The Long Game

Daily Habits are a long game with short term benefits.

Practicing guitar once doesn’t really do you any favors. Practicing guitar 300 days in a row is a different story. Of course, the quality of those practice sessions matters a great deal. Deliberate practice is what most people (Cal Newport for example) call this nowadays. Are you being intentional about your practice, pushing yourself, increasing repetitions, and going outside of your comfort zone?

The longer you stick to your daily habit, the more benefits you will see. Let’s say you master the guitar in five years (complete guess) (plus you really ever master something completely?). In five years, you are really good at guitar. But imagine what your skills are in the years leading up to mastery.

Skill acquisition doesn’t live in isolation. It’s not off (no skill) and then on (professional). Skill is a spectrum.

You’ll be able to play and learn many songs. Maybe you’ll come up with your own songs. You’ll be able to pick up a guitar and jam with some friends.

That goes with any habit. At first, you won’t see much benefit or progress. But as you keep going, you’ll start to accumulate skill, and the more you do it, the more that skill becomes a part of your DNA. You’ll start to think through the lens of your habit(s) and come up with ideas and perspectives that you likely wouldn’t otherwise have.

That’s the true benefit of a daily habit—short term benefits compounded into medium and long term gains.

STAY BOLD, Keep Pursuing — Josh Waggoner | Daily Blog #1302

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What to do When you Get Derailed

“If you’re going through hell, keep going.”Winston Churchill

It’s really hard to get back on top of things when you get derailed.

You build up all this momentum—finally working out consistently again, or making progress on an idea, or two weeks of taking an online coding class—then something gets in the way and whoosh—you face plant.

I find it helpful to think of failing and being inconsistent with a habit (or goal) as part of the process. It reminds me of meditation. The goal isn’t to remove your thoughts, but be aware that you are thinking them, and then going back to your breath.

The goal of any habit isn’t to do it perfectly, the goal is to stick to it, no matter what. (Including messing up or missing a day.)

Actually the goal of any habit isn’t the habit at all, it’s what the habit does for us. Every habit, good or bad, creates an outcome. Journaling every day has it’s day-to-day benefits, but the true benefit is having years worth of your own thoughts and ideas you can look back on and let guide you forward.

Getting lazy (or more likely overbooked) and skipping a week of working out or practicing your code isn’t going to do you any favors, but it’s not a dead end either. Fail, get back up. Fail, try again.

The goal isn’t to be perfect, but to keep going.

STAY BOLD, Keep Pursuing,

— Josh Waggoner | Daily Blog #1215

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Failure to Launch

Isn’t it funny (ironic, tragic, silly) that often the very thing we need is the thing we won’t give ourselves permission to do. And because we won’t do it, we end up stuck in a place we don’t want to be.

We want it, but don’t think we can have it (or aren’t willing to go after it) because X, Y, Z reason.

We want to (finally) eat healthily and lose weight (or fix a health issue that’s constantly bothering us) but we never actually do it (or quit as soon as we glance at a piece of cake).

Or we have the desire to be an entrepreneur, but we sideline ourselves by convincing ourselves that we don’t know enough yet or we don’t have a good idea yet.

And because we don’t do it, we are dissatisfied and judgment to ourselves, stuck in a loop of wanting something we won’t give ourselves!


Because trying something new or going after a dream is scary and it might not work.

Because it’s easier to play it safe and not get what we want than to do something hard or that might fail.

But honestly, all we are doing is failing and mentally blocking ourselves before we even try.

Ask yourself—what am I convincing myself of that is “impossible” or that I “can’t do”?

If we’re already failures for not trying, then why not try anyway and keep trying?

What do we have to lose?

Failure is a part of learning. It’s painful and messy and uncomfortable, but it can also make us better if we allow ourselves to learn and grow from the experience.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1156

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Go Easy on Yourself

That fresh, clean feeling of the start of a New Year always makes me want to resolve to do a hundred things. Exercise more. Be a better friend. Write better stories. Stop eating sugar. Go to bed early… you get the idea.

Whether you are as intoxicated by New Year’s Resolutions like me, or just intoxicated (hey-o!!) remind yourself that you are only human.

It does us no good to self-judge ourselves when we make mistakes or miss the mark.

Go easy on yourself—

Learn to be more self-compassionate.

Good habits aren’t built in a day, they are built every day.

So if you mess up and eat a cookie, don’t quit. Start back up immediately with enthusiasm and desire to be better next time. Don’t let bad habits win.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1155

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No Pressure Habits

When it comes to sticking to daily habits, I find it helpful to not set a strict deadline on what time in the day I should do them.

Ideally, I’d write in the morning when I’m feeling fresh and caffeinated, but the ideal isn’t always in the cards.

You would think that having a precise time in the day for a habit would be good (sometimes it is) but often it can derail and undermine our efforts.

Missing a deadline we give ourselves and easily feel like failure in our minds.

When 9 AM rolls around, and yet you still haven’t gone on your 8 AM run (because of X Y Z reasons) then you’ll stress out about it all day until you go for a run (or give up and get ice cream instead).

I find it helpful to have a loose schedule of when I want to do something, but only have the hard-set rule of practicing each day. If I can’t get to writing until 11:58 PM, then so be it.

I have a morning routine and evening routine, but if something comes up and I don’t chastise myself for not doing it when I expected too.

After all, good habits and supposed to be beneficial, not cause anxiety.

Once you build up enough days under your belt, you begin to trust yourself enough that you will check off your habits.

Because once you’re committed to something, you know you’ll get it done when you need to.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1141

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

“Character is simply habit long continued.”


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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Practice What You Want To Be Good At

“If you really want to be world class – to be the best you can be – it comes down to preparation and practice.”

Robin S. Sharma

After 3+ years of writing a blog each day, I can officially say that my writing has improved. Am I the best writer in the world? Heeeeeeeell Nah. But I’m better than I was 3 years ago. I’ve also gotten better at knowing what’s good work versus bad. Reading helps, surround yourself with great prose and eventually you’ll absorb some of the magic.

What’s eye-opening is what consistent practice can give you. I have a long way to go before I can earn the title of “pretty great writer” but that’s part of the journey. Not to say that improvement is inevitable on its own. We have to work and challenge ourselves every day in order to discover mastery.

As long as we keep consistently practicing, then it’s inevitable that our skills will improve.

If something is important to you, be it a skill or something that brings you joy (like hiking or listening to music or staying connected with friends) then you need to make it into a practice. What your practice will look like is up to you. It doesn’t have to be daily. It just needs to be integrated into your life.

The same goes for things we want to change.

For example, there’s something I’ve noticed about myself that I’m not happy about—

I suck at talking about myself and articulating my ideas.

I know to get my ideas across with words on paper or a screen, but when it comes to words flopping out of my mouth, I’m a joke. Not always. But a noticeable amount. I’d like to blame it on being tired or stressed, but those are just excuses.

The reason for this is pretty obvious:

I’m not practicing speaking. I’m not practicing communicating.

We only get better at what we practice.

It’s a simple idea, but one that’s easily overlooked.

I don’t expect my golf swing to improve by working on my dance moves. Why should I expect otherwise with writing and talking?

Writing is to talking as learning the piano is to learning drums. They’re in the same category of skills, but they have their own unique sub-skills.

Writing has improved my thinking, but it hasn’t improved my articulation.

The only thing that can do that is practice.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1036

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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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Building Character

“Habits change into character.”


Have you ever strongly identified with a character in a novel or film? One that comes to mind for me is Kvothe from The Name of the Wind, written by Patrick Rothfuss.

He’s someone I admire and relate to in many ways. Kvothe is a true Renaissance (and larger than life) character. What draws me to him is his desire for knowledge in, well, everything. Creativity, engineering, finance, love, etc. He’s flawed and far from perfect, but neither am I ;).

I won’t go into much more detail (Just in case you want to pick up a copy of the book and read it) but Kvothe also frequently gets in his own way and lets negative control him.

I’ve been in my head, psyching myself out too much this past week. I’ve got some good things going, but I can’t help but feel dragged down by my (thoughtless) thoughts. I’m actively trying to avoid this. Meditation helps. Focusing on one task at a time helps. Working on fun projects helps.

But I haven’t been able to shake it yet.

Negative or discouraging thoughts are like toxins in the body. They cause all sorts of damages (and some you can’t see) and wreak havoc on your ability to change and move forward. Detox is possible, but it’s not immediate. It takes work to clean up toxic thoughts and override them with helpful ones.

Sooner or later, you realize that in life, everything is about mindset. And your mindset reflects your habits.

And all of a sudden, the person you currently are is holding back and suppress the better person you could be.

If you get into the bad habit of thinking you’re not doing enough, or you’re not good enough, eventually, you’ll start to believe it. And that believe will ripple across your life in harmful ways.

But the same can also be said about good thoughts too.

Thoughts, actions, habits, and character traits are all on the same spectrum.

Thoughts are the most malleable. They can easily be changed by internal and external events—which also means they can also be honed to work for you instead of against you.

Actions are next. They are malleable too but take effort (or sometimes whim) to see them through. Actions are powerful because they are thoughts converted into reality.

Habits are less malleable than thoughts and actions and take some time to sink in. They’re really just actions done consistently. The more consistent actions you take in something, the more likely it will become a habit.

Character is ridged but can be overridden by habits if done consistently enough.

The battle for change starts in the mind.

Negative thoughts are a part of life, but they are also in your control. There’s always going to be a scared, worrisome, sometimes crazy little version of yourself instead of your head who wants to keep your life bubble-wrapped. But that doesn’t mean you have to let them win.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #998

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Simple Habits

“Moral excellence comes about as a result of habit. We become just by doing just acts, temperate by doing temperate acts, brave by doing brave acts.”


Simple habits often make the biggest impact. They are small, misunderstood, and often overlooked things we almost dismiss as being too basic to do anything, but end up having a huge impact—good or bad. Reading a little every day, for example. Reading opens you up to new ideas and new worlds. It lets you explore not only the minds living across the world but also the minds spanning history. If you wanted, you can read the thoughts of the last great Roman emperor, A book from a reluctant businessman, and a tale of dragons all at the same time.

Journaling is another simple habit that can have a big impact if done consistently.

Often our heads are full of other people’s thoughts and ideas. We are chatting online with friends, reading other people’s thoughts in the form of books, articles, posts, captions, hearing the opinions of others around us. It’s enough to drown out your own voice and your own ideas.

A moment of solitude and a good pen and notebook will open up a whole new world of who you are. It doesn’t matter if you suck at writing. Great writing isn’t the point. The idea is to have a conversation with yourself and discover things you might be missing because you haven’t been listening. Like perhaps the low-grade anxiety you feel is because of not liking your job. You don’t know what you aren’t listening too. Your future self will also thank you for your journaling habit, because she/he will be able to see your growth over the years and what you were thinking at each stage in life.

Walking, Drinking more water, brushing your teeth, getting a full night’s sleep, gratitude practice, breathing exercises, play…

Simple habits are, well, simple, but they are far from useless.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #993

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