The top 5 reasons why you should be a "Jill of all Trades"

Photo by Aidan Finlayson      

Photo by Aidan Finlayson



Like most teenagers, when I was in high school I was deeply confused by the notion of choosing a single career path to follow. My passion resided in the arts, and my efforts revolved around my school schedule - filled with Music, Drama, Visual Art, Photography and Com-Tech. Though my happiness was fuelled by expressive artistic creation, I still felt somewhat guilty that I wasn't enrolled in what seemed like "smart" courses. I was experiencing a degree of disillusioned societal pressure, and thought that in order to "succeed" I would need to abandon the majority of my interests, and pursue the perfection of just one.

It was my rebellious nature that ultimately rejected these fear based thought patterns, and I still remember the joyful day when I rushed home and pronounced, "Mom, I am going to school for music - I want to be a beautiful person!" 

Photo by Jill Stella       

Photo by Jill Stella



After graduating from music school, (the hardest and most gratifying accomplishment of my life) I can now say that I intentionally revert back to nurturing all of my high school rooted interests. I am committed to being an active student and adventurer in this scientific, artistic and expressive playground we call life. 

After recently discovering the podcasts and writings of world renowned author, athlete and educator Tim Ferriss, my path to entrepreneurialism feels immeasurably empowered.

Below is a summary of the key points from Tim's "Top 5 Reasons to be a Jack of all Trades" podcast. I wanted to share this with you, as it spoke deeply to where I am at and where I want to go.


1. The statement "jack of all trades, master of none" is an artificial pairing.

  • In Tim's podcast he claims that being a jack of all (or many) trades, or what he calls "generalist," is making a come back.

  • He argues that specialists tend to over estimate the amount of time it takes to master a skill, and often confuse "mastering" a skill set with "perfecting." 

  • Generalists seem to recognize the 80/20 principle when it comes to learning a skill. 

  • Tim exemplifies that when learning a language, 20% of the languages vocabulary will enable you to communicate and comprehend at least 80% of the time, and 20% of the moves in a sport account for 80% of the scoring.


2. In a world of dogmatic specialists, the generalist often ends up running the show.

  • Tim states that it is often (not always) that the big picture generalists predict, innovate and rise to power the fastest.
  • At the highest levels in a business, one needs certain "soft skills" or "connective tissue" to be able to communicate and be a proper leader.

  • It is the CEO's like Steve Jobs - who have a broad range of skills, that see the interconnectivity of everything.


3. Boredom is failure. 

  • Happiness is the opposite of boredom.

  • Tim argues that depression and "emotional bankruptcy" is the direct result of a lack of stimulation.

  • When one has their emotional identity invested in one skill set, they are likely to fall into depressive states of the mind, where as the generalist seems to have more stimulating pursuits to fall back on.


4. Diversity of intellectual playgrounds breeds confidence, not fear.

  • Tim argues that diversity in intellectual playgrounds breeds empathy with the broadest range of human condition, and appreciation with the broadest range of human accomplishments.

  • "Defensive smugness" is often related to those who pursue incremental gain out of obligation instead of enjoyment.


5. It's more fun!

  • Lastly Tim states that the Jack of all (or many) trades maximizes his or her number of peak experiences in life.

  • He or she learns "the pursuit of excellence" unrelated to material gain, all while finding the things that he or she is uniquely suited to dominate.

  • The curious generalist often consistently measures improvements in quantum leaps, rather than seemingly stagnant incremental steps.


a handful of hobbies, Countless career choices, and a palette of passions. Invest in every one of them, and in their own time. Celebrate your unsubscription to the seemingly set architecture of society. Live an unconventional life.
- Jill STella


Thank you for reading this blog post and I leave you with this message from Walk off the Earth.