This post accompanies my most recent youtube post:

I’ve started posting video stories. This is my second of hopefully many. They’re not short, and they really go deep. If you haven’t seen the first one, click here. They’re a bit of fun, a bit of freestyle thinking out loud, and they’re longer-form than anything I’ve ever made. 20ish minutes. This is partly because I don’t want to tempt busy people to watch them, and partly because I really like the kind of story I have the chance to tell with 20 full minutes. I’m having a blast making them.

That said, this one specifically talks about ideas like having fun with the things you do professionally. It’s idealistic. It makes a lot of big claims. If you know me well, you know I have moments like this pretty regularly.

I realize it’s super easy to lose people talking like that. The thing that frustrates me most about experts, successful people, rich people, politicians, and even some hippies is that they often talk completely past the issues that they care most about, or worse they just sound like lunatics. I realize that as I work on unusual projects (which we’ll cover in future videos – subscribe to my YouTube channel if you haven’t yet) I’m likely to start sounding less and less relatable. I want to combat any incoherence, idealism, or oversimplification in my video monologues with posts like this, where I cut out the usual entrepreneurial spin. In this post I’ll try to tell my story like you would see it as an objective onlooker into my life.

I also just wanted to write a post to accompany this video because it might lose people or will simply be too long for some to watch.

The video and this blog post each work on their own, so you won’t hear me repeat myself. These are two different messages, but they compliment each other well. Enough preface. On with it.

Failing Sucks

What do I mean by failing? The grim reality of not meeting your own goals. The always-looming feeling that things you set your mind to never quite work out like you had first imagined. Etc. So on.

Failing sucks because when we set goals, we expect to achieve them. Unfortunately, we’re rarely right about what it will take to achieve our goals on the first try.

I ran into an interesting quote recently (from a book called How Will You Measure Your Life) that I think applies very well:

93% of all companies that ultimately become successful had to abandon their original strategy—because the original plan proved not to be viable. In other words, successful companies don’t succeed because they have the right strategy at the beginning; but rather, because they have money left over after the original strategy fails, so that they can pivot and try another approach.

What I’m trying to highlight is that everyone fails to meet their goals. If 9 out of 10 companies fail initially and have to start over, so will you. So how do you turn the fact that you will fail into a strategic advantage? That’s what I want to explore in this post.

First, I’d like to talk about my own goals, but to do that I have to introduce you to a new term.

Most people find out that the goals they set aren’t even worth reaching once they get part way there. I call goals that turn out to be ultimately pointless or uninteresting “stupid goals.”

I set stupid goals. I’m the champion of stupid goals. The king and reigning emperor.

Stupid Goals

Remember that Project 365 I started 2 days into the new year of 2015? Still stuck in February, it’s November as I write this.

My plan to post on this blog weekly and huffpost monthly? Down the drain.

How about making my book a “national curriculum.” I ran around saying that for an entire year and it’s absolutely never going to happen. What does that even mean?

Heck, at one point I decided that buying a Lamborghini by the time I was 20 was a brilliant goal, and I still couldn’t buy a ford if I wanted to. I’m 23.

Hold that inner smirk you’ve just developed. We’ll come back to that.

See, that’s not even the tip of the iceberg when it comes to my stupid, unrealistic, unachieved goals.

But my goals aren’t the reason I’m writing this.

I’m writing this for you.

Staying Motivated

I know so many wonderful, beautiful people who care about making the world better for the people around them.

And I see them heartbroken when it doesn’t work the first time. Or when they forgot to get started.

Or when they’ve been putting it off. Or when they don’t know where to start.

I’ve seen friends grow tired of trying and failing. They opt for the easy route. They start only trying things they know they can succeed at. They end up changing course, second guessing themselves, and throwing themselves into mental and physical illness. Bedridden and depressed.

And I’ve done the very same thing to myself. I still wake up depressed some days, feeling like my work and my contributions are useless.

But I have an unfair advantage: I got a head start at pursuing my own goals independently, so I’ve had time to practice managing the emotional turmoil of entrepreneurship, or really any independent venture.

I’ve been picking myself up out of that slump on a regular basis for about 5 years now. And I have friends and family that are far better to me than I deserve.

But I know a ton of people who don’t have the tools, skills, practice, or support to pull of that turn-around. So I see them keep sabotaging themselves and wishing something would change.

I can’t fix everything, but I hope this post helps.

So, back to goals.

The No Spin Zone

I know more want-to-be entrepreneurs than any other class of people. And I don’t mean this in a derogatory sense at all.

I myself am one. I want to change the world for the better, and I haven’t succeeded at hardly any of my goals yet.

Some people don’t even know what their goals are! And that’s okay. (That’s a link to my purpose post, but you might also like reading this post called “finding your calling” about why it’s okay to not find you calling.)

To make matters worse, I personally have gotten really good at hiding my failures and talking about my successes. I focus only on the bits and pieces of progress I find along the way.

I noticed people of all kinds tend to hide their failures and talk up their successes, so I started doing it myself. I don’t like it.

I’m worried that’s hurting the people around me. So I talked briefly above about how ridiculous my goals can get to give you a sense of just how dramatically I can fail, and do so regularly.

Telling Your Story

By telling detailing just a few of my failures, I’m making different use the single most important tool in life’s journey: the tool of re-crafting my own narrative. Telling my own story differently.

See, you get to decide what your failures are about, and what your successes mean.

I think being brutally honest might be less impressive, but more helpful for the people I care about. Most entrepreneurs get so carried away telling the story of their success that it starts to lose relevance. They start to sound out of touch. They lose sight of what actually caused their success, and start to imagine that they can take all the credit for their own blessings.

So yes, I’ve learned to think of my failures as opportunities and talk about them as lessons learned. This way I preserve my own illusion of dignity, and I get to make up a compelling heroes journey along the way. Many people learn to put the narrative fallacy to work for their own purposes.

So far, I have gotten to learn something meaningful from each failure and weave that into my story without ever talking about my failures directly. But the narrative fallacy can cause you to lose touch with the world around you, and that’s something I want to be wary of.

I’m concerned that as more and more people become aware of my business-building (or business-breaking, as it may turn out) journey, the lack of discussion about failures along the way will set up unrealistic expectations.

I want my entrepreneurial friends to feel encouraged and inspired by my hustle, but I don’t want them to expect anything they try to work on try #1.

Nothing big should work on the first try, because often you’re aiming at the wrong goal to begin with!

But that’s okay because you can make your own version of the story along the way.

The Value Of Big Goals

Things might work out on your first try, but if they do it wouldn’t be as rewarding. The real reason to get into the game of changing the world (as I mentioned briefly in the video) is because it’s a game. You want to play it because it’s FUN, and winning is awesome, just like any other game.

If you can’t see life as a game, setting big goals isn’t going to be very fun.

Furthermore, if you don’t set stupid goals, you’re going to set boring goals. It’s not a very fun game if you have boring objectives.

Which brings us to an interesting discovery.

Boring or Stupid

Boring or stupid: As far as I can tell those are the only two options.

So no one is going to follow through on boring goals because they’re not fun. They don’t spark your imagination. They don’t make you dream. Which leaves …stupid goals.

See, stupid goals only look stupid if they don’t work out. If your crazy goals do work out they call you a visionary.

Need an example? Think about MLK without an audience, Steve Jobs without Apple, or any presidential hopeful. Crazy people with lofty, unrealistic goals by all counts.

But that’s why their goals mattered. On the off chance that you make your dreams a reality, you can actually change the world. Because if that’s what they you out to do, you don’t care if you look a little (or a lot) silly along the way.

Of course, for every visionary there are a lot of people that just seem crazy. But you don’t get to decide which one of those you get to be, you only get to keep trying.

And that’s what I’m trying to do. So I apologize if I sound crazy along the way, but I’d really like you to join me. It’s a blast.

Keep At It

So what do you do with this?

Stop trying boring things. Stop applying for jobs you know you can get. Aim higher. Stop paying money to get a degree if you wouldn’t be willing to show up to class if it were free. Be honest with yourself.

Then go where you don’t belong and start asking questions. Get uncomfortable. Make moves. Stop complaining.

Actually just giving up complaining and asking one question in a place you don’t belong every day will change your life in a week. For example, ask for a tour of a company you’ve always been curious about! (I toured Space X twice recently with seven different friends thanks to an old friends’ sibling who was a very generous Space X intern!)

Do it. Try it. See what happens. The worst that can happen is you end up right back where you are now. There are no repercussions to asking questions. I’ve talked face to face with billionaires, I’ve shadowed university chancellors, and I’ve failed a lot. I’ve embarrassed myself a few times. But never have those experience caused anything but a spike in my own anxiety. No one has ever said “stop” or “no” or “you shouldn’t be here” – and sure some of that is privilege, but much of it is just showing up. So I can’t encourage you enough to find ways to show up wherever you think you might want to be.

Why? Because you live just about the best life of anyone on the planet. You ARE the 1%. (Your family only needs to make around $34k a year to be in the global 1%) You can read, you have internet access, a place to live, you’ve probably even eaten today. I know you know that, but every time we complain or we take our lives for granted we’re forgetting how much of an undeserved privilege that is. So maybe we’re obligated to do something worthwhile with this opportunity we have at life. Do something inspiring, sure, but make sure it’s fun, so that failing is worth it. Because you’re gonna fail over and over and over just like the greats, and it’s gonna be awesome.

If you don’t know where to start, check out my purpose post. Or if you haven’t already, watch this: