Chances are, the following sentence will be something you can relate to. The career ladder you have been picturing looked like this: you get a degree, find a company to work for, and begin one steady climb. But now, a larger share of unemployed people spend more than a year searching for work, and full-time roles are harder to come by. In this environment, upskilling and reskilling are possible paths to new success.
This article by professional development magazine Training calls upskilling and reskilling “essential pillars of workforce strategy.” Upskilling expands your current skill set to do a better job in your current role, growing along a linear path. Reskilling means learning entirely new skills outside your usual area so you can shift gears and move into a different job.
If you’re feeling inner resistance to these processes
First, it’s crucial not to treat this change as a sign of failure. Richard N. Bolles writes in What Color Is Your Parachute? that many high achievers took winding paths rather than committing early to one lane. J.K. Rowling worked a string of unrelated jobs into her thirties before publishing Harry Potter, while Andrea Bocelli didn’t break through as a singer until 34, after years as a lawyer. Our personalities and interests keep changing. Since you can’t accurately predict who you’ll be in ten or twenty years, betting everything on a plan made today is riskier than staying ready to pivot.
Where to start?
Once you’ve accepted that building new skills is worth doing, the next challenge is deciding where to put your energy. You need to figure out who you are before deciding what you want to do, as outlined in Richard N. Bolles’s classic career guide, What Color Is Your Parachute?. Skipping this step is how people end up chasing in-demand skills that don’t fit them.

Bolles warns that focusing on “what” jobs are out there before discovering “who” you are lets others dictate your path, leaving you feeling completely unfulfilled. To break free from this, you can map your favorite fields of interest and transferable skills on a single sheet of paper to spot unique career niches where they overlap.
Remember to stay agile
To build on this self-discovery, you should avoid rushing to specialize too early, a key piece of advice from David Epstein’s book, Range.

Epstein argues that although early narrow specialization is a popular strategy, it is a misconception. A “sampling period” where you try different skills helps you find your true calling and sharpen your overall abilities. In a complicated world full of unpredictability, you need cognitive flexibility. It is the ability to take what you learn in one field and apply it to another.
Instead of making rigid, long-term plans that ignore how much your personality, values, and interests will change as you grow older, you should focus on what is highly engaging right now and keep your options open. Epstein shows that amazing breakthroughs often happen when generalists think outside the box and use an unconventional approach.
How to actually learn the skill
Once you have mapped out your direction, you can speed up your skill acquisition by using the strategy described in Scott H. Young’s book, Ultralearning.
Young points out that traditional education often fails because of “failed transfer,” where we study in artificial environments and struggle to apply that knowledge in the real world. To beat this problem, you must practice skills in the exact environment where you will use them, or in a setup that mimics it.

A helpful practice is first to spot your weaknesses, then drill those specific bottleneck areas. You must also cut out passive study habits like highlighting or rereading, because they create a false illusion of learning. Prioritize active retrieval by testing your memory without looking at notes. You could also benefit from seeking out corrective feedback that identifies your mistakes and tells you how to fix them.
Focus and balance are your friends in the process
With your learning engine running, you must protect your focus. We recommend productivity principles from Gary Keller and Jay Papasan’s book, The ONE Thing.
Have you heard that multitasking reduces your efficiency by a third and wastes hours of your day? This is due to the mental switching time required to jump between tasks. Keller and Papasan tell us to apply the 80/20 rule, recognizing that 80% of your success comes from just 20% of your efforts. To find your highest-leverage tasks, ask yourself the Focusing Question: “What is the ONE thing I can do right now such that by doing it, everything else will be easier or unnecessary?”

To keep this momentum going without burning out, you must stop trying to achieve a perfect work-life balance. Outstanding achievements require you to go all in, which naturally throws your life out of balance. The secret to staying on track is “counterbalancing” — balancing intense periods of career focus with scheduled rest and time to recharge.
Career development is a step-by-step journey of positive change. By taking things slow and steadily building your skills, you can master complex areas and build a truly rewarding career.
Putting it together
Upskilling and reskilling don’t have to be a one-time emergency response to a layoff or a stalled career. You can perceive them as an ongoing habit, and one the modern job market increasingly rewards.
Let’s say it together one more time: changing direction does not mean you’ve failed. You just need to identify the one skill that would make the biggest difference, and understand your own strengths and interests well enough to choose wisely. Then, learn that skill using methods that actually build lasting ability.
None of this requires quitting your job or going back to school full-time. What you need is to start treating your own learning like any other priority. You can also turn to books for specific career and skills advice. Here is our list of books about professional development to gather inspiration from.
Photo credits:
- Photo by Peggy Sue Zinn on Unsplash










