Briefing Notes: Training Day

Published: February 16, 2020

“The only thing that interferes with my learning is my education.” — Albert Einstein


It’s not just good ol’ training anymore. The new buzz words are upskilling and reskilling. And with good reason.

Case in point: In the US, we closed the decade with a million MORE job openings than unemployed workers. Add to that the fact that it’s pedal to the metal on automation and other tech advances. And we are in for a huge talent mismatch. McKinsey estimates about 14% of workers across the globe will need to switch occupations — not just jobs — by 2030.

New jobs will be available but people will need to find their way into these jobs.

So, on the one hand, lots of opportunities. Yay! On the other… are we even positioned to take advantage of them? 🤔

This isn’t just a problem for us sapiens. Companies are facing the same issue too — if they want to remain competitive in a rapidly changing world.

For once, the stars seem to be aligned: We want to get retrained AND companies want us to get retrained. Giants like Amazon and AT&T have announced massive retraining dollars for their staff. Hopefully, your company’s doing some level of that too.

So, reskilling, upskilling, outskilling… these are three words we all need to understand – wherever we are in our career ladder or journey.

👉🏼 And just because you run a business or are self-employed does not exempt you from thinking about this. Maybe even more so as you have to budget for the training yourself.

Some definitions to level set:

Reskilling programs are designed for workers who need to move into an entirely new type of job and career. They don’t just need additional skills; they need entirely new ones. Employers are increasingly using it as a way to avoid layoffs and costly hiring initiatives.

Upskilling initiatives target workers who need additional training to remain relevant or to advance in their existing company or industry. Think of the marketer who needs to learn how to use new digital tools or the engineer who needs to master a new coding language.

Outskilling is a last-resort form of training for folks who simply won’t be able to find a new role at their current companies or industries. It’s offered as a severance benefit for employees being laid off or bought out.

Here’s a deeper dive, plus two more training approaches gaining popularity among companies.

Bottom line, if you’re:
Employed: You’ll want to understand what your company is offering and make sure you’re in the queue to take advantage. If no official retraining opportunities have been announced, do your own research and suggest training programs that will make you more relevant to the company’s direction.

Self-employed: You’ll want to understand where your industry is and where it’s heading. Be on the lookout for tech developments that may impact your line of work (e.g., availability of AI tools that may automate the work that you do for your clients). Then set aside time and resources for appropriate training to pick up new skills.


Switching from climbing a corporate ladder to starting a small business meant I was in for a steep learning curve. Back in the day, this would have meant investing loads of money on a business program and going to school nights and weekends. Thankfully, the world has evolved and we now have access to JIT training and bite-sized programs that fit our busy schedules. I couldn’t have done it without the online classes at CreativeLive.

If you’re starting out in your self-employment or business ownership journey, you’ll want to review the list of best-selling business basics classes.* Good luck on your new venture!

*This is an affiliate link.

  • “It’s the difference between writing a certain way because you want to or because you feel you have to.” Women often hear that our emails are ‘too friendly, not confident enough’ and that we should email like a man. Perhaps a better approach isn’t to write like a man, or for that matter, like a woman. Instead, focus on saying what we really want to say.
  • “Not to get angry and keep a smile on your face,” says the world’s oldest living man, who shared his secrets to making it to 112. That guy definitely knows something about longevity.


“Who are you trying to impress? What do you have to force yourself to do? What would you like to never, ever do again?” — Danielle Laporte


You’ve heard, don’t you? Civilization is going interplanetary. In just a decade or two, the billionaire rocket bros say, there’ll be celestial cruises (courtesy of Virgin Galactic), lunar mining operations (run by Blue Origin), and permanent settlement on Mars (SpaceX is all in). As Branson, Bezos and Musk spend their fortunes on the tech that will get us into orbit and beyond, one question remains unanswered: What are we going to eat in space?


… when Blackberry was it and Crackberry addiction was a thing? The blue one with the track wheel on the side — who remembers those? 🙋🏻‍♀️ While the company stopped making its own hardware in 2016, it’s been licensing the brand to TLC for the last four years. Earlier this month though, TLC announced that the relationship is ending in August. This might just be it. The final nailing of the coffin on Blackberry devices once and for all. Let’s file this under ‘slow death’.


The podcast is on a brief break as I go into production for the next season. In the meanwhile, you can check-out the just-ended series on Side Gigs and Side Hustles. That season started with Ep 107 through 121. Check out the backlist on your mobile device.


As someone in love with the process of learning, all this up- and re- skilling is just heaven for me. And so my challenge is to be more intentional (dare I say strategic) about where my training monies go. Especially given that as a self-employed person, I’m financing it all.

I definitely take advantage of less expensive methods of learning, such as books, webinars, short-term online programs on platforms like CreativeLive and SkillShare.

And don’t count podcasts out. One of the reasons I started one is because I benefitted and learned a lot from podcasts myself. With over 900K podcasts available on iTunes, there are many that provide timely information.

We haven’t got any excuses for not retraining ourselves and getting in position to catch the wave, really. So, get on it!

Best wishes for a productive week. Send comments, training grounds, gourmet MREs, email hacks, and blackberry jokes.

Cool beans,
Lou Blaser


A former management consultant and IT leader, Lou Blaser is the editor of Briefing Notes and the host of the Second Breaks podcast. She is also the author of Break Free: The Courage to Reinvent Yourself and Your career. Lou’s work is focused on helping experienced professionals navigate an evolving work landscape so they can continue their impact and relevance in a changing world.

The world of work is changing.

Stay smart about it.

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