Purpose, Tools

How to be great at your job – have a side gig

Creative pursuits after hours give you surprising advantages in the workplace

  • By boosting your cognitive flexibility you will increase your chance of breakthrough thinking and creative problem solving.
  • Flexible, creative thinking gets stronger with time and practice. You control these outcomes!
  • Side gigs, passion projects, hobbies and play can all contribute to a more creative mind.


Emma Watson is a highly accomplished actor. She is also an Oxford graduate with an English degree, she’s modeled for the likes of Burberry and Lancôme, is famously active as a Goodwill Ambassador for the United Nations, and a global advocate for gender equality. Ms. Watson turns 30 next year.

You may know that former NFL player Terry Crews is now an actor but did you know he also went to college on an art scholarship? Terry Crews has regularly painted on commission, and even worked as a courtroom sketch artist.

Emma Watson and Terry Crews are examples of people who are accomplished in more than one field, often called “multi-hyphenates.” Are these individuals born – erm – multi-hyphenated with an innate talent for many things? Or did they pursue many interests first and that pursuit lead to success building upon itself? The answer is likely a bit of both, but more of the latter than you might think.

Multi-hyphenate: A person – particularly one with notable success – with several professions or skills. E.g. ‘Shaquille O’Neil is a NBA Star – actor – business professional’

Skills build upon themselves

If you stop to notice, there are actually a surprising number of people who achieve in more than one area of life. Perhaps some of this can be explained by personality – the drive and intensity it takes to become excellent as a concert pianist would also lend toward a successful career as Secretary of State (Condoleezza Rice). At some point though you have to ask yourself – is it the very act of going after more than one passion that allows these individuals to go into overdrive and stand out?

Steve Jobs on multi-hyphenate product teams being best in class

Steve Jobs, Apple co-founder and infamous technology disruptor, was also known for his appreciation of fine arts. Indeed, this appreciation can be seen in his focus on simple, sophisticated design in Apple products. In talking about one of Apple’s earlier disruptive technologies, the Macintosh personal computer, Jobs noted the link between the success of the Mac and the number of multi-hyphenates working on that product team:

“I think part of what made the Macintosh great was that the people working on it were musicians and poets and artists and zoologists and historians who also happened to be the best computer scientists in the world.” Steve Jobs — PBS’s “Triumph of the Nerds: The Rise of Accidental Empires” (1996)

Computer scientist – zoologist? Why not? The pattern begins to emerge – a correlation can be made between people who explore more than one interest deeply and highest self performance.

The Other Flexibility

We know that staying physically flexible is one of the keys to aging gracefully. If you can bend, stretch, maintain full range of motion and balance you are more likely to stay active and avoid accidents later in life. The same holds true for your brain. When we are young, first in college, we are learning a skillset (among other, possibly more nefarious pursuits) and many of us seek to achieve mastery of that skill so we can jumpstart a career. This works because it helps us specialize but practice in only one area of study doesn’t make us very mentally flexible. Studies have shown however that cognitive flexibility, the ability to shift thoughts or adapt behaviors to changes in environment, is linked to higher performance no matter the industry. So the ability to maintain or bring back those hobbies and creative play is critically important to staying mentally limber.

  • Curiosity is a basic yet critical form of cognitive flexibility – the ability to ask ‘why not?’ Learner mode opens us up to new possibilities.
  • Critical thinking conversely uses this same skillset to ask ‘why?’ Independent analysis allows us to validate the information we receive.
  • Being able to connect seemingly separate concepts and create a correlation is a third form of cognitive flexibility often used to see the world differently. Entrepreneurs may use this strategy to brainstorm new, unique product offerings.

The good news is that flexible, creative thinking gets stronger over time – like a muscle. You control these outcomes!

Cognitive Flexibility: The ability to shift thoughts or adapt one’s behaviors to changes in environment

Christopher Bergland, Psychology Today

I was talking with a respected technical colleague last week who had broken a finger. Not great when you work in front of a computer all day. Turns out he’d done this playing jazz piano in his band with such intensity that his finger required setting. Ok – ouch! But also – he clearly excels at his technical profession as far away from jazz piano as it gets. How much does his side gig help him set a problem aside, focus his brain elsewhere, and then be able to come back and look at the issue in a new way after working through solutions in his subconscious during that critical break period? This is cognitive flexibility at work – he can shift from one subject to a vastly different area and spark different brain functions while giving others a rest.

Curiosity is cognitive flexibility in action

If you are flexible in your thought pattern you tend to think creatively. Creative thinking allows a person to connect seemingly unrelated ideas to create new thought patterns and spark breakthroughs. You can be more than adequate in any profession by deeply understanding that skillset. To truly stand out however you need to be able to uniquely apply your own mental models and experiences to the profession. Cognitive flexibility should not be under-estimated.

Side gigs, hobbies, and play

This is where side gigs come in – and to be fair – any other activity that can regularly stimulate your brain and put you into that deep sense of engaged concentration that allows you to put your other work fully aside. Whether it’s a hobby that brings you joy (in our family we call this ‘soul food’) or taking purposeful time to put away the work to go and play (those vacation days should not be skipped!), the point is to shift your thinking and wake up the other areas of your brain.

Optimally side ventures come with other perks like secondary income. That said, if you are an English teacher passionate about rebuilding classic cars in her spare time for fun – go do that! A passion project is a great example of flexing your brain in a fully engaged way. As long as what you do absorbs your concentration and takes you fully out of the typical skillset you tap into for work then you are gaining cognitive flexibility. Classic car rebuilds have nothing to do with that curriculum you need to create for next semester. Even still, you are allowing the task to be worked by your subconscious as you are installing those upgraded fuel lines and it’s likely that a spark of curriculum inspiration will hit you an hour or two after you finish your garage project.

In summary

There are examples across history and modern day of people celebrated in one area who are also highly talented in another skillset. The ability to shift your thinking between vastly different types of tasks gives you greater cognitive flexibility and creativity which makes you better at *both* your core work and your side gig. Want to level up? Don’t work another 5 hours a week at your job. Instead – spend those 5 hours on a hobby, passion project, or out in play and exploration. To be great at your job – enjoy the creativity and cognitive flexibility that comes with a side gig.

About the author: Hi! My name is Jess Anderson, I am a technologist based in Louisville, Ky. I lead technology product and project management teams and am ‘mom’ to two school aged kids.

Check out this article and related author content on Medium.

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