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.

Subscribe

    Latest Post

    Cooking with Simple Ingedients

    There are few things in life better than a loaf of freshly baked bread.

    At least for me, there’s a good chance that if there’s fresh bread in the house, I’ll eat pretty much nothing else until it’s gone.

    Part of fresh bread’s appeal comes down to its tangible attributes. The smell it fills the house with as it bakes, the way it feels in your mouth as you bite through the hard crust into the soft, still-warm center, and of course, the flavour, understated though it may be.

    Another part of the appeal, however, is its hearty simplicity.

    Fresh bread is humble, unpretentious, made of simple ingredients that have remained largely unchanged over centuries if not millennia.

    In an increasingly experimental culinary world highlighted by flashy, exotic, Instagram-worthy ingredients and presentations, good simple bread persists—and in many cases remains uniquely capable of stealing the show out from under a more ostentatious main course.

    Perhaps part of the magic of good bread is that it defies our expectations of what a few simple ingredients are capable of adding up to.

    Or perhaps we’re presented with so much bland, mundane, mass-produced bread that when it’s done right, we can’t help but take notice.

    Whatever it is, for all its simplicity, good bread is–often literally–remarkable.

    Bread is not alone in its simple, durable remarkability.

    Beer, wine, cheese, olive oil, a steaming bowl of soup, stew or goulash—all of which pair excellently with a fresh loaf of bread by the way—are just a few products of simple ingredients that have continued to persist, comfort, and delight through the centuries.

    In a world that is changing ever more quickly, the fact that these foods, made often from just a few simple ingredients have not only endured in their appeal is incredible.

    But what if these foods have persisted not in spite of their simple, pedestrian, unassuming ingredients but because of them?

    And if so, what can we learn about cooking with simple ingredients when it comes to our creative practices?

    Simplicity is a Feature Not a Bug

    A basic loaf of sourdough bread is made from just three ingredients, flour, salt, and water.

    For most of us, these ingredients are not only easily-accessible, but ubiquitous. If we don’t already have our cupboard stocked with them, we can get them quickly and cheaply.

    The basic building blocks of creative work are even more ubiquitous.

    At its core, all creative work comes down to just two basic ingredients:

    1. A novel idea
    2. A way to express it

    We’re all equally capable of finding good ideas if we’re willing to learn how to look for, notice, and develop them.

    And while there are certainly complex and expensive ways of expressing ideas, most of us have the ability, both physically & technically, to share our ideas in either written or recorded form.

    Writing, in particular, has persisted as a durable form of communicating ideas for millennia.

    Despite the limited number of prerequisites, we have a hard time believing that these simple ingredients are enough to succeed creatively.

    And so we start adding in trendy, exotic, and flashy ingredients, thinking that what our recipe is missing is more spice, more garnish, or more “Wow” factor.

    In the hands of a skilled chef, these finishing touches might elevate a dish from great to extraordinary.

    In the hands of an amateur, they lead to a dish that may look impressive… but leaves a disappointing taste in your mouth.

    Perhaps it’s the most skilled chef of all who is able to deliver an extraordinary, remarkable experience without the ornamentation. With nothing but a few simple ingredients, prepared masterfully.

    And indeed, it’s precisely the method of preparation that has the ability to transform many a set of simple ingredients into something exponentially greater than the sum of their parts.

    The Magic is in the Process

    For all the joy a loaf of fresh bread is capable of bringing us, it’s surprising we don’t bake them more often.

    The reason, I think, is that while the ingredients may be simple and readily available, the process required to transform those ingredients into something special requires more time, patience, and commitment than we’re typically willing to invest.

    A single loaf of sourdough, for example, can take over a week to create, with regular attention and adjustments to the fermenting sourdough starter mix.

    So instead, more often than not, we settle for an off-the-shelf, pre-packaged loaf that—while it might occupy the same space in our stomach—lacks the substance and the magic of the carefully and attentively prepared alternative.

    It turns out, sourdough is not alone in its patient magic.

    The same slow, caring, attentive process transforms all kinds of simple ingredients into something special.

    Wine, whiskey, beer, barbecue, stew, cheese, and many other foods all improve with age. Many even require it.

    Balsamic vinegar, for example, takes anywhere from 12-25 years to prepare from scratch.

    The same concept holds true for us as creators, both in regard to our individual ideas and projects as well as our broader careers.

    Applying Time & Patience to Your Creative Work

    Every full-time creator I know has a slew of ideas for blog posts, podcast episodes, or videos they’ve been patiently allowing to ferment for multiple years without publishing.

    On the surface, these ideas are almost always simple, mundane, quotidian.

    And yet… for one reason or another, there’s something about the idea they can’t quite shake or articulate.

    And they begin to obsess over it.

    When the time finally comes to publish, the process of fermentation has done what it always does: Transformed the simple base ingredients into something entirely unrecognizable and, perhaps even, remarkable.

    The same process of fermentation occurs at the career level as well.

    It’s absurd to think that someone who’s been creating around a topic, genre, or medium for two years would have anywhere near the level of nuanced insight, mastery of the tools, or ability to articulate ideas as effectively as someone who’s been baking with those same ingredients for a decade (let alone three, or five).

    The most successful creators are often those who dedicate an entire body of work to a simple topic others overlook as unworthy of more than a single blog post or podcast episode.

    Think Ryan Holiday with Stoicism applied to modern life.

    Brene Brown with vulnerability.

    Krista Tippett with what it means to be a human today.

    None of their work is defined by exotic spice or extravagant garnish, but instead, a few simple ingredients, given decades to ferment and transform into something magical.

    Which is all any of us needs.

    The ingredients are all around us. In fact, we likely already have them.

    Which means the surest path to success might be to stop looking outward for the ingredients we feel we’re missing and instead look inward.

    To the simple ingredients that have already been fermenting, perhaps for years, unseen, waiting patiently to be combined, nurtured, and distilled into something entirely magical.


    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

        More Posts

        What We Carry With Us

        Every month or so, I pack my life up into a suitcase.

        It’s a pretty smooth routine by now. The items I bring with me remain relatively static and everything has its usual place where it always goes.

        Sometimes I surprise myself by packing just a little differently and stumbling on a way to save some space, but mostly each packing is the same as the previous.

        When it’s not rushed, late at night or early in the morning, the process can be meditative, cathartic even.

        That’s because a big part of the packing process is an assessment of each of the things I carry with me, and a decision as to whether I want to carry it with me any more.

        Your Relation To Things Changes When You Travel Full-Time

        I’ve been traveling full-time for three and a half years now.

        I run my company, Counterweight Creative, a podcast production agency from coworking spaces. I go to the office every day, have an apartment, and live life on a pretty much identical schedule to anyone who has a job in any city in the world.

        The places, people, cultures and time zones change, but it’s a pretty normal day-to-day life otherwise.

        The biggest difference might be the mindset shift around physical things that occurs when you aren’t rooted anywhere. When any acquisition must either be carried with you, or shipped somewhere for pickup, use, and enjoyment at some undetermined, future date in some undetermined, future place.

        Undoubtedly, it adds several layers of thought to any purchasing decision. Far more relevant than price become questions like, “Will I use this enough to warrant carrying it around? Will it fit in my luggage? If I get this what will I no longer have room for?”

        But beyond the added thought around new acquisitions, the practice of regularly packing your existing possessions produces an opportunity for reflection on what we bring with us and why.

        An Expanding Suitcase

        Over the years, I expanded my kit from the minimalist essentials I brought with me on a three-month cycle trip of Europe on my first trip, to a minimalist work setup when I first started Counterweight Creative and started traveling full-time.

        More recently, I’ve traded in the backpack for rolling luggage, filled out my work setup including laptop stand, keyboard, mouse, fancy noise-canceling headphones, hard-drives, as well as bringing a wider variety of clothing, tools for hobbies, and other comforts.

        What Our Things Say About Us

        Along with these comforts and necessities, I have a habit of collecting postcards, pamphlets, maps, and brochures from the places I visit. When I first started traveling, I journaled daily and would often use these local finds to cut up and turn my journals into scrapbooks.

        I love those old journals, but I haven’t journaled regularly in over two years at this point. Despite that, until recently I continued to add to my collection of loose papers, lugging them across the globe, and with them, the belief that one day I’d take the time to catch up on two years of journaling and scrapbooking.

        During a stopover at my Mom’s house recently, I emptied my bag out entirely and was confronted with the 5lb stack of papers.

        “Why am I still carrying these around with me?” I asked.

        I realized that this random assortment of papers was tied to my idea of who I was.

        Scrapbooking and journaling had been central to the way I not only traveled, but lived my life during my first trips, and I hadn’t yet moved on from that version of myself, even though I no longer had the need or desire to continue those practices regularly.

        As a result, I was carrying around extra weight that served no purpose towards improving my current life or moving me toward my future goals. A small, even trivial weight to be sure, but who’s to say this wasn’t happening elsewhere.

        Pruning Your Possessions

        After this realization, I took a new eye to everything else I owned and carried with me, and realized that there were a surprising number of items I was jamming into my pack that were less practical than they were representative of a vision of myself.

        I carried books around that I never read, carried my rock climbing shoes around the world for a year and only once ever even looked for a climbing gym. I had keepsakes and mementos from my past and aspirational items that I thought would hold me accountable to some practice or task in the future.

        Even with my limited space, I managed to fill the nooks and crannies with stuff that served no purpose in increasing my happiness, often doing the opposite by reminding me of the guilt I had for carrying these things around with me and not making use of them.

        I’m grateful that I only have a limited amount of space to fill with these items. But I haven’t always traveled full-time and I won’t live this way forever. I know how easy it can be for the things, the beliefs, the routines, either those from our past or those designed to encourage a future we’re not really that excited about to crowd out the present.

        If we’re not careful, our baggage can fill up and take over all our space, physical, emotional, relational and spiritual, leaving no room for the new, for the necessary, for the vital.

        My advice is to make a habit of taking stock of your life, your things, your thoughts and ask, “Why am I still carrying this with me?”

        If no good reason exists, you might be better leaving it behind.


        The Hard Stuff

        Most of us want to do the work.

        We thrive on the feeling of meeting a worthy challenge and our best self rising up to face it, and best it. Of fighting through the hard stuff.

        The harder the hard stuff, the better.

        Why then, if we take such pride in doing the hard work, do we so often stall, get stuck, or abandon our pursuits when the going gets tough?

        Shouldn’t these be the moments that excite us most? That pull our best selves to the surface to meet this new challenge and create our best work?

        I think there are a couple of reasons.

        Validation Of Our Struggle

        While we can certainly feel pride in ourselves, pride feels a whole lot better when we’re acknowledged and lauded by others.

        For so many of us, the hard parts in our work are creative, technical or abstract challenges that may not be relatable or understood by a single person we know.

        As far as our friends and family might be concerned, one website is pretty much the same as any other, a sales letter is just a bunch of words you jotted down over 30 minutes, and your online course is just you talking about something they don’t understand in front of a camera.

        God help you if you create music, art or poetry…

        Sure, if we’re massively successful with our creations we may get some of that validation, when they see that we’re making a good living from our work and our art, and creating an impact along the way.

        But there’s no guarantee that will happen.

        And if our work does fall flat, there’s no consolation prize and perhaps not even an understanding or acknowledgment of our efforts.

        That’s a lonely place to be.

        Best not to risk it.

        Fear Of Not Being Enough

        The second reason is that while we want to show up as our best selves, call on all our strength and wit, and truly test ourselves, we also want to know that we’re going to come out on top.

        This means that we have to understand going in what the work will consist of, how it will challenge us, and hopefully be similar to something we’ve faced — and bested — before.

        By taking on something new and unknown, by stepping beyond the light of the campfire we’ve been sitting warmly around, we risk showing up fully, bringing every fiber of our being to the table and finding that it’s not enough.

        That we’re not enough.

        This is a truly scary thought.

        A thought that can keep us playing small, and safe. Ocassionally tiptoeing up to the edge of the darkness, but only just. Staying within the realm of what we already know we can achieve.

        Because if we step outside the firelight, if we’ve brought our best and fallen short in pursuit of work that is meaningful to us and impactful to our communities, what does that say about us?

        More than a rejection of our skills and knowledge, failures like these feel like a direct rejection of our vision for the world, and our ability to bring it in to being. A rejection that strikes to the core of who we are and all that we encompass.

        Most definitely best not to risk going there.

        Better to stay by the campfire with the familiar, the known, the manageable.

        How Do We Create Work That Matters?

        So what do we do as people with big ideas that will surely consist almost predominantly of hard, emotional, risky work?

        First, I think, we need to go into the work knowing that the work hasn’t really begun until we get to the hard stuff.

        More, we need to understand that while “the hard stuff” will probably test us mentally, and may even test us physically, it will most definitely test us emotionally.

        The hard stuff will expose us in some way, and may even slice down to the core of our very idea of oursleves, leaving it open, raw, vulnerable.

        That idea of ourselves might even be broken.

        This is the price of admission to dance with the hard stuff.

        If we need to ignore this price, ignore the hard stuff in order to begin our work, we probably don’t care enough about the outcome of the work to see it through when the going gets tough.

        That’s fine. Better to move onto something else now than waste the time.

        But if we’re willing to pay that price, knowing what it is and being prepared for it can help us build up our resources, support and courage for when the time comes to stare it down.

        We Don’t Need To Face The Hard Stuff Alone

        Secondly, we can accept the fact that we can’t — and don’t have to — get through the hard stuff alone.

        We can accept that we probably don’t have all the skills, knowledge, resources and emotional bandwidth to complete our work alone, and we can assemble our support team.

        These don’t need to be employees or contractors, they don’t have to be doing the work with or for you. While this type of person or people might be helpful, more important are those that will keep you accountable, motivated, inspired, and supported emotionally.

        While we might not want to admit that outside acknowledgment and emotional support matters, for most of us, that’s a lie.

        Surround yourself with people who understand both your vision and the work it will take to get there. People who will cheer you on through your successes, and pick you up without judgment after your failures and help you analyze what happened and why.

        Understand that the hard stuff will test your ego, will require you to ask for help, to look beyond yourself for answers.

        Find teachers, guides, mentors, and use them.

        We Don’t Have All The Answers… Yet

        Lastly, we need to understand that when we’re taking on the hard stuff, we will fall short.

        There’s no way around, over or under it.

        At some point, we will be forced to confront the fact that in our current iteration, we are not enough.

        But we also need to understand that falling short is not a rejection of us, our work, and our vision for the world. And that our current iteration is not the extent of our potential.

        We need to understand that in reality, falling short, even when we’ve brought everything we have to the table, is nothing more than a sign that our current knowledge, strength or resources are insufficient to overcome this current challenge.

        Our work then, is to build up our knowledge, our strength, and our resources further before facing down the hard stuff again.

        If we believe our work is vital, we’ll return to face down the hard stuff again and again and again and again, as many times as necessary, showing up stronger, smarter, more resilient each time until we’ve become the people we need to be to push through.

        The only way to get there is by stepping outside the firelight.

        Build Up Your Bravery

        You don’t have to confront the truly hard stuff before you’re ready, but I believe we all have some dream inside us that will require us to face it at some point if we’re going to realize that dream.

        So take one small step beyond the known. Challenge yourself the tiniest bit further than what you know for sure you can handle.

        Then do it again.

        Build your fire, and with it your ability, your knowledge, and your belief ever outward.

        Don’t think it will be easy.

        It takes true bravery to step beyond your known limits and put yourself on the line.

        But it’s the only way to prepare yourself for when the time comes to do the work that really matters to you, and facing down the hard stuff that comes with it.


        Why You Aren’t Coming Up With New (or Good) Ideas

        Ideas are nothing without action, so the saying goes.

        It’s a little glib, but I’m not going to argue with it.

        It’s also true, however, that action is nothing without an idea, and more often than not, even action and idea together amount to less than we hoped for or maybe even nothing at all.

        It’s a disheartening reality, but as anyone who’s started a business and kept it going for any amount of time will tell you, the first (or second, third, fourth…) thing you try rarely works out as you’d hoped.

        And even if you do hit it big once, that’s probably not enough.

        Most of us can only squeeze so much life out of our individual hits before being relegated to the category of One-Hit Wonders along with Psy, Gotye, and Baha Men…

        The key then to both getting off the ground and then remaining aloft once we’ve done so is to ensure we have a steady stream of ideas ready to get to work on when the time is right.

        Coming Up With Ideas Is Hard

        When I made my first foray into the world of podcasts, one of my favourite shows was Question Of The Day, with Stephen Dubner (of Freakonomics fame) and James Altucher (of James Altucher fame…).

        It was a short, daily show in which the two friends would have a lighthearted discussion around a topic, often presented by a listener. I’d often binge-listen through 4 or 5 episodes a day while working full-time as a landscaper.

        James mentioned on multiple occasions the practice he had developed of coming up with 10 ideas a day as being central to his success in his life as an entrepreneur.

        Being young, impressionable and in the beginning stages of figuring out how to start my own business, I took this advice as truth and started keeping a daily journal of ideas.

        The first day I wrote down maybe 6 ideas. They weren’t very good. They may not have even been real ideas, and they definitely weren’t original.

        I knew they weren’t good, but I figured that as I built up the idea-generating muscle, I would only get more and better ideas each day until by day 100 I would understand how to cure cancer, have built out mental blueprints of a light-speed capable rocket engine, and be primed for fame, fortune, and accolades from the highest echelons of society.

        Fast forward 100 days and I had given up on the idea journaling exercise about 87 days earlier…

        Where I had assumed that conjuring ideas would become easier with time, I instead found that after a couple of weeks, I had exhausted the ideas that had already been kicking around the back of my head (none of them very good), picked the low hanging fruit, and was left with nothing new.

        What Does An Idea Even Look Like?

        It had been my understanding that big ideas would appear in the form of a lightning bolt, lightbulb, or some other obvious (and light-based) signal that would alert me to their presence.

        And so, when none appeared despite my keen 13-day surveillance, I accepted the fact that I wasn’t the idea-generating type and moved on.

        What I realized much later, was that the issue was not, in fact, that I wasn’t the idea-generating type, but that my conception of what an idea even looks like was flawed.

        Part of it was that I was impatient.

        I was ready to have my million-dollar idea and get to work on bringing it to life.

        And so, in my impatience and naivete, I was on the lookout — and only on the lookout — for fully-formed business ideas, ready to download from the ether and convert into paying customers.

        It turns out that big ideas, the ones that do seem to strike you like a bolt of lightning are exceedingly infrequent and subject to the same rules as all other ideas.

        That is, there’s a better than not chance that they won’t work out as well as you’d hoped.

        Generating ideas like this is neither reliable, nor scalable for most of us.

        Real Ideas Are Subtle

        What I’ve come to learn and embody is that the most reliable way to find and develop ideas into something useful (and maybe even impactful or profitable), is not to go looking for the lightning bolts.

        Instead, keep your eyes peeled and your ears pricked for the slight tickling of curiosity. For the end of a ball of string that you can unravel and see where it leads.

        For me, these usually show up as a random thought, or observance that strikes me as interesting and worth more exploration.

        In all likelihood, most of those ideas won’t lead anywhere “productive” or profitable. But that doesn’t mean they’re not worth exploring. If nothing else, you’ll have exercised your mind, satisfied your initial curiosity about the idea, and can move on to the next one.

        Often, however, in unspooling one ball of string, you’ll find the beginnings of another 7 balls along the way.

        This is how you become an idea-generating machine. Not by waiting for lightning to strike, but by actively following and exploring the tiniest sparks of ideas you come across.

        Commit To Idea Exploration

        In my experience, the ideas that amount to the most are the ones that stick their tiny hooks in you, and then force you to grapple with them, unroll them, turn them over, flex them, view them from every angle, break them open before putting them back together.

        These ideas are not fully formed. They take time, sometimes months or even years, to wrestle with or to grow into before they become useful.

        They can be frustrating, the timing never being quite right, the pre-requisite pieces never quite being in place, never quite fitting into the space we have for them at the moment.

        But if we ignore these idea threads in favour of the lightning bolts, we risk passing up the thousands of unexplored ideas, that would have revealed their potential if only we’d taken the effort to give the thread a slight tug to see where it leads.

        So pull your conception of ideas down off its pedestal. Write down every thought or observance that seems interesting you, and then commit to exploring it further.

        Do this, and you’ll have no shortage of ideas.

        They won’t all be good. They won’t all be useful.

        But some will both, and they’ll be worth putting the work in to unravel.

        Shit-Disturbing: A Beginners Guide For Creatives + Visionaries

        Let’s face it. You’re a shit-disturber. A contrarian. An instigator.

        Maybe you’re not getting in bar fights every weekend (although maybe you are…), but if you spend your days creating, whether that’s business, art, or ideas, my guess is that at the root, at least some of your motivation comes down to changing people, the culture, and maybe even the world in some way.

        Chances are, many, if not most of those people have no interest in being changed, however.

        They’re perfectly happy with the way their existence is currently playing out, or if they’re not, they’re not truly ready or committed to seek out change themselves.

        Thus, in your efforts to change them, to make them see things your way, you have to become something of a shit-disturber. To upend their worldview and show them that with you, your ideas, your creations, a better way forward is possible.

        I know calling you a shit-disturber might not be a polite way to start off this article, but I say it with love.

        We need you. The world needs you.

        There are myriad problems facing us both collectively and individually, ranging from war, famine, disease, and climate crisis in the extreme all the way down to not having any good new music on your phone.

        The status quo is not going to solve these problems, at least not in a timely manner. Checklists, manuals, and reasoned debate are not going to solve these problems.

        You are going to solve these problems, and you’re going to do it by going against the grain, breaking the rules, and surprising us all with something unexpected and new.

        In other words, you’re going to seriously disturb some shit.

        But again, most people aren’t looking for you to change them and their way of life. They’re happy with the old, the safe, the familiar.

        Most people are happy with their current music, current art, current technology, current conception of the world and ideas about life and their place in the universe.

        “Nothing new, please. Another round of the same. Don’t rock the boat, things are good here.”

        So how do we bring our radical, shit-disturbing ideas to people who don’t want to hear them and show them our vision of a better way forward that resonates with them and invites them to come on board?

        How can we create something unlike what’s come before and find an audience for it that will help us create more?

        Indoctrinating Them Slowly

        Give them something they’re familiar with but subtly slip in some of your art, your fresh ideas, your rebellion.

        Package your work in a wrapper people already know and like, but include something unexpected and surprising. Something that might just expand their idea of what’s possible.

        Sure some people might hate it. But some people will like it. And if you’re lucky, some people might really like it. And they might ask for more.

        “Yes, please. More of that. I can’t get this anywhere else.”

        Suddenly you have license to take your art a little further, to push the boundaries of what’s familiar and acceptable out a little more, be a little bolder in your work.

        And not only do you have an audience who’s ready for your ideas, your art, your rebellion, they may actually be hungry for it. Messaging you daily asking when you’ll have new music, a new book, a new product.

        Playing The Long Game

        As a shit-disturber, this might be a frustrating strategy.

        You want change now.

        You know the problem, see the solution and if the rest of these knuckleheads could just see it we could solve it and move on to the next one.

        But world-changing is a long game.

        And chances are, your ideas could still use some refinement, and will only benefit from challenge, push-back, competition and collaboration.

        If you just want to be different, go ahead and commit to publishing your work in its rawest most unrefined form. It might be art in its highest form, but it might not find an audience.

        History is filled with near-unknowns who were too radical, too unfamiliar, too soon.

        If you truly want to change peolpe, the culture, and the world however, commit to the long game.

        Pique their interest by pushing just a bit outside their comfort zone, and once they give you permission to continue, spoon-feed them a little more, at their pace, as they’re ready for it.

        Do it with kindness, do it with generosity, do it with empathy, and do it with patience.

        Now go build your rebellion and change the world.


        Sometimes You Just Need To Collect Data

        My family loves games, and we’re competitive about them.

        We’re not game nerds per se. We don’t buy new games every month, we’re not into complex strategy games, we don’t collectively attend game meetups and wipe the floor with the competition*.

        *Although that sounds awesome…

        We mostly play cards and classic board games that you’re probably familiar with to some extent.

        And while we may not be extremists, we have our favourites and we take them seriously.

        At any family gathering, game playing is almost the default activity over which to catch up, eat, and spend time with each other.

        So when my mom recently visited my girlfriend and me, it was just a matter of hours before the deck of cards came out.

        After running through some family favourites, my girlfriend suggested a family classic of her own, Spades, which I had never played before.

        Now Spades is similar in concept to a number of the trick-taking card games I’m familiar with, and yet the feeling and strategy of the game are quite different.

        Being a competitor, I was of course, interested in winning out of the gate.

        Every Game Is Different

        A few hands in, however, I realized that while the rules were similar to other games I was familiar with, the same strategies and mindsets didn’t necessarily work.

        When learning many games, not only is there a process of learning the hard and fast rules that contain and guide the flow of play, but also a more abstract “feeling out” process required to gain a level of proficiency.

        This feeling out process relates both to the game as a whole, as it would be played with any other players, as well as the individual players with whom you are playing in the moment.

        A game with one or more aggressive, risk-taking players will have a drastically different feel than one with generally conservative players, and those variables will change how you show up and play the cards you’re dealt.

        On top of learning how to compete at a basic level, a game often doesn’t begin to feel fun until you’ve really gained the feel for it.

        This means that sometimes when you’re new to a game or new to your fellow players, the correct strategy is to put aside your competitive nature and just gather data.

        Test The Boundaries

        Commit to losing every hand, but testing different modes of play until you develop your feel for it.

        Play aggressively, conservatively, randomly, trust your gut, trust a system, play based on your opponents, play based on your hand, try anything that comes to mind. Push the boundaries of how someone might play a given hand and note the outcome.

        Note how your opponents alter their play in response.

        Note what’s most fun for you personally. It’s a game after all, and games should be fun.

        Then once you’ve gathered sufficient data and developed your feel, you can enter the next round with an intentional strategy that you have some confidence in being effective for the given situation with the given players.

        Always Be Testing

        The same is true for so many aspects of our work and lives.

        We want to jump into different areas of our businesses, be that marketing, management, our product or service itself, or maybe even the business we want to start but haven’t yet and have every action we take be successful the first time through.

        Life rarely works like that.

        Instead, we should commit to relentlessly experiment and test the boundaries in ways both big and small, and always be gathering and analyzing the data we get back from those tests.

        Some tests might fail. Some tests might cost us money. Some tests might cost us relationships and even clients or customers.

        Testing can be scary.

        But we can’t begin to build and grow intentional businesses until we develop our feel for our business, our clients, our customers, our teams until we know where the boundaries for each are, and how the various inputs affect the outputs.

        And my guess is that if you do enough tests you’ll realize that the boundaries of your potential are a lot bigger than you had thought, and you might just hit on something truly special you never would have known was possible otherwise.

        So make a list of possible tests to run and start collecting data. Put your ego aside, be prepared for many of your tests to fail, or even commit to it if you’re really brave.

        Note how your leads, clients, and customers respond.

        Note how your team responds.

        Note what’s most fun for you personally.

        It’s a business after all, and business should be fun.

        A Resolution For Kindness

        Like many others, I’m entering this new year — and new decade — with a heady list of goals and resolutions.

        However, along with our typical business goals, health goals, and personal goals, there’s one resolution I think we could all benefit from making.

        What if we all resolved to treat each other with just a little more kindness?

        In light of how this past decade has come to an end with politics dividing us across the world, opinions growing more entrenched and extreme, and those opinions (often weaponized) being easier than ever to share anonymously, even a marginal increase in kindness from each of us would be a breath of fresh air.

        It doesn’t have to be giving up your weekends to volunteer, donating money to charities and organizations, or even the classic act of holding open the door for an old lady at the grocery store.

        I’d argue these options are easy ways to make yourself feel good while ignoring the impacts our everyday interactions have on others, our communities, and the world.

        What might resolving to be kinder look like?

        What if instead of arguing with those we disagree with (whether online or off), we started by asking questions and gaining an understanding of their background and why they believe what they believe?

        What if instead of focusing on all the seemingly myriad topics that divide us, we remembered that life is not entirely made up of political opinions and dug deeper to find and focus on all the beliefs, goals, causes, affiliations, and histories we share?

        What if we diversified our media intake to include opinions from the “other side”?

        What if we resolved to remember that everyone has reasons behind their opinions and that while attacks and arguments won’t change many minds, compassion, understanding, and kindness just might?

        None of these are easy resolutions, but isn’t that the point of resolutions? If they were easy we would have already done them.

        Kindness, like gratitude, restraint, or mindfulness is a practice that strengthens the more you use it. Luckily for us, there are probably hundreds of opportunities every week for us to exercise that muscle.

        I’m convinced that when used authentically and generously, kindness is the key to not only making the world a little better as a whole, but to radically transforming our businesses, communities and lives.

        Where to start?

        A good first step is to just take two breaths the next time you feel your emotions rising up and asking “how can I treat this person with kindness?”

        So what do you say? Care to join me in making the next decade a little bit the kinder than the one we just came from?

        Creative Wayfinding For Ambitious Optimists.

        Relax, This Won’t Work

        What if every time we started a new project, we went in with the mindset that it in all likelihood wouldn’t work?

        Would it kill our motivation? Lead us to produce a sloppy final product because it was never going to work anyway, so what was the point of trying?

        Or would it set us free?

        Would we finally be able to create our best, most inspired work, because we’ve already taken our biggest fear — that our efforts would be wasted when our work falls flat — off the table?

        If there were no fear of judgment, because they were just crazy ideas to begin with, would we feel a little freer to push the boundaries, experiment wildly, create intuitively, and say our crazy ideas out loud?

        If the stats didn’t matter, the revenue, the pageviews, the downloads, would we appreciate the joy of creating for the sake of creating a little more? To show up and say, “Here, I made this” and release it without any hope or expectation as we turn around and go back to work to create something new?

        What if we knew before we started, that our work was worth doing even if it fell flat? That there were returns besides acclaim, status, and money that would pay out regardless of the broader reception of the finished product?

        Sure, it sounds idyllic. It’s most definitely easier said than done.

        But it might be worth trying with each new project, to distance ourselves a little further from the outcome, and do work that’s worth doing simply because it’s worth doing.

        What We Carry With Us

        Every month or so, I pack my life up into a suitcase.

        It’s a pretty smooth routine by now. The items I bring with me remain relatively static and everything has its usual place where it always goes.

        Sometimes I surprise myself by packing just a little differently and stumbling on a way to save some space, but mostly each packing is the same as the previous.

        When it’s not rushed, late at night or early in the morning, the process can be meditative, cathartic even.

        That’s because a big part of the packing process is an assessment of each of the things I carry with me, and a decision as to whether I want to carry it with me any more.

        Your Relation To Things Changes When You Travel Full-Time

        I’ve been traveling full-time for three and a half years now.

        I run my company, Counterweight Creative, a podcast production agency from coworking spaces. I go to the office every day, have an apartment, and live life on a pretty much identical schedule to anyone who has a job in any city in the world.

        The places, people, cultures and time zones change, but it’s a pretty normal day-to-day life otherwise.

        The biggest difference might be the mindset shift around physical things that occurs when you aren’t rooted anywhere. When any acquisition must either be carried with you, or shipped somewhere for pickup, use, and enjoyment at some undetermined, future date in some undetermined, future place.

        Undoubtedly, it adds several layers of thought to any purchasing decision. Far more relevant than price become questions like, “Will I use this enough to warrant carrying it around? Will it fit in my luggage? If I get this what will I no longer have room for?”

        But beyond the added thought around new acquisitions, the practice of regularly packing your existing possessions produces an opportunity for reflection on what we bring with us and why.

        An Expanding Suitcase

        Over the years, I expanded my kit from the minimalist essentials I brought with me on a three-month cycle trip of Europe on my first trip, to a minimalist work setup when I first started Counterweight Creative and started traveling full-time.

        More recently, I’ve traded in the backpack for rolling luggage, filled out my work setup including laptop stand, keyboard, mouse, fancy noise-canceling headphones, hard-drives, as well as bringing a wider variety of clothing, tools for hobbies, and other comforts.

        What Our Things Say About Us

        Along with these comforts and necessities, I have a habit of collecting postcards, pamphlets, maps, and brochures from the places I visit. When I first started traveling, I journaled daily and would often use these local finds to cut up and turn my journals into scrapbooks.

        I love those old journals, but I haven’t journaled regularly in over two years at this point. Despite that, until recently I continued to add to my collection of loose papers, lugging them across the globe, and with them, the belief that one day I’d take the time to catch up on two years of journaling and scrapbooking.

        During a stopover at my Mom’s house recently, I emptied my bag out entirely and was confronted with the 5lb stack of papers.

        “Why am I still carrying these around with me?” I asked.

        I realized that this random assortment of papers was tied to my idea of who I was.

        Scrapbooking and journaling had been central to the way I not only traveled, but lived my life during my first trips, and I hadn’t yet moved on from that version of myself, even though I no longer had the need or desire to continue those practices regularly.

        As a result, I was carrying around extra weight that served no purpose towards improving my current life or moving me toward my future goals. A small, even trivial weight to be sure, but who’s to say this wasn’t happening elsewhere.

        Pruning Your Possessions

        After this realization, I took a new eye to everything else I owned and carried with me, and realized that there were a surprising number of items I was jamming into my pack that were less practical than they were representative of a vision of myself.

        I carried books around that I never read, carried my rock climbing shoes around the world for a year and only once ever even looked for a climbing gym. I had keepsakes and mementos from my past and aspirational items that I thought would hold me accountable to some practice or task in the future.

        Even with my limited space, I managed to fill the nooks and crannies with stuff that served no purpose in increasing my happiness, often doing the opposite by reminding me of the guilt I had for carrying these things around with me and not making use of them.

        I’m grateful that I only have a limited amount of space to fill with these items. But I haven’t always traveled full-time and I won’t live this way forever. I know how easy it can be for the things, the beliefs, the routines, either those from our past or those designed to encourage a future we’re not really that excited about to crowd out the present.

        If we’re not careful, our baggage can fill up and take over all our space, physical, emotional, relational and spiritual, leaving no room for the new, for the necessary, for the vital.

        My advice is to make a habit of taking stock of your life, your things, your thoughts and ask, “Why am I still carrying this with me?”

        If no good reason exists, you might be better leaving it behind.


        The Hard Stuff

        Most of us want to do the work.

        We thrive on the feeling of meeting a worthy challenge and our best self rising up to face it, and best it. Of fighting through the hard stuff.

        The harder the hard stuff, the better.

        Why then, if we take such pride in doing the hard work, do we so often stall, get stuck, or abandon our pursuits when the going gets tough?

        Shouldn’t these be the moments that excite us most? That pull our best selves to the surface to meet this new challenge and create our best work?

        I think there are a couple of reasons.

        Validation Of Our Struggle

        While we can certainly feel pride in ourselves, pride feels a whole lot better when we’re acknowledged and lauded by others.

        For so many of us, the hard parts in our work are creative, technical or abstract challenges that may not be relatable or understood by a single person we know.

        As far as our friends and family might be concerned, one website is pretty much the same as any other, a sales letter is just a bunch of words you jotted down over 30 minutes, and your online course is just you talking about something they don’t understand in front of a camera.

        God help you if you create music, art or poetry…

        Sure, if we’re massively successful with our creations we may get some of that validation, when they see that we’re making a good living from our work and our art, and creating an impact along the way.

        But there’s no guarantee that will happen.

        And if our work does fall flat, there’s no consolation prize and perhaps not even an understanding or acknowledgment of our efforts.

        That’s a lonely place to be.

        Best not to risk it.

        Fear Of Not Being Enough

        The second reason is that while we want to show up as our best selves, call on all our strength and wit, and truly test ourselves, we also want to know that we’re going to come out on top.

        This means that we have to understand going in what the work will consist of, how it will challenge us, and hopefully be similar to something we’ve faced — and bested — before.

        By taking on something new and unknown, by stepping beyond the light of the campfire we’ve been sitting warmly around, we risk showing up fully, bringing every fiber of our being to the table and finding that it’s not enough.

        That we’re not enough.

        This is a truly scary thought.

        A thought that can keep us playing small, and safe. Ocassionally tiptoeing up to the edge of the darkness, but only just. Staying within the realm of what we already know we can achieve.

        Because if we step outside the firelight, if we’ve brought our best and fallen short in pursuit of work that is meaningful to us and impactful to our communities, what does that say about us?

        More than a rejection of our skills and knowledge, failures like these feel like a direct rejection of our vision for the world, and our ability to bring it in to being. A rejection that strikes to the core of who we are and all that we encompass.

        Most definitely best not to risk going there.

        Better to stay by the campfire with the familiar, the known, the manageable.

        How Do We Create Work That Matters?

        So what do we do as people with big ideas that will surely consist almost predominantly of hard, emotional, risky work?

        First, I think, we need to go into the work knowing that the work hasn’t really begun until we get to the hard stuff.

        More, we need to understand that while “the hard stuff” will probably test us mentally, and may even test us physically, it will most definitely test us emotionally.

        The hard stuff will expose us in some way, and may even slice down to the core of our very idea of oursleves, leaving it open, raw, vulnerable.

        That idea of ourselves might even be broken.

        This is the price of admission to dance with the hard stuff.

        If we need to ignore this price, ignore the hard stuff in order to begin our work, we probably don’t care enough about the outcome of the work to see it through when the going gets tough.

        That’s fine. Better to move onto something else now than waste the time.

        But if we’re willing to pay that price, knowing what it is and being prepared for it can help us build up our resources, support and courage for when the time comes to stare it down.

        We Don’t Need To Face The Hard Stuff Alone

        Secondly, we can accept the fact that we can’t — and don’t have to — get through the hard stuff alone.

        We can accept that we probably don’t have all the skills, knowledge, resources and emotional bandwidth to complete our work alone, and we can assemble our support team.

        These don’t need to be employees or contractors, they don’t have to be doing the work with or for you. While this type of person or people might be helpful, more important are those that will keep you accountable, motivated, inspired, and supported emotionally.

        While we might not want to admit that outside acknowledgment and emotional support matters, for most of us, that’s a lie.

        Surround yourself with people who understand both your vision and the work it will take to get there. People who will cheer you on through your successes, and pick you up without judgment after your failures and help you analyze what happened and why.

        Understand that the hard stuff will test your ego, will require you to ask for help, to look beyond yourself for answers.

        Find teachers, guides, mentors, and use them.

        We Don’t Have All The Answers… Yet

        Lastly, we need to understand that when we’re taking on the hard stuff, we will fall short.

        There’s no way around, over or under it.

        At some point, we will be forced to confront the fact that in our current iteration, we are not enough.

        But we also need to understand that falling short is not a rejection of us, our work, and our vision for the world. And that our current iteration is not the extent of our potential.

        We need to understand that in reality, falling short, even when we’ve brought everything we have to the table, is nothing more than a sign that our current knowledge, strength or resources are insufficient to overcome this current challenge.

        Our work then, is to build up our knowledge, our strength, and our resources further before facing down the hard stuff again.

        If we believe our work is vital, we’ll return to face down the hard stuff again and again and again and again, as many times as necessary, showing up stronger, smarter, more resilient each time until we’ve become the people we need to be to push through.

        The only way to get there is by stepping outside the firelight.

        Build Up Your Bravery

        You don’t have to confront the truly hard stuff before you’re ready, but I believe we all have some dream inside us that will require us to face it at some point if we’re going to realize that dream.

        So take one small step beyond the known. Challenge yourself the tiniest bit further than what you know for sure you can handle.

        Then do it again.

        Build your fire, and with it your ability, your knowledge, and your belief ever outward.

        Don’t think it will be easy.

        It takes true bravery to step beyond your known limits and put yourself on the line.

        But it’s the only way to prepare yourself for when the time comes to do the work that really matters to you, and facing down the hard stuff that comes with it.


        Why You Aren’t Coming Up With New (or Good) Ideas

        Ideas are nothing without action, so the saying goes.

        It’s a little glib, but I’m not going to argue with it.

        It’s also true, however, that action is nothing without an idea, and more often than not, even action and idea together amount to less than we hoped for or maybe even nothing at all.

        It’s a disheartening reality, but as anyone who’s started a business and kept it going for any amount of time will tell you, the first (or second, third, fourth…) thing you try rarely works out as you’d hoped.

        And even if you do hit it big once, that’s probably not enough.

        Most of us can only squeeze so much life out of our individual hits before being relegated to the category of One-Hit Wonders along with Psy, Gotye, and Baha Men…

        The key then to both getting off the ground and then remaining aloft once we’ve done so is to ensure we have a steady stream of ideas ready to get to work on when the time is right.

        Coming Up With Ideas Is Hard

        When I made my first foray into the world of podcasts, one of my favourite shows was Question Of The Day, with Stephen Dubner (of Freakonomics fame) and James Altucher (of James Altucher fame…).

        It was a short, daily show in which the two friends would have a lighthearted discussion around a topic, often presented by a listener. I’d often binge-listen through 4 or 5 episodes a day while working full-time as a landscaper.

        James mentioned on multiple occasions the practice he had developed of coming up with 10 ideas a day as being central to his success in his life as an entrepreneur.

        Being young, impressionable and in the beginning stages of figuring out how to start my own business, I took this advice as truth and started keeping a daily journal of ideas.

        The first day I wrote down maybe 6 ideas. They weren’t very good. They may not have even been real ideas, and they definitely weren’t original.

        I knew they weren’t good, but I figured that as I built up the idea-generating muscle, I would only get more and better ideas each day until by day 100 I would understand how to cure cancer, have built out mental blueprints of a light-speed capable rocket engine, and be primed for fame, fortune, and accolades from the highest echelons of society.

        Fast forward 100 days and I had given up on the idea journaling exercise about 87 days earlier…

        Where I had assumed that conjuring ideas would become easier with time, I instead found that after a couple of weeks, I had exhausted the ideas that had already been kicking around the back of my head (none of them very good), picked the low hanging fruit, and was left with nothing new.

        What Does An Idea Even Look Like?

        It had been my understanding that big ideas would appear in the form of a lightning bolt, lightbulb, or some other obvious (and light-based) signal that would alert me to their presence.

        And so, when none appeared despite my keen 13-day surveillance, I accepted the fact that I wasn’t the idea-generating type and moved on.

        What I realized much later, was that the issue was not, in fact, that I wasn’t the idea-generating type, but that my conception of what an idea even looks like was flawed.

        Part of it was that I was impatient.

        I was ready to have my million-dollar idea and get to work on bringing it to life.

        And so, in my impatience and naivete, I was on the lookout — and only on the lookout — for fully-formed business ideas, ready to download from the ether and convert into paying customers.

        It turns out that big ideas, the ones that do seem to strike you like a bolt of lightning are exceedingly infrequent and subject to the same rules as all other ideas.

        That is, there’s a better than not chance that they won’t work out as well as you’d hoped.

        Generating ideas like this is neither reliable, nor scalable for most of us.

        Real Ideas Are Subtle

        What I’ve come to learn and embody is that the most reliable way to find and develop ideas into something useful (and maybe even impactful or profitable), is not to go looking for the lightning bolts.

        Instead, keep your eyes peeled and your ears pricked for the slight tickling of curiosity. For the end of a ball of string that you can unravel and see where it leads.

        For me, these usually show up as a random thought, or observance that strikes me as interesting and worth more exploration.

        In all likelihood, most of those ideas won’t lead anywhere “productive” or profitable. But that doesn’t mean they’re not worth exploring. If nothing else, you’ll have exercised your mind, satisfied your initial curiosity about the idea, and can move on to the next one.

        Often, however, in unspooling one ball of string, you’ll find the beginnings of another 7 balls along the way.

        This is how you become an idea-generating machine. Not by waiting for lightning to strike, but by actively following and exploring the tiniest sparks of ideas you come across.

        Commit To Idea Exploration

        In my experience, the ideas that amount to the most are the ones that stick their tiny hooks in you, and then force you to grapple with them, unroll them, turn them over, flex them, view them from every angle, break them open before putting them back together.

        These ideas are not fully formed. They take time, sometimes months or even years, to wrestle with or to grow into before they become useful.

        They can be frustrating, the timing never being quite right, the pre-requisite pieces never quite being in place, never quite fitting into the space we have for them at the moment.

        But if we ignore these idea threads in favour of the lightning bolts, we risk passing up the thousands of unexplored ideas, that would have revealed their potential if only we’d taken the effort to give the thread a slight tug to see where it leads.

        So pull your conception of ideas down off its pedestal. Write down every thought or observance that seems interesting you, and then commit to exploring it further.

        Do this, and you’ll have no shortage of ideas.

        They won’t all be good. They won’t all be useful.

        But some will both, and they’ll be worth putting the work in to unravel.

        Shit-Disturbing: A Beginners Guide For Creatives + Visionaries

        Let’s face it. You’re a shit-disturber. A contrarian. An instigator.

        Maybe you’re not getting in bar fights every weekend (although maybe you are…), but if you spend your days creating, whether that’s business, art, or ideas, my guess is that at the root, at least some of your motivation comes down to changing people, the culture, and maybe even the world in some way.

        Chances are, many, if not most of those people have no interest in being changed, however.

        They’re perfectly happy with the way their existence is currently playing out, or if they’re not, they’re not truly ready or committed to seek out change themselves.

        Thus, in your efforts to change them, to make them see things your way, you have to become something of a shit-disturber. To upend their worldview and show them that with you, your ideas, your creations, a better way forward is possible.

        I know calling you a shit-disturber might not be a polite way to start off this article, but I say it with love.

        We need you. The world needs you.

        There are myriad problems facing us both collectively and individually, ranging from war, famine, disease, and climate crisis in the extreme all the way down to not having any good new music on your phone.

        The status quo is not going to solve these problems, at least not in a timely manner. Checklists, manuals, and reasoned debate are not going to solve these problems.

        You are going to solve these problems, and you’re going to do it by going against the grain, breaking the rules, and surprising us all with something unexpected and new.

        In other words, you’re going to seriously disturb some shit.

        But again, most people aren’t looking for you to change them and their way of life. They’re happy with the old, the safe, the familiar.

        Most people are happy with their current music, current art, current technology, current conception of the world and ideas about life and their place in the universe.

        “Nothing new, please. Another round of the same. Don’t rock the boat, things are good here.”

        So how do we bring our radical, shit-disturbing ideas to people who don’t want to hear them and show them our vision of a better way forward that resonates with them and invites them to come on board?

        How can we create something unlike what’s come before and find an audience for it that will help us create more?

        Indoctrinating Them Slowly

        Give them something they’re familiar with but subtly slip in some of your art, your fresh ideas, your rebellion.

        Package your work in a wrapper people already know and like, but include something unexpected and surprising. Something that might just expand their idea of what’s possible.

        Sure some people might hate it. But some people will like it. And if you’re lucky, some people might really like it. And they might ask for more.

        “Yes, please. More of that. I can’t get this anywhere else.”

        Suddenly you have license to take your art a little further, to push the boundaries of what’s familiar and acceptable out a little more, be a little bolder in your work.

        And not only do you have an audience who’s ready for your ideas, your art, your rebellion, they may actually be hungry for it. Messaging you daily asking when you’ll have new music, a new book, a new product.

        Playing The Long Game

        As a shit-disturber, this might be a frustrating strategy.

        You want change now.

        You know the problem, see the solution and if the rest of these knuckleheads could just see it we could solve it and move on to the next one.

        But world-changing is a long game.

        And chances are, your ideas could still use some refinement, and will only benefit from challenge, push-back, competition and collaboration.

        If you just want to be different, go ahead and commit to publishing your work in its rawest most unrefined form. It might be art in its highest form, but it might not find an audience.

        History is filled with near-unknowns who were too radical, too unfamiliar, too soon.

        If you truly want to change peolpe, the culture, and the world however, commit to the long game.

        Pique their interest by pushing just a bit outside their comfort zone, and once they give you permission to continue, spoon-feed them a little more, at their pace, as they’re ready for it.

        Do it with kindness, do it with generosity, do it with empathy, and do it with patience.

        Now go build your rebellion and change the world.


        Sometimes You Just Need To Collect Data

        My family loves games, and we’re competitive about them.

        We’re not game nerds per se. We don’t buy new games every month, we’re not into complex strategy games, we don’t collectively attend game meetups and wipe the floor with the competition*.

        *Although that sounds awesome…

        We mostly play cards and classic board games that you’re probably familiar with to some extent.

        And while we may not be extremists, we have our favourites and we take them seriously.

        At any family gathering, game playing is almost the default activity over which to catch up, eat, and spend time with each other.

        So when my mom recently visited my girlfriend and me, it was just a matter of hours before the deck of cards came out.

        After running through some family favourites, my girlfriend suggested a family classic of her own, Spades, which I had never played before.

        Now Spades is similar in concept to a number of the trick-taking card games I’m familiar with, and yet the feeling and strategy of the game are quite different.

        Being a competitor, I was of course, interested in winning out of the gate.

        Every Game Is Different

        A few hands in, however, I realized that while the rules were similar to other games I was familiar with, the same strategies and mindsets didn’t necessarily work.

        When learning many games, not only is there a process of learning the hard and fast rules that contain and guide the flow of play, but also a more abstract “feeling out” process required to gain a level of proficiency.

        This feeling out process relates both to the game as a whole, as it would be played with any other players, as well as the individual players with whom you are playing in the moment.

        A game with one or more aggressive, risk-taking players will have a drastically different feel than one with generally conservative players, and those variables will change how you show up and play the cards you’re dealt.

        On top of learning how to compete at a basic level, a game often doesn’t begin to feel fun until you’ve really gained the feel for it.

        This means that sometimes when you’re new to a game or new to your fellow players, the correct strategy is to put aside your competitive nature and just gather data.

        Test The Boundaries

        Commit to losing every hand, but testing different modes of play until you develop your feel for it.

        Play aggressively, conservatively, randomly, trust your gut, trust a system, play based on your opponents, play based on your hand, try anything that comes to mind. Push the boundaries of how someone might play a given hand and note the outcome.

        Note how your opponents alter their play in response.

        Note what’s most fun for you personally. It’s a game after all, and games should be fun.

        Then once you’ve gathered sufficient data and developed your feel, you can enter the next round with an intentional strategy that you have some confidence in being effective for the given situation with the given players.

        Always Be Testing

        The same is true for so many aspects of our work and lives.

        We want to jump into different areas of our businesses, be that marketing, management, our product or service itself, or maybe even the business we want to start but haven’t yet and have every action we take be successful the first time through.

        Life rarely works like that.

        Instead, we should commit to relentlessly experiment and test the boundaries in ways both big and small, and always be gathering and analyzing the data we get back from those tests.

        Some tests might fail. Some tests might cost us money. Some tests might cost us relationships and even clients or customers.

        Testing can be scary.

        But we can’t begin to build and grow intentional businesses until we develop our feel for our business, our clients, our customers, our teams until we know where the boundaries for each are, and how the various inputs affect the outputs.

        And my guess is that if you do enough tests you’ll realize that the boundaries of your potential are a lot bigger than you had thought, and you might just hit on something truly special you never would have known was possible otherwise.

        So make a list of possible tests to run and start collecting data. Put your ego aside, be prepared for many of your tests to fail, or even commit to it if you’re really brave.

        Note how your leads, clients, and customers respond.

        Note how your team responds.

        Note what’s most fun for you personally.

        It’s a business after all, and business should be fun.

        A Resolution For Kindness

        Like many others, I’m entering this new year — and new decade — with a heady list of goals and resolutions.

        However, along with our typical business goals, health goals, and personal goals, there’s one resolution I think we could all benefit from making.

        What if we all resolved to treat each other with just a little more kindness?

        In light of how this past decade has come to an end with politics dividing us across the world, opinions growing more entrenched and extreme, and those opinions (often weaponized) being easier than ever to share anonymously, even a marginal increase in kindness from each of us would be a breath of fresh air.

        It doesn’t have to be giving up your weekends to volunteer, donating money to charities and organizations, or even the classic act of holding open the door for an old lady at the grocery store.

        I’d argue these options are easy ways to make yourself feel good while ignoring the impacts our everyday interactions have on others, our communities, and the world.

        What might resolving to be kinder look like?

        What if instead of arguing with those we disagree with (whether online or off), we started by asking questions and gaining an understanding of their background and why they believe what they believe?

        What if instead of focusing on all the seemingly myriad topics that divide us, we remembered that life is not entirely made up of political opinions and dug deeper to find and focus on all the beliefs, goals, causes, affiliations, and histories we share?

        What if we diversified our media intake to include opinions from the “other side”?

        What if we resolved to remember that everyone has reasons behind their opinions and that while attacks and arguments won’t change many minds, compassion, understanding, and kindness just might?

        None of these are easy resolutions, but isn’t that the point of resolutions? If they were easy we would have already done them.

        Kindness, like gratitude, restraint, or mindfulness is a practice that strengthens the more you use it. Luckily for us, there are probably hundreds of opportunities every week for us to exercise that muscle.

        I’m convinced that when used authentically and generously, kindness is the key to not only making the world a little better as a whole, but to radically transforming our businesses, communities and lives.

        Where to start?

        A good first step is to just take two breaths the next time you feel your emotions rising up and asking “how can I treat this person with kindness?”

        So what do you say? Care to join me in making the next decade a little bit the kinder than the one we just came from?

        Subscribe

        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.