Freestyling through life

Today I put on Ol Dirty Bastard’s Return to the 36 Chambers: the dirty version. Ol Dirty Bastard is my favourite rapper of all time. Not because of his rhyme skill but because he was always unapologetically himself (we now have Kanye and Joe Budden but they apologise or try to explain any statement that falls wrong). I put on the album so I can fall back into nostalgia and learn from the mindset the teenage me, had in 1995. I was freestyling through life!

Quick definition of what freestyle rapping in HipHop was circa 1995.

Freestyle rapping is reciting (spitting) lyrics in a group (ciphers) or alone that you make up on the spot.

(For a whole rundown on how the definition changed over the years check the following Wikipedia link

Freestyle in this form is full of successes and failures. Your improvisation skills had to be impeccable if you could pull off a freestyle without error. That said most also threw in rhymes that were pre-written. 15 year old me was fine with any successes and also any failures life brought with it at that time. Somewhere along the path of becoming an adult I (like many of us) started to do everything in my power to avoid failures. Everything had to be perfect. The results I delivered to management, the CV used for job applications, Linkedin profile, public image and being the perfect partner and example to my children. Not only did I expect perfection from myself but I started expecting it from those around me.


This mindset caused failures to be interpreted as a burden instead of a lesson. It also delayed any words from being said until what would be conveyed is “perfect”. Delayed any decision from being made until everything was “perfect”.  And then during a mentally taxing time, listening to Ol Dirty Bastard’s Return to the 36 Chamber I decided to be more like the teenage me! I started freestyle rapping to the beats. With my mind tuned to “perfection” and not having done it in years I can tell you it was not a very successful freestyle. But instead of focussing on what went wrong my thoughts automatically focussed on which rhymes were good and the tweaks needed to improve the others. I  started to celebrate my successes and learn from my failures.


Fast forward some years and here I sit “freestyling” my website in order to get this blog up.  I now use the Freestyle rap as one of my tools to help others create and celebrate successes but also to accept and tweak their failures!

Contact me and learn how HipHop can inspire and motivate you and/or your organisation!