Make Your Own Mistakes

“Often any decision, even the wrong decision, is better than no decision.”

Ben Horowitz

The worst decisions you can make are from a place of non-decision. A non-decision is a self-thoughtlessness one. Meaning, without consideration of why you are saying yes (or no) to something.

This comes from a place of not knowing what you want, and/or not taking the time to ask yourself what you want.

By not knowing what you want, big life decisions are made for you by the people in your environment.

In some regard, this can be a good thing. If you are surrounded by wise and thoughtful people, then they’ll want the best for you, and their influence will reflect that.

But what someone else thinks is the best for you and what you think is the best for you isn’t always the same thing.

Plenty of people have gone down the path of being a doctor or lawyer, not out of passion, but because that’s what their parents told them to do and that doing so would make them successful and happy.

But success and happiness aren’t always the same thing.

Sometimes what others deem as successful actually creates unhappiness.

Take the opinions of people whom you admire and respect into advisement, but make your own decision based on your own dreams and passions.

Even if you’re not sure what you want yet, it’s better to make a mistake by your own hands, than regret a choice by defaulting to someone else’s decision.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1084 ☕️

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Decisions of Fear

“Quick decisions are unsafe decisions.”


What emotion are your decisions coming from?

Are you making decisions from joy or fear?

We mean well when we are making decisions out of emotions like desire or fear. We naturally (usually) want the best for ourselves. But if we listen to the wrong emotions we can end up making dumb mistakes. Buying something you can’t afford, for example.

If my finances suck, buying a Tesla would bring me great joy, but this is a “desire” decision, not a “joy” decision. That joy would quickly turn into dread once the bill comes due.

Decisions of fear come from the place of feeling like you “have to do something.” We pin ourselves against a wall, thinking its the only way.

“I have to stay up late and study otherwise, I’ll fail the test.” But what if you don’t? What if there was a way to prioritize sleep AND study enough to get could grades?

“I have to get an MBA before I start my own company / I have to learn X Y Z before I start my own company.” But what if you just started instead and surrounded yourself with people smarter than you?

“I’m old, I have to retire.” Do you?

It doesn’t help that may people are actively pushing us to make decisions out of fear (some people we know, others we don’t). Whenever you hear yourself say “I have to because X” pay attention. There’s always another option out there.

Our decisions make our life.

Before making any decision, make sure you’re coming from the right emotional headspace. Whenever you find yourself in a headspace of fear, failure, negativity, stress, etc., then don’t make a call right away, get into a better mindset first or even sleep on it if can.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1077

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Today’s the Day

“Yesterday is gone. Tomorrow has not yet come. We have only today. Let us begin.”
Mother Teresa

Freedom is one of those invisible things you can easily take for granted until you experience the opposite. Seeing the persecution of others who live outside of a free society, for example. Or personally feeling the restrictions of debt or the anxiety of saying yes to too many things,

I don’t normally consider decisions as freedom, but they are. We are free to choose what we say yes or no to. Responsibilities, obligations, desires, dreams, persuasion, and incentive sway us one way or another. But at the end of the day, our decisions are our own.

The frightening thing about decisions is we can’t take them back—good or bad.

Most of the time, anyway.

A few years ago I was helping a friend decide between taking a job opportunity in town or taking a job in a different city. Both options were equally solid. Both were something worth doing. And my friend wasn’t sure what to do.

While we were discussing the options with the other people around us, a thought occurred to me that ultimately helped him make a decision:

Which decision was less permanent? What’s a way you choose option B if you decide not to enjoy option A?

In my friend’s case, the job out of town was actually an open invitation. Meaning, he could test out the job in town and if he found it not a good fit, he could call up the other one instead. So he took the job in town.

Was it the right call?

Impossible to say.

Even when we strategize and lessen the risk, we can still end up making the wrong call sometime.

“Wrong” applies to our failures, but failures often become turning points and opportunities to be better. Unless we let our mistakes drown us and keep us living in the past.

Failure is only a moment. And even when dealing with the fallout of failure, we still can find a way forward. But first, we have to start looking forward. Otherwise, we are enslaved to our past.

What are you willing to give up in order to be free?

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1073

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Regret-free Decisions

Plenty of folks would look at my plate (interests/projects/dreams) and say that I say yes to too many things.

I’ve always been someone who has been interested in many subjects. Art, music, sports, exercise, technology, learning, etc. I also occasionally feel slightly envious of the people who can stick in one lane for most of their lives (for example, just graphic design). But I enjoy too many things to be that kind of person.

But you can’t do everything (at least not all at once 😜). So there’s always a matter of which pursuits to spend your time on.

I try to say yes to as much as I can tolerate without sacrificing health or quality. And if I walk outside of that tolerance range I rebalance.

Right now I’m less concerned about quantity and more about quality. Meaning, how can I say yes more to the right things (and no to the wrong things) instead of saying yes to things that don’t matter?

Ultimately what we decide is worth our time comes down to each of us. A question I ask myself is what I’ve found helpful is “would I regret not doing this in a year (or five years) from now?” Or said the opposite way, “would I regret saying yes to this after a year has passed?”

Pay attention to where you’re answers are coming from. Make sure they are coming from the heart and not from your wallet or from someone else’s mouth. Not that there is anything wrong with making money or following the path of another great leader—quite the contrary. And yet still. When it comes to making important decisions, make sure you know why or why not you’re saying yes.

Think of a decision like it’s not yours but a close friend making them. What would you advise them? Would you give them the same advice that you are giving yourself?

Consider all sides. And at the end of the day, if it turned out to be a bad call, then learn from it. Mistakes are scars earned. They can be something we try to hide and ignore, or something we learn from and wear like a badge that tells a story for others.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #1050

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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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True Yes

“Saying no frees you up to say yes when it matters most.”

Adam Grant

It’s not that loose threads are inherently bad or good—like many things it depends on the context. On the road to success, there will be many opportunities we could say yes or no too.

The problem is, most opportunities look pretty great! How the heck do you know what’s a good opportunity versus a bad opportunity?

Simple (..but far from easy): compare the opportunity to yourself—who you are, what you value, and what kind of life you want to have.

The question is whether it’s leading you towards or against what you’re looking for.

Is this opportunity and/or obligation distracting me from what I actually want to do?

If someone is dangling money or fame In front of you, but it doesn’t align with who you want to be, will you take it or turn it down? Tough call. Knowing what you want, no—discovering what you want through experience and practice will make tough decisions much easier.

Is this yes a true yes or more like an easy/fun distraction?

Of course, in order to answer questions like these, you have to know who you are. And, equally important, you have to learn to act on self-interest. Self-interest isn’t selfish. You can be caring and compassionate about others AND have an opinion and say what you want your life to look like.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #980

Recommended Reads:

Hell Yeah or No

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Test What You Think You Can’t Do

“Because your own strength is unequal to the task, do not assume that it is beyond the powers of man; but if anything is within the powers and province of man, believe that it is within your own compass also.”

Marcus Aurelius

“Most of our assumptions have outlived their uselessness.”

Marshall McLuhan

I’ve never had a good experience by making a decision based on an assumption. Assumptions are guesses, backed only by our own wish for how things should be. 

Assumptions are lazy decisions, or better yet, non-decisions. They are subtle and get us into more trouble than in many ways:

“I assumed you emailed them already.”

“Oh, I assumed you would go to the store to pick up what we needed.”

“I assumed you wouldn’t mind / I assumed you wouldn’t care. /I assumed you already knew.”

And it’s not just assumptions we have about others but assumptions we have about ourselves:

“I’m not confident enough to ask her/him out on a date.”

“I’m too old to learn a new language.”

“I’m too poor to start my own company.”

“I’m not smart enough / talented enough / pretty enough / brave enough … etc.”

But just because we assume something, doesn’t make it the truth. In fact, it’s likely the opposite that’s true.

If you think you can’t do something, there’s only one way to find out for sure —

Test it. 

Experiment. Give it the proper time to make sure. Spend a weekend testing one assumption. Go for a full week. Try a month. Make sure. Because otherwise, you are living your life by jumping from one guess to the next.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #915

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Never Second-Guess Yourself

“All my big mistakes are when I try to second-guess or please an audience. My work is always stronger when I get very selfish about it.”

David Bowie

How do you know if you are making a decision for the right reason?

Intuition? It’s almost always the best decision to go with in the moment. (That’s easier said than done of course.) Think of it like a hunch that’s backed by experience—who we are, our values, our culture, our beliefs, our sense of what’s right and wrong, and our likes and dislikes, all rolled up into one “feeling”.

We usually know when we’ve made a bad decision (and certainly know afterward).

“I knew I should have said no to the project, but the money was too good to pass up…”

“I thought he was the one, but my gut was telling me otherwise…”

“I knew college wasn’t right for me, but my family convinced me otherwise.”

Intuition is something that we know is true (personal truth), and yet somehow second-guess and let fear, worry, and vices drive us to ignore it. But intuition isn’t perfect.

In the fascinating book, The Body Keeps the Score, Bessel van der Kolk M.D. explains how our intuition is normally great, but when we experience trauma, we can shut ourselves off from reality: “Our gut feelings signal what is safe, life-sustaining, or threatening, even if we cannot quite explain why we feel a particular way. Our sensory interiority continuously sends us subtle messages about the needs of our organism. Gut feelings also help us to evaluate what is going on around us. They warn us that the guy who is approaching feels creepy, but they also convey that a room with western exposure surrounded by daylilies makes us feel serene. If you have a comfortable connection with your inner sensations—if you can trust them to give you accurate information—you will feel in charge of your body, your feelings, and your self. However, traumatized people chronically feel unsafe inside their bodies: The past is alive in the form of gnawing interior discomfort. Their bodies are constantly bombarded by visceral warning signs, and, in an attempt to control these processes, they often become experts at ignoring their gut feelings and in numbing awareness of what is played out inside. They learn to hide from their selves.”

Bad decisions are hard to recover from. Intuition is our first line of defense for blocking bad decisions and making smart ones. But we need to stack it with second and third defenses.

First, we must never second-guess ourselves. Second, we verify. 

We must surround ourselves with people who have our back and want to see us succeed. The majority of my past mistakes could have likely been avoided if I had someone advising my decision and ideas, telling me “Hey, that’s probably not a great idea, here’s why…”. Perhaps that’s wishful thinking on my part. Perhaps my past self wouldn’t have listened. But that’s why it’s massively important to have a group of “life advisors” (I picked this phrase up from my conversation with Alex Lavidge on The Renaissance Life Podcast) who can help guide you in the right direction.

The third defense is self-examination. Periodically take stock of your life as if it wasn’t your own. If your sister or friend were going through the problem(s) you are facing, what advice would you give to them? When we are dealing with something—like lack of motivation or health problems— it’s hard to come up with solutions because we are so close to the issue (Plus the stress it’s causing us.) When we take ourselves out of the equation it’s much easier to come up with ideas for our problems. 

Have the courage to believe in yourself. But be intentional.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #911

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Practicing Character

“Character is doing the right thing when nobody’s looking. There are too many people who think that the only thing that’s right is to get by, and the only thing that’s wrong is to get caught.”

J. C. Watts

When you do something nice for others, like donating money to medical causes or treating the checkout clerk like a human being, you’re doing it out of kindness, but you are also doing it for yourself. And I don’t mean selfishly. Rather, our actions are a byproduct of our character. And the same is true said in reverse— our character is spoken through our actions.

Character and action are two way streets. What you do is a reflection of who you are. Not just what you do for a living (although that’s a piece of it) but everything you do (or don’t do).

Which means every decision is an opportunity to practice building our character.

Patience, generosity, sincerity, persistence, optimism, ambition, courage, charm, humility, encouragement— these are all things we can practice in our daily lives.

If we don’t practice them, how else would we except to get good at them? Magic beans?

One simple practice I like to do is whenever I’m leaving the grocery store, I take my cart back to the store’s entrance. It’s so tempting to unload your groceries in your car, and they peel out of the parking lot, leaving your buggy next to where you parked. What the big deal anyway? I don’t have time to bring it back. It’s someones job to gather up all the loose carts anyway. Why should I do their job for them?

Because you are doing it for youself as much as you are doing it for them.

Everything we do not only sends a message about who we are to those around us, but also ourselves.

By leaving your empty cart where you parked and driving away, you are telling yourself that you are lazy. Alternatvely, by taking the cart back to the store’s queue, you are telling yourself you are hard-working and not to mention caring to boot.

The same is true for anything we do. Holding the door for others. Not letting our angry control us when someone cuts us off or someone loses their temper. Cleaning up after ourselves. Following through with a promise or conversation. Staying true to what we value.

It’s like the old saying goes, “How we do anything is how we do everything.” Especially when no one’s around to keep us accountable.

That’s why I adopted a “Do it Now” mentality. Not everything has the same amount of importance and priority, but taking care of things when they need taken care of is a great way to practice character. If there’s a pile of dirty dishes in the sink, I’m going to clean them now, instead of later. Even if that means I have to unload the clean dishes from the dishwasher first before I can put the dirty ones in. If there’s a thing around the house that needs to be taken care of, I jump on it. If I’m in the middle of something, I’ll focus all my efforts on that one thing, before I jump to the next.

These are tiny things, but they make all the difference.

Because your actions are telling yourself that “I’m the type of person that get’s things done.” This isn’t a blame game. Just because someone else isn’t doing it doesn’t mean I get to point a finger at them for being lazy. Because if I did I would only be practicing characteristics I don’t want to be.

I’m far from perfect, of course. Some days I can barely manage to do my nightly routine and don’t have the energy to clean up the house or put away my fresh laundry. So then I double down the next day. But if I do manage to put away my clothes when I don’t feel like it, I know I’m working my character mental muscles and showing myself what I’m made of.

Remember, It matters less what you’ve done and more what you do.

If you want to be strong, practice strength. If you want to be resilient, learn everything you can about how to persevere in chaos and get back up when you fail.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #902

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Yes Yes Yes No No No

When is an idea or decision worth saying yes to? I can think of 6 ways a decision can go:

1. Yes—I would love to do this.

For the majority of the time, these are the easiest decisions to say yes to. These are the decision’s we should say yes too, but there are quite a few situations that often make saying yes to what we love extremely difficult.

The first reason is bad timing, luck or lack of self-awareness — which I’ll discuss as #4.
The second reason being fear—which I’ll discuss as #5.

2. Yes — but you want to say no.

There are our most innocent and humbling decisions. Whether out of love, force, pity or magic, we agree, but would rather say no. As innocent as they appear, these types of decisions can quickly take over our entire lives. This the number one regret of the dying, “I wish I’d had the courage to live a life true to myself, not the life others expected of me.” It’s great to help others, but if you are only living your life by the expectations of what others want for you, you aren’t making decisions for yourself or living at all.

Sometimes we say yes, but don’t know we should have said no. This is tricky because now we’ve said yes and are beholden to that choice. If there’s an opportunity to get out of it, do it. There’s no sense wasting our time on something we clearly don’t want to do. But if you’ve backed a yes with your word and reputation, see it through. We never want to waste our time, but we also want to make sure our actions also align with our words.

There’s a version of this type of yes that I’ve personally experienced. (Well, I’ve experience all 6 of these types of decisions, but this one was a real doozie.) Sometimes when you say yes, but you don’t want to (or you eventually figure out you don’t) AND then you keep doing it anyway—out of fear or obligation etc.—then you are on a short unfortunate path to burnout. There are many flavors of burnout, but one of the surest ways to burn yourself out is to continuously do something you don’t want to do.

Eventually you hit a wall and you’re body forces you to stop. That’s what happened to me anyway. My body’s response was—“Oh, I see. You’re going to keep working at this even though you know we don’t want to? The Nerve of this guy. He think’s he’s the boss. We’ll show him whose the real boss around hear.” Don’t let yourself be steamrolled by a decision you don’t even like doing.

3. Yes — but your future self won’t.

These’s are also painful decisions, usually based around an event, agreement or project in the future. It sounds so lovely (and distant), but when the moment arrives you completely dread it to your core. Ugh! Why did I agree to this?!

The key is asking yourself what your future self would want to do. “If this thing (that I’m about to agree to) was tomorrow, would I still want to do it?

It’s great to plan for the future, but keep decision locked in the immediate.

4. No — but you want to say yes.

In essence, you wish you could say yes, but the timing isn’t right or you’ve already committed and said yes to another earlier opportunity. Decisions like these aren’t worth your time dwelling over. Stick with what’s in front of you, and keep learning about yourself and your dreams. The better we know ourselves, the more accurate we can be in our decision making.

5. No — not right now.

This is a slight variation of the last decision (#4) and again comes down to timing. There’s only so many things we can say yes too. There’s only so much time to go around. If the timing isn’t right, it’s better to say No—not right now. And try to revisit it later.

For me, there’s a million-billion things I want to learn and experiment on, but if I tried doing them all at the same time, I’d make no progress on anything (and likely go insane). This idea is often called your “not right now list”. A list of things you want to do or see, but right now you are prioritizing other things instead.

6. No — I’d rather get dirt.

Knowing when to say no might be the hardest decision of them all. But saying no is also the most exhilarating and uplifting decisions we can make. It’s easy to say yes. It’s easy to say yes to things we want to do AND don’t want to do. But it takes training and discipline to say no.

No free’s up our time.

No gives us room to think, dream and play.

No opens up more opportunities.

In a backwards, up is down, left is right sort of way, by pursuing less, we end up gaining more.

STAY BOLD, Keep Pursuing,
— Josh Waggoner | Daily Blog #875

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No “yes.” Either “HELL YEAH!” or “no.” | Derek Sivers

8 Ways to Say No Without Hurting Your Image | Adam Grant