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Reskilling? Here’s how to manage choice paralysis

By Saga Briggs

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Reaching the decision to reskill or upskill is one thing; taking the necessary steps to do it is quite another. In an age where the question is no longer “What do you want to become?” but “What do you want to learn?”, we have even more options to choose from and even more potential for choice paralysis. Do we learn software development? UX design? Digital marketing? Should there be coherence to our skillsets and experience, or should we be well-rounded and widely familiarised?
Benefits of upskilling and reskilling include future-proofing your career, positioning yourself for promotion and raises, staying abreast of industry trends, and gaining the knowledge and experience to fall back on consulting or freelancing should you ever need to.

Companies like Amazon, Walmart, PwC, and JPMorgan Chase have upskilling programs underway, and Quartz estimates that most Fortune 500 companies will have launched a program in the next year.But when it comes to taking charge of your own professional future, and deciding whether to reskill in areas that may be brand new to you, it’s important to know what will and will not be worth your time, effort, and money in the end.

PwC conducted the largest global survey of workers on digital skills, inclusivity, and job flexibility. It revealed that by learning new digital skills and quickly adapting to remote work, most believe that they can meet the challenges of automation. Despite this, approximately only 4 out of 10 workers think that their job is at risk or that their job will be obsolete within the next five years. Acquiring new skills (read our blog on why you should invest in upskilling) that enable workers to think and work in different ways is necessary as companies accelerate their plans and jobs continue to be remote. Where opportunity exists, almost 8 out of 10 workers are ready to learn new skills or completely retrain to a new industry or role according to the same survey. Further stating that “younger people are twice as likely as older people to get opportunities to improve skills, and people in cities are 1.5 times as likely as people in towns.”. This, in turn, generates demand and puts pressure on companies to create more inclusive, flexible, and relevant opportunities to upskill. 

The U.S. is also seeing demand for Behavioural Health Technicians, Sales Development Representatives, Robotics Engineers, Chief Revenue Officers, Cloud Engineers, and Javascript Developers.

In Europe, employers are hiring Data Protection Officers, Human Resources Partners, Commercial Real Estate Agents, Community Relations Managers, Big Data Developers, Building Information Modeling (BIM) Specialists, Enterprise Account Executive, and Content Designers.

In Asia, add to that DevOps Engineers, Partnership Specialists, Clinical Specialists, E-commerce Specialists, Creative Copywriters, Robotic Process Automation Consultants, Growth Managers, Digital Marketing Specialists, and Lead Generation Specialists.

When taken together, the top skills needed for these jobs are as follows:
Python, CRM, Salesforce, SaaS, Amazon Web Services, Apache Spark, Data Science, Machine Learning, Account Management, JavaScript, Information Technology & Services, and Marketing & Advertising.

With these in mind, it appears well-worth your time to 1) learn programming, 2) become a machine learning expert or data scientist, 3) specialise in service-based IT, and/or 4) study account management or sales.

You’ll notice that half of those skills are service-based or human-centred. And, in fact, the report notes that demand for soft skills will increase as automation becomes more widespread:
“Skills like communication, creativity, and collaboration are all virtually impossible to automate, which means if you have these skills you’ll be even more valuable to organisations in the future,” writes Guy Berger, LinkedIn’s Principal Economist. “If you have these skills, make sure they’re on your LinkedIn profile so hiring professionals can find you for relevant opportunities.”

Let’s take a look at how you might reskill or upskill in both “hard” and “soft” areas.

Reskilling in machine learning

The number-one most in-demand job, anywhere in the world, is Artificial Intelligence Specialist. Businesses are recruiting AI Specialists for a wide range of projects, from designing crop-harvesting robots to modeling risk in finance.

Element AI in Montreal estimates that in the United States, there are around 144,000 AI-related job openings but only about 26,000 developers and specialists looking for work. One reason may be that people who are, in fact, qualified for these jobs don’t realise they are. But that’s starting to change.

“The most common jobs that AI Specialists held prior to labeling themselves with the title include ‘software engineer,’ ‘data scientist,’ ‘research assistant,’ and ‘data engineer,’” says Jonathan Vanion, writing for Fortune. “This suggests that people may be updating their job titles to include artificial intelligence, to put themselves in a better position to capitalise on the current AI boom.”

This advice is gold: Call yourself what you want to be, not what you are, and you’ll grow into the role. After all, hiring managers often post unreasonable lists of qualifications that describe no real candidate.

“Employers’ list of desired skills often doesn’t make much sense—for instance, a request for ten years’ experience with a framework that has existed for only two,” says Jilles Vreeken, machine-learning researcher at the Helmholtz Center for Information Security and the Max Planck Institute for Informatics in Saarbrücken, Germany. “So make sure you tick lots of the boxes, but don’t feel inhibited if you don’t tick every one.”

To get started with machine learning or AI, you’ll most likely need to know Python and have a solid grasp on data science and deep learning fundamentals. Traditionally, AI Specialists have a degree in computer science, though it doesn’t have to be a PhD. A background in math and statistics is helpful.

“Focus on learning the fundamentals: good linear algebra, probability, and software engineering skills,” says Ian Goodfellow, a research scientist at OpenAI. “The state of the art in machine learning changes from one year or even month to the next, but the fundamentals stay the same for decades.”

That said, you don’t have to be an AI Specialist to work in AI.
Many AI companies are hiring subject matter experts in a wide variety of fields to guide AI development in specific industries like healthcare, insurance, and finance.

“AI designed for simple tasks like image recognition can be trained on data alone, but AI assigned to more specialised tasks needs input from human experts,” explains Antony Brydon, CEO and co-founder of Directly. “Post-doctoral researchers, data scientists, and other AI specialists may be brilliant people with diverse skill sets, but rarely do they have insight into the nuances of product design, the delicacies of customer service, or the subtleties of concierge hospitality.”

According to Nature, businesses such as LinkedIn, Kixeye, and Nextdoor are already using non-technical experts to develop their AI platforms.
The point is that working in AI may not necessarily mean programming machines. It could instead mean consulting AI companies in your area of expertise, like mental health or banking. Still, you could gain an edge as a consultant by studying the fundamentals of AI yourself.

Reskilling in programming

The top programming languages and frameworks mentioned in the LinkedIn report are Python, JavaScript, React.js, Node.js, CSS, and AngularJS. You can learn any of these online, at your own pace. You may even be able to learn a language on the company dime, depending on your employer’s professional development policy.

To get started, be prepared to learn. Voraciously.
“You must have an insatiable appetite for knowledge,” says professional programmer Rob Walling. “This usually means reading a programming book every few weeks in the early days, and moving on to more conceptual books like The Pragmatic Programmer, Code Complete, and Facts and Fallacies after 6-12 months of full-time coding. I can’t stress enough the value of reading, nor the value of immersing yourself in code early in the process.”

Consider doing a software apprenticeship, which involves learning to program alongside a mentor. You’ll pick up not only the fundamentals but insights, knowledge, and insider tips that normally take years to uncover. You may also get a job out of it if you’re a savvy networker.

Next, sign up for a course in the programming language that’s most often required for the job you want. For instance, if you want to work in machine learning or back end development, choose Python. You can learn it as a beginner programmer, although it helps to know programming basics at least in theory. If you want to become a UI Designer or Front End Developer, choose JavaScript or CSS. Both are “core technologies” of the web, so you won’t waste your time with these.

Estimates for “time to proficiency” for Python are eight weeks. For JavaScript, nine months. Tackle both if you want to become a Full Stack Engineer.
Finally, some words of wisdom from Data Scientist Freddie Odukomaiya: “Pick one programming language and stick to it. Don’t go back and constantly change your choice of language to study. If you do, you will slow your progress down.”

Reskilling in data science

To become a Data Scientist, you do not necessarily need a degree in a field like engineering, computer science, mathematics, or statistics. What matters most of all are your skills and experience. This is especially true in a market where demand vastly outweighs supply.

DJ Patil, who built the first data science team at LinkedIn before becoming the first Chief Data Scientist of the United States in 2015 and coined the term “Data Scientist” with Jeff Hammerbacher (Facebook’s early data science lead) in 2008, tweeted the following in 2016:

“Data science doesn’t care about what you majored in or if you even got a degree. It’s what you do with data that matters.”

You could, in fact, be a data journalist (emphasis on the “journalist”) and get hired as a Data Scientist. It’s all about your familiarity with three things: statistics, programming, and business.

“A data scientist needs to know statistics and math to analyse patterns in data and to manipulate it with different treatments,” says Roger Huang, CEO and co-founder of CyberSecure. “They need to use programming skills to deal with data at scale that can take up terabytes of space. They need to understand business fundamentals in order to communicate their findings and drive other teams to action based on their insights.”

What this means is that you don’t have to start from scratch as a computer science student. You can simply take a course in statistics, learn a programming language, and enrol in an online business or entrepreneurship course to learn the basics of each. You can then combine these skills to work on projects with fellow learners and mentors. Remember, you can always volunteer to complete your first project for a company for free to gain experience.

“The one thing a bootcamp can deliver that a really good university can’t is a really thorough understanding of how to build something from ideation to deployment—that’s a full-fledged capability I don’t see often from Ph.D.s,” says Daniel Carroll, a principal data scientist at Aetna. “If you can bring that to light in a CV or interview, that will make you shine.”

Reskilling in account management

Account Managers and Customer Success Specialists are in high demand around the world. If you like to work with people, or at least to manage relationships, then this is a promising field for you. Businesses know they need to become more service-oriented as basic processes go digital, so they will be looking for candidates with strong customer service, communications, and HR management backgrounds.

It doesn’t matter if you’ve only worked as an Account Manager in one industry—your skills are transferrable. And if you’re just beginning your journey in account management, there’s no reason for concern. As you may have guessed by now, you don’t need a specific degree for this field either.

LinkedIn’s Emerging Jobs report lists Customer Success Specialist as an especially fruitful area. Unlike Customer Service, which is more reactive, Customer Success focuses on working proactively to understand client needs on behalf of the company.

“Australian consumers have some of the highest service expectations in the world,” the report explains. “So, it is not surprising that Australian companies have been early adopters of customer relationship management (CRM) tech. According to Gartner, in 2018, local companies spent a record A$2.3 billion on CRM technologies, up 20 percent on the previous year and outpacing the global growth of 15 percent. The rise of Software as a Service (SaaS) business has been a big contributor to the growth in this job. Product adoption & utilisation and customer retention & growth are key success factors for this job.”

The main skills needed for this job are account management, CRM, customer retention, strategy, and Salesforce. If you have experience in any of these areas, or in project management, you’re qualified to apply for a Customer Success Specialist role. Another skill, which we’ll explore below, can push you in the account management direction: Service design.

Reskilling in service design

Service design is an increasingly popular field for professionals in Australia, and will draw higher demand more globally in the next few years. As businesses move from product-orientation to service-orientation, they will need more people to understand how clients interact with those services to help improve their experience.

“Just as an industrial designer designs chairs and water bottles, a service designer designs experiences,” explains the report. “A good service designer can work with a broad sweep of the organisation to ensure that its service is designed to make life more enjoyable for its users.”

Top skills needed for service design include design thinking, user experience design, user research, user-centred design, customer experience design, and customer journey mapping. However, they are not requirements for getting started. If you have a background in the service industry, you can tack on a UX course and start redesigning your CV to help usher in your dream job. You can also take a service design course which, on top of experience in the hospitality or restaurant industry, will set you up for success in your job search.

Upskilling in communication

Good communication skills create a positive experience at work, build team morale, and help you build your own leadership skills. They’re not about taking the floor and delivering monologue after monologue until your conversation partner’s eyes glaze over. They’re about slowing down and being present, listening closely, asking questions, being clear, anticipating confusion, knowing when and when not to crack a joke, using body language that’s aligned with the message you want to send, and making the people around you feel comfortable.

“Good listeners ask questions, challenge assumptions, and generally check for understanding throughout a conversation,” writes Celeste Mora, Grammarly’s Senior Content Strategy Manager. “They cultivate a two-way conversation where they’re constantly trying to improve their understanding of what the other person is saying.”

Communication experts also recommend “over-communicating” sometimes, as we tend to assume people understand us more than they actually do. Balance that, however, by being as clear and concise as possible in your messages. You’ll be rewarded for it:

“Twenty years ago, the smartest person in the room at work was the one who had gathered more and better information than anyone else,” says Dean Brenner, president of The Latimer Group, an executive coaching agency in the U.S. “Today, the smartest person in the room…is the one who can simplify all the things that are going on and create a path through the complexity and toward a simpler solution.”

Brenner adds that when you’re talking about something you do or something you know, most people want to know one thing: how it can apply to them.
“The real mistake is to assume that everybody cares about the nitty-gritty of the data as much as you do,” Brenner says. “What you have to realise is everybody’s listening to what you’re saying and thinking in their heads about how they can apply it to what they’re doing.”

An online course in written or spoken communication could be an interesting option. Foreign language courses are always useful too, as employers will increasingly be looking for multi-lingual candidates who can liaise with global clients.

Upskilling in creativity

How do you become more creative?
Research shows one big predictor of creative output is a trait called “openness to experience.” Part of the Big Five personality scale, openness to experience is pretty much what it sounds like: exploring new places, meeting new people, going outside your comfort zone, taking up new activities and skills, and generally exposing yourself to new stimuli. Some people are naturally more comfortable with this way of being than others, but it can be learned and honed like any other skill. The more you seek variety and witness the creative fruits of your efforts to do so, the more comfortable you’ll become with this way of being and the more incentive you’ll have to continue with it.

“Multiple psychological studies suggest that a crucial trigger of creativity is the experience of unusual and unexpected events,” says psychologist Scott Barry Kaufman. “Unexpected events can certainly mix emotions, and mixed emotions… can increase sensitivity to unusual associations and ideas.”

A 2012 study published in the Journal of Experimental Social Psychology concluded that any life experience, from the traumatic to the joyful, can lead to creativity “as long as it diversifies your experiences and pushes you outside your normal thought patterns.”

For the study itself, researchers placed participants in a virtual reality world where they took a three-minute tour through a university cafeteria. They were divided into two groups: experiencers of a weird reality where events violated the laws of physics or experiencers of a normal reality with standard laws of physics. For example, people in the first group might walk up to a suitcase resting on a table only to watch the size of it decrease, then increase as they walked away.

Afterwards, researchers asked participants to take a test of cognitive flexibility where they came up with as many answers as possible to the question, “What makes sound?”

Participants who had been immersed in the weird virtual reality scored higher on the test, coming up with more creative answers, than those who had been immersed in a normal version of the virtual world.

Kaufman says the “core feature” of an experiment like this is “actively experiencing a violation of how things are supposed to happen.”

These findings have implications for team managers as well.
“The latest research on the role of emotions in creativity suggests that instead of focusing exclusively on bringing out positive emotions among employees—or attempting to dispel negative emotions—managers may want to consider additional factors,” Kaufman says, “such as whether the environment brings out emotional ambivalence (Is the environment unusual? Will it tap into a wide range of seemingly contradictory emotions?) and motivational intensity (Will it broaden or narrow someone’s focus?) when trying to stimulate creativity.”

Other research suggests that taking walks, doodling, feeling at ease, solving problems, tapping into mixed emotions, cultivating interdisciplinary thinking, and switching up your environment can all help you boost your creativity.

Simply put, employers want creative teams because, in an age of automation, creativity is a distinctly human trait. It won’t become obsolete—at least, not any time soon. Time to skill up.

Upskilling in collaboration

Collaboration will trump competition as the world becomes more globalised. We’re already witnessing the rise of the collaborative economy with the phasing out of solo entrepreneurship and siloed teams, the move toward partnerships between companies and consumers, and the democratisation of income through startups like Uber and Airbnb. Organisations know that collaboration is the faster route to growth, and that’s why they’re hiring people who can help build relationships with customers and partnerships with other businesses.

“The real driver of success in the collaborative economy is not technological innovation,” says Andrew Reid, founder and president of Vision Critical. “Collaborative startups like Lyft and Instacart aren’t getting billion-dollar valuations because they’re more technologically advanced than the big transportation and hospitality services that existed long before them. These startups are dominating because they’ve uncovered insight about today’s customers. Ultimately, that understanding of the customer is what will give companies sustained competitive advantage in the age of the collaborative economy and beyond.”

As customers themselves demand more authentic experiences from companies, what it means to “understand the customer” will increasingly require interacting with that customer and building a real relationship with them. If you plan to work in the customer-facing side of a business, you’ll need strong collaboration skills.

You’ll also need to be a team player, enthusiastic about learning from and teaching your colleagues. Teams that work well together simply get more done, and are able to be more creative during brainstorming sessions and meetings. Collaboration doesn’t mean being best friends with the people you work with; it means knowing how to bring out people’s strengths, make people feel heard, challenge people respectfully, stay receptive and open-minded, accommodate different personalities and communication styles, and guide idea sharing in a productive direction.

To become a skilled collaborator, try gaining experience as a community or events manager, customer success specialist, human resource manager, or employee experience designer.

Upskilling in emotional intelligence

Yes, this is a valid soft skill. Yes, employers are looking for candidates who have it. What does it look like, exactly?

As defined by Psychology Today, emotional intelligence is “the ability to identify and manage one’s own emotions, as well as the emotions of others.”

It’s made up of three skills: “the ability to identify and name one’s own emotions; the ability to harness those emotions and apply them to tasks like thinking and problem solving; and the ability to manage emotions, which includes both regulating one’s own emotions when necessary and helping others to do the same.”

How do you improve at something that requires so much sensitivity, especially in a professional environment?

To cultivate better self-awareness, Mark Manson recommends understanding yourself and your behaviour on three levels: 1) know what you’re doing, 2) know how you feel about it, and 3) know what you don’t know about yourself.

“Schedule time in your day to get away from [distractions],” he advises. “Do your morning commute with no music or podcast. Just think about your life. Think about how you’re feeling. Set aside 10 minutes in the morning to meditate. Delete social media off your phone for a week. You’ll often be surprised by what happens to you.”

Next, learn to channel your emotions well. This means reserving judgment over the way you or another person feels and focusing on how to respond.

“The whole point of this is to be able to channel your emotions into what psychologists call ‘goal-directed behavior’—or what I prefer to call ‘getting your shit together.’”

Learning to motivate yourself can also boost emotional intelligence. Manson recommends acting early to get things simmering:

“If you don’t feel like anything motivates you, do something,” he writes. “Draw a doodle, find a free online coding class, talk to a stranger, learn a musical instrument, learn something about a really hard subject, volunteer in your community, go salsa dancing, build a bookshelf, write a poem. Pay attention to how you feel before, during, and after whatever it is you’re doing and use those emotions to guide your future behavior.”

Once you’ve built a healthy amount of self-awareness, you’ll be able to tune into the emotions of others to create relational health around you.

“You do this by connecting and empathising with others. By both listening to others and sharing yourself honestly with others—that is, through vulnerability.”

Finally, Manson recommends “infusing your emotions with values.”

“Emotional intelligence is meaningless without orienting your values,” he writes. “You might have the most emotionally intelligent CEO on the planet, but if she’s using her skills to motivate her employees to sell products made by exploiting poor people or destroying the planet, how is being emotionally intelligent a virtue here?”

Being clear about your own values will allow you to guide your emotional energy in a positive, constructive direction.

It’s a new decade. Time for a new you (or maybe just the 2.0 version). As challenging as it may be to decide which direction you’ll go in, rest assured that you can’t, really, make a wrong choice when it comes to upskilling or reskilling in any of these areas. The only mistake you can make is to take no action at all. So give yourself permission to do what feels right, whether it “makes sense” now or not. The reason you chose that new skill will become crystal clear when you land your dream job later on down the road.


If you want to future-proof your career and learn in-demand skills, we’ve got a variety of online courses available in Human-Centred Design, Business and Marketing and New and Emerging Tech.

Saga Briggs is a journalist covering trends in learning, creativity, intelligence, and educational technology. Follow her @SagaMilena