Creative Wayfinding For Ambitious Optimists.

How Your Identity As A Creator Will Elevate or Undermine You

March, 5, 2022

🧭 This blog post is adapted from my Creative Wayfinding Newsletter.

Last week I shared this post outlining the advantages that come with embracing the mentality of an underdog.

I got a number of great messages in response from people who resonated strongly with the sentiment. That didn’t surprise me, as I think most of us here identify as underdogs, struggling for attention amid much larger, better-funded, better-staffed companies, publications, and creators.

What did surprise me, however, was one email I got from a long-time reader and PMA alumni, Kelle Sparta, in which she–point by point by point–flatly refuted my encouragement of embracing the underdog mentality.

What surprised me even more, however, was that I found myself agreeing wholeheartedly with every point she made.

While there are certainly benefits to embracing the mentality of the underdog–it takes a certain level of defiance and even audacity to create change with our creative work after all–Kelle’s email shed light on some of the problems associated with holding onto the underdog mentality too tightly and for too long.

So today, I want to share Kelle’s letter along with some further reflections on the identities we choose to adopt and put to work for us.

Kelle’s Letter

As someone who works with people on their identity, I am fluent in identity issues.

Here’s the problem with identifying as an underdog.

You are beginning from the assumption of you being “less than”.

You see the entire world as your enemy that you have to overcome.

You are assumed to be the loser and you have to overcome this assumption.

While people may root for you, they will bet on the other guy – giving him all the resources.

You are living in a state of lack all the time, fighting for scraps.

This sets up an assumption that you must fight for everything so that when things do come easily, you reject or distrust them. When help is offered, you turn it down.

There is an inherent assumption that you have to beat someone much bigger and stronger than you to be taken seriously.

The odds are always against you. (If they weren’t, you wouldn’t be the underdog.)

You’re constantly fighting for your place in the world. And this leaves you no space to be vulnerable and held, no place to be cared for.

Because this is your identity, you will always magnetize to you people to serve in the role of your Goliath.

This identity is a dominant/dominated roleplay with you always trying to be on top. This isn’t an evolved identity because to overcome and become the oppressor still leaves a winner and loser.

This is a Young Warrior identity.

Instead, consider the Spiritual Warrior identity where the only thing/person the overcome is yourself.

Where you start from believing in your right to take up space in your own life.

Where you are in competition with no one.

Where the only person you need to be better than is your former self – and even that isn’t required.

Where you are calm and in tune with yourself and the world around you.

Where you have no natural predators.

Where you are not choosing a winner and loser, but everyone gets to win.

Where there is always enough and you can manifest more whenever you need it.

Where you can share your true self and know that while you may be making yourself vulnerable, there are safe places in which to do that and that no one can hurt you without your permission.

There are energies associated with the identity you pick.

Choose wisely.

Mind Your Identity

I was immediately struck by the distinction between what Kelle described as the Young Warrior identity of the underdog and the Spiritual Warrior she describes in the second half.

The underdog can be a valuable identity to own early on in our creative careers. We can use it to help us prove our worth and skill (to ourselves as much as others) and to build up confidence.

But it’s always meant to be a way station en route to a more mature, evolved identity.

The underdog is scrappy, daring, and resourceful, all traits that are needed–perhaps in abundance–early on.

But while these traits may remain useful throughout our lives, as we mature as people and creators, we should aspire to rely more on our perspective, wisdom, and belief in the abundance of opportunities.

Personally, I feel myself currently existing somewhere between these two identities.

I’ve relied on (and benefited from) the underdog mentality to start and grow a successful creative business. But six years in, I’m beginning to realize the limits of just how far this mentality can take me.

For one, fighting for everything is exhausting and unsustainable.

As I’ve approached these limits, however, I’ve also begun to experience the benefits of (reluctantly at times) adopting the more ease- and abundance-focused mindset of Kelle’s Spiritual Warrior.

One of the great lessons for me of the past year is that the biggest gains we stand to make as creators come through self-understanding and mastery.

By looking inward instead of outward.

Doing so gives helps us understand the environments, projects, and commitments in which we thrive and those in which we don’t. This allows us to put ourselves in positions where success will come more naturally.

Similarly, self-awareness allows us to recognize that when we’re not getting the results we’re wanting, chances are, we ourselves are complicit in the problem.

This understanding then gives us the power to shift our posture, and thus our results.

Shift Your Stance to Shift Your Results

As I’ve become more self-assured in myself, my work, and the unique place it occupies in the world, opportunities have started to show up with surprising consistency, and of a scale beyond what I would have imagined a couple years ago.

Whereas I used to feel like I had to claw and fight for every scrap of progress, in relaxing my approach, things are flowing more easily with less effort.

On the one hand, there’s no doubt that my work is simply better now, both when it comes to this newsletter as well as my work in podcasting. With that in mind, perhaps it’s not surprising that more opportunities are showing up now.

But my stance around my work has also shifted significantly.

Whereas I used to be defensive and protective of my work, forever looking over my shoulder that someone was going to come along and steal my ideas or do a better job of executing on the same concept, I no longer worry about that.

I’ve realized that as long as I keep my gaze directed forward, and continue to put one foot in front of the other, there’s no possible threat of competition.

I’m walking my own path, and everyone else is walking theirs.

No one else can create in the way I do because they haven’t walked the same path to get here.

The only way to guarantee failure is to try and walk the same path as someone else.

An underdog mentality might be empowering (and even necessary) during a certain phase of our life cycle as creators.

But it pales in comparison to the more mature, evolved identity of standing tall, confident that we’re doing the work that no one else could possibly create. The work that will go uncreated if we choose not to pursue it.

Embodying this identity isn’t easy, however.

As an underdog, it’s hard to let go of the feeling that we always need to be working just to keep our heads above water, let alone get ahead.

The idea of competition is so ingrained into our culture that it’s hard to entertain, let alone embrace the idea that competition is optional, and that all we need to do is choose to approach our work that way.

Like so much of creative work, this process takes time.

In the meantime, I still believe there are distinct advantages to adopting and embracing the underdog mentality, especially when we’re first starting out.

But I also now believe that holding on to the identity for too long will keep us stuck.

So embrace the mentality of the underdog fully and fiercely for as long as it serves you.

But know that a time will come when that mentality that has served you well for so long will become a burden.

And when it does, don’t be afraid to shed it as you step into the new, more mature, more complete, more fully-formed version of yourself.


Explore how to navigate a creative life that matters

This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

It’s something I’m proud to create and I’d be honoured to share it with you.


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    Hi, I'm Jeremy, I'm glad you're here.

    No matter what you create, I'm guessing you spend a good amount of time feeling lost, hopeless, and unsure about how to get from where you are to where you want to be.

    So do I. And so does everyone doing creative work.

    This is the Creative Wilderness.

    Every week, I publish a new article in my Creative Wayfinding newsletter about how we as creators and marketers can navigate it with more clarity and confidence.

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