Are you playing chess with your career? Or Connect Four?

In Wednesday’s newsletter after sharing the biggest career lie of them all – that we are what we do – I asked the following:

If you could design your dream career, would you prefer to specialize in a single craft? Or instead pursue a variety of different interests?

Let’s just say the responses just about broke my inbox! Boy did I touch a nerve…

  • This is the single biggest lie for sure…many who have “traditional” careers live everyday regretting being stuck in an endless loop not of their own calling.
  • I don’t wanna stick with one job. I want to be continuously exposed to learning and forced outside my comfort zone.
  • My dream career would allow me to [work in] the scripted world but balance it with unscripted, documentary, YouTube shorts, commercials or even corporate work. It would be enough so that I can see my friends/family in the evenings and on weekends.
  • I have always been a person that liked so many different things, partially because I have ADHD, and just partially who I am.
  • Only a year ago I realized that it’s okay to want to pursue different interests and don’t just have to find the ONE thing that fits. I feel more at peace in my mind now…even if I feel like I’m walking aimlessly into the world.
  • Your point reminds me of a successful dermatologist who also had his own off-broadway musical. Some people are able to figure out how to be the best version of themselves, for many others it’s just a slog getting through one goal at a time.
  • I’d prefer a life filled with adventure, twists and turns, and pursuing various interests and passions. But I feel so out of touch with my passions and interests, I just cannot fathom what else I could do.
  • I want to be good at the things I do but be a jack of all trades that’s good at its trades.

And therein lies the real fear 👆…

The path of the generalist means being labeled as “A Jack of all trades, master of NONE.”

This mentality couldn’t be further from the truth. As humans, being generalists is an evolutionary advantage that literally increases our likelihood of survival.

“It is not the strongest of the species that survive, nor the most intelligent, but the ones most responsive to change.”
– Charles Darwin

It’s only since the Industrial Revolution that we’ve been (falsely) led to believe specialization is what maximizes our safety & security.

As creatives, I believe ALL of us have the hidden potential to thrive not only as generalists but simultaneously as specialists.

Once you identify the intersections between your:

  • Work & life experiences
  • Skills & abilities
  • Interests, knowledge, & passions
  • Character traits & core values

You can then generalize and diversify how you make a living (i.e. make money several different ways and no longer depend on a single industry to support yourself) while also providing value to the world via a specialization unique to only you.

Once you learn how to tap into your hidden potential, you then have the freedom to become a Jack of all trades, master of ONE.

Here’s the problem…

We were neither trained nor educated properly to thrive as generalists. Navigating the world today is a complex game of 3-dimensional chess.

Yet we’ve been trained to navigate life like a game of Connect Four.


At best we’ve been trained as square pegs to fit into square holes…even when we know that deep inside we’re circles, triangles, trapezoids, parallelograms, and every other shape in between.

Thriving as a creative generalist in today’s freelance economy requires you to think beyond the next paycheck gig and instead become the CEO of your own life.

And thinking like a successful CEO means playing a game of chess with every aspect of your career.

  • You need a vision
  • You need goals (big & small)
  • You need a purpose
  • You need a strategy
  • You need to prioritize what’s truly important
  • You need clearly defined values (and boundaries)

And most importantly…

  • You need to believe that success is possible.

If you’re stuck in the gap between who you’re supposed to be and you you desperately want to be, I’m here to help you build the bridge that leads to the more balanced, sustainable, and fulfilling creative career that you deserve.

Stay tuned…

Next week I’ll be releasing a brand new 5-day email series to help you design your dream career and become the CEO of your own life, one small step at a time.

Imagine no longer relying solely on a single job (or even an entire industry) as your only means for survival but instead having the freedom to choose only the best projects you’re excited to work on. And the ability to pursue multiple skills, interests, & passions without feeling guilty they are “just a distraction.”

In order to help you optimize your true creative potential, I’ll be releasing a variety of educational resources throughout 2024 (and beyond) to help you:

  • Optimize Your Career Path
  • Optimize Your Network
  • Optimize Your Brand
  • Optimize Your Time (& Well-Being)
  • Optimize Your Finances

As the CEO of your own career, which area above do you need to optimize first? And why?

Zack Arnold (ACE) is an award-winning Hollywood film editor & producer (Cobra Kai, Empire, Burn Notice, Unsolved, Glee), a documentary director, father of 2, an American Ninja Warrior, and the creator of Optimize Yourself. He believes we all deserve to love what we do for a living...but not at the expense of our health, our relationships, or our sanity. He provides the education, motivation, and inspiration to help ambitious creative professionals DO better and BE better. “Doing” better means learning how to more effectively manage your time and creative energy so you can produce higher quality work in less time. “Being” better means doing all of the above while still prioritizing the most important people and passions in your life…all without burning out in the process. Click to download Zack’s “Ultimate Guide to Optimizing Your Creativity (And Avoiding Burnout).”