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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    Pushback Rallies: How to Do More with the Creative Opportunities You’re Given

    Ever since Roger Federer announced his retirement a few weeks ago, I’ve been going back and watching through highlight reels from his career.

    Many of Federer’s highlight reel moments are of him masterfully dictating the flow of the game and utterly dominating his opponents.

    In these clips, Federer feels like some mix of artist, chess master, and evil genius.

    Through precise and strategic shot-making, he guides his opponents around the court, setting up the pieces with subtle manipulation… before dropping the hammer with an elegant, seemingly effortless checkmate.

    These clips clearly display a master of his craft at the height of his powers.

    But there’s another, very different type of highlight reel rally that appears again and again in these compilations of Federer’s career. One where it’s Federer being chased around the court.

    These rallies are defined less by skill and more by a certain type of grit.

    I think of them as Push Back Rallys. And there’s a lot we can learn from them.

    Specifically, there’s a certain decisive shot in the middle of these rallies that we all need to learn to make as creator-entrepreneurs as well.

    Let’s set the scene.

    Hitting Off the Back Foot

    In a typical Push Back Rally, the opponent has taken control of the pace and it’s all Federer can do to simply return the ball in play.

    He’s clearly on the defensive, struggling to keep up, constantly hitting off his back foot, unable to plant and step into his shots in order to generate more power or accuracy.

    You can tell it’s only a matter of time before he cracks, handing his opponent the point.

    And then the decisive moment.

    His opponent attacks. Federer lunges to get into position, but he’s half a step too slow.

    You can almost see the same calculation we as the viewers are making play out in his head.

    “Is it even worth fighting to keep this rally going? I’m in a weak position… Maybe I’d be better conceding the point, conserving my energy, and resetting for the next one “

    But just as you think he’s giving up, something in his posture shifts, almost imperceptibly.

    He’s off-balance, unplanted, and out of position. The safe shot is to simply get the ball back over the net, extend the rally, and hope for a better opportunity on the next shot.

    Instead, through force of will alone, he goes on the attack.

    With this one shot, he manages to swing control of the rally in his favour, and a few shots later the point is his.

    Examples of Push Back Rallys abound in tennis.

    It’s a sport governed by momentum where single shots can—and often do—change the complexion of points as well as entire games, sets, and matches.

    But the idea applies elsewhere as well, including our creative work.

    Don’t Wait for the Perfect Setup

    Unlike Federer, most of us default to waiting for the circumstances to be perfect—feet planted firmly in a position of power with ample time to pick our spot, step in, and swing with perfectly controlled form—before making our move.

    These opportunities rarely if ever present themselves to us, however.

    And so we spend most of our creative lives on our back foot, reacting to what comes our way, just trying to get the ball back over the net, without ever pressing the offensive without making our opponent react to our will.

    There’s certainly a time to defend.

    To do what we can to keep the ball in play, extending the game while conserving and building up our energy.

    But as a larger strategy, simply extending the game is unlikely to win us many points.

    Sooner or later, we have to shift to the offensive, to assert ourselves and seize control of the flow of play.

    We won’t be given an obvious or advantageous opening to do so.

    When the time comes, we’ll likely be on our back foot, out of position, without as much time as we’d like to step up and really swing through our shot.

    In watching Federer, it strikes me just how many of his career-defining winning shots came during Pushback Rallies, where the odds were stacked against him and the logical choice seemed to be to wait for a better opportunity.

    It makes me wonder.

    How many of the losses or draws we settle for in our lives and work could actually be winning points if we were willing to dig a little deeper, get a little more uncomfortable, and go on the offensive, even when all the circumstances are telling us to do the opposite?

    Because in the end, these are the opportunities we’re given.

    What we do with them is up to us.


    Explore how to navigate a creative life that matters

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

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

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

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


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        Sometimes Your Work Sucks

        Photo by Maria Teneva on Unsplash

        It’s true.

        I won’t sugarcoat it and tell you it’s great, good, or even passable because it’s not.

        Today your work really sucks.

        But maybe that’s not important.

        Maybe what’s more important is both of us knowing that you have the potential to do better work tomorrow than the work you did today, and that I won’t let you off the hook or expect less than I believe you’re capable of.

        Maybe what’s important is to do dig our way through the work that sucks in order to get to the work that sucks a little less.

        Maybe if we do this long enough we’ll get to work that is passable. Maybe even good. Maybe even great.

        So yes sometimes your work sucks.

        Don’t dwell on it. Don’t hide it. Don’t quit.

        I know you’ve got better inside you and I won’t let you settle for less than that.

        And when my work sucks, I hope you’ll do the same for me.

        How Can We Make Business Magical?

        Photo by Karly Santiago on Unsplash

        Last year I saw a talk by a magician that changed the way I think about my business, relationships and daily experience.

        Nate Staniforth, the magician in question, is the first to acknowledge that the title “Magician” carries with it some less-than-helpful connotations.

        This is especially when attempting to be taken seriously at say, a (non-magic-related) conference where you’re presenting a keynote talk, but applies to many other more mundane, but perhaps equally stressful situations as well (meeting future in-laws comes immediately to mind).

        What I took away, however, first from Nate’s talk and then from his excellent book, Here Is Real Magic, is that real, true magic does exist, perhaps not in the way we often conceive of it, and that each of us has the transformative power to create it.

        I’ve become convinced that if we can harness this power and apply it to our businesses, work and lives, we can transform them — and those of the people we interact within those contexts — forever.

        Ok So What Is Magic?

        First, we need to do away with our unhelpful present ideas of what constitutes magic.

        Figures like Harry Potter, and Gob Bluth, the Arrested Development character (both of whom I love by the way), while entertaining, are not what we’re shooting for here.

        Real, applicable magic is not about illusions, sleight of hand, or elaborate performances and stage shows (although feel free to use those if the situation calls for them…)

        Rather, the magic we can create is about giving the people we interact with the sense of awe, wonder, inspiration and hope that good magic achieves.

        Imagine if this was the feeling your clients, customers and collaborators associated with interacting with you.

        Magical types of experiences are the ones that people rave about.

        How To Create Magic In Your Business

        Magical experiences should speak uniquely to your customers and the relationship you have. They’ll take thought and work to create and might sometimes feel like they’re not worth the time and expense you put into them.

        The fact that they go above and beyond the normal course of business is part of what makes them magical.

        So while I don’t have a defined, repeatable framework, let’s have a look at some traits that magical experiences have in common.

        Awe/Wonder: This is at the core of magical experiences. Moments like this make us realize that the world is a little bigger than we previously thought. That the unknown isn’t just a place of fear and uncertainty, but of excitement and possibility.

        Inspiration/Hope: Good magic raises the bar of what’s possible, both for ourselves and the world. When I find myself in the middle of a magical moment I feel inspired both that I can do more, and that I must do more. Good magic destroys cynicism.

        Surprise + Subversion Of Expectations: Magical moments and experiences catch us off guard and surprise us. This could be through the timing of the delivery or by subverting expectations of how a certain process will go. If you’re able to turn a process that’s typically uncomfortable or painful into something that feels magical, you’re on to something.

        How did they do that? This is one of the hallmarks of magic tricks, where we find ourselves analyzing and guessing at how it was done. Perhaps you make note of some off-hand remark about a client loving a specific hard to find flavour of ice cream, and have a tub delivered to them (yes ice cream delivery exists, I’ve looked into it for this very purpose) leading them to ask, “how did they know I liked this?”

        (In this case, we’re hoping they’ve forgotten they ever mentioned it, which is hard to ensure, but amazing when it happens.)

        Personalization

        Beyond these common traits, I’m convinced that when it comes to creating moments that feel like magic in our businesses, we need to pay special attention to personalization.

        We want our clients and customers to know that we created this specifically with them in mind. That we went out of our way. That not everyone gets the attention and experience that they’re getting right now.

        One of my favourite things about the concept of personalization is that it can be low cost but feel thoughtful and unique.

        I attended a conference a couple years ago, and waiting for me when I checked in was a bottle of my favourite beer.

        Just one. Just for me.

        I remembered later that they had asked on the registration form what my favourite beverage was to kick back and relax, to which I had responded with this beer.

        The fact that I had supplied the information myself didn’t diminish the experience.

        I would have been excited and surprised to get any bottle of beer at a conference check-in. The fact that it was unique to me, however, elevated the experience into the realm of magic, where for a few moments I was filled with awe and the question, “how did they know??”

        By the way, I rave about that conference and tell almost everyone I know that they should go…

        I’ve since started incorporating similar questions into my own client and team member intake forms and surveys to slowly build up information that I can use later (hopefully once they’ve forgotten that they supplied the information) to create unique, special, hopefully even magical experiences.

        A Word About Intention

        I want to make sure to say that while I really believe that creating moments that feel like magic for our teams, clients, customers and colleagues has the potential to have huge returns in how people talk about, interact with, and refer our businesses, for it to be effective, you need to be doing it for the right reasons.

        Manufacturing magic to achieve an end result doesn’t work and isn’t scalable or sustainable, at least not while retaining a true sense of magic.

        Hopefully, you already care deeply about those you work with and believe that creating an experience for them that feels magical is worth it if only to show your appreciation. Maybe you even believe that they deserve to have this type of experience.

        Your people need to believe that the act is coming from a sincere place in your heart. These experiences won’t cover over or patch up past or consistent shortcomings, but they will elevate an already solid relationship to an extraordinary one.

        Let’s Make Magic

        One of my missions in our work at Counterweight Creative is to make the experience of both our team members and clients feel as far from “business as usual” as possible.

        I want to create team and client experiences that subvert expectations about how employee/employer and client/supplier relationships work.

        I make a point to send out handwritten thank yous, postcards, and letters, I’ve sent out cases of client’s favourite beer, whiskey, ice cream and other gifts to mark special occasions.

        We’ve sent out congratulatory videos from our team to clients who’ve hit milestones, and recently even sent a custom, framed platinum record to a client who passed the million-download milestone on her podcast.

        It’s not easy to keep on top of and prioritize these experiences. They often cost money, always take time, and there’s no clear return.

        Nevertheless, I want to build a company that’s known for going above and beyond in both the work we do and the experience we deliver, so if that’s the goal, why not go a little further and strive to make the experience truly magical?

        I’d love to hear how you create magical experiences for your team, clients, customers or anyone else. I’d also love to hear if you’ve been on the receiving end of a magical experience, whether personal or professional that was orchestrated by someone else.

        Ideas Need Leaders

        If we’re going to use our unique talents and ideas to change the world around us for the better, sooner or later we need to realize that we have to step up and own our roles as leaders.

        There are countless people with ideas. Ideas that have the potential to change the culture, move it forward to somewhere better than it is now.

        But ideas need leaders.

        Without leaders, ideas are left to either sit stationary as they are, or bounce around aimlessly and hope that someone else will recognize their value and lead them where they need to go.

        We don’t need to walk around with a spotlight on us every second of the day, smoke cigars in boardrooms, and ensure we’re regularly rubbing elbows with the right people.

        But at some point, to move our ideas into the world, we need to champion them, to put them in front of people, the right people, people who see our work and ask, “How can I help?”

        The idea of stepping into the spotlight might scare us.

        We might be more comfortable staying in the background, creating our work and then moving on to the next thing.

        Sure, we might feel slightly unfulfilled. We might recognize that our work doesn’t get the attention we feel it deserves. We might even feel bitter when lesser talents and ideas get recognized.

        But it also feels safe to stay just outside the light. Free of scrutiny, judgment, and responsibility.

        What if leadership isn’t what we’ve made it out to be in our heads, however?

        What if leadership isn’t all about decisive action, clarity, force, and unwavering charisma?

        What if leadership, true leadership, leadership that inspires is about leading with vulnerability?

        About inviting others in and saying, “I don’t know where to go from here, what do you think?”

        About understanding that we can’t change the culture by ourselves and that real leadership is about uniting, finding and inviting in the people who are needed to solve the problem we’re facing. People who believe in our cause as much as we do.

        Maybe that’s a kind of leadership we can step into.


        We Should Say “I Don’t Know” More Often

        Photo by Greg Rakozy on Unsplash

        There’s a lot of stuff in the universe. A lot of stuff.

        There may even be multiple universes, existing in parallel to ours.

        I like to think that’s the case.

        It stokes my curiosity, my wonder, my awe at the existence of myself, the Earth, and this, and any other as-yet-undiscovered universes.

        But while I may hope for the existence of alternate universes, I don’t really have an opinion on the topic, I’m far from being whatever kind of physicist studies that kind of thing.

        What do I know?

        The fact that a universe filled with so much stuff also contains so many opinions about said stuff is more than a little absurd.

        How is it possible that in a universe full of so much complexity, unknown and perhaps even unknowable, that to simply admit we don’t know or have an opinion on any given subject is to subordinate ourselves to others with more conviction?

        I suppose it’s not entirely unexpected.

        Opinions are easy to come by and our culture encourages their development and their sharing, our rights to free speech are co-opted to justify the sharing of any opinion, no matter how wrong or harmful.

        Opinions are an easy substitute for original thoughts, with what’s lacking in substance made up for in volume.

        Opinions are comforting. They help us feel like we have some control, like we understand what’s going on around us, like we’re smarter, better, and more in the know than those around us.

        Opinions do not help us create better, more meaningful work, however.

        To make work that’s new, that makes an impact, that has substance, we need to start with not knowing, being in the dark, without an opinion.

        It’s uncomfortable, to be sure.

        But nothing great begins at a place of comfort and certainty.

        It’s getting comfortable with the not-knowing, grappling with the uncertainty and really, truly seeking to understand the problem we’re trying to solve that leads to work that matters.

        It’s the unknown that fuels our sense of wonder, curiosity and awe, which in turn fuels our creativity.

        Lucky for us, there are likely dozens of opportunities every day to start getting comfortable with all we don’t know and embracing it.

        Next time you’re asked for your opinion on the economy, the housing market, foreign policy or any other complex system that few, if any, truly understand, say it out loud.

        “I don’t know.”

        Do it again. Build the muscle. Admit again and again how little you know until it becomes second nature.

        Then, with every unknown, find wonder, curiosity, and magic in life’s mysteries and dive in and explore them

        Take pride that while others are busy forming opinions, you’re forming your best work.

        How You Do The Work Matters

        Photo by Jamie Street on Unsplash

        At the end of each of his fantastic Akimbo podcast episodes, Seth Godin fields one or more voice recorded listener questions.

        Listeners typically introduce themselves, ask their question and then thank Seth for the work he does.

        I was struck on a recent episode by a listener who signed off her question with “Thanks so much not only for the work you do but the way you do it.”

        If you’re at all familiar with Seth’s extensive body of work, it will come as no surprise to you that he has built up a lot of fans by changing the way we — as business owners, freelancers, entrepreneurs, and marketers — think about marketing.

        Marketing is a topic towards which many in the general public — and more than a few heart-centered business owners and freelancers — have a deep-seated sense of suspicion and antipathy.

        Bad marketers have given the word a connotation of deceit and trickery, often leaving us feeling like we’ve been cheated after dealing with them.

        Given that this is not an uncommon impression of his craft, the fact that Seth has been able to build up not only the size but the quality of audience that he has is remarkable at first glance.

        Look closer, however, and you’ll quickly realize that while there are a million and one marketing gurus in the world, there are few, if any doing it the way Seth is.

        At the core of his work is a deep thread of empathy, generosity, honesty, heart and love for the work he does and those it is intended to help.

        The How Changes People

        When I heard the listener-submitted question above, it sent a chill through me.

        There’s was an emotion in the questioner’s voice when she said “the way that you do it,” that conveyed much more than a simple thanks for good, even impactful, work done.

        It hinted at an inspiration, and a motivation to show up bigger and more fully in her own work. That she had been changed not just by consuming the content of Seth’s work, but by interacting with him in the way he interacts with every member of his audience.

        Showing Up Generously

        When we believe in the work we’re doing it’s easy to justify straying from our values, treating people a little less like people, and taking the occasional short cut if it means moving closer toward creating our vision for the world.

        But What we achieve, accomplish, and create is not the only way to change our communities, cultures, and people we interact with.

        By showing up to our work generously, vulnerably, honestly, with heart, compassion, and empathy for those we work with, those the work is for, and the work itself, we have the opportunity of inspiring a more generous, honest compassionate world.

        Imagine for a second that Elon Musk, Peter Thiel, Reid Hoffman and the rest of the PayPal Mafia had been united by the same generous, honest, empathetic value set that drives Seth Godin’s work.

        The impact and reach of the work that group did together and has now gone on to do individually stretches into every corner of our culture and has undoubtedly changed the world. No doubt each and every one of their successive companies has spun off additional founders who will continue to shape our world through ever more integrated technology.

        How would our world today be different if at the core of all that work, the work it spawned, and the work it will continue to spawn was a focus on compassion and heart?

        Yes, the What matters.

        Do work that excites you, that means something, that makes the world a better place, for one person or for everyone.

        But know that if you’re only focusing on the What you’re missing out on creating impact that has the potential to go far beyond the product of your work.

        The How matters every bit as much as the What.

        It’s the How that moves, that inspires, that changes people from the inside out.

        And so the challenge, if we truly want to be leaders in the world is this:

        Do work that means something in a way that means something.


        Want to hear more about building an audience around work that matters? I think you might enjoy these reads!

        https://medium.com/@jeremyenns/ideas-need-leaders-25950eaa90bhttps://medium.com/@jeremyenns/ideas-need-leaders-25950eaa90b

        What Do You Believe?

        Photo by Katrina on Unsplash

        It seems like a simple enough question.

        But would you be able to cogently sum up your life philosophy and rationale behind your daily actions if put on the spot?

        I’m guessing that for most of us, the answer is no.

        We probably have a vague, intuitive sense behind the beliefs that guide our actions, but those feelings are not always easy to put into words.

        Most businesses have a defined set of core values designed to guide their decision-making processes to not only ensure they’re staying on-brand but true to the traits that they stand for.

        A defined set of core values also provides a measuring stick when mistakes are made. More often than not, big mistakes can be traced back to a decision that strayed from one or more of the values.

        So if businesses realize the value of defining and committing to the core values that guide their decisions, why don’t we as individuals?

        Sure, businesses often have reach and influence beyond that of an individual.

        But as ambitious people looking to create change in our communities and the world, shouldn’t we be equally aligned and consistent in our actions?

        Sure, businesses often consist of more than one person, maybe even thousands of people, and a central set of defined values are necessary to ensure each of those individuals understands how to show up and do the work and represent the company.

        But in doing our own work, many of us will bring on others at some point to help advance our cause. Isn’t co-ordination equally important for us?

        Whether you’re a business, freelancer or individual, defining your core values and beliefs about how you show up in the world and do the work that’s important to you is a valuable tool to ensuring consistency in your decisions.

        It’s also a crucial piece to attracting better clients, collaborators, and team members who buy into what you’re doing and how you’re doing it.

        Tribes, communities and movements form around shared values.

        They are essential if you want to create better work and a bigger impact.

        Make them true, make them you, and make them public.

        Tell us what you believe.

        …But Is It Useful?

        Photo by Ehimetalor Unuabona on Unsplash

        The problem for most people with art isn’t that it’s not impressive.

        It’s not that it’s not interesting, beautiful, remarkable even.

        The problem is that they don’t understand what it’s for.

        “What’s the point? What do I do with it? How will it help me?”

        To the average person, the average piece of art is little more than a pleasing piece of canvas that costs hundreds, thousands, or even millions of dollars more than that piece from IKEA they currently have making that space on their living room wall feel a little less empty.

        How Does This Affect Us?

        Ok, so most people aren’t art lovers, so what? Why should we as creators, makers and entrepreneurs care? How is this information useful?

        Well, I’d argue that for most of us, art plays a significant roll in the work we do.

        For most of us, there is an artistry, a craft to our work that we’ve spent a lot of time developing, but which isn’t always outwardly apparent to the uninitiated.

        At some point, we all need to convince a customer or client that our work is worth them paying for, and paying at a rate we know it’s worth.

        Which means that a core part of the work we do if we want to reach new audiences needs to be explaining to the uninitiated how our work will help them.

        Conveying Our Work’s Value

        Luckily for us, we have some advantages over pure artists when it comes to reaching a broader audience.

        Most of us as business owners, entrepreneurs, freelancers and creators have a product or service for which there is already a market. Even if it’s small or competitive or both, there are probably people out there who are looking to hire someone to do work similar to the work we do.

        Sometimes we connect with these people, their budget matches our asking price and we’re able to create great work together and get paid a fair price for it.

        More often, we connect with a potential client looking for what we’re selling but who doesn’t see the value in the price we’re charging.

        We know that the reason we charge what we do is because of the art in our work.

        The art is the piece that makes our work that crucial 10% more effective, pleasing to use, or profitable for our clients than a cheaper alternative from Fivver or UpWork.

        But our potential client doesn’t know that.

        Our job then, is to be prepared to educate them on what sets our work apart. On why the extra cost of working with us is really a bargain compared to the returns they’ll get as a result of doing so.

        Considering how often these potential client interactions come up, most of us are woefully ill-equipped to deal with them when they do.

        This is a skill we must hone if we want to do more work and create a bigger impact with it.

        Educating The Masses

        Finally, there are aaaalllll the people who have no idea what we do and no idea how our work could potentially help them.

        These are the people who feel alienated by the “pretentious” art community.

        They’re not in on it.

        “What is it you even do online all day? I can make really great designs in Canva on my own. So as a copy writer does that mean you deal with trademark stuff? Isn’t there already an app for that that works fine?”

        How is this thing you do useful or relevant to me?

        Too many of us write these people off as lost causes, not worth the effort of detailing the process, goals, and impact of our work.

        That’s a short term view.

        If we took the long view, we would realize that if we were able to speak concisely and engagingly about the impact that our work has on the people we interact with every day, we are expanding the pool of potential future customers and clients, and raising the perceived value of the work we do.

        We may never work directly with any of the people we take the time to educate, but if we believe in the work we do, we benefit by spreading awareness, appreciation and even excitement about it.

        Invite People In

        To educate in a way that engages the people we talk to and doesn’t leave people feeling like idiots takes thought. We need to understand deeply the true benefits and impact of our work and why it matters beyond giving us a paycheck.

        But we also need empathy. We need to understand where the average person is coming from, their blindspots, the gaps in their knowledge, as well as their goals and desires.

        Once we know this, we can begin to have a real honest conversation about what we do, and hopefully create one more new art fan.

        More than simply being great, maybe even the best at the work you do, this is what being a leader in your field is about.

        Getting Paid Vs. Getting Reps

        Photo by John Arano

        We all want to get paid for our work.

        And sometimes we do.

        Sometimes we get paid what our work is actually worth.

        Most of the time we get paid less.

        Rarely we get paid more, but these are elusive gigs and not to be counted on.

        And then there’s all the work we do for which we never see a dime. Maybe we even pay to do the work.

        Maybe we create a product that doesn’t.

        Maybe we learn a skill that we never get hired to use.

        Maybe it’s all the hours of practice we put into our craft on our own time, when no one’s watching, judging, applauding, critiquing, or, you guessed it, paying.

        There’s getting paid and there’s getting your reps in.

        Both are essential to doing our work to move the culture forward.

        Occasionally you get to do both at the same time, but for the most part, each has their place and it’s better not to mix the two.

        Each form of the work has it’s own limitations and its own benefits.

        Neither is better than the other, they are, in fact co-dependent. The more progress you make with one, the more the other will benefit.

        So make sure you’re clear on which type of work you’re doing in the moment and own it. Accept its limitations and embrace its benefits.

        Build a habit around each form of work.

        Now go get your reps in and then go get paid.


        Want to hear more about building an audience around work that matters? I think you might enjoy these reads!

        https://medium.com/@jeremyenns/dont-rush-to-get-found-before-you-have-a-foundation-5add284779cahttps://medium.com/@jeremyenns/dont-rush-to-get-found-before-you-have-a-foundation-5add284779ca

        Make Space For Doubt

        One of my goals for this year is to build up my confidence further.

        While I feel like I’m generally pretty confident in my ability to bring my ideas to life, I, like most people am prone to comparison, imposter syndrome, and any number of less-than-confident thought distortions.

        In taking stock of where I want to go over the coming years, it was clear to me that in order to be the leader, CEO and person I aspire to be, an increase in confidence, in ownership of my ideas talents and perspectives, is necessary.

        One of my other goals for this year, however, is to make room for a little more doubt, specifically in some key areas.

        Why Doubt is Important

        While confidence is a useful trait, even a necessary one for certain pursuits, it can get in the way.

        Last year, for example, I charged headfirst, investing considerable time and money into creating a product that ultimately underwhelmed significantly.

        I’d seen the model for the product work in other niches and was exceedingly confident that it would work in mine as well.

        In hindsight, I could have used a healthy dose of doubt about a number of aspects of that product.

        Granted, I probably would have done it anyway, but I would have done it differently, with a more complete picture of what would drive its success or failure.

        As Your Potential Impact Grows so Should Your Healthy Doubt

        As my team, client base, and impact grows, I want to be thoughtful and intentional about the choices I’m making.

        “Why won’t this work? How will this impact my team, clients and others?” and, “Why shouldn’t I do this?” are all equally important questions as, “What do I stand to gain?” and “What do I need to do to make this successful?”

        The Role of Doubt in a Societal Context

        Beyond making smarter decisions in business and life, however, I think doubt can play a larger and more powerful role in how we interact with others and our communities.

        As a straight, white, English-speaking male from a middle-class family in Canada, I’m not short on privilege.

        In most categories, I’d rank myself as average to a little above average. I’m pretty smart, decent looking, maybe an above-average work-ethic, but nothing crazy.

        What I attribute any success I’ve had so far to would be my curiosity, perspective, positivity and friendliness. In other words, not skills that are necessarily confidence-inducing or easy to measure.

        Despite my average confidence and mostly average skill set, I’ve been increasingly aware that my privilege and the point of view that comes with it has been more than enough to make up for that lack of above-average confidence in certain social situations.

        I’ve been more aware that I’ve likely been going through life with little regard for my blind spots, speaking up when I should have listened, not leaving (or making) space at the table for others, and have generally done more taking than giving or empowering. All without even noticing.

        Maybe a little less confidence and a little more doubt in my ideas, beliefs, and opinions might serve me, and those around me better. Might make a little more space for others. Might allow me to hear other perspectives and experiences that will help me grow and evolve further.

        And so my seemingly contradictory goals.

        To increase my confidence in my abilities a little more.

        And to add a little doubt about my own importance, opinions, and ideas.

        Maybe with a little more doubt, we’d be encouraged to listen more, collaborate more, and create work that’s a little more helpful to a few more people.

        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.

        Creative Wayfinding For Ambitious Optimists.

        How To Solve Creative Problems In A Way That Resonates

        Photo by Eunice Lituañas on Unsplash

        When it really comes down to it, almost everything we do in our work boils down to solving problems.

        Solving problems for other people, for our teams, for ourselves.

        Problems, problems, problems, everywhere we look.

        Given that this is our reality, it helps to have a framework before we begin to work on a given problem to determine how to best go about attempting to solve it, and indeed if we should even be the ones working on it in the first place.

        Before accepting any project, or beginning to solve any problem we should ask ourselves 3 questions to help calibrate our view of what needs to happen and how it needs to be done.

        Who is it for?

        Most of us are not in the business of mass-market product or service manufacturing.

        Who we are doing the work for, be that our audience, a client, a client’s audience, or anyone else will have a huge effect on the final product.

        Designing a new website for Nike is not going to look the same as designing a new website for Ford, let alone designing a website for the new podcast you’re launching for your own audience.

        Too often we think we’re making something for a client, when we’re really making it for their audience.

        We need to dig deeper, because who it’s really for matters.

        What’s it for?

        At the start of a new project, especially one we’re excited about, it can be easy to get ahead of ourselves and dive in headfirst without taking the time to ask what the bigger purpose is behind it.

        Sometimes the reason is obvious, such as building a landing page with the sole purpose of selling a product, but it isn’t always so clear.

        When it comes to the website for your podcast, for example, there’s a lot to consider.

        You may be launching the podcast to educate your audience, build a loyal following for yourself, create and sell products and services, level up your network by connecting with interesting guests, and build up clout in your industry.

        How will the website serve each of those goals? A website that focuses only on one of those goals will be a lot different than one that supports all of them.

        Why Am I Doing It?

        The first side of this question addresses whether you should actually be the person doing this project.

        It’s more than likely on any number of potential problems that you get invited to solve that you may not be the best person to take it on.

        Knowing that you’re not the ideal choice and taking on the project regardless has a way of backfiring, if not in the form of failed or underwhelming project results, then in the form of intense periods of stress while trying to keep your head above water on a project you’re ill-equipped for.

        Part of doing work that people rave about is knowing your strengths and capabilities and operating within them.

        This question takes on additional meaning when it’s not just you doing the work.

        As our team at Counterweight Creative has grown, I’ve been finding myself asking this question more and more about tasks I’ve always done but should perhaps no longer be doing.

        Every month I look at my time tracking report and for each task-category ask myself why I am the person handling that task.

        Sometimes it’s because I’m the only one who has the skills, knowledge, or relationships to do it.

        But sometimes it’s habit, fear of handing it off, or because I just haven’t created the training resources and structure to hand it off.

        Regardless of what the reason is, it’s essential to be aware of it.

        If you’ve decided that you are the person to be taking on a project, this question can be asked from an additional angle as well.

        Why am I DOING it?

        In a perfect world, every project we took, every problem we solved would be in the service of changing the world for the better, and the impact of our work would be obvious.

        But let’s not kid ourselves. There are a lot of reasons that we might agree to solve a problem, either for someone else or for ourselves.

        Sometimes we do take on projects that we believe deeply in with an obvious impact.

        Even when that’s the case, money usually plays some factor in our decision to sign on.

        Some projects we take on only for the money.

        Others we forgo money entirely either to give back or to gain experience or skill.

        There are no universal “wrong” reasons to do the work you do, just so long as you’re clear on why you’re doing it.

        Remind yourself that if the only reason you’re doing a project is for the paycheque, it may not be worth getting as emotionally attached to the work, especially when the client starts making meaningless revisions that reduce the value of your contributions.

        I’m not saying to detach yourself from your work entirely.

        Care about the work you do. Care deeply and fight for it when you need to.

        But understand which projects are worth the extra energy of championing and fighting over, and which you’re better letting go and moving on from.

        Knowing why you’re doing the work will help you maintain the appropriate temperament, make the work more enjoyable, and keep you sane.

        Revisit These Questions Regularly

        While it’s essential to ask these questions and get clear on your reasoning before beginning on a project, it’s equally important to build a habit of revisiting these questions at regular intervals throughout the project.

        This keeps you on track, making decisions that serve the audience and the goal of the project and helps ensure you’re doing your best work, which when it comes down to it, is solving problems in the most appropriate way possible.

        Sometimes Your Work Sucks

        Photo by Maria Teneva on Unsplash

        It’s true.

        I won’t sugarcoat it and tell you it’s great, good, or even passable because it’s not.

        Today your work really sucks.

        But maybe that’s not important.

        Maybe what’s more important is both of us knowing that you have the potential to do better work tomorrow than the work you did today, and that I won’t let you off the hook or expect less than I believe you’re capable of.

        Maybe what’s important is to do dig our way through the work that sucks in order to get to the work that sucks a little less.

        Maybe if we do this long enough we’ll get to work that is passable. Maybe even good. Maybe even great.

        So yes sometimes your work sucks.

        Don’t dwell on it. Don’t hide it. Don’t quit.

        I know you’ve got better inside you and I won’t let you settle for less than that.

        And when my work sucks, I hope you’ll do the same for me.

        How Can We Make Business Magical?

        Photo by Karly Santiago on Unsplash

        Last year I saw a talk by a magician that changed the way I think about my business, relationships and daily experience.

        Nate Staniforth, the magician in question, is the first to acknowledge that the title “Magician” carries with it some less-than-helpful connotations.

        This is especially when attempting to be taken seriously at say, a (non-magic-related) conference where you’re presenting a keynote talk, but applies to many other more mundane, but perhaps equally stressful situations as well (meeting future in-laws comes immediately to mind).

        What I took away, however, first from Nate’s talk and then from his excellent book, Here Is Real Magic, is that real, true magic does exist, perhaps not in the way we often conceive of it, and that each of us has the transformative power to create it.

        I’ve become convinced that if we can harness this power and apply it to our businesses, work and lives, we can transform them — and those of the people we interact within those contexts — forever.

        Ok So What Is Magic?

        First, we need to do away with our unhelpful present ideas of what constitutes magic.

        Figures like Harry Potter, and Gob Bluth, the Arrested Development character (both of whom I love by the way), while entertaining, are not what we’re shooting for here.

        Real, applicable magic is not about illusions, sleight of hand, or elaborate performances and stage shows (although feel free to use those if the situation calls for them…)

        Rather, the magic we can create is about giving the people we interact with the sense of awe, wonder, inspiration and hope that good magic achieves.

        Imagine if this was the feeling your clients, customers and collaborators associated with interacting with you.

        Magical types of experiences are the ones that people rave about.

        How To Create Magic In Your Business

        Magical experiences should speak uniquely to your customers and the relationship you have. They’ll take thought and work to create and might sometimes feel like they’re not worth the time and expense you put into them.

        The fact that they go above and beyond the normal course of business is part of what makes them magical.

        So while I don’t have a defined, repeatable framework, let’s have a look at some traits that magical experiences have in common.

        Awe/Wonder: This is at the core of magical experiences. Moments like this make us realize that the world is a little bigger than we previously thought. That the unknown isn’t just a place of fear and uncertainty, but of excitement and possibility.

        Inspiration/Hope: Good magic raises the bar of what’s possible, both for ourselves and the world. When I find myself in the middle of a magical moment I feel inspired both that I can do more, and that I must do more. Good magic destroys cynicism.

        Surprise + Subversion Of Expectations: Magical moments and experiences catch us off guard and surprise us. This could be through the timing of the delivery or by subverting expectations of how a certain process will go. If you’re able to turn a process that’s typically uncomfortable or painful into something that feels magical, you’re on to something.

        How did they do that? This is one of the hallmarks of magic tricks, where we find ourselves analyzing and guessing at how it was done. Perhaps you make note of some off-hand remark about a client loving a specific hard to find flavour of ice cream, and have a tub delivered to them (yes ice cream delivery exists, I’ve looked into it for this very purpose) leading them to ask, “how did they know I liked this?”

        (In this case, we’re hoping they’ve forgotten they ever mentioned it, which is hard to ensure, but amazing when it happens.)

        Personalization

        Beyond these common traits, I’m convinced that when it comes to creating moments that feel like magic in our businesses, we need to pay special attention to personalization.

        We want our clients and customers to know that we created this specifically with them in mind. That we went out of our way. That not everyone gets the attention and experience that they’re getting right now.

        One of my favourite things about the concept of personalization is that it can be low cost but feel thoughtful and unique.

        I attended a conference a couple years ago, and waiting for me when I checked in was a bottle of my favourite beer.

        Just one. Just for me.

        I remembered later that they had asked on the registration form what my favourite beverage was to kick back and relax, to which I had responded with this beer.

        The fact that I had supplied the information myself didn’t diminish the experience.

        I would have been excited and surprised to get any bottle of beer at a conference check-in. The fact that it was unique to me, however, elevated the experience into the realm of magic, where for a few moments I was filled with awe and the question, “how did they know??”

        By the way, I rave about that conference and tell almost everyone I know that they should go…

        I’ve since started incorporating similar questions into my own client and team member intake forms and surveys to slowly build up information that I can use later (hopefully once they’ve forgotten that they supplied the information) to create unique, special, hopefully even magical experiences.

        A Word About Intention

        I want to make sure to say that while I really believe that creating moments that feel like magic for our teams, clients, customers and colleagues has the potential to have huge returns in how people talk about, interact with, and refer our businesses, for it to be effective, you need to be doing it for the right reasons.

        Manufacturing magic to achieve an end result doesn’t work and isn’t scalable or sustainable, at least not while retaining a true sense of magic.

        Hopefully, you already care deeply about those you work with and believe that creating an experience for them that feels magical is worth it if only to show your appreciation. Maybe you even believe that they deserve to have this type of experience.

        Your people need to believe that the act is coming from a sincere place in your heart. These experiences won’t cover over or patch up past or consistent shortcomings, but they will elevate an already solid relationship to an extraordinary one.

        Let’s Make Magic

        One of my missions in our work at Counterweight Creative is to make the experience of both our team members and clients feel as far from “business as usual” as possible.

        I want to create team and client experiences that subvert expectations about how employee/employer and client/supplier relationships work.

        I make a point to send out handwritten thank yous, postcards, and letters, I’ve sent out cases of client’s favourite beer, whiskey, ice cream and other gifts to mark special occasions.

        We’ve sent out congratulatory videos from our team to clients who’ve hit milestones, and recently even sent a custom, framed platinum record to a client who passed the million-download milestone on her podcast.

        It’s not easy to keep on top of and prioritize these experiences. They often cost money, always take time, and there’s no clear return.

        Nevertheless, I want to build a company that’s known for going above and beyond in both the work we do and the experience we deliver, so if that’s the goal, why not go a little further and strive to make the experience truly magical?

        I’d love to hear how you create magical experiences for your team, clients, customers or anyone else. I’d also love to hear if you’ve been on the receiving end of a magical experience, whether personal or professional that was orchestrated by someone else.

        Ideas Need Leaders

        If we’re going to use our unique talents and ideas to change the world around us for the better, sooner or later we need to realize that we have to step up and own our roles as leaders.

        There are countless people with ideas. Ideas that have the potential to change the culture, move it forward to somewhere better than it is now.

        But ideas need leaders.

        Without leaders, ideas are left to either sit stationary as they are, or bounce around aimlessly and hope that someone else will recognize their value and lead them where they need to go.

        We don’t need to walk around with a spotlight on us every second of the day, smoke cigars in boardrooms, and ensure we’re regularly rubbing elbows with the right people.

        But at some point, to move our ideas into the world, we need to champion them, to put them in front of people, the right people, people who see our work and ask, “How can I help?”

        The idea of stepping into the spotlight might scare us.

        We might be more comfortable staying in the background, creating our work and then moving on to the next thing.

        Sure, we might feel slightly unfulfilled. We might recognize that our work doesn’t get the attention we feel it deserves. We might even feel bitter when lesser talents and ideas get recognized.

        But it also feels safe to stay just outside the light. Free of scrutiny, judgment, and responsibility.

        What if leadership isn’t what we’ve made it out to be in our heads, however?

        What if leadership isn’t all about decisive action, clarity, force, and unwavering charisma?

        What if leadership, true leadership, leadership that inspires is about leading with vulnerability?

        About inviting others in and saying, “I don’t know where to go from here, what do you think?”

        About understanding that we can’t change the culture by ourselves and that real leadership is about uniting, finding and inviting in the people who are needed to solve the problem we’re facing. People who believe in our cause as much as we do.

        Maybe that’s a kind of leadership we can step into.


        We Should Say “I Don’t Know” More Often

        Photo by Greg Rakozy on Unsplash

        There’s a lot of stuff in the universe. A lot of stuff.

        There may even be multiple universes, existing in parallel to ours.

        I like to think that’s the case.

        It stokes my curiosity, my wonder, my awe at the existence of myself, the Earth, and this, and any other as-yet-undiscovered universes.

        But while I may hope for the existence of alternate universes, I don’t really have an opinion on the topic, I’m far from being whatever kind of physicist studies that kind of thing.

        What do I know?

        The fact that a universe filled with so much stuff also contains so many opinions about said stuff is more than a little absurd.

        How is it possible that in a universe full of so much complexity, unknown and perhaps even unknowable, that to simply admit we don’t know or have an opinion on any given subject is to subordinate ourselves to others with more conviction?

        I suppose it’s not entirely unexpected.

        Opinions are easy to come by and our culture encourages their development and their sharing, our rights to free speech are co-opted to justify the sharing of any opinion, no matter how wrong or harmful.

        Opinions are an easy substitute for original thoughts, with what’s lacking in substance made up for in volume.

        Opinions are comforting. They help us feel like we have some control, like we understand what’s going on around us, like we’re smarter, better, and more in the know than those around us.

        Opinions do not help us create better, more meaningful work, however.

        To make work that’s new, that makes an impact, that has substance, we need to start with not knowing, being in the dark, without an opinion.

        It’s uncomfortable, to be sure.

        But nothing great begins at a place of comfort and certainty.

        It’s getting comfortable with the not-knowing, grappling with the uncertainty and really, truly seeking to understand the problem we’re trying to solve that leads to work that matters.

        It’s the unknown that fuels our sense of wonder, curiosity and awe, which in turn fuels our creativity.

        Lucky for us, there are likely dozens of opportunities every day to start getting comfortable with all we don’t know and embracing it.

        Next time you’re asked for your opinion on the economy, the housing market, foreign policy or any other complex system that few, if any, truly understand, say it out loud.

        “I don’t know.”

        Do it again. Build the muscle. Admit again and again how little you know until it becomes second nature.

        Then, with every unknown, find wonder, curiosity, and magic in life’s mysteries and dive in and explore them

        Take pride that while others are busy forming opinions, you’re forming your best work.

        How You Do The Work Matters

        Photo by Jamie Street on Unsplash

        At the end of each of his fantastic Akimbo podcast episodes, Seth Godin fields one or more voice recorded listener questions.

        Listeners typically introduce themselves, ask their question and then thank Seth for the work he does.

        I was struck on a recent episode by a listener who signed off her question with “Thanks so much not only for the work you do but the way you do it.”

        If you’re at all familiar with Seth’s extensive body of work, it will come as no surprise to you that he has built up a lot of fans by changing the way we — as business owners, freelancers, entrepreneurs, and marketers — think about marketing.

        Marketing is a topic towards which many in the general public — and more than a few heart-centered business owners and freelancers — have a deep-seated sense of suspicion and antipathy.

        Bad marketers have given the word a connotation of deceit and trickery, often leaving us feeling like we’ve been cheated after dealing with them.

        Given that this is not an uncommon impression of his craft, the fact that Seth has been able to build up not only the size but the quality of audience that he has is remarkable at first glance.

        Look closer, however, and you’ll quickly realize that while there are a million and one marketing gurus in the world, there are few, if any doing it the way Seth is.

        At the core of his work is a deep thread of empathy, generosity, honesty, heart and love for the work he does and those it is intended to help.

        The How Changes People

        When I heard the listener-submitted question above, it sent a chill through me.

        There’s was an emotion in the questioner’s voice when she said “the way that you do it,” that conveyed much more than a simple thanks for good, even impactful, work done.

        It hinted at an inspiration, and a motivation to show up bigger and more fully in her own work. That she had been changed not just by consuming the content of Seth’s work, but by interacting with him in the way he interacts with every member of his audience.

        Showing Up Generously

        When we believe in the work we’re doing it’s easy to justify straying from our values, treating people a little less like people, and taking the occasional short cut if it means moving closer toward creating our vision for the world.

        But What we achieve, accomplish, and create is not the only way to change our communities, cultures, and people we interact with.

        By showing up to our work generously, vulnerably, honestly, with heart, compassion, and empathy for those we work with, those the work is for, and the work itself, we have the opportunity of inspiring a more generous, honest compassionate world.

        Imagine for a second that Elon Musk, Peter Thiel, Reid Hoffman and the rest of the PayPal Mafia had been united by the same generous, honest, empathetic value set that drives Seth Godin’s work.

        The impact and reach of the work that group did together and has now gone on to do individually stretches into every corner of our culture and has undoubtedly changed the world. No doubt each and every one of their successive companies has spun off additional founders who will continue to shape our world through ever more integrated technology.

        How would our world today be different if at the core of all that work, the work it spawned, and the work it will continue to spawn was a focus on compassion and heart?

        Yes, the What matters.

        Do work that excites you, that means something, that makes the world a better place, for one person or for everyone.

        But know that if you’re only focusing on the What you’re missing out on creating impact that has the potential to go far beyond the product of your work.

        The How matters every bit as much as the What.

        It’s the How that moves, that inspires, that changes people from the inside out.

        And so the challenge, if we truly want to be leaders in the world is this:

        Do work that means something in a way that means something.


        Want to hear more about building an audience around work that matters? I think you might enjoy these reads!

        https://medium.com/@jeremyenns/ideas-need-leaders-25950eaa90bhttps://medium.com/@jeremyenns/ideas-need-leaders-25950eaa90b

        What Do You Believe?

        Photo by Katrina on Unsplash

        It seems like a simple enough question.

        But would you be able to cogently sum up your life philosophy and rationale behind your daily actions if put on the spot?

        I’m guessing that for most of us, the answer is no.

        We probably have a vague, intuitive sense behind the beliefs that guide our actions, but those feelings are not always easy to put into words.

        Most businesses have a defined set of core values designed to guide their decision-making processes to not only ensure they’re staying on-brand but true to the traits that they stand for.

        A defined set of core values also provides a measuring stick when mistakes are made. More often than not, big mistakes can be traced back to a decision that strayed from one or more of the values.

        So if businesses realize the value of defining and committing to the core values that guide their decisions, why don’t we as individuals?

        Sure, businesses often have reach and influence beyond that of an individual.

        But as ambitious people looking to create change in our communities and the world, shouldn’t we be equally aligned and consistent in our actions?

        Sure, businesses often consist of more than one person, maybe even thousands of people, and a central set of defined values are necessary to ensure each of those individuals understands how to show up and do the work and represent the company.

        But in doing our own work, many of us will bring on others at some point to help advance our cause. Isn’t co-ordination equally important for us?

        Whether you’re a business, freelancer or individual, defining your core values and beliefs about how you show up in the world and do the work that’s important to you is a valuable tool to ensuring consistency in your decisions.

        It’s also a crucial piece to attracting better clients, collaborators, and team members who buy into what you’re doing and how you’re doing it.

        Tribes, communities and movements form around shared values.

        They are essential if you want to create better work and a bigger impact.

        Make them true, make them you, and make them public.

        Tell us what you believe.

        …But Is It Useful?

        Photo by Ehimetalor Unuabona on Unsplash

        The problem for most people with art isn’t that it’s not impressive.

        It’s not that it’s not interesting, beautiful, remarkable even.

        The problem is that they don’t understand what it’s for.

        “What’s the point? What do I do with it? How will it help me?”

        To the average person, the average piece of art is little more than a pleasing piece of canvas that costs hundreds, thousands, or even millions of dollars more than that piece from IKEA they currently have making that space on their living room wall feel a little less empty.

        How Does This Affect Us?

        Ok, so most people aren’t art lovers, so what? Why should we as creators, makers and entrepreneurs care? How is this information useful?

        Well, I’d argue that for most of us, art plays a significant roll in the work we do.

        For most of us, there is an artistry, a craft to our work that we’ve spent a lot of time developing, but which isn’t always outwardly apparent to the uninitiated.

        At some point, we all need to convince a customer or client that our work is worth them paying for, and paying at a rate we know it’s worth.

        Which means that a core part of the work we do if we want to reach new audiences needs to be explaining to the uninitiated how our work will help them.

        Conveying Our Work’s Value

        Luckily for us, we have some advantages over pure artists when it comes to reaching a broader audience.

        Most of us as business owners, entrepreneurs, freelancers and creators have a product or service for which there is already a market. Even if it’s small or competitive or both, there are probably people out there who are looking to hire someone to do work similar to the work we do.

        Sometimes we connect with these people, their budget matches our asking price and we’re able to create great work together and get paid a fair price for it.

        More often, we connect with a potential client looking for what we’re selling but who doesn’t see the value in the price we’re charging.

        We know that the reason we charge what we do is because of the art in our work.

        The art is the piece that makes our work that crucial 10% more effective, pleasing to use, or profitable for our clients than a cheaper alternative from Fivver or UpWork.

        But our potential client doesn’t know that.

        Our job then, is to be prepared to educate them on what sets our work apart. On why the extra cost of working with us is really a bargain compared to the returns they’ll get as a result of doing so.

        Considering how often these potential client interactions come up, most of us are woefully ill-equipped to deal with them when they do.

        This is a skill we must hone if we want to do more work and create a bigger impact with it.

        Educating The Masses

        Finally, there are aaaalllll the people who have no idea what we do and no idea how our work could potentially help them.

        These are the people who feel alienated by the “pretentious” art community.

        They’re not in on it.

        “What is it you even do online all day? I can make really great designs in Canva on my own. So as a copy writer does that mean you deal with trademark stuff? Isn’t there already an app for that that works fine?”

        How is this thing you do useful or relevant to me?

        Too many of us write these people off as lost causes, not worth the effort of detailing the process, goals, and impact of our work.

        That’s a short term view.

        If we took the long view, we would realize that if we were able to speak concisely and engagingly about the impact that our work has on the people we interact with every day, we are expanding the pool of potential future customers and clients, and raising the perceived value of the work we do.

        We may never work directly with any of the people we take the time to educate, but if we believe in the work we do, we benefit by spreading awareness, appreciation and even excitement about it.

        Invite People In

        To educate in a way that engages the people we talk to and doesn’t leave people feeling like idiots takes thought. We need to understand deeply the true benefits and impact of our work and why it matters beyond giving us a paycheck.

        But we also need empathy. We need to understand where the average person is coming from, their blindspots, the gaps in their knowledge, as well as their goals and desires.

        Once we know this, we can begin to have a real honest conversation about what we do, and hopefully create one more new art fan.

        More than simply being great, maybe even the best at the work you do, this is what being a leader in your field is about.

        Getting Paid Vs. Getting Reps

        Photo by John Arano

        We all want to get paid for our work.

        And sometimes we do.

        Sometimes we get paid what our work is actually worth.

        Most of the time we get paid less.

        Rarely we get paid more, but these are elusive gigs and not to be counted on.

        And then there’s all the work we do for which we never see a dime. Maybe we even pay to do the work.

        Maybe we create a product that doesn’t.

        Maybe we learn a skill that we never get hired to use.

        Maybe it’s all the hours of practice we put into our craft on our own time, when no one’s watching, judging, applauding, critiquing, or, you guessed it, paying.

        There’s getting paid and there’s getting your reps in.

        Both are essential to doing our work to move the culture forward.

        Occasionally you get to do both at the same time, but for the most part, each has their place and it’s better not to mix the two.

        Each form of the work has it’s own limitations and its own benefits.

        Neither is better than the other, they are, in fact co-dependent. The more progress you make with one, the more the other will benefit.

        So make sure you’re clear on which type of work you’re doing in the moment and own it. Accept its limitations and embrace its benefits.

        Build a habit around each form of work.

        Now go get your reps in and then go get paid.


        Want to hear more about building an audience around work that matters? I think you might enjoy these reads!

        https://medium.com/@jeremyenns/dont-rush-to-get-found-before-you-have-a-foundation-5add284779cahttps://medium.com/@jeremyenns/dont-rush-to-get-found-before-you-have-a-foundation-5add284779ca

        Make Space For Doubt

        One of my goals for this year is to build up my confidence further.

        While I feel like I’m generally pretty confident in my ability to bring my ideas to life, I, like most people am prone to comparison, imposter syndrome, and any number of less-than-confident thought distortions.

        In taking stock of where I want to go over the coming years, it was clear to me that in order to be the leader, CEO and person I aspire to be, an increase in confidence, in ownership of my ideas talents and perspectives, is necessary.

        One of my other goals for this year, however, is to make room for a little more doubt, specifically in some key areas.

        Why Doubt is Important

        While confidence is a useful trait, even a necessary one for certain pursuits, it can get in the way.

        Last year, for example, I charged headfirst, investing considerable time and money into creating a product that ultimately underwhelmed significantly.

        I’d seen the model for the product work in other niches and was exceedingly confident that it would work in mine as well.

        In hindsight, I could have used a healthy dose of doubt about a number of aspects of that product.

        Granted, I probably would have done it anyway, but I would have done it differently, with a more complete picture of what would drive its success or failure.

        As Your Potential Impact Grows so Should Your Healthy Doubt

        As my team, client base, and impact grows, I want to be thoughtful and intentional about the choices I’m making.

        “Why won’t this work? How will this impact my team, clients and others?” and, “Why shouldn’t I do this?” are all equally important questions as, “What do I stand to gain?” and “What do I need to do to make this successful?”

        The Role of Doubt in a Societal Context

        Beyond making smarter decisions in business and life, however, I think doubt can play a larger and more powerful role in how we interact with others and our communities.

        As a straight, white, English-speaking male from a middle-class family in Canada, I’m not short on privilege.

        In most categories, I’d rank myself as average to a little above average. I’m pretty smart, decent looking, maybe an above-average work-ethic, but nothing crazy.

        What I attribute any success I’ve had so far to would be my curiosity, perspective, positivity and friendliness. In other words, not skills that are necessarily confidence-inducing or easy to measure.

        Despite my average confidence and mostly average skill set, I’ve been increasingly aware that my privilege and the point of view that comes with it has been more than enough to make up for that lack of above-average confidence in certain social situations.

        I’ve been more aware that I’ve likely been going through life with little regard for my blind spots, speaking up when I should have listened, not leaving (or making) space at the table for others, and have generally done more taking than giving or empowering. All without even noticing.

        Maybe a little less confidence and a little more doubt in my ideas, beliefs, and opinions might serve me, and those around me better. Might make a little more space for others. Might allow me to hear other perspectives and experiences that will help me grow and evolve further.

        And so my seemingly contradictory goals.

        To increase my confidence in my abilities a little more.

        And to add a little doubt about my own importance, opinions, and ideas.

        Maybe with a little more doubt, we’d be encouraged to listen more, collaborate more, and create work that’s a little more helpful to a few more people.

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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.