Learning New Tricks

“You can’t teach the old maestro a new tune.”

Jack Kerouac

It’s weird getting older. As I’m writing this, I’m 31. Which, depending on what said of the aisle you fall on will likely either sound really old or really young to you.

In some ways, I feel old. Part of that is the aches and pains I’ve accumulated over the years (for example I’ve been dealing with some chronic jaw pain this past year).

But in some ways I feel young, still working to find myself and create success and meaning in my life.

One thing I’ve learned (and will hopefully continue to keep in mind) is that there’s always a new chapter of your life after your current chapter ends. No matter where you are in life, there’s always room for change and reinvention. Not only room for it, but a necessity.

No matter where you are in life, there’s always an opportunity to reinvent yourself.

Why can’t you teach an old maestro a new tune? Because their head is too full of old tunes.

Failures accumulate. Fears accumulate. Debt, Mistakes, Memories, Habits, Patterns, Rigidness—accumulate.

Reinventing yourself requires letting go of who you were (and ultimately forgiving where applicable), or at least pieces of who you were, in order to create space for new things.

Pouring water into a glass that’s already full will just immediately spill out.

If you’ve wanted to change something about your life for a while now, perhaps a part of you—a past version of you—isn’t letting you do that.

If you want to get healthy and fit, maybe your past unhealthy self is still stuck in her old habits.

If you want to change your career, are you following the same decision patterns you did previously?

If you want to be a better writer, are you challenging yourself or just looping past ideas on repeat?

STAY BOLD, Keep Pursuing — Josh Waggoner | Daily Blog #1567

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Dosey Doe

I tried therapy for the first time the other day. It was just the initial interview or-what-have-you, so I don’t have too much to write home about. But there was one nugget of advice I took away and have been thinking about ever since.

I was talking about various things—you know, as you do—and I mentioned that I’ve been feeling overwhelmed lately and that usually is because (or correlates) with low energy days and/or not sleeping well.

And then the therapist said something along the lines of—

“Did you know that energy creates energy? Doing things you would be doing if you were energetic often leads you to actually feeling like you have high energy.”

Or put another way, energy meets you where you are.

Low energy actions will give you low energy. Just as high energy actions create high energy outputs. Exercise being the key example—exerting energy makes us energized.

The idea is to focus on doing the things that bring us more energy, instead of the things that take/drain decrease our energy.

I wonder if this idea is true for all aspects of our lives.

Does stress create more stress? Does wealth generate more wealth? Does overwhelm spawn more overwhelm?

What if all we need is to simple *do* what we need?

Instead of waiting to feel right or to feel ready, we can simply act first.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1187

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Reaching for Nostalgia

Whenever I am feeling low or unmotivated, I like many, will reach for nostalgia.

I’ll listen to my favorite songs, or full albums from the past that hit me in just the right time and place, such as Yellowcard’s Ocean Avenue album, Logic’s Under Pressure, or Back Breaker by The Showdown (I have very eclectic tastes ;).

I’ll rewatch my favorite shows and films (like Bleach, the anime series. I find Ichigo’s “never give up” resolve quite uplifting).

I’ll reread some of my favorite books, like The Kingkiller Series and The War of Art.

But I have to be watchful. Because as great as nostalgia is, it can also be a crunch for escape.

Finding relief, motivation, energy, and inspiration in our past is wonderful, but escaping to our past to avoid our future only traps us in the past and keeps us from improving our reality.

It’s like eating dessert—there’s nothing wrong with a little cheesecake now and then. But having (needing) sugar to get through the day is a sign that something is out of balance.

Are you eating some cheesecake to enjoy it or are you pounding the cake to avoid/ignore/release your pain?

Create the strength you need to get up and make a change. Be that having a heart to heart, going to therapy, reaching for things that make you help energized and inspired. But don’t lose sight of why you are doing what you are doing.

Focus on the small changes, little ice picks to the ice burg in your path. Even just a few good strikes can break a way forward.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1158

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Loving Uncertainty

Facing the unknown is uncomfortable.

No one said it would be easy to start your own business, or finish your book idea, or lose weight.

That feeling of not knowing what to do, or how to do it, or what decisions will lead to success is part of the creative process.

Going to school, smart decisions, honing our skills, and asking for wise counsel can set our course (and give us a better chance to succeed), but we’re still the ones who have to figure out how to climb the mountain(s) we are facing.

Even if we have someone guiding us all the way through, the path will be different, because the timing is different, and we’re different and our purpose is different.

This is not a lonely course, because everyone who is pursuing creative work outside the norm has to experience this.

Most people won’t choose this.

They would rather have someone else choose their path for them. Is this a bad thing? Who am I to say.

For me, it comes down to doing things that fulfill me and help others.

Does this thing I want to do light me up with joy and add a spark to my eye?

Is this person I want to be someone whom I would admire?

Am I helping others with my gifts?

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1152

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Waste of Time

I’ve been thinking a lot about what it means to live a meaningful and intentional lifestyle. The details would look different for each of us (depending on what’s important to us) but there’s gotta be some overarching principles for a meaningful life.

Let’s look at the opposite of a meaningful life—wasted time.

If our life is made up of time (our most valuable resource) then wasting our time leads us down a path of regret and unhappiness.

But what does wasted time look like?

Again, not so easily answered universally. We all value certain things over others.

Here are some questions to reflect on whether or not you are using your time wisely:

Q: Am I spending my time or investing my time?

Entertainment is incredible. But it’s also about balance. Enjoy the things you love, but not let your love of short term pleasure and experience crowd out the long term benefits of investing your time more wisely. Ask yourself, “Am I enjoying this? Am I gaining some value from this experience?”

Q: Will I care about this a month from now? How about a year? 3 years?

If not, then it’s likely a waste of valuable resources. For example, if you’re angry about something critical or hateful someone said to you, are you really going to care about it a year from now? Not really—you likely won’t even remember the mean spirited comment. Then, it’s not worth the time to dwell on it! Easier said than done, of course. But even knowing that it’s a waste of time is a helpful way to reset yourself and give yourself the space to move on from it.

Q: Is this part of my current environment’s lifestyle? Or, put more generally, is this something in my immediate control or not?

If you live in New York, then taking the subway, walking long distances, paying for a taxi or a Lyft, and/or paying top dollar for parking is a way of life. In this case, commuting isn’t a waste of time, because it’s a necessity for living in the city. That’s not easily changeable. But the upsides of living in a thriving city might be worth it for you. Otherwise, why are you there?

If so, then I should either stop stressing or regretting the cost or change my environment that aligns better with what a meaningful life looks like for me.

Q: What can I learn from this experience?

There’s always going to be moments in our lives where we cave or unintentionally waste our time. We aren’t perfect. Mistakes will be made. But failure isn’t a waste of time unless we stubbornly refuse to learn from our mistakes and misfortunes.

Wasted time is only wasted time if we refuse to learn from it.

This requires our ego to take a knee and humble itself enough to be open to change, to moving forward, to emotion, to uncomfortable conversations and hope for a better version of ourselves going forward. But if we loop our wasted time over and over again in our heads, not only are we not learning from the past, we aren’t moving forward (aka we’re wasting even more precious time.)

Am I running on default or am I living intentionally?

Default is:

  • Doing things other people tell you without regard to why.
  • Not making decisions (allow other people to make them for you.

Living intentionally is having an active say in who you want to be and how you want to live.

A meaningful life is a well-invested life.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1117

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The Zen of Dogs

Some valuable lessons can be learned from dogs. I know that’s not the most original thought, but I can’t help but think it every time I’m playing catch or just being around my dog.

The immediate observation is how present and happy they generally are. But looking beyond that, it’s not just living in the moment that’s striking, but the lack of concern or stress from the past.

My dog can go from thing to the next without loss of enthusiasm. Her favorite thing to do is play, but she’s always ready for the next thing when the next thing comes.

Sure, they bark at everything, get anxious in the car, lick their privates, and poop in public.

But there’s something special about the way dogs go about living.

She’ll chase a squirrel and not catch it, but she won’t dwell on the ”failure”, and she’s immediate back into enjoying the walk, enjoying the moment.

It reminds of the quote from Churchill, Success is the ability to go from one failure to another with no loss of enthusiasm.

Failure sucks, but dwelling on it is worse, and if we’re honest with ourselves, unhelpful. It’s better to learn from them, and then do what dogs do—move on and be enthusiastic about the next things.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1112

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The Cost of Lying to Yourself

“The first principle is that you must not fool yourself — and you are the easiest person to fool.”

Richard Feynman

The biggest lies are the ones we believe about ourselves.

Who you are and who you want to be aren’t the same.

You don’t have to fake it to be who you want to be. You need to start acting how you want to be, and slowly stretch your life towards that reality.

For example, think of how we can easily wash over or even boast about our lives and how we feel to others, yet the opposite is true.

“Oh hey! How are you?”

(Everything sucks) “I’m great, you doing well?”

“Yeah! things are good.” (I hate my job. My back is killing me.)

I don’t necessarily see this as lying to others. Technically yes, but these kinds of opposing inner thoughts and outer dialogue are more like a protective mechanism. Whether or not you think this is an example of lying to others, it is an example of how we lie to ourselves.

The cost of lying to ourselves is staying stuck—right where we don’t want to be.

We hold in pain and anger so we don’t have to explain how we got here and protect ourselves from looking stupid. But by brushing off how we feel to others—especially people who are close—we do a disservice to ourselves. We’re avoiding our problems by pretending like things are normal.

Think about, how many people have you actually confided in with your problems and goals? Does anyone actually know what you are going through?

Maybe that’s why no one seems to not care to help you. Because they don’t know.

How does that help you be the person you want to be?

We can begin removing these barriers that are holding us back in three stages:

  1. Acceptance
  2. Assessment
  3. Action


Acceptance isn’t about giving up to your situations, it’s taking a bow and respecting the good, the bad, and the fugly of your life.

Accept things as they are. Accept who you are. Accept the moment, so that you can move beyond it.


Assessment is about turning over every rock, shining a light into every dusty cobweb filled corner, and looking head-on at the things you’ve been avoiding.

Things like looking at where your money is going and how much debt you owe. And journaling about what values and principles you’ve been living by. And assessing where you’re time is going. Comb through every aspect of your current life and see how it relates to the life you want to have.

It isn’t fun, but it can often be a relief, because at least now you know and have something specific to work towards, versus a mystery blob of problems and fears.


After accepting where you are and looking at the state of things, the last step is to take immediate action.

Make a list, prioritize that list, then focus on knocking out one thing at a time.

The key is building up momentum. The more momentum we have, the easier it is to keep stepping forward.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1075

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Embrace Uncertainty

“You create your life, and you can recreate it, too. In times of economic downturn and uncertainty, it’s more important than ever to look deep inside yourself to fathom the sort of life you really want to lead and the talents and passions that can make that possible.” — Sir Ken Robinson

Pain is an interesting sensation. It hurts, obviously. Even small pains can sting—like burning your hand on a hot pan on the stove, or whacking your funny bone while closing the bathroom door. Sometimes pain lingers, and we are left to pick up the pieces while also continuing to preserve in the face of a feeling that doesn’t know when to leave. But despite the discomfort, pain also is a signal.

A sign that something needs to change. Or a moment of healing. Or a lesson and story that enables us to grow.

Not that I’d wish pain on anyone of course. Nor is all pain an “opportunity” or a good thing. Caveat caveat. But when we are personally facing pain, we have to do something with it. If not healing then what? If not a chance to change or help others change then we just what? Give up? No. It won’t be an overnight change, but gradually we will move forward, day by day until we find a way to use the pain.

One flavor of pain is uncertainty. We try to avoid uncertainty. But forcing uncertainty to be certain is like wearing a two-sizes too small sweater—half of you is still cold, you’re still stressed and uncomfortable and everyone is in on the joke but you.

2020 has been anything but certain. Personally and culturally. But if you’re reading this, you’re still alive. And if you’re still alive there are endless opportunities you can take.

Recently I was not chosen for a job opportunity. I had three rounds of solid interviews and ultimately someone else was chosen. I asked for feedback, but there wasn’t really any. There was no reason I wasn’t chosen—I just wasn’t. There was only room for one. Their intuition choose someone else. Good. I’m happy for that other person. The company is great, so I’m happy for them as well. Again, there are plenty of other opportunities out there. Now I can focus on them.

There’s very little in life that is truly certain. And many things we deem as certain, such as our career or direction in life, are only certain at a surface level. I’m not trying to be pessimistic. Once you realize that the unexpected is normal, then you have room to embrace all aspects of life and let go of the outcomes.

There’s a difference between external and internal certainty. Just because the world is shaky doesn’t mean we have to be.

Are we focused on our personal essentials? Eating clean. Moving and exercising. Surrounding ourselves with good books and good friends. Meditating. Sleeping well.

Are we making intentional decisions? Choosing work because we want to be, not because the money is good. Hanging out with friends that lift us up instead of tearing us down. Standing for our values.

Are we prioritizing what matters to us?

Part of being a creative person is turning uncertainty into something new and different.

Original ideas are built from uncertain outcomes. We can stack the decks in our favor, but it still takes a leap of boldness to pursue a dream.

Ironically embracing uncertainty makes everything certain.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1061

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Get to the Heart of It

I’ve been dealing with sleep issues for the last couple of years. I can fall asleep like the best ‘em them. But my quality of sleep hasn’t been great. Honestly, I’m still trying to figure it out. My best guess is allergies, not breathing well at night.

The reason I’m telling you this is I made a mistake. A simple mistake, but one easily made. Instead of focusing on the main issue—my quality of sleep— I tried to optimize everything else around it.

My sleep hygiene is on point. Cold room temperature, bed, blackout shades, Magnesium citrate, air filter—the works. But as nice and beneficial as those are, it doesn’t address the underlying problem. Instead of optimizing everything to death first, I should get an at-home sleep study and figure out what the real issue is so I can focus on solving it.

When you’re dealing with a problem—be it health, work, relationships— take a moment to think of the underlying issues that are bothering you.

Optimizations all the minute details won’t necessarily move the needle.

Save yourself some time and get to the heart of things, instead of tiptoeing around it.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1043

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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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