The Pros and Cons of Being a Jack of All Trades

Andrew Pratt
4 min readMay 21, 2020

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We have all heard the term “Jack of all trades, and master of none.” While some consider being a Jack of All Trades the highest of compliments, many intend it as an insult. On one hand, being multi-faceted and versatile is useful. On the other hand, many specialists would argue that narrowing focus to one skill is better.

What is a Jack of All Trades?

A Jack of All Trades refers to a person with a wide-ranging skillset. Whereas specialists focus on being great with a particular set of tools, Jacks see every new experience as adding a new tool to an ever-growing toolbelt. Despite never developing any skill to mastery level, their proficiency across disciplines gives them the potential to be great problem solvers, critical thinkers, and leaders. Learning and trying new things make Jacks useful in a handful of situations and are great people to know when something goes wrong.

For all their good qualities, Jacks tend to have trouble following through on new career paths, especially in industries that value high technical knowledge and specialized skills. Jacks are more focused on being able to do a job that they can lose focus on being able to do it well. If Jacks are aware of both their strengths and weaknesses, though, they can be some of the most influential people on the planet.

The Upside

Quick Learners

Becoming a Jack of All Trades requires learning all sorts of new skills. Being able to bounce from job to job requires being a quick learner who can make connections fast. Just as machine learning is attempting to replicate, the more we learn new skills and concepts, the more that we make connections across concepts. Essentially, as we continue learning, we add to our existing framework for “how to learn” and become better primed to continue making more connections. For these reasons, Jacks are great on the job learners and candidates for cross-promotions.

Leadership

Leaders must understand the people and organizations they are leading. The best way to understand an organization and its people is to have experienced first-hand what they do. Working jobs in different companies, departments, or industries give a competitive edge when looking at how a company should be run. Making decisions across an entire organization takes the type of big-picture understanding that Jacks naturally accumulate throughout their lives.

Adaptability

Having a varied skillset means marketability. When layoffs or automation lay off specialized workers, finding a new job can be quite difficult. A multi-faceted Jack may lose a desk job and hop into the manual labor market. As long as a person can demonstrate competency or experience in a field and there are jobs available, unemployment is not a fear. Even within a company, being flexible enough to cover for an employee in another department or take work off a manager’s hands can provide leverage and job security in many cases.

Relatability

The narrow focus that specialists must have to reach mastery can also make them a bore in conversation. Being more of a generalist, Jacks are relatable to people of all different backgrounds. Bouncing between jobs and hobbies give them a chameleon-like quality to blend in with anyone. Of course, with all their experiences, they probably have plenty of good stories to keep the party rolling.

The Downside

Technical Knowledge

Most career paths are designed to support a highly specialized division of labor. With more specialization comes more technical jargon, more necessary education and experience, and more barriers for entry. Getting into many industries is not possible just because someone is a quick learner. This lack of specialization is the opportunity cost of trying new things.

Specialized Job Functions

In a world inspired by the assembly line, the fact that an employee can provide a wider variety of functions is not always relevant. Managers are inclined to value employees who do one function very well rather than many functions well. Jacks may need to place added focus on learning technical skills to stand out and succeed within certain jobs to avoid replacement.

Compensation & Promotions

Switching fields and trying new jobs means trading off the steady climb up the corporate ladder and the pay increases that come along with it. Being entry-level in a new job might be new and exciting but the pay and benefits are not.

Losing Interest

People who are always looking for new things often do so from a struggle to stay engaged. Jacks need new stimulation and are prone to losing what they have in search of something new. Erratic or inconsistent behavior can be alarming for companies hiring or loved ones who fear losing someone close to them. Jacks must understand how others may interpret their behavior to put things into context.

Exhaustion

Trying to do too much and be part of too many things can cause stress and burnout. It is great to want to be all that you can be, but health must be the number one priority if you want a long life full of new experiences.

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Andrew Pratt

I am an accountant turning Software Engineer. I am passionate about learning, meeting new people, and creating things.