The 12 Challenges of Creative Giants

Do you have the vision to see how the world might be, the courage to act, and the capability to actually change the world?

Far better is it to dare mighty things, to win glorious triumphs, even though checked by failure … than to rank with those poor spirits who neither enjoy much nor suffer much, because they live in a gray twilight that knows neither victory nor defeat. — Theodore Roosevelt

Have you spent a lifetime being frustrated by people telling you that you should do just one thing rather than explore all of the different interests and talents you have?

Or perhaps you tire of people wondering why you prefer to stay home and read or work on something that matters rather than go out to clubs, bars, or the sports event du jour.

Or deep down, you have problems committing to doing something because you know you could do just about anything but are scared that you’re going to pick the wrong thing.

If so, you’re not alone. You’re probably a Creative Giant.

Creative Giants are naturally compassionate, creative people who have the vision to see how the world might be, the courage to take action, and the capability to actually change the world. These people aren’t just the black-beret-wearing artists that we might typically think of when we hear the word “creative”; they’re engineers, doctors, programmers, and scientists, as well as painters, musicians, designers, and writers. Actually, because they’re Renaissance people, they’re often both engineers AND musicians.

In fact, one of the distinguishing features is that they are AND people who get tired of trying to present themselves to a very limiting EITHER/OR world. It’s not that they’re trying to be difficult; it’s that they just don’t see the world that way or show up with an easy EITHER/OR label. They always need a few extra circles for whatever Venn diagrams people try to use to categorize them.

The aforementioned exasperation came from some questions that interviewers who weren’t Creative Giants would ask about you. “So, they’re people who are wanting to be more creative?”

Uhm, no. Being more creative is never a pain point for Creative Giants. Every breath comes with a new idea or two to figure out what to do with. Figuring out where to put the ideas and which ones to pursue is the challenge.

While not all Creative Giants are entrepreneurs — and there’s no need to buy into the pressure to be entrepreneurs — they’re almost always entrepreneurial because they’re always seeking ways to better use what’s in front of them to create more value. In organizations that employ them, they’re the intrapreneurs, linchpins, trust agents, or whatever term trends next year to describe the same thing.

Lastly, Creative Giants are usually reluctant and accidental leaders. They didn’t set out to be leaders but fell into it. Because they don’t see themselves as fitting “the leader archetype,” they discount the fact that a) they’re leading, b) there are many ways to be an effective leader, and c) most of the principles of leadership are learnable and practicable. I know, because I’ve been mentoring reluctant and accidental leaders for a little over 25 years. (I had an early start through youth leadership programs and continued in Boy Scouts and military training.)

The Creative Giant’s Challenges

In my mind, the best way to understand who Creative Giants are is to talk about their challenges and the way their creativity, intelligence, compassion, and personal power generate tensions and polarities. I’ll list the major challenges, which will help me explain where the “Giant” part comes from later on:

  1. They can do just about anything they set their minds to. They’re scared they’re going to pick the wrong thing.
  2. They chronically overcommit because people turn to them for a lot of help or to see projects through and because most things are easy for them to do. They forget the cumulative costs of small commitments, and they often forget that everything takes longer than they think it will.
  3. They half-finish projects because they’ve worked out the puzzles or adventures before finishing them. The projects have thus lost their appeal, and Creative Giants have other commitments to attend to. (See #2 above.)
  4. Their compassion gets in the way of their personal power. They suck at receiving, they undervalue themselves so that others can afford them or don’t feel small, they can’t “win” because that means other people lose, they can’t “move on” because they’d have to leave someone behind, etc. They spend an inordinate amount of time either hiding their power or throttling it so that they can play nicely with others.
  5. They learn and grow quickly, so relationships are hard for them to maintain. Even when they have the patience for people who aren’t continually expanding, they still don’t understand why people wouldn’t want to grow.
  6. Because they are socially adaptable, they often struggle with keeping to their core. They adopt worldviews quickly and sometimes forget that someone else’s worldview isn’t their own.
  7. Success is an ever-evolving thing for them. They accomplish things that other people could only dream of, but it’s not enough for them because they know they could do more or they know what they could’ve done better if they’d had more time. They’re great builders of never-ending ladders.
  8. They crave simplicity at the same time that they reject it. Their native creativity and intelligence thrive on the tension of complexity and novelty, oftentimes obscuring their experiential knowledge (wisdom) that simplicity, structure, flow, and sufficiency form the broad, plain path that enables them to thrive.
  9. They’ve created conceptual tension between strategy and compassion and often don’t see that being better in the world means that they can better serve and lead others.
  10. Busy, accomplished people always get more responsibility than everyone else, so it’s easy for them to be overwhelmed. An evergreen problem is that they have more demands on them than they have the capacity to meet, and every time they satisfy one more demand, another one or two are placed on them.
  11. They have a chronic problem with over-delivering. Good enough is never good enough, especially if someone has paid them to do something.
  12. Cultivating their physical health has to be an intentional practice that they remain vigilant about because they work with their minds. Because they often get pulled into travel, extended projects, or caregiver roles that disrupt their routines, they easily fall off the exercise wagon.

If you’re reading that list and thinking that everyone has those problems, I have two things to tell you: a) you’re wrong and b) you’re a Creative Giant. Welcome to the club. Coffee is in the back, the bathroom is down the hall, and we’ve been meaning to get equipment in the fitness center for a few years now.

Why “Giant”?

I recognize my limits but when I look around I realise I am not living exactly in a world of giants. — Giulio Andreotti

Now, about the “Giant” part. That really comes from items 4 and 5 above, and the term addresses a recurring pattern I’ve seen for years in conversations with my clients, colleagues, friends, co-mentors, and mentors. In private conversations and in workshops, I talk a lot about superheroes because the metaphor provides such a rich and clear lens for the stories we can tell ourselves, AND the superhero is a concept that female Creative Giants have had a harder time getting into, so I started looking for more accessible language.

What so many of my conversation partners were describing was the feeling of having to tiptoe around people lest they end up triggering, hurting, or enchanting them. It’s as if they were giants having to pretend to be normal people so that they didn’t step on others, scare them, or awe them. Additionally, Creative Giants are just as often introverts as they are extroverts, so while they might not actively smallify themselves, their gianthood is still not readily apparent. Until you get them talking. (I’m thinking of Chris Garrett here, who’s a known Creative Giant and one of those guys I can never hear enough from.)

To add further insult to a long life of injuries, Creative Giants who show up to events and conferences that put on a big show often find themselves sorely disappointed but unable to really talk about it. While everyone else is having a great time and/or having their minds blown, the Creative Giants are trying to figure out a) how not to show their internal discomfort, b) what’s wrong with them that they’re not getting it, c) whether to cut their losses and leave or hold out for that “one idea” that may be a game-changer for them, and d) how to find other Creative Giants so the trip isn’t a bust. Yes, they’re doing that all at once. (It’s for this reason that I tell Creative Giants to decide whether the conference or event is worth it if all they do is meet a handful or two of people they click with or want to finally meet; if not, pass.)

The other reason that they’re giants, though, is that they really are powerful. As I’ve mentioned in Foundations Are to Be Built Upon, Not to Be Flown Over, this is also a perennial downfall for them: they can do so much without trying hard that they simply don’t cultivate self-mastery skills.

I’ll pause here, though, because the story about your personal power is the story you want to and like to hear. The story you don’t want to hear and be held accountable to is the one that says you’re scared of being the best version of you and that you should dial it back so you don’t have to deal with the social fallout of revealing your gianthood. Mediocrity is safe for you because your mediocre level of results and performance is at the level of very good for other people. Let’s move past those easy A-minuses.

Marianne Williamson said it best:

Your playing small does not serve the world. There is nothing enlightened about shrinking so that other people won’t feel insecure about you.

Standing Tall

I used the term “Giants” behind the scenes for years before I used it publicly. I didn’t want to share it because I was afraid you’d hate the name. I got it, Team PF got it, everyone I’ve talked to about it got it, but still, there was a fear that it’d be yet another name or concept that wouldn’t stick.

I’ll also not sidestep the truth that showing you who you are also means showing you who I am. Those 12 challenges I listed above? I struggle with them, too. I’m a lot better with some than with others, but I’m here in the trenches with you.

Over the years, many of you have sent me personal notes about how much you’ve appreciated what I’ve written. I’ve also gotten a few “I’m glad you wrote that but I’m a little mad at you for pointing it out” notes. I’ll take a little bit of groaning from you if the end result is your standing a little taller and feeling truly seen. I’ll tell you the same thing I told my troops: you may not always like me, but we will succeed and I will do my best to take care of you.

It’s the tension of “doing my best to take care of you” that compelled me to share this and that continues to get me up in the morning. I know there’s a part of you that won’t like the “Giant” bit. I know why that part is there: the superficial elitism of the label, your self-criticism, your seeing that you’re not the “expert” or authority, and so on. I could dance around the idea for the next few years. I could dance around your gianthood indefinitely without ever directly holding up the mirror so that you see what I see and what the world would see.

But I don’t think that’s the best I can do to take care of you. I can’t encourage you to move past that A- if I’m not going to do it myself. I can’t really encourage you to Stand Tall if I’m not doing it myself. I don’t want you to get by just on your raw power and I don’t want you to excel at a game that doesn’t tap into the best of who you are and what you can truly do when you play the game that fits you.

I want you to stand taller so you can step bigger.

And as I said above, I intend on standing taller with you. My goal is to prototype and ship sooner and faster than I have in the past. Rather than spend a year figuring it out on my own, I’m showing more rough sketches, prototypes, and outlines to the people I’m building them for and doing this three or four months earlier than I have in the past. It’s awkward to not have it all figured out, but, anymore, it’s more uncomfortable to leave the people I care about hanging. I’m leaning into the former discomfort, which means that some things might not work. I’m okay with that — I trust that you’d rather have roughs that work sooner rather than later and that the cream will rise to the top.

Let’s stand tall, together.


This post was also recorded as an episode for the Productive Flourishing podcast (listen below!). Hear more episodes and subscribe on iTunes here.


Charlie Gilkey is an author, business advisor, and podcaster who teaches people how to start finishing what matters most. Click here to get more tools that’ll help you be a productive, flourishing co-creator of a better tomorrow.