Planning to Fail

“If you do not change direction, you may end up where you are heading.”

Lao Tzu

Whenever I’m feeling stressed or overwhelmed, it’s usually because either A) I’m trying too many things at once, B) I’ve said ‘yes’ to something I should have said ‘no’ to, C) My intention/direction is vague and-or D) All the above.

A. Doing too many things at once is something I’m constantly rebalancing. Curiosity can lead you down to thousands of wonderful (and occasionally bizarre) places. This can spark a countless number of ideas and opportunities, but if you let curiosity run on a rampage all the time, you’ll wake up a week later after being lost in a deep Reddit or YouTube rabbit hole.

The important thing is to have a firm grasp on the few major things that are important to you, so you can pare back when you become aware that you’re a few hundred pounds over your elevator capacity, so to speak.

B. This one is similar to A. Saying yes is easy. It’s nice when someone asks you to do something for you. But too many of these, and you’ll end up doing everyone’s work except your own. It’s hard to say no, but it’s essential if you want to still have the time and energy to focus on what’s most important to you.

C. If there’s a centralized theme to this observation, it’s that only having a vague idea of what you want can easily lead you off into a direction you may or may not have wanted to go.

Sometimes vagueness is what you want. You want the surprise and spontaneity that an unknown direction will bring. Traveling (remember traveling?) to a new place, for example. It’s a delight when you can discover an unknown (to you) restaurant that is divine in a city you’ve never been to before. Movie spoilers is another one. If there’s a movie or tv show I’m interested in seeing, I don’t want to know anything about it. Don’t give me the plot. I don’t want any details. I want to be surprised (and hopefully delighted) which I wouldn’t be if I knew what was going to happen beforehand.

But what about when you’ve got a problem you need to fix or when hazy ideas are holding you back?

When in doubt, make a plan.

The method can be simple. Grab some paper and a pen and start writing. Make a todo list. Ask yourself questions. Get specific. Dig. Come up with some potential action steps.

The true benefit of planning is clarity. We’ll rarely actually reach the exact goal we set out to achieve, but taking time to understand our next steps will move us in the right direction.

If we only have a vague sense of what we’re after, how can we possibly know what we can do to get there?

Planning gives us specific actions to take. No—it gives the next action we need to take. Our destination might be completely different after we finish that action, but by then we are ready for the next one.

Planning is about playing the chessboard. The next move is critical, but only when combined with the next several moves and countermoves in the future. The idea isn’t just to have one fixed thing we’re after. We’re thinking about all the potential outcomes—worst-case and best-case scenarios. We’re trying to nudge the outcome in a particular direction, but if it doesn’t work at least we have an idea of what a bad scenario looks like and what we can do to handle it.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1013

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‘No’ is Better Than ‘Maybe’

—And that goes both ways (you saying no, or someone else telling you no).

The question is, which is scarier?

Getting a no, or never knowing because you never asked?

At least with a no, you can move on. You can try something new and different.

With a maybe, you don’t know what you need, and you feel stuck and overwhelmed. With a no, you understand where you stand and what you can do going forward.

To take charge of your life, you must fear maybe’s more than you fear no’s.

You must fear inaction — or lack of change — more than you fear action — what you might experience with action, such as failure, embarrassment, rejection, and criticism.

Otherwise where will you end up?

Exactly where you are and have been. Nowhere you want to be.

“There are risks and costs to action. But they are far less than the long range risks of comfortable inaction.”

John F. Kennedy

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1012

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Let Yourself Have It

“Start by doing what’s necessary; then do what’s possible; and suddenly you are doing the impossible.”

Francis of Assisi

It’s been said that the moment you learn to worry is the moment you become an adult. Growing up I was a rambunctious kid.

I bit my tongue and had to get stitches when I was really young. I broke my left leg in an ATV accident with my dad. I fractured my right wrist rollerskating at the skating rink. But I never worried about it. I felt pain, but I never once thought about whether or not I’d be okay.

It wasn’t until much later, when I injured my neck (and am still dealing with today) that I faced worry in a real way. Hello, world. It is something that is a piece of my story, but it doesn’t define me. Well—not completely. It’s similar to a job or a hobby. You may be a photographer but that doesn’t completely describe who you are.

Worry (And it’s friend Anxiety) is the problem. You can work it away. You can play it away. But the only true way to get rid of a worry is to let go of what’s bothering you, or what might/could happen.

What if you suffer an injury you can never recover from? Well, so be it. There’s always hope, but if worst comes to worst, you make do with your new normal.

There is joy to be found if you let yourself have it. If you open up to what you have, what you can do, what you can dream of—instead of being stuck in the past or what you had.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1011

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Joyful

“Always turn a negative situation into a positive situation.”

Michael Jordan

In order to thrive, we need stability. In order to have stability, we need to thrive. A catch-22. (Or perhaps an ouroboros.)

And yet, maybe not. What is stability? What does thriving mean? Is it something external? Free from harm? A hot meal and a warm bed?

Anyone who has started their own company knows that the stability of a job is abstracted away from the business’s finances. An employee at a company that’s doing well is secure. And an employee at a company doing poorly is also secure. The employee at the thriving company will more likely keep her job than the other employee, but both could end up unemployed if something goes unexpectedly wrong.

A job is an external thing. It provides for our basic needs, but it’s not what gives us stability or the ability to thrive. That comes from within. If we cultivate our minds and learn to let go in the face of uncertainty and things that aren’t in our control, no amount of instability will hold us back from long.

Thriving starts is in the mind.

You can see it radiating out of people into their lives, but it starts with the thought of knowing that despite everything challenging going on, you’ll be okay. The sun will rise. The birds will sing. And we can begin anew, wherever we are and use what we’ve got as an opportunity to do great things and keep on living.

The happiest people in the world aren’t happy because of all the things they own, or because of their success and accomplishments. They are happy—no, joyful—because they decided to be.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1010

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Missing a Day

“Right discipline consists, not in external compulsion, but in the habits of mind which lead spontaneously to desirable rather than undesirable activities.”

Bertrand Russell

It’s a sad day when you break a daily habit streak. The other day, I was on day 240 of sketching every day, but I flubbed it. I could give you a million reasons why I forgot, but that doesn’t change the fact that I broke my streak. It happens to the best of us. 

Practicing a habit always has its ups and downs. Doing anything worthwhile is never easy. The two most difficult moments of keeping a habit are: 

1. The first couple of weeks of starting a new habit:

A new habit isn’t sticky when you are just beginning. There’s nothing really pulling you forward beyond the excitement and motivation of trying something new. That’s why I find daily streaks so powerful. 3 days in a row is cool, but no one would feel remorse for missing day 4. But what about day 30? Day 100? Day 300? When day 301 rolls around, you better believe you’ll do whatever you can to make it happen.

2. The day after you miss:

Missing a day can be crushing. There’s a million reasons, obstructions, and excuses that can prevent us from practicing. It’s easy to feel demoralized and unmotivated to start over. But here’s the thing—

A habit is a means to an end.

Practicing daily is fantastic, but it’s not the end-all-be-all. Drawing every day will improve your artistic abilities—which is a great reason why to do it—but there needs to be a goal beyond that. It goes down to the core of why you want to learn and become great at something in the first place. Practicing music everything day will improve your song muscles which can flourish into you becoming a musician and writing songs people love.

Missing a day sucks, but so be it. It’s not the end of the world. It doesn’t change our passions. It doesn’t change the goal. If it happens—it happens. The only thing we can do is look forward and think of it as a fresh start. We know what we have to do. There’s no time to sulk. Our daily streak may be back to Day #1, but that’s just a tool that keeps us accountable to our dreams. The daily count doesn’t matter—what matters is what we do with the skills we are cultivating.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1009

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Cats & Dogs

“My ‘fear’ is my substance, and probably the best part of me.”

Franz Kafka

There are many things in life that seem like one thing, but can actually the other. For example, exercise is fantastic for your health, but if you don’t know what you are doing, you can easily hurt yourself. Without depth and guidance, we can quickly become closed off (and sometimes clotheslined) by our assumptions and generalizations. As the Sociologist, Marshall McLuhan (1911 – 1980) once quipped, “Most of our assumptions have outlived their uselessness.”

1. Sometimes advantages are disadvantages and disadvantages are advantageous.

Think of talent. Talent can be a crutch just as it can be a benefit. Being naturally born gifted at sports or music can take us far, but only for a while. Sooner or later practice outraces talent and if we lean to heavy on our gifts without putting in the time, we’ll quickly be left in the dust of less-talented hardworking people. (I learned this from the book The Talent Code by Daniel Coyle.)

Talent is a crutch. Consistent practice and drive lead to mastery.

It takes dedication and work to succeed in a skill. If you don’t have a knack for something (or perhaps even suck at it), but you are so passionate about it, then your “disadvantage” will drive you to seek mastery and achievement. (Nobody puts Baby in the corner.)

2. Fear is a guiding force.

It leads us away from danger, but it also can lead us toward challenge. Distinguishing which is straightforward when you ask the question: “Am I in danger? Is this going to kill me?”

If the answer is yes, then get the heck out of there. But if you’re not in danger, then perhaps your fear is telling you something. Fear of speaking in front of the crowd is understandable (it makes me sweat just thinking about it), but it won’t kill you. In fact, your fear of public speaking is a social fear that’s holding you back. Imagine what you could do in every aspect of your life if you had the confidence of someone who can get up on stage and be the center of attention for a moment. Things would certainly change. Social fears are challenges we can use to improve and become better versions of ourselves.

3. Pain is a (wretched) gift.

I would never wish pain on anyone, but it’s one of the great eye-openers of life. Pain humbles you, removes your ego, and shows you a world you didn’t know existed. Pain can isolate us if we let it, but it can also connect us—to others, to something bigger and to ourselves. It’s difficult to feel the pain someone else has experienced, without feeling the sting of it yourself. Anyone who has injured themselves—a back, neck, or foot injury for example—will know difficult it is to deal with.

We rarely realize how important something is until we’ve lost it.

Pain is a beginning, as much as it is an ending. Your pain may fade, but you’ve changed because of the experience. Or your pain may never go away, but it becomes part of your story and has woken you up to a world of others who have experienced something similar to you. Your story connects and heals us.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1008

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Just Finish

“It’s the job that’s never started as takes longest to finish.” — J. R. R. Tolkien

My head is pounding. It’s been a long day, although it doesn’t feel like I did much. Some days are like that—you make progress, but it’s a small accomplishment in a sea of todo’s and planning towards a long-term goal. But it still counts. The day still adds up to something.

I probably overdid it today (as per usual 🙂 I started learning Wim Hoff breathing, Dual-n-Back training, Procreate illustration courses on SkillShare, and started learning Japanese. (Learning Brag?) Normally I’d only start one new habit at a time, but I was feeling scattered today, so instead, I just started learning everything.

If you are a multi-disciplinary like me, that’s one thing you have to be vigilant about—whether or not you are learning too many things at once. If you have to ask yourself the question, “Am I learning too many things at once?” then you definitely are. There are only so many hours in the day, so it’s easily doable. Plus you’re a human being—don’t forget to take breaks and stay hydrated (half-kidding). Otherwise, you’ll end up with a headache like me. Everything in balance.

There’s nothing wrong with trying new things. Just make sure you are still putting in time with the things that are important to you. It’s better to finish what you start than constantly start new things and never finish anything. You don’t want to be that person who is known for their half-started ideas.

Of course, some things aren’t finish-able. You never “finish” learning a language or skill. You either stop or keep improving and using it. Stopping is an acceptable thing to do, particularly if it’s something you’ve been holding onto and need to let go of. But if you want to be great in a skill, you have to keep cultivating it.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1007

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Cultivating The Whole

“The whole is more than the sum of its parts.”

Aristotle

I spend a lot of time on my mind. Meaning, not in my thoughts—I do that too—but on developing my mind and the skills regarding the mind. Which usually means I’m taped to a computer (or device of some sort) most of the day. I wouldn’t say I’m addicted to screen (I’m addicted to creating and learning). I don’t feel separation pains if I leave my phone at home. I spent over a year off of social media. But, my work, side project, and entertainment center around mental things.

There’s a touch of heart and body, of course, but most of the things I enjoy—coding, design, writing, music creation, not to mention reading and writing—all revolve around the mind.

This feels very one sided.

There is no mind without a body, just as there is nobody without a mind (they’re kind of a package deal). Even computers have physical hardware somewhere, what makes us think we can invest everything into our minds and leave everything else in our lives malnourished?

Day and night. Awake and rest. We need to find balance with all aspects of ourselves and our surroundings. Mind, Body, Spirit, Connection, Community—all pieces of the puzzle that can bring us joy, meaning, and creativity when we make them significant to us. Otherwise, things start to break down. Relationships crumble or fade, and suddenly you’re left without a support system when you fall and friends to call when you are feeling lonely. The body stops functioning properly and suddenly your mind wasn’t what it used to be. (So much for all the time you spend cultivating it). You

Action Question: How much time do you roughly spend cultivating your mind and mental skills? How does that compare to the time you invest in your relationships? What about body, spirit, and love?

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1006

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Wilting

“Nature does not hurry, yet everything is accomplished.” — Lao Tzu

Have you noticed that in modern society we barely (if at all) live by the seasons anymore? If it weren’t for school, seasonal allergies, marketing, and Christmas, we’d probably have gotten rid of them years ago.

We’ve abstracted nature out of the equation.

We eat out of season. Pasta in the summer. Fruit in the winter.
We use AC to have a more comfortable local atmosphere.
When the sunlight fades, we light up the night sky with electricity.

Taking control of nature allows us to work and live however we want to. This gives us more power and ownership over our lives. But it potentially throws out of alignment with our needs. Perhaps we need to live more seasonally.

My fiancée and I recently had a conversation about this idea. She’s hot-natured, so living in the South during the summer is almost unbearable for her. If she’s out in the humid sun too long she turns into a cooked vegetable. She’s a much happier and productive camper when fall comes along.

I wonder if seasonality goes deeper than what food we can grow. What if the seasons are built into our DNA as earthlings?

Sure, different parts of the world have a different climates. To each their own.

There’s a time for things to bloom and things to wither. There’s a time for rest and for work. There’s a time for reflection and play and community and adventure. Are we respecting that in ourselves? How can we incorporate seasonality into our lives?

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1005

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Analysis Paralysis

“Our nature consists in motion; complete rest is death.”

Blaise Pascal

Momentum requires movement. Think of a fire—a spark is nothing and everything. A spark can keep you warm, it can take out a house, a forest, even cities. It doesn’t take much, but a little is enough.

The hardest parts are:

  1. Starting
  2. Restarting (another form of starting)

Starting something new can feel like quicksand, particularly when we are scared or worried. But once you get moving, fear turns into excitement. Water starts to flow. Ideas pour out. Dust and cobwebs start to clear. Muscles warm up in anticipation.

Restarting is similar to starting, but harder. Whenever you stop doing something, like a diet or journaling, or an online design course, not only you lose momentum, you also add weight to your shoulders. How many times have you thought of the past when things about your life— your health, happiness, finances—were better? We pine after the “good old days” and whenever we attempt to restart our habits we fail because we put too much pressure on ourselves.

The key to starting is starting fresh. Don’t focus on what you had and what you’ve lost. Focus on what you can do right now and the potential of where you can be once you begin again.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1004

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