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!

6 Replies to “Freestyling through life”

  1. Freestyling has helped me so much in my life and the concept applies well beyond rhyming and can be applied to pretty much everything that people do. Words and being cognitive jsut appealed to me most personally. It’s shown me what I think and who I am without the filter of my conscious mind. Being forced (by the beat or any other time pressure for that matter) to put your mind out there without having the time to reconsider is a powerful exercise in letting go and being unapologetically yourself (although I’ve heard plenty of rappers who use lots of their freestyle bars apologizing for what they’ve just said, in awe about what just came out of them – what an amazing opening into therapeutic or coaching conversations – Freud would stand in awe (see below))

    However, I’m not a big fan of the idea of “success” when it comes to freestyling. Success is when stuff comes out of your mouth and flows (however you define flowing). If it feels good for you, it’s a success. If it’s well received by others, even better, but that’s not the goal post. or is it? Depends how the rapper gains a sense of self-worth. Worth a (separate) discussion. Reflecting on what you’re feeling when you’re freestyling (rapping or otherwise – this is important to make the link if you’re writing for non-rapping audiences) is such a valuable opportunity to learn. What are my views of success, how did I feel. Freud’s technique of “free association” as a tool to access the unconscious comes to mind. Worth a reference?
    Similar to success, I don’t see any failure in freestyling. You either show up and offer a piece of yourself, or you don’t. The only failure is choking. Everybody else represents at whatever level of skill and practice they’re at at this time of their lives. I hate it when experienced rappers mock newbies for their lack of skill. I’ve never seen that happen among bboys (just as HipHop). Everybody who steps into the cypher and does a move gets respect. Every dancer seems to remember well how it was when they started out (and yes, I’m sure there’re plenty of exceptions to this). Every writer was a toy at some point. Practice makes masters. Freestyling is the beginning of everything and the essence of authenticity. And definitely a powerful tool to learn about yourself if used right and given the appropriate space to reflect on the experience afterward.

    Keep up the good work! 🙂

    1. You’re welcome to post your question. Would love to hear your feedback

  2. Do you have any pointers for writing posts?
    That’s where I constantly battle and I simply wind up looking empty display
    for lengthy time.

    1. Hey Catharine,
      My pointer is to write piece by piece and later make 1 whole article of it. When seeing the different pieces you will put it together like a puzzle.
      Good luck and would love to read your posts when they are up.

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