2020 is the Year of Upskilling

Feb 2020 Update! If you’re curious about upskilling, check out my LinkedIn Live session, WTF is Upskilling?

Last August, I spent the month teaching my audience how to upskill themselves. Upskilling is one of those words that’s still a little bit out of reach for most people. It hasn’t entered mainstream just yet.

That’s all about to change in 2020. Upskilling is going to go mainstream in people’s professional lives. First, people love to kick off a new decade with big, bold moves. People are eager to build on ideas from the previous decade and start again, both in their professional and personal lives.

Second, the pace at which change is happening in our workplace is staggering. LinkedIn featured two posts this past week that highlighted the shifts we’re already seeing in the workplace. The first, “Where have all the secretaries gone?” covered the disappearance of administrative assistant jobs, often staffed by women without degrees. There was a quote in that article that really struck me:

Rita Maxwell had no idea she was about to lose the job she’d had for nearly 20 years when her boss told her to meet him in the conference room at the end of the work day. “I was completely taken aback when he called me into the meeting room to let me know my position had been eliminated,” said Maxwell, who was let go in early 2017. “There’s just not a lot of loyalty anymore.” Administrative assistant jobs helped propel many women into the middle class. Now they’re disappearing.


The death of employee loyalty is just one of many changes happening in our workplace.

The second article that LinkedIn highlighted was on the teacher shortage. More teachers are opting out of teaching because of low pay. While our lack of teachers is a national problem, it struck me because teaching used to be a sure fire fulfilling career path. It was the secure job that people often changed into when they wanted an escape or were burned out. Now days, not so much.

In addition to the two articles, I also stumbled on this map of the fastest disappearing jobs in the US by state.

On top of that, we see more articles about the new types of jobs created by new technology. Articles like this one, which highlights architects working in video game design as a creative way to apply their skills. It’s yet another traditional career path that’s adapting to our new world of work.

It’s also enough to get any burnt out architect thinking, how do I get into that?!

New career advice book: Punch Doubt in the Face: How to Upskill, Change Careers, and Beat the Robots
I wrote a book to teach people how to upskill.

It’s time to upskill yourself

The result is that a lot more people are starting to see the impact, good and bad, of new technology in their workplace. And they’re looking for ways to adapt.

Upskilling is adaptation. Though upskilling isn’t a household term just yet, it will be in 2020 thanks to the impact of recent changes in the workplace.

Upskilling is a verb and a mindset. It’s the act of learning new skills to improve your professional life. It’s also a willingness to accept that things are changing, take charge of your learning and development, and not burry your head in the sand.

While the term upskilling is frequently thrown around in articles as if one can just upskill tomorrow, upskilling is not an easy process. Every time I read an article in a big publication (looking at you HBR) by a corporate leader declaring that our collective workforce simply needs to upskill, I roll my eyes. Often these articles are written by people who haven’t actually upskilled themselves.

In fact, upskilling is downright hard. I say this as someone who is doing it and as someone who just wrote a book teaching people how to upskill. It’s hard because we haven’t been taught how to do it.

It makes me think of a quote I read last year from Tech in Asia, How to stay relevant in today’s rapidly-changing job market:

The benefits of the comfort zone are appealing. Steady (though not always satisfying) incomes, “secure” jobs, relaxed routines, and predictable schedules are as comforting to humans as they are to animals. In this phase, people limit their learning to things they learn on the job, not knowing that yesterday’s lessons rarely solve tomorrow’s challenges… Without skill upgrades or a willingness to learn, people are caught in a rut. They are unable to see when the next trend is about to catch up or when the current one is about to die. For the few that can see the new trend, the pain of having to upgrade their skills far supersedes the pleasure of staying in the comfort zone.


The comfort zone is cozy. But it’s the opposite of adaptation. A lot of mid-career professionals need to escape the comfort zone.

Making a plan in 2020 to upskill yourself

If you’re curious about how to upskill yourself, follow me on LinkedIn where I’ll be hosting trainings in January and February. You can also dive into some of my previous posts to get a handle on where we’re headed in the future of work (or get my book):

AI is Going to Wreck Your Carefully Planned Career

The Pain of Upskilling

If listening is more your style, here’s recent podcast I did on how to outsmart artificial intelligence and develop your future.

If you’re looking to upskill your workforce, take a look at how I teach employees how to upskill and invite me to speak to your employees.

Is LinkedIn a Learning Platform?

Full confession: I spend more time on LinkedIn than Instagram. My friends make fun of me when I tell them this. It’s embarrassing because LinkedIn is easily the least exciting social platform to spend your precious internet time on. But I speak and write about emerging careers and trends in upskilling, so LinkedIn is part of my daily internet consumption routine and embrace the awkwardness of it.

This week LinkedIn popped a recommended course into the top my feed.

That action reminded me that LinkedIn has an entire catalogue of courses on offer, a fact that I’d totally forgotten. Clearly this was the intent of the designers. They wanted to remind users like me that LinkedIn isn’t just a place to read professional #inspo stories of people you don’t know.

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