Stephen Baines
5 min readMay 19, 2016

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Jack of All Trades, Master of None: An Optimal Career Pathway?

No one career path is ever directly the same. Situation impacts on us all differently. Therefore, mirroring your currently CEO’s career path will almost certainly offer vastly different outcomes:

  • Did you work as hard?
  • Were you presented with the same opportunities?
  • Did you have the same level of knowledge, insight and experience?
  • Were you in the same personal situation?

These questions are important if you look up your leaders today as a source of a guide for your own career path. Fundamentally, you need to forge your own path. Not follow one already cut-out for you.

What Options are Available to Me?

Well, the new good news is, endless opportunities! It is all about grasping the opportunity for you. It does not even have to be the right opportunity at the time. Afterall, how many of the World’s current leaders do you think knew they would where they are today? Quite possible very few of them.

It introduces the questions which leaders are so often asked… Should I Specialise?

The questions bring about two distinct pathways in itself:

  • Generalist (‘Jack of All Trades, Master of None’)
  • Industry or Capability Specialist

What is the Difference Between a Generalist and a Specialist?

A Specialist has a deep, often unmatched insight, knowledge and experience into one narrow, but deep industry or capability. The focus may be a niche such as ‘Lean Manufacturing Capabilities, in the Aerospace Industry with a specific focus on Turbine Production’. Others may be as simple as ‘Fruit & Veg Procurement in the Retail Industry’.

A Generalist has a broad, often shallow insight across a diverse range of Capabilities, Industries or Sectors. Often Specialisms too. The focus may be a capability such as ‘Business Model Design in the Technology Sector’. Others with a degree of specialism may include ‘Technology Investor focusing on FinTech Start-Ups’.

Is it better for me to become a Specialist?

There are arguments for and against specialising and generalising:

A Specialist for a specific topic will be needed so long as there is a demand for their services. In contrast, when the banking industry collapsed in 2008, many banking Specialists were out of work. The Specialist can comfortably dive to the very bottom of the Ocean but may struggle to tread water in the roughest of seas.

A Generalist will always be able to draw upon broad experiences as and when the demand exists. In contrast, the specialist will often need to call upon the Specialist when the waters become too deep. The Generalist can comfortably tread water in the roughest of seas but has limited capability to dive to the bottom of the Ocean.

The simple answer is… a ‘Jack of All Trades, Master of Many’, or a ‘Generalist Specialist’.

How do I become a Generalist Specialist?

There are a number of steps to becoming a specialist in a subject

1. Understand the Mechanics of Specialising

The focus of developing a specialism is about understanding the mechanics of how skills are development. Generalists recognise that the 80/20 principle applies to skill development:

  • In learning a language, 20% of the vocabulary will enable you to communicate and understand 80% of the language
  • In learning a new sport, 20% of the moves will account for 80% of the scoring

The key is in recognising this. Then applying the skills/knowledge gain practices effectively. Not going out to learn everything about everything. Picking your subject matters and focusing on the key aspects which will teach you the most about them. Suggestions indicate you can become ‘World-Class’ within one year.

2. Recognise the Benefits and Pitfalls of a Generalist

Ask yourself a question. Was Steve Jobs a better programmer than the top coders at Apple? Is Elon Musk the best Aerospace Engineer at Space-X? No! But they have a broad range of skills which go far beyond any specialism. They are able to bring specialists together, motivate them and get results. They are able to lead them. It is the big-picture generalist who will predict, innovate, and rise to power fastest, as Tim Ferriss notes. Recognise that as a Generalist, you will NOT get far on your own whilst as a Specialist, without a Generalist you may become lost in direction.

A generalist therefore needs the leadership and man management capabilities that specialists often do not need. Turn on your EQ. Focus on your visionary skills. Look at it from 10,000 feet. Become that Jeff Bezos, Steve Jobs, Larry Page.

3. Work to Resolve Boredom

Boredom may arise through a confinement towards a single specialism, explored to the lowest depths with limited broadness to thinking. What happens if a new technology makes your specialism obsolete? Think of Kodak and Dark Room specialists. How many of these specialists were thinking about the Digital era? They were likely treating their specialism as a means to an end. Something that would bore a generalist to death.

The key is to think outside the box. In a specialism, how can you introduce other generalisms to broaden your horizons. Maybe you could form the next Kodak moment! In contrast, as a generalist, becoming bored presents new options: learn a new skill; apply your expertise elsewhere; switch industries/capabilities.

4. Realise that Diversity of Intellect Breeds Confidence

Holding a diverse knowledge offers an opportunity to deeply empathise across a range of situations. Empathy breeds confidence. Both from a personal perspective and the belief of others. In contrast, the alternative is a defensive xenophobia and smugness which may arise from a deep-lying but narrowly diverse specialism. Think of those hiding behind their job title with no real substance to what they contribute other than a perceived negativity. You know those people… those who blatantly hate their job but have a big paycheck.

The breeding of confidence is something to really learn to develop. There is no magic switch for either a specialist or generalist. It is all about believing more in yourself and the value you add.

5. Have LOTS of Fun!

The Generalist maximises their peak experiences in life. Generalists tend to learn to enjoy the pursuit of excellence unrelated to material gain, all while finding the few things to truly dominate. The Specialist often pursues an impossible perfection. A sometimes one-dimensionality. A focus on incremental rather than radical improvements.

Have some fun in what you do. Make it a passion. It is difficult not to when you experience something different almost every day of your life. Attaching a profound mission will make all the difference

Reference: http://fourhourworkweek.com/2007/09/14/the-top-5-reasons-to-be-a-jack-of-all-trades/

About Stephen

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#Mentoring #Personal Development

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Stephen Baines

Founder at Stephen Baines Coaching & Mindfulness Evangelist at Salesforce.