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2×4: An Interview With Brett Kelly

2×4: An Interview With Brett Kelly


    2×4: One series that examines two topics, creativity and productivity, by asking those who make things on the web the same four questions on both subjects.

    We all want to change our circumstances; we want to make more money or get a better job. For most of us, it’s simply a fantasy, something we’ll imagine ourselves doing, something we may even try for, but more likely than not, it’s something that will never happen. Why? We don’t do what it takes to make that happen. Brett Kelly of Bridging The Nerd Gap made that happen when he got his job at Evernote.

    Many of us sit around and scheme. We try to find any easy route to improve our circumstances. What most of us don’t do: the work. We don’t do what it takes to get ourselves noticed and get in the door. Brett did. Brett wrote the user guide that was missing, Evernote Essentials. It was downloaded 12,000 times and caught the attention of the team at Evernote so much so that they hired Brett full-time to write and maintain their user documentation. It was a chain of events that enabled Brett’s wife to be a full-time mother, empowered him to work from home and helped them get to a place where Brett was no longer working two jobs (or when he is, it is now in pursuit of his own projects).

    Brett’s story is more than a bit of hard work or a spot of good luck; it wasn’t just about writing the right book at the right time. It’s about consistently looking for ways to make things that matter and delivering the goods. Evernote Essentials is a great resource and the site he created to support it, “Bridging The Nerd Gap” is consistently a useful site. Brett is a hell of a writer, especially for those of us who enjoy our Mac geekery. He brings the goods, but he is also grounded in a way that is rare amidst us Apple and GTD fanatics. Look no further than his recent take on minimalist writing apps. Where most of us get excited and exuberant, Brett finds clarity and makes sense.

    Without further ado, here’s a look at how Brett Kelly consistently does what it takes to make things happen.

    Creativity

    Have you always considered yourself a creative person?

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    No, not really. Though, when I was growing up, “creative” was a word used to describe poets, musicians and sculptors. I’ve enjoyed writing in some form or another going back to high school, but it wasn’t until many (many) years later that I saw it as a creative pursuit on par with the other, more obviously “artsy” endeavors I mentioned a second ago. Now, I would say that I’m certainly a creative person, but I don’t necessarily think that makes me terribly unique. The lesser-sung outlets for creativity, I think, are things like problem-solving. My six-year-old son isn’t going to be writing sonnets anytime soon, but he can certainly figure out a way to eat the last cookie without technically breaking the rules.

    What mediums and inspirations do you gravitate toward to realize your creative goals?

    My creative expression can be wrapped up in precisely two gerunds: writing and programming. I can’t paint, draw or play a musical instrument. I deal in words and characters (the kind you access via the Shift key, not the kind you develop as a novelist) because the parameters are fairly well understood and agreed-upon, particularly when talking about software. All the creativity in the world isn’t going to save you if your program doesn’t compile or generates three screenfuls of error messages. You’re working in a known universe. I like it that way. English is arguably quite similar, though there’s definitely more flexibility. When I’m writing, my goal is to say something that the reader can understand. If I fail at that, then it’s time to re-examine the execution a bit and figure out where things went south.

    The inspiration part is easy: people who are better craftspeople than I am. Thanks to the Internet, you can hardly swing a dead eCat without hitting somebody who is a hell of a lot better than you at just about everything. Having ready access to the works of my heroes—both writers and programmers—is like looking out toward what I may become one day, if I work hard and take every opportunity to improve.

    If you had to point to one thing, what specific posts or creations are you most proud of and why?

    I guess I’d have to say my eBook Evernote Essentials is my current front-runner for the achievement of which I’m most proud. This is mostly because it’s far and away the longest single work I’ve ever produced and, well, it’s earned me some money. Plus, lots of people really like it, which helps.

    Any suggestions for those who feel they may not be creative enough to unlock their inner artist?

    Creativity isn’t about being able to paint or write or make music; it happens every day on a much smaller, less glamorous level. When I discover that I can use a binder clip to hold my iOS charging cable firmly to my desk, that’s creativity applied to problem solving (except people don’t usually use the world “creativity”).

    You’re a unique little snowflake of a person that’s walking around having had different experiences than everybody else. These experiences combined with your personality give you a particular take on any number of problems or topics. After all, a butcher’s apprentice is going to be a very different hunting partner than a taxidermy student. Use your specific brain and emotional makeup to take a look at existing situations/problems and see if you don’t have different spin on it (because that’s exactly what creativity is — a different spin on the stuff we all see/feel/use).

    Productivity

    Can you describe your current personal and professional responsibilities?

    By day, I’m the Technical Communications Manager for a startup called Evernote. The title is a little ambiguous, but my duties include generating user documentation and doing a bit of programming—some things for the web, some internal tools. If you’ve ever used the Evernote Knowledge Base, you’ve probably read words that I’ve written.

    Personally, I’m the undeserving husband to my first wife and we have two great kids. I also write a blog called Bridging the Nerd Gap where I talk about all sorts of different things, mostly relating in some way to technology or productivity. I also co-host a weekly podcast with my good buddy Myke Hurley called Cooking with Brett and Myke where he and I talk about anything and everything that happens to tickle our fancy on a given day. Lastly, I’m the one-man show behind my little ebook business where I handle everything from marketing, customer support, product development and—most importantly—the office coffee equipment.

    I’ve got other self-imposed responsibilities in the form of unannounced projects and such, but those are the biggies.

    How do you go about balancing the personal, professional and digital?

    This is one area where I could definitely use some work, but I’ve got a reasonably good handle on things. Every day I eat a quick breakfast with my family before walking down the hall to work (I work at home). I don’t usually take a real lunch break, but having taken a couple of strategic breaks to hug my wife and kids, who are also usually at home, I knock off around dinner time and have dinner with the family, followed by family hang-out time until my kids go to bed a couple hours later. Then, I’ll either spend time writing, reading or working on something. I’ve got far more ideas than I have time to execute on them, though, and that’s hard.

    The more tactical parts where I need help involve getting to bed at a reasonable hour and doing a better job “defining my work” (to borrow an expression from David Allen). I’m routinely bitten in the ass by a poorly defined project or task, so I’m trying to make fewer mistakes there and spend less time tuning my task manager (which will lead to knocking more tasks out in the time I’ve got and not crawling into bed at 1:30am).

    What tools and techniques do you find yourself counting on to get through your workload?

    I’m a big proponent of GTD. We’ve had a rocky relationship in the past, but it’s definitely how I like to roll. The best part about it, I think, is that it makes it possible to move everything forward, even if it’s only a little bit.

    As far as tools, you’ll almost always find me in one of these applications: OmniFocus for tasks on my Macs and iOS devices, Evernote for all sorts of different things, Vim for writing code and prose and Apple’s Mail. Without OmniFocus and Evernote, I’d probably be 40 pounds heavier, single and in therapy.

    What is the best starting point for the unproductive amongst us, who are looking to get more organized?

    I’ve probably bought more copies of David Allen’s Getting Things Done for desperate friends than I care to remember, but that’s what I tell just about everybody to do. Yeah, I know it’s become cliché and lots and lots of people won’t shut up about it, but it’s really such a great antidote for the stressed out everyman (or “everylady”, if that’s a thing).

    Tactically, do what David Allen calls a “mental sweep”; essentially, sit down with a big stack of paper and a pen and completely empty your head of every single thing that’s got your attention, one item per sheet. You can read his seminal book for more info on what to do after this, but the point is that your brain is really good at solving problems and creating things, but it positively sucks at holding information such that it can be called back up on command.

    If I’m ever feeling overwhelmed, I’ll sit down and do exactly this mental sweep activity until I’ve cleared everything out of my brain and it can relax.

    More by this author

    2×4: An Interview with David Sparks 2×4: An Interview with Myke Hurley 2×4: An Interview With CJ Chilvers 2X4 Interviews 2×4: An Interview With Gabe Weatherhead 2×4: An Interview With Brett Kelly

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    1 Why You Have the Fear of Failure (And How to Overcome It) 2 How to Break Out of Your Comfort Zone 3 How to Cope with the 5 Common Stressors In Life 4 How to Achieve Goals and Increase Your Chance of Success 5 This Is Why Taking Action Creates Success

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    Last Updated on May 12, 2020

    Why You Have the Fear of Failure (And How to Overcome It)

    Why You Have the Fear of Failure (And How to Overcome It)

    Nobody enjoys failing. Fear of failure can be so strong that avoiding failure eclipses the motivation to succeed. Insecurity about doing things incorrectly causes many people to unconsciously sabotage their chances for success.

    Fear is part of human nature. As an entrepreneur, I faced this same fear. At times, I forgot that who I was wasn’t what I did. My ego and identity became intertwined with my work, and when things didn’t go as planned, I completely shut down. I overcame this unhealthy relationship with fear, and I believe that you can too.

    Together we’ll examine how you can use failure to your advantage instead of letting it run your life. We’ll look at what a fear of failure is, where it comes from, and how to overcome it so that you can enjoy success in your work and life.

    What Is Fear of Failure?

    Fear causes you to avoid potentially harmful situations. Fear of failure keeps you from trying, creates self-doubt, stalls progress, and may lead you to go against your morals.

    What causes fear of failure? Here are the main reasons why fear of failure exists:

    • Patterns from childhood – Hyper-critical adults cause children to internalize damaging mindsets.[1] They establish ultimatums and fear-based rules.This causes children to feel the constant need to ask for permission and reassurance. They carry this need for validation into adulthood.
    • Perfectionism – Perfectionism is often at the root of fear of failure.[2] For perfectionists, failure is so terrible and humiliating that they don’t try. Stepping outside your comfort zone becomes terrifying.
    • Over-personalization – The ego may lead us to over-identify with failures. It’s hard to look beyond failure at things like the quality of the effort, extenuating circumstances, or growth opportunities.[3]
    • False self-confidence – People with true confidence know they won’t always succeed. A person with fragile self-confidence avoids risks. They’d rather play it safe than try something new.[4]

    How the Fear of Failure Holds You Back from Suceeding

    Unhealthy Organization Culture

    Too many organizations today have cultures of perfection: a set of organizational beliefs that any failure is unacceptable. Only pure, untainted success will do.

    Imagine the stress and terror in an organization like that. The constant covering up of the smallest blemishes. The wild finger-pointing as everyone tries to shift the blame for the inevitable cock-ups and messes onto someone else. The rapid turnover as people rise high, then fall abruptly from grace. The lying, cheating, falsification of data, and hiding of problems—until they become crises that defy being hidden any longer.

    Miss out Valuable Opportunities

    If some people fail to reach a complete answer because of the lure of some early success, many more fail because of their ego-driven commitment to what worked in the past. You often see this with senior people, especially those who made their names by introducing some critical change years ago. They shy away from further innovation, afraid that this time they might fail, diminishing the luster they try to keep around their names from past triumph.

    Besides, they reason, the success of something new might even prove that those achievements they made in the past weren’t so great after all. Why take the risk when you can hang on to your reputation by doing nothing?

    Such people are so deeply invested in their egos and the glories of their past that they prefer to set aside opportunities for future glory rather than risk even the possibility of failure.

    High Achievers Become Losers

    Every talent contains an opposite that sometimes makes it into a handicap. Successful people like to win and achieve high standards. This can make them so terrified of failure it ruins their lives. When a positive trait, like achievement, becomes too strong in someone’s life, it’s on the way to becoming a major handicap.

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    Achievement is a powerful value for many successful people. They’ve built their lives on it. They achieve at everything they do: school, college, sports, the arts, hobbies, work. Each fresh achievement adds to the power of the value in their lives.

    Gradually, failure becomes unthinkable. Maybe they’ve never failed yet in anything that they’ve done, so have no experience of rising above it. Failure becomes the supreme nightmare: a frightful horror they must avoid at any cost.

    The simplest way to do this is never to take a risk, stick rigidly to what you know you can do, protect your butt, work the longest hours, double and triple check everything and be the most conscientious and conservative person in the universe.

    If constant hard work, diligence, brutal working schedules and harrying subordinates won’t ward off the possibility of failing, use every other possible means to to keep it away. Falsify numbers, hide anything negative, conceal errors, avoid customer feedback, constantly shift the blame for errors onto anyone too weak to fight back.

    The problems with ethical standards in major US corporations has, I believe, more to do with fear of failure among long-term high achievers than any criminal intent. Many of those guys at Enron and Arthur Andersen were supreme high-fliers, basking in the flattery of the media. Failure was an impossible prospect, worth doing just about anything to avoid.

    Loss of Creativity

    Over-achievers destroy their own peace of mind and the lives of those who work for them. People too attached to “goodness” and morality become self-righteous bigots. Those whose values for building close relationships become unbalanced slide into smothering their friends and family with constant expressions of affection and demands for love in return.

    Everyone likes to succeed. The problem comes when fear of failure is dominant. When you can no longer accept the inevitability of making mistakes, nor recognize the importance of trial and error in finding the best and most creative solution.

    The more creative you are, the more errors you are going to make. Get used to it. Deciding to avoid the errors will destroy your creativity too.

    Balance counts more than you think. Some tartness must season the sweetest dish. A little selfishness is valuable even in the most caring person. And a little failure is essential to preserve everyone’s perspective on success.

    We hear a lot about being positive. Maybe we also need to recognize that the negative parts of our lives and experience have just as important a role to play in finding success, in work and in life.

    How to Overcome the Fear of Failure (Step-By-Step)

    1. Figure out Where the Fear Comes From

    Ask yourself what the root cause of your negative belief could be.[5] When you look at the four main causes for a fear of failure, which ones resonate with you?

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    Write down where you think the fear comes from and try to understand it as an outsider.

    If it helps, imagine you’re trying to help one of your best friends. Perhaps your fear stems from something that happened in your childhood, or a deep-seated insecurity.

    Naming the source of the fear takes away some of its power.

    2. Re-Frame Beliefs About Your Goal

    Having an all or nothing mentality leaves you with nothing sometimes. Have a clear vision for what you’d like to accomplish but include learning something new in your goal.

    If you always aim for improvement and learning, you are much less likely to fail.[6]

    At Pixar, people are actually encouraged to “fail early and fail fast.”[7] They encourage experimentation and innovation so that they can stay on the cutting edge. That mindset involves failure, but as long as they achieve their vision of telling great stories, all the stumbling blocks are just opportunities to grow.

    3. Learn to Think Positively

    In many cases, you believe what you tell yourself. Your internal dialogue affects how you react and behave.

    Our society is obsessed with success, but it’s important to recognize that even the most successful people encounter failure.

    Walt Disney was once fired from a newspaper because they thought he lacked creativity. He went on to found an animation studio that failed. He never gave up, and now Disney is a household name.

    Steve Jobs was also once fired from Apple before returning as the face of the company for many years. [8]

    If Disney and Jobs believed the negative feedback, they wouldn’t have made it.

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    It’s up to you to notice your negative self talk and identify triggers. Replace negative thoughts with positive facts about yourself and the situation. You’ll be able to create a new mental scripts that you can reach for when you feel negativity creeping in. The voice inside your head has a great effect on what you do.

    4. Visualize all Potential Outcomes

    Uncertainty about what will happen next is terrifying. Take time to visualize the possible outcomes of your decision. Think about the best and worst-case scenarios. You’ll feel better if you’ve already had a chance to mentally prepare for what could happen.

    Fear of the unknown might keep you from taking a new job. Weigh the pros and cons, and imagine potential successes and failures in making such a life-altering decision. Knowing how things could turn out might help you get unstuck.

    5. Look at the Worst-Case Scenario

    There are times when the worst case could be absolutely devastating. In many cases, if something bad happens, it won’t be the end of the world.

    It’s important to define how bad the worst case scenario is in the grand scheme of your life. Sometimes, we give situations more power than they deserve. In most cases, a failure is not permanent.[9]

    For example, when you start a new business, there’s bound to be a learning curve. You’ll make decisions that don’t pan out, but often that discomfort is temporary. You can change your strategy and rebound. Even in the worst case scenario, if the perceived failure led to the end of that business, it might be the launching point for something new.

    6. Have a Backup Plan

    It never hurts to have a backup plan. The last thing you want to do is scramble for a solution when the worst has happened. The old adage is solid wisdom:

    “Hope for the best, prepare for the worst.”

    Having a backup plan gives you more confidence to move forward and take calculated risks.

    Perhaps you’ve applied for a grant to fund an initiative at work. In the worst-case scenario, if you don’t get the grant, are there other ways you could get the funds?

    There are usually multiple ways to tackle a problem, so having a backup is a great way to reduce anxiety about possible failure.

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    7. Learn from Whatever Happens

    Things may not go the way you planned, but that doesn’t automatically mean you’ve failed. Learn from whatever arises.[10] Even a less than ideal situation can be a great opportunity to make changes and grow.

    “Sometimes you win, sometimes you learn.”

    Ask yourself:

    • What did I learn?
    • How can I grow from this?
    • Did anything positive come from this situation?

    Dig deep enough, and you’re bound to find the silver lining. When you’ve learned that “failure” is an opportunity for growth instead of a death sentence, you conquer the fear of failure.

    Final Thoughts

    Together we’ve learned what fear of failure is, and how it can have a crippling effect on our ability to achieve. This fear often stems from childhood, perfectionism, ego and over-personalization, and a lack of confidence.

    Luckily for us, there are plenty of ways to tackle this fear. We can start by figuring out where it comes from and re-framing the way we feel about failure. When failure is a chance for growth, and you’ve looked at all possible outcomes, it’s easier to overcome fear.

    Stay positive, have a backup plan, and learn from whatever happens. Your failures will be sources of education and inspiration rather than humiliation.

    “I have not failed. I’ve just found 10,000 ways that won’t work.” – Thomas A. Edison

    Failures can be blessings in disguise.

    Go boldly in the direction of your dreams and goals. Don’t allow fear to stand in your way.

    More Tips for Conquering Fear

    Featured photo credit: Vecteezy via vecteezy.com

    Reference

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