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.
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Commit to the Pour (Or Commit to Failure)
Chances are, you’ve at some point encountered a scenario where you’ve poured too much liquid into a cup and needed to find a way to get it back into the bottle.
If you were lucky, it was water from a wide-mouthed bottle that you could easily transfer back.
If you weren’t so lucky, it was 60-year-old Macallan single-malt scotch whisky, each teaspoon of which is worth more than $13,000.
Regardless of the stakes, you probably considered two options of how to proceed:
- Hold the lip of the cup right up against the mouth of the bottle and tilt slowly and steadily.
- Hold the cup above the mouth of the bottle, decisively commit to the pour, and hope to direct the thin, focused stream back through the narrow opening of the bottle.
At first glance, the second option feels unnecessarily risky.
With the first, more cautious approach, we have the security of knowing we can pull back on our the pour at any time and limit our losses.
By tilting the cup far enough to produce a focused stream of liquid, on the other hand, we’re committing to losing a significant amount of our overall store should our aim be off.
And yet, if you’ve attempted each of these approaches yourself, you’ve probably realized your instinct to take the cautious approach was wrong.
That more often than not, the timid, measured approach often results in more liquid dribbling down the side of the cup than actually ending up in the bottle.
If you’re like me, you’ve experienced this situation enough times to know better.
And yet we often continue to make the cautious, timid approach to our own detriment, time and time again.
The problem, I think, is the level of transparency of the risk involved with each approach.
The risk of committing to the pour is immediately obvious.
The risk of the timid approach, on the other hand, is obscured by an illusion of control and safety.
And so we consistently opt for the option with the veneer of safety rather than the option that’s actually more likely to give us the outcome we’re hoping for.
Minimum Viable Commitment
This flawed approach to decision-making plays out well beyond attempting to transfer liquid from one vessel to another.
In fact, it shows up in almost any decision that revolves around committing our time, energy, and resources.
In our creative work, this most often plays out in how we approach our marketing strategies.
Whether it’s starting a new content channel like a newsletter, YouTube channel, or podcast, or experimenting with a new social platform, we tend to go in with a “test and assess” mentality before committing fully.
This approach makes sense.
With so many potential options available to us, we want to make sure we’re investing our time and resources wisely. We want to see some proof of our effort in order to justify our continued investment.
The problem is that with many endeavours, it’s almost impossible to see any positive result without fully committing to the process.
Content marketing is a perfect example.
There’s almost zero chance that you’ll see a meaningful return on your investment before publishing 50 or 100 videos, podcast episodes, or newsletter issues.
Similarly, there’s almost zero chance you’ll have any success on a given social platform without showing up meaningfully on a consistent basis for 3–6 months.
Upfront commitment, it turns out—without any proof or promise of future results—is often a prerequisite for the results we’re chasing.
In other words, we have to commit to the pour first, and then do our best to direct that stream of energy and effort toward our desired result.
How to Know Where to Commit Your Resources
Of course, we all have a limited amount of time and energy available.
Which means committing ourselves fully to one area will leave us unable to commit to others.
So how do we choose where and when to commit to the pour when we can’t base our decision on results?
I think there are two considerations.
1. Confidence In Your Ability to Hit the Target
If a given project or practice requires more than we suspect we have the ability or bandwidth to fully commit to–financially, energetically, or otherwise—we’re better off avoiding it.
That might mean intentionally choosing an alternative with lower potential upside, but which we have more confidence in our ability to attain.
A podcast has much lower discoverability potential than YouTube, for example. But if creating a sufficiently high-quality podcast to be seen as legitimate by your audience would take you half as long and cost half as much as achieving the same standard on YouTube, it’s likely a better option.
2. Self-Knowledge, -Awareness & Intuition
While dabbling in a practice might not be enough to get you meaningful results, it’s often enough to light the spark of curiosity and excitement in you as a creator.
That spark is as good a sign as any of a practice worth committing to.
This is because in many cases, the length of commitment required to get the results we’re after demands that we actually enjoy the practice we’ve committed to if we have any hope of keeping it up in the absence of meaningful results in the short term.
A good approach, then, is to dabble just enough to identify the spark of a delicious challenge we’re excited to sink our teeth into.
Then, once we find it, commit to the pour fully, and without hesitation.
All Or Nothing
Results have a way of coming to those willing to commit with no guarantee that their effort will amount to anything.
On the surface, choosing to commit in this manner feels irrational, if not outright irresponsible.
When you commit to the pour, after all, there’s no way back.
No way to recover the expenditure of time, money, and energy we’ve now put forth.
But perhaps recovery shouldn’t be a consideration in the first place.
If we’re truly willing to commit the resources required to achieve an outcome, we should commit them upfront, without caveat or safeguard, and then do what we can to focus and direct them to our intended target.
Directing the pour accurately requires confidence, faith, a steady hand, and often a little luck.
Occasionally, we’ll miss the mark and spill those resources out across the floor.
But in the end, it’s better to suffer the occasional wasted effort while making an honest, committed attempt than to slowly and consistently let our time, energy and effort dribble down the side of the cup, never giving ourselves a real shot at success.
It’s mildly annoying to let water run down the side of the cup and into the sink.
Heart-breaking to do the same for a $1.9M bottle of whisky.
But I can think of nothing more agonizing than letting a life dribble away because we were afraid to ever commit it fully to a goal worth pursuing.
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.
Subscribe
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Do It To Do It
Don’t do it for the success.
Don’t do it because it could be your ticket to fame and fortune.
Instead,
Do it for the experience.
Because once you’ve done it once, you can do it better the next time.
Or because the experience itself was worth it, even if you never do it again.
Do it because maybe you’ll realize that it’s not what you really wanted in the first place.
That it won’t take you where you want to go.
That there’s a better route to your destination.
Do it because regardless of the outcome, you’ll learn something.
About your craft.
About the world.
About your audience.
About yourself.
Do it because it helps someone or something in some small, little way.
Do it because it matters.
To you.
And if you’re lucky, it will matter to someone else too.
Questions To Ask Before Starting a New Project
It’s tempting to jump into a new project the moment you feel inspiration strike and the excitement in running hot. After all, it’s not hard to be excited when you only have a vague idea of what’s really going to be involved.
But before starting down a path that will take you away from your current priorities, it’s worth asking yourself some questions about the project.
What does success look like?
So often we take on work without knowing what the end result we’re really working toward is. Without having thought through what success to us really looks like, we might succeed in building a product or business that we don’t actually want to be involved with.
Ask yourself what success looks like for you with this project, and set your compass accordingly.
What are the challenges on the way to success?
There are two types of challenges that you’ll face with any project: Those you can see from the start and plan for, and the unexpected variety that you have to adapt to in the moment.
You can save yourself time and stress later by deciding upfront whether or not those challenges are challenges you want to face, and if so, how you’ll address them when they show up.
What skills are required to succeed?
You might have all the skills required to get started on the project, but those likely aren’t all the skill required to see it through.
What skills or tools are you going to need to acquire to see this project through?
Who do I need to get involved in order to succeed?
Some projects are possible to see through entirely on your own. More often, however, you’re going to need to bring on help.
Maybe it’s hiring a freelance designer, bringing on a VA or even building up an entire team around yourself.
Maybe it’s finding the right partner to help bring the idea to life.
Or maybe it’s not about splitting the labour but about mentorship, guidance, support or accountability.
Regardless, know who you’re going to need and when you’re going to need them so you can keep a lookout for potential fits.
How long will it take to achieve the result?
One of the biggest reasons we quit projects is that we don’t realize going in how long it will take to achieve our end goal.
And so, when the excitement wears off and we realize that it’s going to take years of consistent, mundane work to see the project to fruition, we cut our losses to pursue something we’d rather be doing.
At some point, the fun is going to wear off on every project, and what’s required in order to achieve success is no longer creativity and innovation but labour, consistency and implementation.
It’s worth knowing what you’re signing up for from the start and deciding whether it’s a commitment you’re willing to make.
Will the work make me feel good?
Some projects may be enticing in every other way, but if the work required doesn’t make you feel good, may be worth passing on.
Maybe the path to success involves sweatshop labour, or multi-level marketing, or marketing something you don’t truly believe in.
Or maybe it involves you spending more time on social media or sales calls than you feel is optimal for you.
Just because a project could work, doesn’t mean it’s a good fit for you.
Can I keep this up?
Once you’ve taken stock of your answers to the previous questions, ask yourself honestly if you can keep up the activities required to achieve success over your projected timeframe.
Maybe your plan requires you to produce a weekly podcast, video or long-form blog post. Can you keep that up for the years it might take to reach your goal?
Maybe it requires you to have 25 sales calls a week. Can you keep that up?
Maybe it requires you to spend 200 days per year on the road. Can you keep that up?
So often, we think about what’s required in the short term. We don’t realize, however, that the hard thing about producing content, having sales calls or traveling for work isn’t doing them once, but doing them consistently again and again and again, well past the time when the novelty has worn off.
Think of a five-pound dumbbell. No doubt, you could easily curl it once, maybe even ten, twenty, or fifty times. Keep curling, however, and sooner or later, no matter how strong you are, even that tiny amount of weight becomes impossible to lift.
Know what size barbell you’re going to be required to lift going in, and decide how long you can keep it up.
Who else is doing this already?
Someone else is doing the same thing you’re planning to do already. They may not be in the same niche, they may not be following the same plan, they may not have the same end goal in mind, but there is someone (probably many someones) doing similar work already.
You need to know who they are.
I know, it’s easy to psych yourself out by looking at someone further along than you, but there are three reasons to seek out others doing the same thing you plan on doing.
- Oftentimes, the only reason we get excited about a project is because we think it’s never been done before.
When we realize that there are other people doing it already, we magically realize that we actually don’t have all that much interest in it and we can save ourselves some time and heartache.
- You can gather a lot of useful information about how to approach the project from looking at how others are already working through the challenges.
This doesn’t mean that you need to follow the exact roadmap they’ve laid out, but it can get you out of your own head and open your eyes to alternative methods, marketing methods, pricing models, and more.
- If your project involves you actively competing against other similar creators or businesses, this research is necessary to help you position and differentiate yourself in a compelling way.
Without knowing what others are doing and what their value propositions are, it’s hard to position yourself as a better alternative for a select group of people.
Decision Time
Once you’ve answered the above questions (and any others you choose to throw in yourself) you have a choice to make.
There’s nothing wrong with realizing that this project isn’t actually a fit for where you want to be spending your time and attention. There are enough shiny objects and ideas bombarding us on a daily basis that you should be saying “no” to most projects.
If, however, you’ve interrogated yourself and your idea and are still excited to dive in, you’re ready to dive in, confident that you know what you’re getting into, and have done everything you can to prepare for the journey ahead.
I’ve created a project dashboard template in Notion that walks me through many of these questions before I start any project. If you’re interested in getting your own, you can snag the template for yourself here.
Where You Need To Be
We’d all like to jump ahead.
To skip the journey and arrive at our destination
Unscathed by the heartbreaks, defeats, and failures we know to be inevitable along the way.
Sometimes we feel we deserve to be there already.
That we’ve put in all the work that should be expected of us,
Made all the sacrifices that could be asked of us,
That after all we’ve done, we should be somewhere other than where we are.
It’s a wonderful lie to tell ourselves.
A lie that lets us off the hook.
That almost allows us to believe we can move forward without confronting the thing we know we must confront.
The truth is that we’re already exactly where we need to be.
That we’ll remain where we are
Until we’ve learned and embodied the lesson available to us here.
It may be painful.
It may take hundreds of attempts and failures.
Or it may come in a single simple aha moment.
Regardless of the method, the lesson must be learned.
Dream and plan for the future.
But live and learn in the present.
You’re already right where you need to be.
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.
What Are You Measuring?
“What gets measured gets managed,” goes the saying.
But often, it doesn’t end there.
It also gets prioritized, optimized for, and sometimes even chased blindly.
For better or worse, what you choose to measure dictates your focus, your choices, and your actions.
This can lead to unintended side effects.
When shareholder value is the only metric that gets tracked, is it any surprise that people, communities, and the environment are negatively impacted?
Likely, that negative impact goes entirely unnoticed by the company that isn’t measuring those metrics.
It’s no wonder we often default to measuring the metrics we do.
Revenue, page views, downloads, followers, and likes all have nice, round easily trackable numbers attached to them, by which we can measure our performance against others or ourselves.
In fact, the fact that these metrics are prominently displayed in the tools we use suggests to us that we should be tracking them.
That these are the numbers by which we should be judging our success or failure as creators, business owners, and humans.
In reality, we can choose to measure our success and failure by any number of variables.
And the variables we choose to measure will dictate the experience of our work, for everyone who engages with it.
The good news is that we can choose to change what we’re measuring at any time.
And when we do this, our measurements act as a trim tab that will bring the ship around and point us in the direction we wish to be moving.
Creativity & Coral Reefs Both Need This to Flourish
I’m a systems nerd.
Not a “everything must be in precisely the right place, happen at precisely the right time, in precisely the right way” kind of nerd, mind you.
No, I’m more of a “build and tweak systems ad infinitum as a way to procrastinate on other work” kind of nerd.
As far as forms of procrastination go, systems-tweaking must surely rank among the best.
This highly-biased personal assessment is based primarily on the unique and wonderful way in which working on systems can grant a deep-seated feeling of productivity… while entirely avoiding moving the needle on the real work that needs to be done.
When it comes to procrastination, that’s pretty much the dream, right?
Of course I know that while I might tell myself I’m being responsible and productive when working on systems, I’m really in avoidance mode. My version of avoidance happens to be accompanied by a positive outcome, but it’s avoidance nonetheless.
Sometimes I procrastinate on client work or admin.
But most of the time, the work I’m avoiding is the difficult, uncertain creative work that goes into advancing my own creative projects.
If I had to guess, I’d say you probably spend a good deal of time avoiding this type of work yourself.
The irony, of course, is that this is the work most of us spend our days wishing we could do more of.
While we might be bogged down in client work or day jobs right now, we convince ourselves that if we work just a little harder, for just a little longer, we’ll reach a point where we can dedicate more time to the creative work we love.
Then, in those rare moments when the time does open up, we do almost everything in our power to avoid it.
There are a number of reasons we might struggle to take action when it comes to our creative work including many of the usual suspects you’ve likely heard before.
Fear of failure, fear of success, fear of disappointing others, fear of disappointing ourselves, fear of being found out as a fraud… the list of fears is long indeed.
But I think the biggest reason for our avoidance is more practical, mundane even.
We simply don’t know where to start.
Whether we’re working on a book, podcast, product, website redesign, or any other creative project, the starting point is almost some form of a blank page.
As you’ve probably experienced, blank pages are far from conducive for sparking creative work.
Fortunately, there’s an incredibly simple solution to bypassing this particular obstacle, and with it, much of the time we spend avoiding the work to be done.
The solution?
Don’t start from a blank page.
Creative work, it turns out, is like a coral reef. The raw materials are constantly floating around in the ether, but require a frame to attach themselves to before they can flourish and propagate.
Knowing this, our job becomes not to fill the blank page facing us with a fully-formed, coherent idea. Instead, it’s to create a structure around which our ideas can attach and organize themselves.
It just so happens that while systems can be a convenient distraction from doing the work itself, they can also provide us with this structure for each new idea we develop.
Systematizing Your Creative Structure
Over the past couple of years I’ve spent a significant amount of time building out my personal life and business operating system in Notion.
If I was a systems nerd before, Notion and the opportunities it presents have turned me into a full-on fanatic.
One of the aspects I continue to spend the most time on is building out and tweaking templates.
Pretty much anything I do more than once has a template associated with it, and if it doesn’t yet, you better believe that before long, it will.
Initially, my templates were productivity-oriented, designed only to help me save time. But I’ve increasingly been focusing on building creativity-oriented templates which provide the initial structure for ideas and projects to build off of.
Take the podcast episode templates from my old show for example.
Instead of a simple list of tasks, the templates include a series of prompts like:
- Why does this topic matter to my audience?
- What are the common cliches to avoid?
- What’s unique about this guest’s story or approach compared to other similar people?
- Why do I resonate with this topic/guest?
- What’s the one thing I want people to take away from this episode?
- Act 1/2/3 themes
- And more…
These prompts not only inform the direction of the episode content and interview questions, they also help me ensure that the episode is worth creating in the first place.
They also ensure that I’m never faced with a blank page when starting to work on a new episode. If I can’t easily answer a single one of the prompts, that’s a signal that I shouldn’t be working on the episode in the first place.
But podcast templates are just the start.
In addition to the podcast templates, I’ve created templates for blog posts, meetings, workshops, and maybe most importantly large, long-term projects, especially those involving a paid offer.
Much like the podcast episode templates, my project templates contain a series of prompts that helps me define the project, both for myself and my audience while guiding me through the process of building out the list of actionable next steps.
Over time (usually as a form of procrastination), I’ve tweaked these templates to add structure to the specific places I know that I personally get stuck when starting a new project.
The result is that I’m now able to map out the important parts of a new project in 30 minutes and have a concrete, tangible path forward.
Compared to how I used to approach projects, this feels like a superpower.
And it’s a superpower that’s accessible to all of us.
By taking note of where we typically get stuck in our creative work, we can build structures to help us avoid those roadblocks, and, like an artificially seeded reef, give our ideas something to latch onto and build around.
Having these structures ready and waiting to be deployed can save us hours, days, weeks, or even years when it comes to developing our ideas.
Creative Coral Comes In Many Shapes & Sizes
While the beginning of a new project is rife with opportunity for distraction and procrastination, most of the time we spend creatively stuck comes later.
Most often, we find ourselves stuck in the middle of projects or in our ongoing day-to-day creative work.
We get stuck writing blog posts, stuck recording podcasts or YouTube videos, stuck with the small stuff as much as the large.
What’s more, we regularly find ourselves stuck in situations we’ve never encountered before, problems for which we have no template to simply fill in the blanks and work through.
While we might not have the specific blueprints, however, approaching these challenges from a structure-first mentality can help us design those structures on the fly to help us work through all kinds of creative roadblocks big and small, familiar and novel.
Structure + Space = Magic
So much of the challenge of doing creative work is the time we spent stumbling around in the dark, searching for the boundaries of the space in which we’re attempting to create.
What we often forget is that we can create those boundaries ourselves.
And we need to.
While open space allows room for possibility, it’s the structure that provide something solid against which we can both latch onto and push off from.
As such, the structure and the boundaries are just as essential to creativity as the space.
A well-built structure gives us a frame in which to focus our ideas, as well as enough space for serendipity, inspiration, and iteration to work their magic.
The next time you find yourself struggling and frustrated with your attempts to channel that swirly sea of creativity into something solid, stop.
Shift your attention from the ethereal and shapeless to the concrete, the raw materials that are easily grasped and assembled.
Much like it’s easier to pour water into an existing bottle instead of building a bottle around the water, the surest path to producing creative work is to first build the structure and then fill it.
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
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 wilderness of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
Better Is Better
We often resist investing in improving our skills because the promised change feels too insignificant.
We could take a course on web design, or copywriting, or Facebook Ads, or any of a hundred other skills that we know would benefit us, both in the short and long term.
But we also know that even after taking the course we’ll be far from mastery of the skill.
To develop the level of mastery that we feel would be truly helpful to us would take many courses, months, or years of study, with a lot of practice along the way.
And so we do nothing, opting for the status quo, telling ourselves we’ll just hire someone who’s already mastered the skill when we need the task in question done.
What we miss is that no matter how small the improvement, better is better.
That even if we can’t charge a client $20k (or $2k, or $200) for a sales page after taking an intro copywriting course, improving our skill is still better than not improving it.
That improvement isn’t just about the skill we’ve chosen to level up, but how that improvement impacts the rest of what we do.
That even if the skill goes entirely unused, we’re still in a better place for having developed it.
There are few big wins, few opportunities to learn one new skill that changes everything for us in a matter of days or weeks.
Far more potent than a few big wins, however, is a series of small wins, consistently strung together over time.
Leveling up, bit by bit by bit, the progress is almost imperceptible until we look back and recognize how far we’ve come.
Even if it doesn’t feel like it in the moment, better is better.
And it’s hard to go wrong pursuing any version of it.
Abstract Learning Requires Abstract Teachers
It’s hard to argue that continual learning is a bad thing.
The relentless pursuit of heaping more onto our ever-growing mountain of knowledge is a core part of today’s entrepreneurial culture.
And if we want to follow in the footsteps of those who have come before, learning from their successes and failures is a good place to start.
But what if we don’t want to follow in their footsteps?
What if we seek a different path?
Not business as usual, but business unusual?
Yes, we need to learn.
But maybe even more important, we need to unlearn.
Unlearn art.
Unlearn business.
Unlearn marketing.
Unlearn what success is supposed to look like in the first place.
Unlearn our beliefs around our potential to create impact in the world.
Unlearn what it means to create work that matters.
It turns out that not all learning builds on itself.
That sometimes the way forward requires us to turn around and walk away from what we thought was our goal.
Back down the path we’ve spent years walking to find that side spur stretching off into the wilderness.
There are fewer guides on this path, fewer teachers.
And they don’t look like the ones we’re used to.
They don’t appear in our newsfeeds with webinars, masterclasses, or 5-day quick-win challenges.
More likely we find them through whispered word of mouth.
A secret too exciting to be kept to oneself.
Rather than give us the answers they challenge us with questions.
Questions we may have never considered.
Questions that don’t feel like they should have anything to do with the work we create.
Questions that force us into uncomfortable territory, confronting the parts of ourselves we’d rather not look at.
The further we walk down this path, the more we come to understand that these teachers are all around us.
In overheard conversations, the coffee shop down the street, the birds on breeze, the tree shrugging off its coat in the autumn and being reborn in the spring.
These teachers are slow, reticent, timeless, true.
And full of boundless wisdom.
In the end, these are the only teachers we need.
Where Does the Time Go?
How many times have you made it to the end of the week and asked the question?
You’ve worked exceedingly long hours on tasks that felt important in the moment.
In hindsight, however, they appear to have been spent merely bailing water.
When it comes to the things that matter, the needle remains unmoved.
So where to start?
What can we do when every task feels both urgent and important?
When we alone are capable of completing them?
When they overwhelm and crowd out the work that truly sets our soul on fire?
The work we know we’re capable of.
The work that has the potential to change things.
The wrong answer is to work harder.
This is not a season that will pass by continuing our current approach.
Change requires intentional action.
Intentional action requires awareness and ownership of the problem and its roots.
So first, reassess the situation.
Start by committing to tracking your time and assessing it at the end of each week.
Ask yourself:
- Which of these tasks are high-value and which are low?
- Which, with a little bit of guidance could be handed off to someone else?
- How much time would that save each week?
If you’re like me, you might be shocked at the result.
As of my most recent weekly time audit, I’m spending 8+ hours per week on tasks better performed by someone else.
This after working relentlessly over the past two years to build a team and outsource the tasks that keep me from my more important work.
What’s your number?
How many hours a week are you spending on tasks that are keeping from doing the work that really matters?
And what action can you take today to begin to shift the tide?
Seek Change
Too often we end up creating only as a reflex.
We have to fill that space on our content calendar with something after all.
So we create with the end goal of filling that space.
We maintain our production streak while failing to say anything worth saying.
So if content production for content production’s sake isn’t what we’re shooting for, what is?
At its core, our work should be created to achieve one purpose.
Change.
If we seek to create work that matters, our goal with each piece of content, each product, each creative endeavor is to create change in some way.
Even if only for one person.
Even if only in the smallest of ways.
Work that matters changes things.
Perspectives, beliefs, mindsets, moods, systems, processes, practices, relationships.
These are all good places to start seeking change.
So the next time you find yourself staring at a blank spot on your content calendar, instead of publishing for the sake of it, ask yourself, “What’s the smallest amount of change I can make with this content?
There’s too much that needs changing in the world to waste a podcast, blog post, tweet, or Instagram post not working to shift it.
What’s Worth Talking About?
Any business or creative endeavor that grows does so because people talk about it.
Which means there needs to be some aspect of your work that is worth talking about.
The challenge is that things worth talking about are those aspects of your work that exceed existing expectations.
Delivering high-quality work on schedule and on budget isn’t going to cut it.
That’s expected.
In fact, getting people talking about your work itself might be the very hardest way to get them talking of all.
Anyone engaging with you has already set their expectations based on your existing body of work.
The bar has been set. And while you’re likely capable of meeting, and even exceeding that bar, at least a bit, that’s not enough.
Work that is truly worth talking about is extraordinary. Transcendent. Expectation-defying.
Sure, it’s possible, but few manage to get there once, let along consistently.
Luckily, there are other ways to get people talking.
While the work itself might be the most obvious element of what you deliver – it is, after all, what people are paying for, in either money or attention – it’s not the only element.
Perhaps equally as important as your defined deliverables is the experience people have when they engage with you.
This experience is made up of your process, your organization, your ability to communicate.
Maybe most important of all, it’s your ability to make people feel seen, heard, and understood.
This experience isn’t easy to create.
It’s not an item to be checked off your to-do list once, but an ongoing process that requires continual time, attention, and effort.
But while expectations may be high for your work itself, expectations about the experience of engaging with you are often low or non-existent.
Which makes it much easier to create an experience worth talking about.
You might tell anyone who will listen about your favourite podcast, even if they’re not interested in the topic itself.
It’s not the information on the show that gets you talking, however.
More likely, it’s the experience, and the community the host creates for and with her listeners.
Similarly, you might gush about a web design agency long before your new website is even finished if the process and experience are worth talking about.
Zappos is legendary for growing not because of its product – shoes that could be found at any number of outlets – but because of its customer service.
That service defied expectations of what shopping on an online marketplace could be like and as a result, was worth talking about.
Your work still needs to deliver. That’s a non-negotiable.
But it’s also just the foundation.
Which means you need to decide, if not your work itself, what’s worth talking about?
Creative Wayfinding For Ambitious Optimists.
Say Something Small
Don’t feel like you need to say something that changes the world.
Few ever utter such words.
And yet we feel like if we can’t say something profound we’re better off saying nothing at all.
But this is not our only option.
We can aim to simply say something small.
Something intimate.
Something that means a lot to only a few.
Maybe only to one.
There’s power in small sayings spoken to a select few.
Start there.
Get good at speaking small.
It’s not about reaching everyone at once.
It’s about planting a seed that gets spread, person to person, ear to ear.
Further and faster, more intimately and personally than you could do yourself.
All big ideas start as small talk between friends.
Do It To Do It
Don’t do it for the success.
Don’t do it because it could be your ticket to fame and fortune.
Instead,
Do it for the experience.
Because once you’ve done it once, you can do it better the next time.
Or because the experience itself was worth it, even if you never do it again.
Do it because maybe you’ll realize that it’s not what you really wanted in the first place.
That it won’t take you where you want to go.
That there’s a better route to your destination.
Do it because regardless of the outcome, you’ll learn something.
About your craft.
About the world.
About your audience.
About yourself.
Do it because it helps someone or something in some small, little way.
Do it because it matters.
To you.
And if you’re lucky, it will matter to someone else too.
Questions To Ask Before Starting a New Project
It’s tempting to jump into a new project the moment you feel inspiration strike and the excitement in running hot. After all, it’s not hard to be excited when you only have a vague idea of what’s really going to be involved.
But before starting down a path that will take you away from your current priorities, it’s worth asking yourself some questions about the project.
What does success look like?
So often we take on work without knowing what the end result we’re really working toward is. Without having thought through what success to us really looks like, we might succeed in building a product or business that we don’t actually want to be involved with.
Ask yourself what success looks like for you with this project, and set your compass accordingly.
What are the challenges on the way to success?
There are two types of challenges that you’ll face with any project: Those you can see from the start and plan for, and the unexpected variety that you have to adapt to in the moment.
You can save yourself time and stress later by deciding upfront whether or not those challenges are challenges you want to face, and if so, how you’ll address them when they show up.
What skills are required to succeed?
You might have all the skills required to get started on the project, but those likely aren’t all the skill required to see it through.
What skills or tools are you going to need to acquire to see this project through?
Who do I need to get involved in order to succeed?
Some projects are possible to see through entirely on your own. More often, however, you’re going to need to bring on help.
Maybe it’s hiring a freelance designer, bringing on a VA or even building up an entire team around yourself.
Maybe it’s finding the right partner to help bring the idea to life.
Or maybe it’s not about splitting the labour but about mentorship, guidance, support or accountability.
Regardless, know who you’re going to need and when you’re going to need them so you can keep a lookout for potential fits.
How long will it take to achieve the result?
One of the biggest reasons we quit projects is that we don’t realize going in how long it will take to achieve our end goal.
And so, when the excitement wears off and we realize that it’s going to take years of consistent, mundane work to see the project to fruition, we cut our losses to pursue something we’d rather be doing.
At some point, the fun is going to wear off on every project, and what’s required in order to achieve success is no longer creativity and innovation but labour, consistency and implementation.
It’s worth knowing what you’re signing up for from the start and deciding whether it’s a commitment you’re willing to make.
Will the work make me feel good?
Some projects may be enticing in every other way, but if the work required doesn’t make you feel good, may be worth passing on.
Maybe the path to success involves sweatshop labour, or multi-level marketing, or marketing something you don’t truly believe in.
Or maybe it involves you spending more time on social media or sales calls than you feel is optimal for you.
Just because a project could work, doesn’t mean it’s a good fit for you.
Can I keep this up?
Once you’ve taken stock of your answers to the previous questions, ask yourself honestly if you can keep up the activities required to achieve success over your projected timeframe.
Maybe your plan requires you to produce a weekly podcast, video or long-form blog post. Can you keep that up for the years it might take to reach your goal?
Maybe it requires you to have 25 sales calls a week. Can you keep that up?
Maybe it requires you to spend 200 days per year on the road. Can you keep that up?
So often, we think about what’s required in the short term. We don’t realize, however, that the hard thing about producing content, having sales calls or traveling for work isn’t doing them once, but doing them consistently again and again and again, well past the time when the novelty has worn off.
Think of a five-pound dumbbell. No doubt, you could easily curl it once, maybe even ten, twenty, or fifty times. Keep curling, however, and sooner or later, no matter how strong you are, even that tiny amount of weight becomes impossible to lift.
Know what size barbell you’re going to be required to lift going in, and decide how long you can keep it up.
Who else is doing this already?
Someone else is doing the same thing you’re planning to do already. They may not be in the same niche, they may not be following the same plan, they may not have the same end goal in mind, but there is someone (probably many someones) doing similar work already.
You need to know who they are.
I know, it’s easy to psych yourself out by looking at someone further along than you, but there are three reasons to seek out others doing the same thing you plan on doing.
- Oftentimes, the only reason we get excited about a project is because we think it’s never been done before.
When we realize that there are other people doing it already, we magically realize that we actually don’t have all that much interest in it and we can save ourselves some time and heartache.
- You can gather a lot of useful information about how to approach the project from looking at how others are already working through the challenges.
This doesn’t mean that you need to follow the exact roadmap they’ve laid out, but it can get you out of your own head and open your eyes to alternative methods, marketing methods, pricing models, and more.
- If your project involves you actively competing against other similar creators or businesses, this research is necessary to help you position and differentiate yourself in a compelling way.
Without knowing what others are doing and what their value propositions are, it’s hard to position yourself as a better alternative for a select group of people.
Decision Time
Once you’ve answered the above questions (and any others you choose to throw in yourself) you have a choice to make.
There’s nothing wrong with realizing that this project isn’t actually a fit for where you want to be spending your time and attention. There are enough shiny objects and ideas bombarding us on a daily basis that you should be saying “no” to most projects.
If, however, you’ve interrogated yourself and your idea and are still excited to dive in, you’re ready to dive in, confident that you know what you’re getting into, and have done everything you can to prepare for the journey ahead.
I’ve created a project dashboard template in Notion that walks me through many of these questions before I start any project. If you’re interested in getting your own, you can snag the template for yourself here.
Where You Need To Be
We’d all like to jump ahead.
To skip the journey and arrive at our destination
Unscathed by the heartbreaks, defeats, and failures we know to be inevitable along the way.
Sometimes we feel we deserve to be there already.
That we’ve put in all the work that should be expected of us,
Made all the sacrifices that could be asked of us,
That after all we’ve done, we should be somewhere other than where we are.
It’s a wonderful lie to tell ourselves.
A lie that lets us off the hook.
That almost allows us to believe we can move forward without confronting the thing we know we must confront.
The truth is that we’re already exactly where we need to be.
That we’ll remain where we are
Until we’ve learned and embodied the lesson available to us here.
It may be painful.
It may take hundreds of attempts and failures.
Or it may come in a single simple aha moment.
Regardless of the method, the lesson must be learned.
Dream and plan for the future.
But live and learn in the present.
You’re already right where you need to be.
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.
What Are You Measuring?
“What gets measured gets managed,” goes the saying.
But often, it doesn’t end there.
It also gets prioritized, optimized for, and sometimes even chased blindly.
For better or worse, what you choose to measure dictates your focus, your choices, and your actions.
This can lead to unintended side effects.
When shareholder value is the only metric that gets tracked, is it any surprise that people, communities, and the environment are negatively impacted?
Likely, that negative impact goes entirely unnoticed by the company that isn’t measuring those metrics.
It’s no wonder we often default to measuring the metrics we do.
Revenue, page views, downloads, followers, and likes all have nice, round easily trackable numbers attached to them, by which we can measure our performance against others or ourselves.
In fact, the fact that these metrics are prominently displayed in the tools we use suggests to us that we should be tracking them.
That these are the numbers by which we should be judging our success or failure as creators, business owners, and humans.
In reality, we can choose to measure our success and failure by any number of variables.
And the variables we choose to measure will dictate the experience of our work, for everyone who engages with it.
The good news is that we can choose to change what we’re measuring at any time.
And when we do this, our measurements act as a trim tab that will bring the ship around and point us in the direction we wish to be moving.
Creativity & Coral Reefs Both Need This to Flourish
I’m a systems nerd.
Not a “everything must be in precisely the right place, happen at precisely the right time, in precisely the right way” kind of nerd, mind you.
No, I’m more of a “build and tweak systems ad infinitum as a way to procrastinate on other work” kind of nerd.
As far as forms of procrastination go, systems-tweaking must surely rank among the best.
This highly-biased personal assessment is based primarily on the unique and wonderful way in which working on systems can grant a deep-seated feeling of productivity… while entirely avoiding moving the needle on the real work that needs to be done.
When it comes to procrastination, that’s pretty much the dream, right?
Of course I know that while I might tell myself I’m being responsible and productive when working on systems, I’m really in avoidance mode. My version of avoidance happens to be accompanied by a positive outcome, but it’s avoidance nonetheless.
Sometimes I procrastinate on client work or admin.
But most of the time, the work I’m avoiding is the difficult, uncertain creative work that goes into advancing my own creative projects.
If I had to guess, I’d say you probably spend a good deal of time avoiding this type of work yourself.
The irony, of course, is that this is the work most of us spend our days wishing we could do more of.
While we might be bogged down in client work or day jobs right now, we convince ourselves that if we work just a little harder, for just a little longer, we’ll reach a point where we can dedicate more time to the creative work we love.
Then, in those rare moments when the time does open up, we do almost everything in our power to avoid it.
There are a number of reasons we might struggle to take action when it comes to our creative work including many of the usual suspects you’ve likely heard before.
Fear of failure, fear of success, fear of disappointing others, fear of disappointing ourselves, fear of being found out as a fraud… the list of fears is long indeed.
But I think the biggest reason for our avoidance is more practical, mundane even.
We simply don’t know where to start.
Whether we’re working on a book, podcast, product, website redesign, or any other creative project, the starting point is almost some form of a blank page.
As you’ve probably experienced, blank pages are far from conducive for sparking creative work.
Fortunately, there’s an incredibly simple solution to bypassing this particular obstacle, and with it, much of the time we spend avoiding the work to be done.
The solution?
Don’t start from a blank page.
Creative work, it turns out, is like a coral reef. The raw materials are constantly floating around in the ether, but require a frame to attach themselves to before they can flourish and propagate.
Knowing this, our job becomes not to fill the blank page facing us with a fully-formed, coherent idea. Instead, it’s to create a structure around which our ideas can attach and organize themselves.
It just so happens that while systems can be a convenient distraction from doing the work itself, they can also provide us with this structure for each new idea we develop.
Systematizing Your Creative Structure
Over the past couple of years I’ve spent a significant amount of time building out my personal life and business operating system in Notion.
If I was a systems nerd before, Notion and the opportunities it presents have turned me into a full-on fanatic.
One of the aspects I continue to spend the most time on is building out and tweaking templates.
Pretty much anything I do more than once has a template associated with it, and if it doesn’t yet, you better believe that before long, it will.
Initially, my templates were productivity-oriented, designed only to help me save time. But I’ve increasingly been focusing on building creativity-oriented templates which provide the initial structure for ideas and projects to build off of.
Take the podcast episode templates from my old show for example.
Instead of a simple list of tasks, the templates include a series of prompts like:
- Why does this topic matter to my audience?
- What are the common cliches to avoid?
- What’s unique about this guest’s story or approach compared to other similar people?
- Why do I resonate with this topic/guest?
- What’s the one thing I want people to take away from this episode?
- Act 1/2/3 themes
- And more…
These prompts not only inform the direction of the episode content and interview questions, they also help me ensure that the episode is worth creating in the first place.
They also ensure that I’m never faced with a blank page when starting to work on a new episode. If I can’t easily answer a single one of the prompts, that’s a signal that I shouldn’t be working on the episode in the first place.
But podcast templates are just the start.
In addition to the podcast templates, I’ve created templates for blog posts, meetings, workshops, and maybe most importantly large, long-term projects, especially those involving a paid offer.
Much like the podcast episode templates, my project templates contain a series of prompts that helps me define the project, both for myself and my audience while guiding me through the process of building out the list of actionable next steps.
Over time (usually as a form of procrastination), I’ve tweaked these templates to add structure to the specific places I know that I personally get stuck when starting a new project.
The result is that I’m now able to map out the important parts of a new project in 30 minutes and have a concrete, tangible path forward.
Compared to how I used to approach projects, this feels like a superpower.
And it’s a superpower that’s accessible to all of us.
By taking note of where we typically get stuck in our creative work, we can build structures to help us avoid those roadblocks, and, like an artificially seeded reef, give our ideas something to latch onto and build around.
Having these structures ready and waiting to be deployed can save us hours, days, weeks, or even years when it comes to developing our ideas.
Creative Coral Comes In Many Shapes & Sizes
While the beginning of a new project is rife with opportunity for distraction and procrastination, most of the time we spend creatively stuck comes later.
Most often, we find ourselves stuck in the middle of projects or in our ongoing day-to-day creative work.
We get stuck writing blog posts, stuck recording podcasts or YouTube videos, stuck with the small stuff as much as the large.
What’s more, we regularly find ourselves stuck in situations we’ve never encountered before, problems for which we have no template to simply fill in the blanks and work through.
While we might not have the specific blueprints, however, approaching these challenges from a structure-first mentality can help us design those structures on the fly to help us work through all kinds of creative roadblocks big and small, familiar and novel.
Structure + Space = Magic
So much of the challenge of doing creative work is the time we spent stumbling around in the dark, searching for the boundaries of the space in which we’re attempting to create.
What we often forget is that we can create those boundaries ourselves.
And we need to.
While open space allows room for possibility, it’s the structure that provide something solid against which we can both latch onto and push off from.
As such, the structure and the boundaries are just as essential to creativity as the space.
A well-built structure gives us a frame in which to focus our ideas, as well as enough space for serendipity, inspiration, and iteration to work their magic.
The next time you find yourself struggling and frustrated with your attempts to channel that swirly sea of creativity into something solid, stop.
Shift your attention from the ethereal and shapeless to the concrete, the raw materials that are easily grasped and assembled.
Much like it’s easier to pour water into an existing bottle instead of building a bottle around the water, the surest path to producing creative work is to first build the structure and then fill it.
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
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 wilderness of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
Better Is Better
We often resist investing in improving our skills because the promised change feels too insignificant.
We could take a course on web design, or copywriting, or Facebook Ads, or any of a hundred other skills that we know would benefit us, both in the short and long term.
But we also know that even after taking the course we’ll be far from mastery of the skill.
To develop the level of mastery that we feel would be truly helpful to us would take many courses, months, or years of study, with a lot of practice along the way.
And so we do nothing, opting for the status quo, telling ourselves we’ll just hire someone who’s already mastered the skill when we need the task in question done.
What we miss is that no matter how small the improvement, better is better.
That even if we can’t charge a client $20k (or $2k, or $200) for a sales page after taking an intro copywriting course, improving our skill is still better than not improving it.
That improvement isn’t just about the skill we’ve chosen to level up, but how that improvement impacts the rest of what we do.
That even if the skill goes entirely unused, we’re still in a better place for having developed it.
There are few big wins, few opportunities to learn one new skill that changes everything for us in a matter of days or weeks.
Far more potent than a few big wins, however, is a series of small wins, consistently strung together over time.
Leveling up, bit by bit by bit, the progress is almost imperceptible until we look back and recognize how far we’ve come.
Even if it doesn’t feel like it in the moment, better is better.
And it’s hard to go wrong pursuing any version of it.
Abstract Learning Requires Abstract Teachers
It’s hard to argue that continual learning is a bad thing.
The relentless pursuit of heaping more onto our ever-growing mountain of knowledge is a core part of today’s entrepreneurial culture.
And if we want to follow in the footsteps of those who have come before, learning from their successes and failures is a good place to start.
But what if we don’t want to follow in their footsteps?
What if we seek a different path?
Not business as usual, but business unusual?
Yes, we need to learn.
But maybe even more important, we need to unlearn.
Unlearn art.
Unlearn business.
Unlearn marketing.
Unlearn what success is supposed to look like in the first place.
Unlearn our beliefs around our potential to create impact in the world.
Unlearn what it means to create work that matters.
It turns out that not all learning builds on itself.
That sometimes the way forward requires us to turn around and walk away from what we thought was our goal.
Back down the path we’ve spent years walking to find that side spur stretching off into the wilderness.
There are fewer guides on this path, fewer teachers.
And they don’t look like the ones we’re used to.
They don’t appear in our newsfeeds with webinars, masterclasses, or 5-day quick-win challenges.
More likely we find them through whispered word of mouth.
A secret too exciting to be kept to oneself.
Rather than give us the answers they challenge us with questions.
Questions we may have never considered.
Questions that don’t feel like they should have anything to do with the work we create.
Questions that force us into uncomfortable territory, confronting the parts of ourselves we’d rather not look at.
The further we walk down this path, the more we come to understand that these teachers are all around us.
In overheard conversations, the coffee shop down the street, the birds on breeze, the tree shrugging off its coat in the autumn and being reborn in the spring.
These teachers are slow, reticent, timeless, true.
And full of boundless wisdom.
In the end, these are the only teachers we need.
Where Does the Time Go?
How many times have you made it to the end of the week and asked the question?
You’ve worked exceedingly long hours on tasks that felt important in the moment.
In hindsight, however, they appear to have been spent merely bailing water.
When it comes to the things that matter, the needle remains unmoved.
So where to start?
What can we do when every task feels both urgent and important?
When we alone are capable of completing them?
When they overwhelm and crowd out the work that truly sets our soul on fire?
The work we know we’re capable of.
The work that has the potential to change things.
The wrong answer is to work harder.
This is not a season that will pass by continuing our current approach.
Change requires intentional action.
Intentional action requires awareness and ownership of the problem and its roots.
So first, reassess the situation.
Start by committing to tracking your time and assessing it at the end of each week.
Ask yourself:
- Which of these tasks are high-value and which are low?
- Which, with a little bit of guidance could be handed off to someone else?
- How much time would that save each week?
If you’re like me, you might be shocked at the result.
As of my most recent weekly time audit, I’m spending 8+ hours per week on tasks better performed by someone else.
This after working relentlessly over the past two years to build a team and outsource the tasks that keep me from my more important work.
What’s your number?
How many hours a week are you spending on tasks that are keeping from doing the work that really matters?
And what action can you take today to begin to shift the tide?
Seek Change
Too often we end up creating only as a reflex.
We have to fill that space on our content calendar with something after all.
So we create with the end goal of filling that space.
We maintain our production streak while failing to say anything worth saying.
So if content production for content production’s sake isn’t what we’re shooting for, what is?
At its core, our work should be created to achieve one purpose.
Change.
If we seek to create work that matters, our goal with each piece of content, each product, each creative endeavor is to create change in some way.
Even if only for one person.
Even if only in the smallest of ways.
Work that matters changes things.
Perspectives, beliefs, mindsets, moods, systems, processes, practices, relationships.
These are all good places to start seeking change.
So the next time you find yourself staring at a blank spot on your content calendar, instead of publishing for the sake of it, ask yourself, “What’s the smallest amount of change I can make with this content?
There’s too much that needs changing in the world to waste a podcast, blog post, tweet, or Instagram post not working to shift it.
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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.