Creative Wayfinding For Ambitious Optimists.

How to Identify Your Keys to Victory (And How They’ll Accelerate Your Creative Success)

November, 13, 2021

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

As so often happens when picking up a new hobby, as I’ve gotten into playing tennis this year, I’ve also been watching a lot of tennis YouTube.

Lately, I’ve been binging through compilation videos of each of the “Big 3” of modern tennis: Roger Federer, Rafael Nadal, and Novak Djokovic, each of whom (depending on who you ask) might be considered the Greatest Of All Time when it comes to men’s tennis.

What’s struck me in watching each of these men play hours of tennis, is that while they’ve all ended up with near-identical career win-totals and legacies, the style of play they’ve each used to get there has been unique.

Federer, for example, beats opponents with his touch, finesse, and what seems to be an ability to read their minds and anticipate shots.

Nadal, on the other hand, wins by never giving up on a point, chasing down balls that should be impossible to catch, and then ripping otherworldly winning shots from ridiculous angles.

Djokovic, finally, simply wears his opponents down with his complete mix of power, precision, consistency, and pure athleticism.

Watching the differing styles of these three greats reminds me of a standard segment at the start of many sports broadcasts, the Keys To Victory.

In the segment, the commentators will outline the specific things each team or player needs to do in order to win.

Of course, the easy answer for most sports is to score more points than their opponents. But as with the Big 3 of tennis, every team or athlete has a unique game plan and style of play that will best allow them to win consistently.

Some highly skilled teams (like my hockey team, the Edmonton Oilers) might win by going all out on the offensive and scoring five or six or seven goals… even if they give up four in the process.

Others might win by playing a tight, disciplined, defensive game and then capitalizing on opponent mistakes.

Depending on the makeup of the team, or the physical, mental, and emotional makeup of the player, the Keys To Victory will differ.

The same is true for us as creators.

While we might not be aiming for the title “Greatest Of All Time” in our fields, each of us is working toward the same goal of building a successful (whatever that means to each of us) and sustainable creative career.

As with athletes and sports teams, while our end destinations may be similar, our personal Keys to Victory, which make up the shortest, most enjoyable, and most effective path to getting there differ for each of us.

Identifying Your Keys to Victory

Our personal Keys to Victory are typically processes-oriented activities that are dictated by many factors including our specific goals, skills, disposition, worldview, experience, values, and more.

More specifically, our Keys are based on how each of these traits intersects with and is interpreted by the audience we seek to serve.

You might be an exceptional writer, for example. But if your target audience isn’t interested in written content, creating an exquisite blog or newsletter is hardly one of your Keys to Victory.

In my experience, the best way to identify your personal Keys is to draw a simple graph and plot the activities that contribute to your work across two axes.

1. Other People’s Response

Before you draw your graph, set a timer for 5 minutes and brain dump a list of every audience-facing activity you’ve ever engaged in.

A short list of some of my personal activities might include:

  • Live video teaching & facilitation
  • Community organization & management
  • Blogging
  • Newsletter writing
  • Podcasting
  • YouTube video creation
  • 1:1 connection calls
  • Twitter
  • Facebook
  • Instagram
  • LinkedIn

Once your list is complete, plot each of those activities on the x-axis of the graph.

The far right edge of the graph represents activities that get an exceptional public response and the far left side is for the activities in which you get no–or perhaps even a negative–response.

Keep in mind that these placements are relative to your own experience, you’re not measuring your results against anyone else’s. A positive response for you might mean just two people reached out with positive feedback.

With that in mind, spread your activities out along the x-axis according to their response relative to one another, with at least one activity near each of the far right and far left edges.

2. Your Response

One of my favourite quotes about winning as a creator is from Khe Hy, the creator of Rad Reads who says, “It’s impossible to compete with someone who genuinely cares, and is having fun.”

Success at any strategy will require us to be consistent with it for years at a time. It’s much easier to be consistent with something we actually enjoy than something that drains us every time we sit down to do it.

With that in mind, the next step to completing your graph is to measure the activities you’ve listed based on your own response to it.

For each activity, ask yourself:

  • Do I enjoy love doing this or dread it?
  • Does it give me energy or drain it?
  • Do I have fun with it or is it a slog?

Based on your responses, move each activity on your graph vertically.

Tasks that are a net positive to you personally (ie. those that are fun, energy-giving, etc) should be placed in the upper half of the graph. Net negative tasks (ie. those that drain your energy, you dread doing, etc) should be placed in the lower half.

A completed graph of my own keys to victory would look something like this:

Interpreting Your Graph

With your activities plotted, you’ll find each of the activities you’ve listed falls into one of four quadrants.

Keys to Victory (Top-Right)

The top right quadrant of your completed graph should clearly show your Keys to Victory.

These are the activities that you both enjoy doing, and that get the most positive reaction from others and should be leaned into every chance you get.

As you can see from my graph, there’s a cluster of activities all related to live presentation or facilitation, either over video or audio. This is a good sign that I should be seeking out more opportunities that allow me to present live.

Pit of Despair (Bottom-Left)

Opposite the Keys to Victory, in the bottom left quadrant is the Pit of Despair, which should be avoided at all costs. Not only do these tasks not bring you any enjoyment, but they don’t garner any kind of positive response from your audience either.

Both the Pit of Despair and the Keys to Victory are pretty straightforward, the remaining quadrants, however, are where things get a bit more nuanced.

Watch & Develop (Top-Left)

The top left quadrant consists of activities you enjoy but your audience doesn’t really care about.

These can still be valuable creative outlets for you personally, and it’s entirely possible that you just haven’t put the reps in to start seeing real results. Often, over time, these activities can move to the right as you improve on them.

Regardless, it’s helpful to see plainly the tasks that aren’t currently adding up to tangible results so you can allocate your time accordingly.

Handle with Care (Bottom-Right)

The bottom right quadrant is perhaps the most interesting.

These are activities that get a good response from your audience but which you don’t necessarily enjoy doing yourself.

If you have a healthy selection of activities in your Keys to Victory quadrant, you might choose to ignore the activities in this quadrant altogether. If you don’t have many Keys to Victory, however, these activities can be useful short-term pursuits to help you grow your audience and get results.

Be warned, however: The fact that you’ve placed these activities in this quadrant means that they are inherently unsustainable.

You might choose to build a short-term strategy around any of them, but avoid any strategy that will require you to commit to it for the long term. This is a recipe for frustration, burnout, and resentment*, hence the title of this quadrant.

*Who me? No, I’m not speaking from experience at all…

Your Keys to Victory Are Fluid & Evolving

Regardless of how many Keys to Victory you’ve identified, remember that this graph is not the be-all, end-all.

While many of your Keys to Victory may continue to be effective throughout your life, others will change positions on your graph as your goals, target audiences, and interests change.

Correspondingly, you’ll also identify many new Keys to Victory as you grow, improve your skills, take on new projects, and evolve as a person.

The best (and perhaps only) way to identify new Keys to Victory is to try things out and see what sticks, both for your audience and for yourself. This is an essential phase in the life cycle of a creator and is where most would-be creators give up.

In the first few years, the most effective use of our time might just be experimenting with every type of tactic, strategy, and activity we can think of in order to give ourselves some baseline data with which to work.

Most of the things we try won’t work all that well for us.

The good news is we only really need to find a few things that do.

If you’re struggling to identify your Keys to Victory, push yourself to get outside your comfort zone and start experimenting with new methods of creating and promoting your work. Identifying your Keys is a numbers game.

Outward & Inward Facing Keys to Victory

It’s worth noting that while many of the Keys to Victory you identify will be outward-facing activities that involve (or are at least visible to) your audience, others may be strictly internal.

These Keys are the habits and activities that contribute to the outward-facing work, but aren’t in themselves visible.

Some of my personal inward-facing Keys to Victory are my daily walks, the content I choose to consume, the people I surround myself with, scheduling in time for reflection, and the systems I use to capture, organize and structure my ideas.

While they might not be outwardly visible, and may not always feel “productive”, I know from experience that each of them has a direct impact on every project I work on, and the work suffers when I neglect them.

If you’re a nerd like me, you might choose to draw up a second graph of these internal Keys to Victory.

Follow Your Game Plan

In most sports, the team or player that wins is often the one who’s able to dictate the style of game being played, forcing their opponent off of their preferred style of play.

Whether it’s Resistance, shiny objects, new tools, tactics, or strategies, we too face a world that is relentlessly attempting to pull us into playing the type of game it wants to play, rather than the one that best serves us.

Having a defined game plan, however, built around our specific Keys to Victory allows us to resist that temptation, block out the distractions, and focus on what we know works for us.

Knowing our Keys to Victory gives us confidence as we move through the fog that so often engulfs our creative work, that if we keep following the path we’ve defined, we’ll get where we’re seeking to go.

And more likely, somewhere unexpected, but even better.


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.

    If you're building something that matters, but aren't quite sure how to take the next step forward, I'd be honoured to have you join us.