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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    The Neglected (But Essential) Facet of Creative Productivity

    The decorations are up.

    Christmas music wafting out of every shop door.

    Mulled wine is being served on seemingly every street corner.

    There’s no ignoring that the holiday season is officially upon us.

    But perhaps the best indicator that the end of another year is here is the one bombarding us on our social media, newsletter, and podcast feeds.

    No, I’m not talking about the recent wave of Black Friday sales notices.

    I’m talking about the stream of content challenging us to “not wait until January 1st to start on our 2023 goals” that crops up around December 1 every year.

    Urging us to push through the end of the year.

    To continue the relentless grind we’ve subjected ourselves to all year in order to continue (or build) our momentum.

    I know the advice is well-intentioned.

    But it still irks me.

    Not just because I think we deserve (and require) a break from the relentless grind it takes to start and grow a creative business.

    But because this type of thinking takes such a narrow view of what it takes to achieve creative progress.

    The Neglected Facet of Creative Productivity

    Let’s not kid ourselves, frequent and decisive action is essential to making progress toward our goals.

    As a result, most productivity advice revolves around how to take more action and get more done.

    More action = more progress the thinking seems to go.

    And at least in part, that’s certainly true.

    But there’s an essential prerequisite for productive action that standard productivity hacks and hustle culture consistently neglect, which is this:

    For action to amount to anything, it needs to be focused and directed in the right direction.

    That requires clarity.

    And clarity rarely finds us when we’re in the thick of implementation & action.

    Rather, it almost always finds us immediately after a period of intense action, when we’re able to slow down, step back, and gain enough distance from the fray to gain some perspective.

    Without taking regular steps back to reorient ourselves, we risk barreling forward, head down… making fantastic progress in the entirely wrong direction.

    Far from slowing our momentum, then, regular rests, reprieves, and reorientations are not only essential to recharging our energy stores, they’re a core component of long-term creative productivity.

    Which means that rather than pushing through December at breakneck speed, the very best thing we can do for our creative work and businesses is to slow down.

    Slow Down to Speed Up

    There are few better opportunities to slow down, step back, and gain perspective on where we’re at, than the end of each year.

    It’s one of the vanishingly rare times we as a society allow ourselves to collectively slow down and reflect.

    If you’re like me, at this time of year you might regularly be finding yourself preoccupied with big-picture dreaming, brainstorming, and idea exploration… at the expense of your daily task list.

    The “push through to the new year” advice encourages us to ignore these frivolous distractions and focus on squeezing just a little bit more productivity out of the year.

    But while the value of big-picture dreaming, visioning, and planning may be hard to quantify, without it, our work tends to lilt toward the mundane, generic, and bland.

    Despite its necessity, however, we rarely make space for it, often deferring to the more tangible outcomes of action.

    It’s worth noting that those in the “push through” camp are often staunch and vocal advocates of completing a structured annual review, a practice I too find an incredible amount of value in. But that review is often boxed into a single day, afternoon, or couple-hour-long time block.

    The problem with this approach is that I’d wager there are challenges, puzzles, and problems in your life and work that will take more than a couple of hours to solve.

    In fact, there’s a good chance the (perhaps only) reason they’ve persisted this long has been a lack of time and space to slow down, sit back, and ponder.

    Nature abhors a vacuum, after all, and big ideas and breakthroughs have an uncanny way of showing up when we create the space for them.

    So while I’m guessing you, like me, still have a long list of unfinished goals and projects on your annual to-do list, it’s possible that the single most productive thing you could do with the remainder of the year is to set them aside.

    Slow down.

    Pause.

    Plant your feet.

    Orient yourself.

    So that when you’re ready, you can push off toward the next goal with energy, focus, and intention.


    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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        Leadership in Times of Crisis

        Photo by CoWomen on Unsplash

        Many entrepreneurs, content creators, and subject matter experts want to be seen as leaders in their niches, industries, even the world, and much of the work they do on a daily basis is aimed at elevating their status as leaders.

        They work incredibly hard to stand out among a sea of similar businesses, creators and experts, going a little bit further, giving a little bit more of themselves, producing content that’s just a little better than everything else out there.

        It’s a long, slow race to the top that takes patience, persistence and generosity.

        Faced with a crisis, however, true leaders can accelerate that process.

        Not by taking advantage of panic and fear, not by profiteering or scamming, but by doubling down on the same generosity they were already practicing and adapting it to the current circumstances.

        Want to know who the leader is? Ask him to decide.

        If you’re looking to serve and lead your audience in a time of crisis, don’t overthink it.

        Too many would-be leaders freeze, unable to see what they have to offer and how they can help.

        Give What You Can

        If you have content, products or expertise that are applicable, share them in the way that makes the most sense. Be generous with your knowledge and if you can afford to, your resources.

        If you don’t have applicable content but you have an audience, organize them.

        In a crisis, people are bombarded with information from every side, much of it contradictory. Do your research and distill what’s relevant to your audience and present it in a rational, cohesive manner, free of hype, panic, and fear.

        You know your audience better than anyone else and are uniquely positioned to give them news in the most actionable way possible. While they can get the major news anywhere, your analysis, as one of them matters.

        Foster Community

        Aside from information distribution and analysis, focus on organizing and building a community.

        Focus on hope, reason, and generosity to build a space that is a reprieve from the craziness in the rest of the world.

        Don’t ignore the crisis, talk about it openly but with a focus on what you can each be doing to work through it, staying sane and productive along the way.

        Empower people to help each other. Consider starting an offer and needs market, where members of your community can share both needs that need assistance with, and offers that they’re in a position to provide.

        Empowering and facilitating connection is one of the most underrated skills of a leader, and times of crisis are the perfect time to apply it.

        Ask

        Lastly, if you have a community, no matter how small and aren’t sure what you can do to help, just ask.

        Acknowledge that this is a tough time for everyone and that you don’t know if you’ll be able to help but ask anyway.

        More often than not you’ll find that people have problems you didn’t even think of, but which you are in a position to help solve, even if that means referring them to another resource or person who can help directly.

        Showing up with generosity, with an attitude to serve, and helping people navigate a difficult time, is one of the surest ways to establish yourself as a leader, a status that will last long after the crisis has passed.


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

        Want to know who the leader is? Ask him to decide.

        Want to know who the leader is? Ask him to decide.

        Why Marketing Hacks Won’t Work for You

        Photo by Stephen Dawson on Unsplash

        It’s easy to listen to your favourite marketing expert talk about the newest, strategy, tactic, or hack and the results it’s gotten for them, and think that it’s the missing piece of your own marketing puzzle.

        All you need to do is learn the strategy, buy the software, read the book or blog post, or listen to a podcast on the topic and you’ll be over the hump and on your way to fame and fortune.

        In all likelihood, the strategy/hack/tool actually does work.

        They’re not lying to you. It worked for them and it worked for all those happy people on their testimonial page.

        But it probably won’t work for you.

        The thing about marketing tactics is that while they often do work as advertised, you need to have a foundation in place first, a foundation that established niche authorities have built up over time, and you, most likely, have not.

        The required foundation is an authentic relationship with your audience.

        Keep in mind, a relationship is more than podcast downloads or website page views. An authentic relationship is built on conversation, on seeing and being seen, of treating each other with respect and empathy.

        On the Entrepreneurial Trek, Embrace the Learning

        Relationships like this aren’t built overnight. They take time, generosity, and consistency, and no marketing tactic can perform the hard, emotional labour required to show up and build them.

        That you have to do yourself.

        Once you’ve put in the work to build that relationship, however, the world opens up to you. It’s at this point that the marketing tactics, tools and strategies start to work and deliver results.

        Tactics and strategies at their best amplify, accelerate, and reduce friction in a process that was already in motion.

        With a strong enough relationship, however, almost no amount of friction will stop your super fans from engaging with you.

        Think about people who fly across the country — or the world — to see their favourite band. Or the ones who buy the ridiculously priced one of a kind collectables offered by their favourite brand.

        We all have those people and brands for whom we would go to extreme lengths to engage with. From an outsider’s perspective, these lengths are likely completely irrational.

        These feelings are likely based on a relationship we feel with the creator.

        These people or their work have spoken to us in a way that deeply resonated, have given us a gift, a feeling that is exceedingly hard to come by, and most likely can’t be bought at any price.

        Is it any wonder that we might be willing to go to irrational lengths to give back?

        This is our goal as creators and marketers, to build a relationship with our audience capable of achieving results despite intense friction.

        If we can then use the latest marketing tactics to ease that friction, all the better, but only as a way to amplify the connection that got us there in the first place.


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

        On the Entrepreneurial Trek, Embrace the Learning

        On the Entrepreneurial Trek, Embrace the Learning

        What Does Perfect Look Like?

        Photo by Jonathan Hoxmark on Unsplash

        As entrepreneurs, creators and marketers, we live in a world where the dominant narrative we’re confronted with often contains some version of, “You will fail.”

        Maybe it’s softened up to the more nuanced “You will most likely fail,” maybe it’s well-meaning questions about what our back up plan is, you know, a real job for when our self-directed creative endeavors fail, or maybe it’s some stat about most new businesses failing within the first 5 years or whatever the going number is these days.

        Needless to say, this isn’t the ideal environment in which to produce our best work, the work that has the potential to change the people who engage with it.

        In the face of this adversity, many creators choose to bow out and abandon the pursuit of their craft as a career.

        For those of us who tough it out and against all the (supposed) odds find a way to build a business, sell our art, or otherwise make a living off our work, it feels like we’ve won, proving the naysayers wrong along the way.

        But despite our seeming victory, those narratives often still have a negative impact on the work we do on a daily basis.

        When facing long odds, it’s natural to water down our dream a little bit, maybe even a lot. If it feels audacious and unachievable to start a business or make a living as a creator at all, we don’t dare think about our real, honest, dream scenario.

        Maybe you dreamed of illustrating gig posters for the biggest bands in the world and wound up as a graphic designer who mostly works with big chain retailers.

        Maybe you dreamed of making documentaries and ended up filming weddings.

        Maybe you dreamed of writing the breakthrough book that taught people around the world how to easily live healthier lives and prevent disease, but ended up with a local medical practice in your hometown.

        Compromises can be useful when looking to gain a foothold in our chosen field, they may even be an essential way to get our reps in as we push onward to something better.

        We can be entirely happy in our chosen compromise as well.

        We can be happy designing web ads for chain retailers, we can feel lucky that we get to work in the film industry and help couples celebrate their special days, we can be fulfilled in the fact that we can see the impact we’re having on our patients on a one to one level.

        But we can also wish for more.

        Too often we settle for lesser dreams because it feels like what we can get away with.

        According to the narrative, we shouldn’t have even made it this far. Do we really want to risk dreaming bigger, asking for more?

        I think we should.

        Every so often, I think it’s worth spending an hour mapping out the current state of your business or work and then asking, “What would this look like if it were perfect?”

        Don’t be reasonable, don’t compromise, don’t scale back your true ambitions.

        Make a map of what perfect looks like and then start moving towards it.


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

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        Break the Streak

        Photo by Jon Tyson on Unsplash

        Building habits is essential to creating a system of living that ensures that you’re continually moving in the direction of achieving your goals.

        Building and tracking streaks is one of the best methods of enforcing the habits you want to be strengthening and embedding in your daily life.

        With each successive day add to your streak, the harder the task becomes to avoid for fear of breaking your hard-earned streak.

        Whether it’s getting your 10,000 steps in, writing a daily blog post, keeping your daily or monthly spending under a certain threshold, the longer you’ve maintained your streak of “good behaviour” the more pressure you’ll feel to continue, and soon, a habit is established.

        Every so often, however, it’s worth breaking the streak.

        By breaking the streak intentionally, even for one day, you can take a moment to reflect on the practice and reassess whether it’s actually something that is serving you and moving you closer to where you want to go. If not, decide whether or not it’s worth continuing or if your mental power is best used elsewhere.

        If the practice is still serving you, you’ll likely be reinvigorated to get back to it and start building a new streak.

        If not, find a practice that is more aligned with your destination and start streaking your way there.

        Streaks are powerful tools to help build and enforce habits, but if you’re not careful, you can end up continuing with a practice for no other reason than to maintain and extend your streak.

        Break the streak. Reassess. Then recommit or recalibrate.


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

        https://medium.com/@jeremyenns/stuck-ask-a-different-question-14bad5fa8ad5https://medium.com/@jeremyenns/stuck-ask-a-different-question-14bad5fa8ad5

        Worry Wisely

        Photo by niklas_hamann on Unsplash

        Like most things in life, we have a lot more agency than we think when it comes to what we choose to worry about.

        We can choose to worry at an instinctual level, giving credence to every negative thought that enters our brain, validating it and building it up into an immovable mental object for which we can see no way around.

        We can choose to be guilted, pressured or shamed into worry, adopting a stance only because it was expected of us. “I bet you’re so mad that Susan got that promotion over you. If it were me, I’d be worried about whether or not there’s an opportunity to ever grow in this company…”

        We might not have even cared about that promotion or our future in the company in the first place, but given the expectation, we might now.

        We can choose to worry at a societal level, adopting the worries and neurosis of those around us, often fanning the flames of misinformation and hysteria that we may not have otherwise worried about, but for the fact that everyone around us seemed so concerned, we figured we should be as well.

        We can choose to worry about nothing, if we want.

        Or, we can choose to worry about the things that matter for the change we’re trying to bring about in the world.

        We can worry about whether we’re bringing our best selves and our best work to the table. About how to enroll others in our vision and empower them to take action. About how to create advocates who will help us build our movement.

        There’s no right thing to worry about, no wrong. But the choice is ours to make.

        And some are awfully more productive.


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

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        Stuck? Time to Ask a Different Question

        Photo by Camylla Battani on Unsplash

        We’re all trying to level up.

        Whether it’s our client list, podcast download numbers, page views, revenue, quality of work or all of the above and more, we each have some goal hovering just beyond our reach.

        The question we most often reach for first when determining how to reach our next elusive milestone is, “What do I need to do to bring about the result I want?”

        This seems like fairly straightforward reasoning, input x to get y. And for some goals, it works.

        “What do I need to do,” is about tools, tactics, and strategies that if you had the blueprint for, you could plug into your work and your problem would be solved

        But for big goals, the kind of goals that cause people to raise their eyebrows when you say them out loud, tools, tactics, and strategies aren’t going to cut it. You may have even tried them already to middling (or less) success.

        The problem isn’t that the tools are faulty. The problem is that for big, hairy, audacious goals, before asking yourself what you need to do, you must ask yourself another question first.

        “Who do I need to become to bring about the result I want?”

        Your existing mindset, beliefs, and biases may have got you this far, maybe even brought you to great heights of success, but at some point, you’ll reach the limits of their effectiveness.

        At this point, your only hope of continuing onward toward your goals is to do the hard work of admitting that in your current iteration, no, you are not enough.

        For whatever reason, so many of us humans find this idea of not being enough as we currently are anathema, ignoring the fact that we, as we are is not the limit of who we can become.

        It might be painful, it might take significant effort, it might require us to leave behind the beliefs, mindsets, and even people that no longer serve us, but each of us is capable of becoming more than we currently are, and achieving more than we currently have.

        If you’re sick of banging your head against the wall, sick of tools, tactics and strategies that fail to work as promised, sick of asking what you need to do next, it might be time to ask a new question.


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

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        Don’t Bank on Being the Outlier

        At some point in your journey as a creator, you’ve probably had the experience of watching a competitor with objectively lesser talent, quality, and utility gain more traction and garner more attention than your higher quality offering.

        It’s easy to throw your hands up in defeat, complain of a rigged system, bemoan the fact that good marketers can get away with delivering lesser value products or blame it all on luck, either your competitor’s good or your own bad.

        These are all fair and understandable reactions to the circumstances. There may be a rigged system, your competition may be better marketers than you, and it’s highly likely that they have been the beneficiaries of a stroke or two of luck along the way*.

        * You almost certainly have as well, but we’ll talk about that another time

        As much as we would like to believe that our society is a strict meritocracy, where the cream rises to the top, and hard work and initiative are rewarded with commensurate success, it’s not, and they’re not.

        The system does not always work fairly, reward the most deserving, and occasionally even elevates the truly deplorable to the highest levels of a field.

        Faced with this reality, there’s another reaction common to creators, one that almost ensures they will never get the big break they seek.

        “If mediocre work is capable of not only outperforming objectively better offers, but gaining broad, mainstream success,” they think, “there’s no point in putting in the time, energy and emotional labour of creating something truly remarkable.”

        This mindset chooses to focus solely on the outlier, ignoring the likely more numerous examples of creators and products that did put in more work and are of higher quality.

        In all likelihood, there is a reason this mediocre-quality outlier slipped through the cracks and hit it big. Maybe they’re fantastic marketers, maybe they got lucky, or maybe they’ve built such a strong and generous relationship with their audience that the ultimate quality of their work is less important than the relationship itself.

        This last point is at the root of effective marketing and should not be ignored by any creator or business.

        Even if there’s no reason at all for your competition’s success and it’s entirely a fluke, choosing to settle for creating work that’s less than the work you’re truly capable of creating — just because someone else got away with it — is a poor assessment of the odds.

        Remember, if they snuck through on mediocre work, they’re the outlier. The odds of you also sneaking through in the same niche is incredibly low, and is not a strategy you can bank on.

        Sure, there’s no guarantee that creating the best work in the world will bring you recognition and success, you still need to do the hard work of marketing it effectively, building an authentic relationship with your audience, and catch some luck as well.

        But creating work that matters, work that resonates, that maybe even changes the people who engage with it is a much more reliable path to success than hoping that out of all the mediocre work in the world, yours will be the one that gets picked.

        Besides, is creating mediocre work really the best way to serve your audience?

        There’s enough mediocrity in the world already. Create something that elevates your niche and raises the bar for everything that comes after it.


        Creating Remarkable Work

        Creating work that spreads requires creating work worth talking about.

        Creating work worth talking about requires creating something remarkable.

        Remarkable is not just something sprinkled on top of an otherwise complete product. Remarkable is baked into the core of anything worth talking about and reinforced at every stage of the design and development process.

        Remarkable work requires us to push outward on the existing frame that our work would otherwise fit into, expanding it and distorting it in some way or another to subvert the expectations of the people who engage with it.

        There are countless edges we might choose to seek out and push outward against, each causing our work to resonate more deeply with some people and less with others. Each with the potential to build raving fans and virulent haters.

        When it comes to creating remarkable work, it doesn’t matter which edge or edges you choose to distort and expand, but if your goal is to create something worth talking about you have to find and choose at least one.

        So what will it be?


        What’s Really Slowing Your Progress?

        Photo by Aubrey Rose Odom on Unsplash

        The next time you find yourself stuck procrastinating on a big project, it might be worth scheduling half an hour to simply work through why you’re not taking action.

        You probably run into these holdups all the time on projects that you ostensibly care deeply about, projects that hold the potential to help you take things to the next level in your businesses and life. No doubt, the sooner you take action on them the better things will be for you overall.

        So why the delay?

        While you might initially think that it’s the scope of the action required to move the project forward, my experience, time and again has taught me that more often than not there’s an unresolved decision that needs to be made about the project that is the real culprit.

        It might be a question about the very nature, scope or purpose of the project, or a tactical decision about the specific part of the project you’re currently working on that needs to be answered. Either way, any doubt or uncertainty about any part of the project has the potential to derail it in its entirety until it’s resolved.

        Without clarity, we can be reluctant to put any work in toward advancing the project, as we worry it will be wasted effort if we end up changing our mind about some foundational element in the future.

        Make a List

        When mapping out a new project, or returning to diagnose a holdup on an existing project, I like to add two sub-sections under each heading or module of my project planning document to help me clearly understand what the issues are that have the potential to sideline the project.

        1. Decisions to Be Made

        In this section, I write down all of the questions about that module or the project as a whole that don’t require research, but do require a decision to be made that, until made will make it difficult or impossible to make progress.

        This list might include questions like:

        • Which sections of my online course will be video and which will be text?
        • Will my supporting documents be PDFs or webpages?
        • Will I host my course on Platform A or Platform B?
        • Do I want the tone of the course to be lighthearted and informal or discerning and authoritative?
        • Where will I record the video segments of the course?

        Once I have the list of questions, I find that I’m often able to, over the course of an hour or so, answer each of them to the level that I can at least begin work on the project.

        Of course, not every question can or should be answered immediately. Some questions are actually best left until you have something to work with, and have something invested in the project.

        Technical or strategic questions and decisions, like where the online course from the example above will be hosted, or what the entire marketing plan for the course will be once it’s completed can and probably should be left until you actually have a course on your hands to put up somewhere and market.

        2. Research

        The second section I’ll create is related to the research I need to do in order to finish off a segment of the project or the project as a whole.

        For the podcast marketing course I’m currently working on, for example, I wanted to learn about PR methods for pitching media outlets to contribute an on-air segment or article as well as the psychology behind why people share content online and how to encourage more of it.

        These questions are often less about the nature of the project as a whole, but when undefined, can still result in procrastination.

        I’ve found that the more amorphous the project is in my brain, the less likely I am to even want to approach it. If feels too unwieldy to chip away at piece by piece when I can’t even tell what the pieces are.

        Clarity Leads to Action

        Since adding these two simple lists to every big project I take on, I’ve found myself moving much more quickly when it comes to getting started and taking action on moving the projects forward.

        When revisiting old stalled projects and applying these lists, I’ve found that most often, the thing that was really truly causing me to procrastinate was not the time or effort required to make meaningful progress, but a simple decision that I didn’t realize was unresolved in the back of my mind.

        Once the right question has been asked, the decisions can often be made instantly, or with five minutes consideration and the work can then move forward.

        Train yourself to get clear on decisions that need to be made and watch your speed of implementation increase rapidly.


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

        https://medium.com/@jeremyenns/not-coming-up-new-good-ideas-c4e09fa31e74https://medium.com/@jeremyenns/not-coming-up-new-good-ideas-c4e09fa31e74

        Creating Inevitable Outcomes

        The word “Inevitable” seems to most often be used to describe some slow backward slide toward a negative outcome.

        “It was inevitable they would get divorced at some point.”

        “With his work ethic, it was inevitable that he would be one of the first to be laid off.”

        “The project was ill-conceived from the start, it was inevitable that it would fall flat.”

        When thinking about the inevitability our actions have the potential to create, the idea that we might create a system for living that inevitability leads to success seems almost laughable.

        But I don’t think it is.

        As surely as consistently making certain decisions will lead to failure, I’m convinced that consistently making other decisions are certain to lead us to success if we’re willing to stick with them long enough.

        No doubt there will be variations in the specifics of those actions and decisions depending on what it is you’re pursuing, but I think the following list is a good starting point.

        Regular Practices to Create the Inevitability of Success

        1. Meet new people, especially those with diverse backgrounds doing diverse, interesting things.
        2. Experiment.
        3. Make note of your behaviour, thought patterns, and the reasoning behind them.
        4. Ask for help.
        5. Find a mentor.
        6. Join a mastermind group.
        7. Do a brain dump.
        8. Write down the problem you’re stuck on, on one side of a cue card, on the other side write, “Solution:” Now solve.
        9. Go for a walk.
        10. Reflect on your goals and where you’re currently at regarding them.
        11. Ask “Why?”
        12. Focus on habits.
        13. Do it poorly until it improves.
        14. Be more generous than you want to be.
        15. Have vulnerable conversations.
        16. Unplug.
        17. Be honest with yourself.
        18. Reach out to people you want to connect/reconnect with. Potential clients, customers, collaborators, mentors, friends, etc.
        19. Commit time to thinking.
        20. Commit time to doing.
        21. Create consistently.
        22. Identify the edges of your comfort zone. Then push.
        23. Say “I don’t know.”
        24. Follow your curiosity.
        25. Quit what isn’t working for or serving you.
        26. Take the long view.
        27. Acknowledge your privilege. Use it to empower others.
        28. Act with intention.
        29. Eat the frog.
        30. Be kind. To others and yourself.

        This is only the start of what I’m sure will be a growing list.

        What habits, actions or decisions do you make to lead to inevitable success over time?


        Creative Wayfinding For Ambitious Optimists.

        Getting the Job Done vs. Changing People

        Photo by Claudio Hirschberger on Unsplash

        We have a couple of options when we set out to create the work that matters to us.

        We can aim to create a solid product that gets the job done, or we can aim higher and shoot to create something that changes the people who engage with it.

        Neither is inherently better than the other, in fact, each may be better for different groups of people.

        What’s important is knowing what we’re creating, who it’s for, and why from the start.

        Work that gets the job done almost certainly has a larger potential audience for us to tap into. There is likely more competition, however, with little differentiating our product from our competitors and we risk the commoditization of our work.

        Work that changes people requires us to narrow our focus down to a tiny, niche within a niche and creating something specifically for them. If we choose the right audience and create something that resonates, we may have created a monopoly for ourselves within that community.

        If we mistarget our niche within a niche, however, we may create something that resonates with no one.

        Creating something that gets the job done requires us to put on our engineering hat and figure out how to create something functional, utilitarian, maybe even robust. It requires cunning, decisiveness and action.

        Creating something that changes people requires us to first understand and empathize with our audience before creating something that not only gets the job done but moves and connects with people emotionally. It requires patience, thoughtfulness, and heart.

        Getting the job done can be achieved with visibility and flashy marketing. People may be quick to engage with us, but equally quick to move on when the next best thing arrives.

        Changing people requires building a relationship with the people we seek to serve over time. Our audience may be slow to engage until a foundation of trust has been established, but once built, they’ll stick with us through our blunders and missteps so long as our intentions remain honest.

        Investing in getting the job done means keeping our audience at a distance. Provider and user, creator and consumer.

        Investing in changing people means enrolling them on a mutual journey. Guiding each other’s actions along the way to our shared destination.

        Getting the job done is hard.

        Changing people is harder.

        The world needs both, and it’s up to each of us to decide what we want to create.


        https://medium.com/@jeremyenns/creating-remarkable-work-c3b57b25ea7chttps://medium.com/@jeremyenns/creating-remarkable-work-c3b57b25ea7c

        Leadership in Times of Crisis

        Photo by CoWomen on Unsplash

        Many entrepreneurs, content creators, and subject matter experts want to be seen as leaders in their niches, industries, even the world, and much of the work they do on a daily basis is aimed at elevating their status as leaders.

        They work incredibly hard to stand out among a sea of similar businesses, creators and experts, going a little bit further, giving a little bit more of themselves, producing content that’s just a little better than everything else out there.

        It’s a long, slow race to the top that takes patience, persistence and generosity.

        Faced with a crisis, however, true leaders can accelerate that process.

        Not by taking advantage of panic and fear, not by profiteering or scamming, but by doubling down on the same generosity they were already practicing and adapting it to the current circumstances.

        Want to know who the leader is? Ask him to decide.

        If you’re looking to serve and lead your audience in a time of crisis, don’t overthink it.

        Too many would-be leaders freeze, unable to see what they have to offer and how they can help.

        Give What You Can

        If you have content, products or expertise that are applicable, share them in the way that makes the most sense. Be generous with your knowledge and if you can afford to, your resources.

        If you don’t have applicable content but you have an audience, organize them.

        In a crisis, people are bombarded with information from every side, much of it contradictory. Do your research and distill what’s relevant to your audience and present it in a rational, cohesive manner, free of hype, panic, and fear.

        You know your audience better than anyone else and are uniquely positioned to give them news in the most actionable way possible. While they can get the major news anywhere, your analysis, as one of them matters.

        Foster Community

        Aside from information distribution and analysis, focus on organizing and building a community.

        Focus on hope, reason, and generosity to build a space that is a reprieve from the craziness in the rest of the world.

        Don’t ignore the crisis, talk about it openly but with a focus on what you can each be doing to work through it, staying sane and productive along the way.

        Empower people to help each other. Consider starting an offer and needs market, where members of your community can share both needs that need assistance with, and offers that they’re in a position to provide.

        Empowering and facilitating connection is one of the most underrated skills of a leader, and times of crisis are the perfect time to apply it.

        Ask

        Lastly, if you have a community, no matter how small and aren’t sure what you can do to help, just ask.

        Acknowledge that this is a tough time for everyone and that you don’t know if you’ll be able to help but ask anyway.

        More often than not you’ll find that people have problems you didn’t even think of, but which you are in a position to help solve, even if that means referring them to another resource or person who can help directly.

        Showing up with generosity, with an attitude to serve, and helping people navigate a difficult time, is one of the surest ways to establish yourself as a leader, a status that will last long after the crisis has passed.


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

        Want to know who the leader is? Ask him to decide.

        Want to know who the leader is? Ask him to decide.

        Why Marketing Hacks Won’t Work for You

        Photo by Stephen Dawson on Unsplash

        It’s easy to listen to your favourite marketing expert talk about the newest, strategy, tactic, or hack and the results it’s gotten for them, and think that it’s the missing piece of your own marketing puzzle.

        All you need to do is learn the strategy, buy the software, read the book or blog post, or listen to a podcast on the topic and you’ll be over the hump and on your way to fame and fortune.

        In all likelihood, the strategy/hack/tool actually does work.

        They’re not lying to you. It worked for them and it worked for all those happy people on their testimonial page.

        But it probably won’t work for you.

        The thing about marketing tactics is that while they often do work as advertised, you need to have a foundation in place first, a foundation that established niche authorities have built up over time, and you, most likely, have not.

        The required foundation is an authentic relationship with your audience.

        Keep in mind, a relationship is more than podcast downloads or website page views. An authentic relationship is built on conversation, on seeing and being seen, of treating each other with respect and empathy.

        On the Entrepreneurial Trek, Embrace the Learning

        Relationships like this aren’t built overnight. They take time, generosity, and consistency, and no marketing tactic can perform the hard, emotional labour required to show up and build them.

        That you have to do yourself.

        Once you’ve put in the work to build that relationship, however, the world opens up to you. It’s at this point that the marketing tactics, tools and strategies start to work and deliver results.

        Tactics and strategies at their best amplify, accelerate, and reduce friction in a process that was already in motion.

        With a strong enough relationship, however, almost no amount of friction will stop your super fans from engaging with you.

        Think about people who fly across the country — or the world — to see their favourite band. Or the ones who buy the ridiculously priced one of a kind collectables offered by their favourite brand.

        We all have those people and brands for whom we would go to extreme lengths to engage with. From an outsider’s perspective, these lengths are likely completely irrational.

        These feelings are likely based on a relationship we feel with the creator.

        These people or their work have spoken to us in a way that deeply resonated, have given us a gift, a feeling that is exceedingly hard to come by, and most likely can’t be bought at any price.

        Is it any wonder that we might be willing to go to irrational lengths to give back?

        This is our goal as creators and marketers, to build a relationship with our audience capable of achieving results despite intense friction.

        If we can then use the latest marketing tactics to ease that friction, all the better, but only as a way to amplify the connection that got us there in the first place.


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

        On the Entrepreneurial Trek, Embrace the Learning

        On the Entrepreneurial Trek, Embrace the Learning

        What Does Perfect Look Like?

        Photo by Jonathan Hoxmark on Unsplash

        As entrepreneurs, creators and marketers, we live in a world where the dominant narrative we’re confronted with often contains some version of, “You will fail.”

        Maybe it’s softened up to the more nuanced “You will most likely fail,” maybe it’s well-meaning questions about what our back up plan is, you know, a real job for when our self-directed creative endeavors fail, or maybe it’s some stat about most new businesses failing within the first 5 years or whatever the going number is these days.

        Needless to say, this isn’t the ideal environment in which to produce our best work, the work that has the potential to change the people who engage with it.

        In the face of this adversity, many creators choose to bow out and abandon the pursuit of their craft as a career.

        For those of us who tough it out and against all the (supposed) odds find a way to build a business, sell our art, or otherwise make a living off our work, it feels like we’ve won, proving the naysayers wrong along the way.

        But despite our seeming victory, those narratives often still have a negative impact on the work we do on a daily basis.

        When facing long odds, it’s natural to water down our dream a little bit, maybe even a lot. If it feels audacious and unachievable to start a business or make a living as a creator at all, we don’t dare think about our real, honest, dream scenario.

        Maybe you dreamed of illustrating gig posters for the biggest bands in the world and wound up as a graphic designer who mostly works with big chain retailers.

        Maybe you dreamed of making documentaries and ended up filming weddings.

        Maybe you dreamed of writing the breakthrough book that taught people around the world how to easily live healthier lives and prevent disease, but ended up with a local medical practice in your hometown.

        Compromises can be useful when looking to gain a foothold in our chosen field, they may even be an essential way to get our reps in as we push onward to something better.

        We can be entirely happy in our chosen compromise as well.

        We can be happy designing web ads for chain retailers, we can feel lucky that we get to work in the film industry and help couples celebrate their special days, we can be fulfilled in the fact that we can see the impact we’re having on our patients on a one to one level.

        But we can also wish for more.

        Too often we settle for lesser dreams because it feels like what we can get away with.

        According to the narrative, we shouldn’t have even made it this far. Do we really want to risk dreaming bigger, asking for more?

        I think we should.

        Every so often, I think it’s worth spending an hour mapping out the current state of your business or work and then asking, “What would this look like if it were perfect?”

        Don’t be reasonable, don’t compromise, don’t scale back your true ambitions.

        Make a map of what perfect looks like and then start moving towards it.


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

        https://medium.com/@jeremyenns/best-in-the-world-66ec53d9adebhttps://medium.com/@jeremyenns/best-in-the-world-66ec53d9adeb

        Break the Streak

        Photo by Jon Tyson on Unsplash

        Building habits is essential to creating a system of living that ensures that you’re continually moving in the direction of achieving your goals.

        Building and tracking streaks is one of the best methods of enforcing the habits you want to be strengthening and embedding in your daily life.

        With each successive day add to your streak, the harder the task becomes to avoid for fear of breaking your hard-earned streak.

        Whether it’s getting your 10,000 steps in, writing a daily blog post, keeping your daily or monthly spending under a certain threshold, the longer you’ve maintained your streak of “good behaviour” the more pressure you’ll feel to continue, and soon, a habit is established.

        Every so often, however, it’s worth breaking the streak.

        By breaking the streak intentionally, even for one day, you can take a moment to reflect on the practice and reassess whether it’s actually something that is serving you and moving you closer to where you want to go. If not, decide whether or not it’s worth continuing or if your mental power is best used elsewhere.

        If the practice is still serving you, you’ll likely be reinvigorated to get back to it and start building a new streak.

        If not, find a practice that is more aligned with your destination and start streaking your way there.

        Streaks are powerful tools to help build and enforce habits, but if you’re not careful, you can end up continuing with a practice for no other reason than to maintain and extend your streak.

        Break the streak. Reassess. Then recommit or recalibrate.


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

        https://medium.com/@jeremyenns/stuck-ask-a-different-question-14bad5fa8ad5https://medium.com/@jeremyenns/stuck-ask-a-different-question-14bad5fa8ad5

        Worry Wisely

        Photo by niklas_hamann on Unsplash

        Like most things in life, we have a lot more agency than we think when it comes to what we choose to worry about.

        We can choose to worry at an instinctual level, giving credence to every negative thought that enters our brain, validating it and building it up into an immovable mental object for which we can see no way around.

        We can choose to be guilted, pressured or shamed into worry, adopting a stance only because it was expected of us. “I bet you’re so mad that Susan got that promotion over you. If it were me, I’d be worried about whether or not there’s an opportunity to ever grow in this company…”

        We might not have even cared about that promotion or our future in the company in the first place, but given the expectation, we might now.

        We can choose to worry at a societal level, adopting the worries and neurosis of those around us, often fanning the flames of misinformation and hysteria that we may not have otherwise worried about, but for the fact that everyone around us seemed so concerned, we figured we should be as well.

        We can choose to worry about nothing, if we want.

        Or, we can choose to worry about the things that matter for the change we’re trying to bring about in the world.

        We can worry about whether we’re bringing our best selves and our best work to the table. About how to enroll others in our vision and empower them to take action. About how to create advocates who will help us build our movement.

        There’s no right thing to worry about, no wrong. But the choice is ours to make.

        And some are awfully more productive.


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

        https://medium.com/@jeremyenns/whats-slowing-your-progress-49268d0627c0https://medium.com/@jeremyenns/whats-slowing-your-progress-49268d0627c0

        Stuck? Time to Ask a Different Question

        Photo by Camylla Battani on Unsplash

        We’re all trying to level up.

        Whether it’s our client list, podcast download numbers, page views, revenue, quality of work or all of the above and more, we each have some goal hovering just beyond our reach.

        The question we most often reach for first when determining how to reach our next elusive milestone is, “What do I need to do to bring about the result I want?”

        This seems like fairly straightforward reasoning, input x to get y. And for some goals, it works.

        “What do I need to do,” is about tools, tactics, and strategies that if you had the blueprint for, you could plug into your work and your problem would be solved

        But for big goals, the kind of goals that cause people to raise their eyebrows when you say them out loud, tools, tactics, and strategies aren’t going to cut it. You may have even tried them already to middling (or less) success.

        The problem isn’t that the tools are faulty. The problem is that for big, hairy, audacious goals, before asking yourself what you need to do, you must ask yourself another question first.

        “Who do I need to become to bring about the result I want?”

        Your existing mindset, beliefs, and biases may have got you this far, maybe even brought you to great heights of success, but at some point, you’ll reach the limits of their effectiveness.

        At this point, your only hope of continuing onward toward your goals is to do the hard work of admitting that in your current iteration, no, you are not enough.

        For whatever reason, so many of us humans find this idea of not being enough as we currently are anathema, ignoring the fact that we, as we are is not the limit of who we can become.

        It might be painful, it might take significant effort, it might require us to leave behind the beliefs, mindsets, and even people that no longer serve us, but each of us is capable of becoming more than we currently are, and achieving more than we currently have.

        If you’re sick of banging your head against the wall, sick of tools, tactics and strategies that fail to work as promised, sick of asking what you need to do next, it might be time to ask a new question.


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

        https://medium.com/@jeremyenns/whats-slowing-your-progress-49268d0627c0https://medium.com/@jeremyenns/whats-slowing-your-progress-49268d0627c0

        Don’t Bank on Being the Outlier

        At some point in your journey as a creator, you’ve probably had the experience of watching a competitor with objectively lesser talent, quality, and utility gain more traction and garner more attention than your higher quality offering.

        It’s easy to throw your hands up in defeat, complain of a rigged system, bemoan the fact that good marketers can get away with delivering lesser value products or blame it all on luck, either your competitor’s good or your own bad.

        These are all fair and understandable reactions to the circumstances. There may be a rigged system, your competition may be better marketers than you, and it’s highly likely that they have been the beneficiaries of a stroke or two of luck along the way*.

        * You almost certainly have as well, but we’ll talk about that another time

        As much as we would like to believe that our society is a strict meritocracy, where the cream rises to the top, and hard work and initiative are rewarded with commensurate success, it’s not, and they’re not.

        The system does not always work fairly, reward the most deserving, and occasionally even elevates the truly deplorable to the highest levels of a field.

        Faced with this reality, there’s another reaction common to creators, one that almost ensures they will never get the big break they seek.

        “If mediocre work is capable of not only outperforming objectively better offers, but gaining broad, mainstream success,” they think, “there’s no point in putting in the time, energy and emotional labour of creating something truly remarkable.”

        This mindset chooses to focus solely on the outlier, ignoring the likely more numerous examples of creators and products that did put in more work and are of higher quality.

        In all likelihood, there is a reason this mediocre-quality outlier slipped through the cracks and hit it big. Maybe they’re fantastic marketers, maybe they got lucky, or maybe they’ve built such a strong and generous relationship with their audience that the ultimate quality of their work is less important than the relationship itself.

        This last point is at the root of effective marketing and should not be ignored by any creator or business.

        Even if there’s no reason at all for your competition’s success and it’s entirely a fluke, choosing to settle for creating work that’s less than the work you’re truly capable of creating — just because someone else got away with it — is a poor assessment of the odds.

        Remember, if they snuck through on mediocre work, they’re the outlier. The odds of you also sneaking through in the same niche is incredibly low, and is not a strategy you can bank on.

        Sure, there’s no guarantee that creating the best work in the world will bring you recognition and success, you still need to do the hard work of marketing it effectively, building an authentic relationship with your audience, and catch some luck as well.

        But creating work that matters, work that resonates, that maybe even changes the people who engage with it is a much more reliable path to success than hoping that out of all the mediocre work in the world, yours will be the one that gets picked.

        Besides, is creating mediocre work really the best way to serve your audience?

        There’s enough mediocrity in the world already. Create something that elevates your niche and raises the bar for everything that comes after it.


        Creating Remarkable Work

        Creating work that spreads requires creating work worth talking about.

        Creating work worth talking about requires creating something remarkable.

        Remarkable is not just something sprinkled on top of an otherwise complete product. Remarkable is baked into the core of anything worth talking about and reinforced at every stage of the design and development process.

        Remarkable work requires us to push outward on the existing frame that our work would otherwise fit into, expanding it and distorting it in some way or another to subvert the expectations of the people who engage with it.

        There are countless edges we might choose to seek out and push outward against, each causing our work to resonate more deeply with some people and less with others. Each with the potential to build raving fans and virulent haters.

        When it comes to creating remarkable work, it doesn’t matter which edge or edges you choose to distort and expand, but if your goal is to create something worth talking about you have to find and choose at least one.

        So what will it be?


        What’s Really Slowing Your Progress?

        Photo by Aubrey Rose Odom on Unsplash

        The next time you find yourself stuck procrastinating on a big project, it might be worth scheduling half an hour to simply work through why you’re not taking action.

        You probably run into these holdups all the time on projects that you ostensibly care deeply about, projects that hold the potential to help you take things to the next level in your businesses and life. No doubt, the sooner you take action on them the better things will be for you overall.

        So why the delay?

        While you might initially think that it’s the scope of the action required to move the project forward, my experience, time and again has taught me that more often than not there’s an unresolved decision that needs to be made about the project that is the real culprit.

        It might be a question about the very nature, scope or purpose of the project, or a tactical decision about the specific part of the project you’re currently working on that needs to be answered. Either way, any doubt or uncertainty about any part of the project has the potential to derail it in its entirety until it’s resolved.

        Without clarity, we can be reluctant to put any work in toward advancing the project, as we worry it will be wasted effort if we end up changing our mind about some foundational element in the future.

        Make a List

        When mapping out a new project, or returning to diagnose a holdup on an existing project, I like to add two sub-sections under each heading or module of my project planning document to help me clearly understand what the issues are that have the potential to sideline the project.

        1. Decisions to Be Made

        In this section, I write down all of the questions about that module or the project as a whole that don’t require research, but do require a decision to be made that, until made will make it difficult or impossible to make progress.

        This list might include questions like:

        • Which sections of my online course will be video and which will be text?
        • Will my supporting documents be PDFs or webpages?
        • Will I host my course on Platform A or Platform B?
        • Do I want the tone of the course to be lighthearted and informal or discerning and authoritative?
        • Where will I record the video segments of the course?

        Once I have the list of questions, I find that I’m often able to, over the course of an hour or so, answer each of them to the level that I can at least begin work on the project.

        Of course, not every question can or should be answered immediately. Some questions are actually best left until you have something to work with, and have something invested in the project.

        Technical or strategic questions and decisions, like where the online course from the example above will be hosted, or what the entire marketing plan for the course will be once it’s completed can and probably should be left until you actually have a course on your hands to put up somewhere and market.

        2. Research

        The second section I’ll create is related to the research I need to do in order to finish off a segment of the project or the project as a whole.

        For the podcast marketing course I’m currently working on, for example, I wanted to learn about PR methods for pitching media outlets to contribute an on-air segment or article as well as the psychology behind why people share content online and how to encourage more of it.

        These questions are often less about the nature of the project as a whole, but when undefined, can still result in procrastination.

        I’ve found that the more amorphous the project is in my brain, the less likely I am to even want to approach it. If feels too unwieldy to chip away at piece by piece when I can’t even tell what the pieces are.

        Clarity Leads to Action

        Since adding these two simple lists to every big project I take on, I’ve found myself moving much more quickly when it comes to getting started and taking action on moving the projects forward.

        When revisiting old stalled projects and applying these lists, I’ve found that most often, the thing that was really truly causing me to procrastinate was not the time or effort required to make meaningful progress, but a simple decision that I didn’t realize was unresolved in the back of my mind.

        Once the right question has been asked, the decisions can often be made instantly, or with five minutes consideration and the work can then move forward.

        Train yourself to get clear on decisions that need to be made and watch your speed of implementation increase rapidly.


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

        https://medium.com/@jeremyenns/not-coming-up-new-good-ideas-c4e09fa31e74https://medium.com/@jeremyenns/not-coming-up-new-good-ideas-c4e09fa31e74

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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.