What’s Better in Today’s Workforce: a Jack of All Trades or an Expert?

Published in
8 min readApr 23, 2024


Blame Shakespeare, the original jack of all trades

Photo courtesy of cottonbro studio

First things first. The idiom “jack of all trades, master of none” is incomplete. The full phrase is:

“a jack of all trades is a master of none, but oftentimes better than a master of one.”

Heather Wolfe, the curator of manuscripts at Folger Shakespeare Library, says the name-calling originated in the Elizabethan era, first appearing in the book Greenes, groats-worth of witte, printed in 1592. The author indirectly called Shakespeare an “Iohannes fac totum,” which means a “Johnny-do-all,” the basis of the phrase “Jack of all trades.”

And in her Forbes article, Jodie Cook says that while the truncated idiom is a bit of an insult, it didn’t start out that way.

“The phrase was originally used to describe a playwright who was always hanging around the theatres,” Cook writes. “He would help with the stage, the set, and the costumes. He would remember lines and try directing. This so-called jack of all trades was in fact William Shakespeare. The full phrase is ‘a jack of all trades is a master of none, but oftentimes better than a master of one.’ It was a compliment.”

Fast forward to today’s workplace: Is it better to be a jack of all trades (a generalist) or an expert?

Read more: Choosing Your Career Path: How to Plan & Pivot Your Way to a Dream Career

Jack of all trades: The pros and cons of being a generalist

Having the multiple skills of a jack of all trades allows you to pivot, whether due to your own interests or from necessity, says clinically licensed social worker Dr. Donna Oriowo. “Pivot became a buzzword in 2020 for many people,” she writes. “In the realm of business those who were able to pivot were able to sustain. Many small businesses had to close because they were unable to make those shifts and changes.”

Being a generalist makes you a quick study too, because you’re constantly learning.

Software engineer and accountant Andrew Pratt compares this state of constant upskilling to machine learning. “Just as machine learning is attempting to replicate, the more we learn new skills and concepts, the more that we make connections across concepts,” he writes. “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.”

Digital creator Issa Jean Marie pulls no punches when it comes to the drawbacks of being a generalist, listing lower salaries, the necessity of continuous learning, slow career growth, and high competition. However, he does recognize the benefits, and one of these is that generalists can become specialists relatively easily. Jacks of all trades have experience in many different fields and “because they already have the foundation, it’s not a hustle for them to master it.”

Read more: How to Make the Business Case for the Work You Do

The pros and cons of being an expert

Being an expert or specialist in your field can make you in-demand and be financially rewarding. According to the team at education platform Emeritus, this is because “subject-specific expertise gaps” are difficult for employers to fill.

An additional benefit, especially as jobs are impacted by artificial intelligence and machine learning, is that “specialists are more equipped to handle any new technological complexity in the field as they dedicate years exploring different facets of the domain.”

Read more: Disappointed at Work? That Might Be a Good Thing

However, while specialists may have a higher mastery of a topic, they also have a higher degree of career inflexibility, says Montse Lorente, a facilitator, coach, and career advisor at coaching services provider Kaelon. Another issue they face is “the possibility of becoming obsolete as technology changes.”

Lawyers, for example, are specialists facing replacement and redundancy by AI. Contractbook cofounder and CEO Niels Martin Brochner says lawyers’ work will change, at the very least, and even disappear. “There will most likely be less administrative work and we will probably need fewer clerks,” he writes. “Lawyers will have to write less, read less, search less and, frankly, also think less. They will become hyper-augmented, which might turn them into overqualified project managers.”

Read more: What Are Career Clusters? A Complete Guide

Is it better to be a jack of all trades in the workplace or an expert?

It depends. It depends on you and your career goals, the industry you’re in, and the nature of that particular field.

“Entrepreneurship and freelancing are examples of fields where having a broad range of skills can be beneficial,” writes Will Owens, an inventor and innovator. “In these fields, being able to pivot and adapt to new situations is key to success. On the other hand, there are fields like medicine or engineering where specialized knowledge is essential. In such fields, being a master of one is necessary for success.”

Even though specialists have more predictable career expectations, sales coach and trainer Justine Beauregard, who is also a business builder, full stack marketer, and entrepreneur, thinks “being a generalist is wonderful.” She says it’s widened her perspective and made her an exceptional problem-solver and critical thinker.

Beauregard explains that jacks of all trades don’t learn by starting out great-they learn through failure. “When you’re a generalist, you have a greater risk tolerance,” she writes. “You open yourself up to more opportunity, which opens you up to more risk of failure. This may not always feel the best, but it’s invaluable.”

How to position yourself when applying for jobs or promotions

Whether you’re a jack of all trades generalist or a laser-focused expert, there are steps you can take to better position yourself when applying for jobs or promotions.

Montse Lorente tells InHerSight that “careers need to be understood as dynamic and malleable, which conception involves a lot of career re-design and transitions.” She gives the example of a teacher who wants to move into the role of an HR specialist or event planner. It’s important that the teacher makes their transversal skills known in their application for the new position.

Read more: Feeling Stuck in a New Job You Hate? Here’s What to Do

“Typically, teachers possess soft skills such as effective communication, adept time management, organizational prowess, cultural sensitivity, among others,” Lorente says. “These soft skills are readily transferable and highly valued in an HR specialist role. Thus, recognizing this and ensuring these skills are highlighted in the updated application materials is paramount.”

“The next step would be to target industries related to education technology (edtech), where a background in teaching or education holds significant value. Consequently, a teacher may prove more relevant to an HR specialist role within an edtech company compared to a candidate lacking experience in the field.”

Read more: How to Create Your Professional Brand (& Love It)

The key factors for success in rapidly-changing environments, Lorente says, are:

Creating a winning narrative

Using the profile narrative underscores your adaptability, versatility, and a proactive approach to career development. It not only increases the likelihood of success in securing new opportunities but also fosters a deeper connection between you and your professional aspirations.

While creating your new narrative, it’s important to ask yourself what are the skills that would help you the most, what are the values you share with the new company (or department), and how much you align with their mission. By doing that, you can reframe your story in a way that puts you in a position for success.

Allying with AI

Instead of being afraid that artificial intelligence will make you redundant, use technology to make your work better. Identify what new technologies are being used in your industry and field of work, get trained on them, or get closer to them as much as possible so you can incorporate it in your practice. Being able to use the technology will keep you as a relevant professional.

Allying with artificial intelligence is a powerful strategy in that it expands your horizons and adopts a generalist mindset, ready for continuous learning and training.

The perception of jacks of all trades is changing

Sarah Gilchriest, chief people officer at Workforce Learning, writes that “specialist skills are still important, but as AI and automation transform workplaces, employers will require more generalists.”

“…[W]here the workplace was once built around specialisation, with employees being hired and promoted based on their level of expertise, the issues facing businesses are now much broader,” Gilchriest writes. “This means that the value of a generalist’s abilities has been elevated.

She adds that a “coefficient between specialists and generalists is fast becoming the most effective approach, with each benefiting from the other.”

Journalist David Epstein, author of RANGE: Why Generalists Triumph in a Specialized World, admits that “for a lot of the 20th century, the biggest contributions came from specialists.”

“But,” he goes on to say, “in the information age, as more information became quickly and easily disseminated, it became easier to be broader than a specialist and the biggest contributions started coming from people who spread their work across a large number of technological domains, often taking something from one and bringing it to another area where it was seen as extraordinary, even if it was more ordinary somewhere else.”

Another point Epstein argues is that “slower development…often results in more success in the long run. That’s because “human development doesn’t always follow linear progressions, making it critical to have a broad training base and conceptual framework.”

If you’re a generalist struggling to get ahead in your career, the bottom line is to change the perception you have of your skills and the value of those skills. Instead of a jack of all trades and master of none, define yourself as jack of all trades and master of most.

Pie in the sky stuff? Not at all. Sonya Bessalel, content marketer and integrated marketer on LinkedIn Learning’s B2B Thought Leadership Team, lists the most in-demand skills for 2024 as:

“The rapid rise of artificial intelligence stands to make your core skills more valuable, not less,” Bessalel writes. “Today, business leaders are looking for uniquely human skills to both work with AI-and drive organizational success.”

About the author

Stephanie Olsen is a freelance writer and copy editor. She writes about everything from women’s issues in the workplace and Ethiopian coffee culture to facilities management and expatriate life. Laughs uproariously at her own jokes.

About the source

Montse Lorente is a Certified Executive Coach, Facilitator and Career Strategist at Kaelon. She’s also part of the CVonline.me team, an online CV builder that generates unique CVs and variations tailored to specific job applications.

Lorente has an academic background in business and applied philosophy plus nearly a decade of international experience in career advisory, HR consulting, facilitation and recruitment, accompanying thousands of bold entrepreneurs and forward-thinking professionals in the design of their careers. Her coaching practice is action-oriented, combining creative methods and rational tools to catalyze the results of the process. In partnership with leading educational institutions, Lorente has designed, developed and facilitated online and in-person programs aimed at the employability and personal development of students and professionals from Europe and Latin America.

Originally published at https://www.inhersight.com.




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