Category: Challenges

There is No Try

“The art of teaching is the art of assisting discovery.” — Mark Van Doren

Part of our jobs as creatives is figuring things out. Discovery and uncertainty are two sides of the same pancake. There’s rarely comfort in uncertainty, but there is excitement. The excitement from learning something new. The thrill of being resourceful or doing something yourself.

It’s one thing to be taught the idea of something, it’s another thing to come to it with your own eyes, ears and hands.

True understanding comes from hands-on experience. There’s a level of wisdom you can’t gain unless you tinker, play, explore and experiment yourself.

That’s true with design and business and coding and well—everything. Of course, it’s not about doing it all yourself, rather using DIY as an approach to learn a skill at a deeper level of compression.

It’s hard to completely get that from a book or tutorial. Teaching is a guide. It opens the door for us, but we are the ones that have to take the extra step and make the connections.

A course might save us time and shortcut our path to understanding and success, but until we get our hands dirty, so to speak, we won’t be at the level of mastery we seek yet.

Ask big questions. Observe the world.

Throw things at the wall. And try things out yourself.

STAY BOLD, Keep Pursuing,

— Josh Waggoner | Daily Blog #1202

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Hard-won Lessons

“A failure is not always a mistake, it may simply be the best one can do under the circumstances. The real mistake is to stop trying.”

B. F. Skinner

If I had the opportunity to peer into a crystal ball and see my future, I don’t that I would. Because some of my best moments have come from my worst failures. And if I knew how hard I would fall and scrape my knees (metaphorically speaking), I’m not sure I would be strong enough to choose failure.

For me, that was learning how vital health is by dealing with the damage of injuring my neck.

I would never wish misfortune and hard lessons on anyone, but they often are the most rewarding lessons we can experience in life. Well, that is if we humble ourselves enough to bend to their insights. (There are plenty of people out there who fail and fail again but never learn and use their mistakes to their advantage.)

But how to move forward after failure? How to move forward after your life falls apart like a sugar cookie in a zip lock bag being crushed by your grade school bully?

You move forward by starting over and by picking yourself up and trying again. Because that’s what life is—a cycle of “trying agains”. Even success ebbs and flows.

There’s never a moment of “making it.” There’s always the next level. Even Oprah and The Rock are aiming for something. Of course, it’s when you think you’ve made it that you start to un-make it. Casey Neistat has a great vlog on this, My Biggest Failure. The worst thing you can do when you fail (or succeed) is nothing.

Earn your failures by turning them into momentum.

And when you are in the midst of despair, look for the good—shift out the dirt and debris and find the gold in your situation. There are no easy answers in difficult circumstances, only hard-won lessons.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1188

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Markable

For over eighty percent of my life (I’m currently thirty) I wouldn’t dare think of writing or underlining in a book. I even loathed opening a book to wide, hating the idea of messing up its pristine structure. Folding a book halfway was blasphemous. I know, I was weird (aren’t we all).

I honestly don’t know where this quirk came from. I just really had the desire to take care of my stuff, and treat my books like they were brand new.

Now I’m the opposite. My younger self would feel whiplashed from the amount of underlining and writing I do in my books. The flip was a gradual process, but there were three defining moments shot me out of the canon.

One was a simple thought: there are thousands—sometimes even millions—of copies of books. My scribbling in a hardback now-and-again isn’t going to marginal have much of a difference.

The second defining moment was learning about the marginalia libraries of grand figures, such as Isaac Newton and Oscar Wilde.

And this leads us to the final defining thought: writing, highlighting, and underlining is like a time capsule of your mind and life at a particular time. And every time you revisit a book, you are layering in another version of who you are in a given moment. By writing out thoughts and underlining passages that stand out to you, you are leaving a lasting impression of who you are for your future self.

Does that mean I’m going to scribble in my signed copy of The Name of the Wind? No! Of course not. But I am going to use the books I own and get the most meaning out of them as I can.

Marking up your books is a small thing, but it highlights (pun intended) a big idea:

Making your mark doesn’t require permission.

Perhaps it used to, before the internet age. But now, anyone can pursue an idea or passion and share it with the world. Of course, being able to share doesn’t mean everything is high-quality. Put it does give us a direction to setting higher standards for ourselves and going after big ambitions.

If there’s something you dream about doing, what’s stopping you?

Are you stopping yourself?

What if you got out of the way?

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1167

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Reacting to Lemons

Every year I like to buy a nice big calendar poster to keep track of my focuses and daily habits.

Last year I had just got my freshly crisp, 2020 calendar in the mail. I gently took it out of its tube and rolled it out on my bed. Brand new. Clean. Not a mark out of place. And then all of a sudden my dog comes rushing at me, excited to see me, and, of course, jumps on the bed and rips a paw print through my new calendar.

I could have been angry. I had barely looked at the thing, let alone used it! Or more likely, I could have been frustrated and let it ruin my whole day.

But I didn’t.

I had recently been reading a lot of Ryan Holiday’s work and Stoic philosophers, such as Seneca and Marcus Aurelius.

In that perfect moment to practice being a better person, a quote from Epictetus came to mind—

“It’s not what happens to you, but how you react to it that matters.”

So instead, I rolled the calendar up, played with my pup, and later playfully labeled the holes as paw prints, hung it up, and went on with my day.

This is such a small moment, but it highlights our reactions can influence, and make-or-break the circumstances we find ourselves in.

I don’t also react well to what life throws at me, but each time I do I mark it as one more step to being the person I want to be.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1147

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Clean Slate Method

Often the obstacles in our way are not (just) the problem(s) we are facing, rather how we are dealing with them.

Basically, we lose our sh🙈t. We worry and loop our problems and mistakes over and over again. We stress ourselves so much we drain all the energy we have (and could have used to solve it.) We’re not thinking about this of course (myself included), we’re too busy dovetailing into the abyss.

At least, that’s how I feel when I have too much on my plate or when I’ve unintentionally said yes to too many things I should have said no to.

But I have found a silly method that has helped me out in times of distress, like when I have stacks of todos and a negative amount of time to do them.

I mentally drop everything.

I pull the tablecloth and swipe away clean everything on it.

I sink all the battleships.

And all I’m left with is a clean slate.

No obligations. Nothing I need to get done. No outside pressures. (And now no inside pressures either!)

Not in reality, just in my mind. I think of it as a factory reset for my brain.

If you’re into paper products (like me) then think of it as a fresh, new sheet of paper, or a blank calendar, unblemished.

As I sit in this mind space, I slowly begin to ask myself questions like:

  • If you could drop everything from your life, what would you want to keep/pick back up?
  • What do you really want to do?
  • If something is holding you back from doing that, what immediate actions are you able to take to open that blockade?

The clean state method is a tool to get you in a better headspace to solve problems and focus on what matters.

Obviously, we can’t actually can’t set everything on fire and start over, but we can stop mentally getting in our way by overwhelming ourselves with the past and our expectations of the future.

Clearing your head gives you much more room to focus on the immediate priority, and tackle things head-on—just not all at once.

It’s had to make anything happen if you’ve psyched yourself out before you’ve even be

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1136

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Day and Night

“I often think that the night is more alive and more richly colored than the day.”

Vincent Van Gogh

The best ideas often come from raw and difficult experiences. It’s like we take everything we are feeling, ball it up and use what skill we have—be it our voice, guitar, words on a page, dance—and creatively express it out of us.

Creativity can be an excellent release valve when the pressure of life starts to build. Making something is a creative way to release what’s bottled inside in a positive way.

Difficult moments in our lives suck—but they also add a little bit more color to our story.

Difficulty is part of being human. At least it’s a big part of being creative and putting yourself out there. When I feel the most comfortable and complacent, my ideas suddenly dry up. Imagine that. It’s like we need challenge in order to be imaginative and create something worthwhile.

Now, challenge is not the same as sabotage or danger. It’s one thing to push yourself to the limit of discomfort, it’s another to sabotage yourself and make life difficult for yourself.

Challenging yourself and stretching your comfort zone is getting you somewhere. Sabotaging your success (and failures) with bad habits (or negativity) is only holding you back.

Remember, there will always happy “days” and hard “nights” in our lives. If you’re going through a rough night, keep your head up because night is always followed by day.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1086 ☕️

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Testing Dependencies

“Success is dependent on effort.”

Sophocles

I’ve written before about how it’s easier to acquire tastes than it is to get rid of them. Something normally that’s exotic or saved for special occasions can quickly become our new normals. Instead of saving that delicious Italian restaurant for your birthday, you start having it once a week.

For me, that’s amplified with a personal tendency to overdo it. A cheat “meal” turns into a cheat “weekend”. Or instead of one newsletter, I make three.

But do we really need our “needs”?

I don’t consider myself a minimalist. I related to some of the core values of minimalism, but I wouldn’t label myself as a minimalist. I’m more of a… “essentialist” “practicalist” “intentionalist” something along those lines (semantics, to be sure, but still).

It’s helpful to put things in perspective. In five years, all of the technology you and I use will be obsolete. Five years is generous. There’s a lot of new and exciting gadgets coming out right now. It’s more likely every piece of tech we own will be obsolete in a few months.

It’s good to test your dependencies regularly.

For example, taking a break from social media or swearing off coffee for a year.

Dependency aren’t evil. But they do make us reliant on them. Once you get used to having a certain quality of something, it’s hard to go back. I think that’s why people in third world countries are so happy with very little. It’s not the stuff that they have or don’t have, it’s the knowledge that something “better” is out there. 

This feeling is what I want to resist. I love luxury, but I don’t want to *need* it to be happy. I want to test my dependencies because you never know what fate my take of you. I’d rather be happy and healthy than rich. But if I can be happy, healthy, and rich that would be great too 😉. As long as that money isn’t controlling me.

What are other things we are reliant on? What are your crutches? 

Clothes? New technology? Habits?

Action: Make a list of things you need and use every day. If you forced yourself to give them up for a month, or six or a year, could you?

To live an unconventional life we must do unconforming things.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1062

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Where’s the bottleneck?

“Most people spend more time and energy going around problems than in trying to solve them.”

Henry Ford

When you’re feeling stuck, look for the main bottleneck. What’s the one thing preventing you from moving forward? 

The problem is we immobilize ourselves by trying to solve the problems 3 moves in advance first. ‘I’d love to save more money each month, but if I did that I wouldn’t have enough to pay for food and expenses, plus I won’t be able to get those new running shoes and I forgot I need to get my oil changed sometime soon.’

Sometimes we even convince ourselves that before we can fix this current problem, we must fix X Y and Z first. ‘I want to get a new job, but first I need to fix my health, but before that, I should really think about going back to school.’

Instead of dealing with the immediate problem, we’re thinking about a hundred other things on our todo list.

Thinking 3 moves in advance is great. But when it comes to solving problems we need to focus on them one at a time. Fixing the main issue may cause other issues down the line, but don’t worry about that now. Focus on the current priority. 

Put everything aside in your mind for a moment and focus exclusively on the priority at hand.

An alternative approach is to go around the problem and reduce complexity by finding a way to nullify multiple problems in one sweep by solving the underlying issue. (I believe this idea is from Tim Ferriss.)What’s one thing I can focus on/do that will nullify all the other (potential) problems.

What we need is a sense of priority. What’s the most important thing you need to focus on right now? We might have to deal with other things later, but that’s for later. Before is before. Later is later. Now—we are dealing with now.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1052

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How to Not Fall Apart After Missing a Day of Your Habit

“Character is simply habit long continued.”

Plutarch

Picture this:

You’re a king when it comes to building habits. You’ve set out to do something good for yourself and you’re doing well and feeling confident. Nothing can go wrong.

But after two weeks without a single drink, you bend to peer pressure on day 15 and have a bottle of wine with a few friends.

Or after journalling every night for the last year, you unintentionally fall asleep and miss a day.

Or you’ve been running every morning for the last 30 days, but on day 31 you sprained your ankle in the back yard and can’t run for a full week and a half.

It’s bound to happen. Eventually, a day will come when you miss a day of a habit you are cultivating. Whether you are working on a daily habit, or doing a 30 habit challenge, it’s almost inevitable that something will throw us off the bandwagon. But this is okay if we plan for it. The key is not panicking and throwing the baby out with the bathwater.

Here are 3 things we can do when we mess up our habit(s):

1. Don’t Give Up

When you’re cultivating a daily habit, missing a day sucks (especially if you break a great streak), but it’s not the end of the world. Backsliding isn’t an excuse to quit. A moment of weakness is just that—a single moment. Simple errors or mistakes aren’t worth giving up something that brings us joy and we find meaning in.

2. Remember Why you Started the Habit

The goal of any good habit is ultimately the benefits it brings us in the long term, not necessarily the immediate experiences. Sure, after a couple of weeks of eating healthy, we might feel more vibrant and energized, but it’s also making us stronger and healthy over our entire lifetime. Stopping now would only be causing us issues in the future.

For me, Writing is a good example. Writing every day is a way I can challenge myself to improve and come up with new ideas. Things I’ve written a year ago might not be worth reading anymore, but each idea builds on to the next.

3. Work Our Resilience Muscles

Don’t think of missing a day as a failure, but as a way to challenge ourselves and find a way around problems. Sprain your ankle? Visualize a run instead until you’re back on your feet. Visualize like your life depends on it. Or start exercising your upper body instead. Whatever barrier you’re facing, there’s likely some clever way around/through/under it.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1042

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Doing What’s Necessary

“Take things as they are. Punch when you have to punch. Kick when you have to kick.”

Bruce Lee

Like many of us today, I’ve been having to make a lot of decisions out of necessity. Health, work, community, institutions, goals… everything is changing quickly.

In some ways, this can make you feel small like you’re compromising and giving up a little of who you are because of the realities you face. No, that isn’t precisely true. When we make decisions out of necessity, we aren’t giving ourselves away, we are holding on tightly to expectations and wants. Our expectations take hold of the reins and say “why me?”

We feel compromised because we refuse to give up our expectations of how our lives should look.

But when we let all of that go, we free ourselves up to move forward.

We aren’t suffering, we’re doing what’s necessary. We may not like it, but at least we are making moves that can lead us to better decisions.

There are three main types of decisions available to us. We can make decisions out of

  • Joy
  • Necessity
  • Or Pain

Joyful decisions are always the happiest because we’re doing them because we want to and we find them fulfilling. Accepting our dream college or dream job. Finding your partner. Building a successful business. Working on your health. Spending your money wisely. Anything that brings Joy into the world.

Necessary Decisions can be tough, but they are usually the most rewarding. This is where we take punches but get grow from the experience. They are sometimes even more rewarding that Joyful decisions because they can make us strong and capable when we lean into them and learn to be uncomfortable. Doing what’s necessary feels like a hard day’s work that fun enough feels good and gives you quality nights of sleep. Whereas Joyful decisions are not always appreciated until much later and can be easily taken for granted if we are paying close enough.

Painful decisions are the worst and should be avoided when possible. This is where hard and painful lessons live. This is where we are so stressed we aren’t pausing to think things through. So we end up making a bad decision or a decision that doesn’t align with us. It’s when we are given the choice between A and B, and forget that we don’t have to choose either because we can do C instead. Or D.

The best thing to do about a painful decision is to step away from the immediacy and intensity and find a calm(er) place to figure out how to rework the problem until it becomes a necessary decision instead.

When left with two bad decisions, come up with a better option. And if that doesn’t work choose neither. Especially if both options are trying to coerce you into something you aren’t. And if nothing works then do what’s necessary and keep an eye out for a better opportunity comes along.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1039

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