sales leader at SAP once said to me you may as well be honest even if you are delivering bad news. He said if you are going to get a “kicking” for dropping your forecast, or making a mistake, you may as well take the pain early and not put it off. I have always believed in being frank, upfront and realistic so that people can rely on you. Accuracy in a forecast, or the expectations you set with customers, or internal team members is critical in such a rapidly changing industry.

Another great sales leader told me to lean into the quarter and be ambitious and this is great advice. In sales you should feel accountable and you should lean forward and set your bar at a high level. Coasting along in sales is not what the job is about. Coasting along was never was never an option for me and I always strove to over achieve and encourage my teams to do the same. Today more than ever you need to adapt and execute quickly in the new world we face.

Over the years I have seen a few over zealous examples of aiming high where a sales leader places a totally unrealistic burden on the teams below. Excess pressure to meet some ridiculous “commit” is a recipe for poor morale especially when there is no let up in each passing quarter. Pressure needs to be applied at key times or it just delivers the law of diminishing returns and breeds mistrust.

I now run my own business and face my own quarterly pressures where I set the bar for what I want to achieve. In 18 short months I have re developed all my content comprising 250 days of effort, released a 4th website, launched on LinkedIn, and connected back with numerous people I once worked with. I have also had the free time to think, write, and create some content that is hopefully interesting for the Tech industry I now serve.

At this juncture Chris James, my new business partner will be joining my journey. Chris is one of the most talented execs in the B2B tech sector and I delighted to have him on board. I have always felt two minds are better than one and we look forward to continuing to develop great training material that works in the real world.

Over the coming 100 days Chris will be highlighting over 100 key points on the attributes of great sales professionals. Over the next 100 days we will be also adjusting our training offer so we can deliver this as an online offer.

Our approach, offer, references and training journey can be found at

Authentic - Training - Delivered

Enjoy and stay safe


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