How to Plan Your Life So It Doesn’t Suck

There is a popular, insane conception that the crux of success is a good idea.  People think great art, inventions, and businesses are manifestations of a blueprint that existed in someone’s head.  That all they need is a sound plan and then they can flow from execution to their goals in a pretty little line.

This is dead wrong.

Why we plan (and why we shouldn’t)

Plans provide a sense of control.  We imagine an outcome.  Plan the steps to get there.  Then execute.  We control our destiny.

It sounds wonderful.  But truthfully, you don’t have a goddamn idea what the world will offer up. Whatever you think is coming your way–in 5 minutes or 5 years–you’re missing something.  Our imaginations are so incredibly limited and the universe is so incredibly vast.

And yet all plans depend on your ability to accurately conjure the future.  Which of course you can’t.   There is no way to plan for the chance meeting at a party or the stroke of insight in the shower.  Yet these un-plannable events regularly contribute to the success or failure of all our endeavors.

In short: Our plans are based on a version of the future THAT WILL PROBABLY NEVER EXIST IN REAL LIFE.  An alternate reality.  No matter how good your plan is, if it was made ahead of time it is based on fiction.  This is a recipe for disaster.

How to plan like a pro

We have to abandon the common notion of planning.  We have to free ourselves up to operate spontaneously.  We need to face the world as it ACTUALLY exists.  To remain open to the opportunities thrown our way.

This is called improvising

  • It is how authors write books
  • It is how improv comedians perform
  • It is how I talk to women
  • It is how companies are run
  • It is how you should live

Now I am not saying that authors never have a story line laid out or that I never know what themes I want to talk about with a girl.  Nor am I saying that predictions for the future should not inform our behavior.

We can still plan, we just have to know how to plan: so we need to stop planning minutiae and instead plan in broad strokes, develop resourcefulness, trust ourselves, and accept all outcomes.

Plan in broad strokes

Have you ever tried to give a speech by memorizing every single sentence?

You were probably stiff.  There was little interaction between you and the audience.  And if things went off track, god forbid, you probably had a hard time getting back into the swing of things.

Contrast with this with a speech you might have planned out THEMATICALLY.  You still cover all your major points.  But this time you’re more fluid.  You connect more with the audience.   And if things go off track, you are able to roll with it.  Maybe it even makes your presentation better!

Check out this Tony Robbins video for a good example:

(go to 5:23 to see til about 6:55)

The advantage of planning in broad strokes is that it lets you stay present.  You don’t have to simply execute a script in a vacuum.  You get to incorporate everything that is going on around you to make it even BETTER than you planned.

IE Did you know that Darth Vader wasn’t Luke’s father until Lucas wrote Empire Strikes Back?

Here’s some more concrete examples:

  • Improv: I don’t have a script, but I decide I’m going to come out and play a dopey character
  • Women: I don’t have a routine stack, but I want to attract her then find out what is awesome about her
  • Business: I don’t have a 6 month plan, but I know increasing exposure is my primary goal
  • Travel: I don’t have a daily itinerary, but I know a few things I want to do and then put myself out there to meet people

Have a system but operate freely within it.  Break the system at times.  After all, it is just a guide, not gospel.

Prepare resourcefulness

Drill your craft.  Get good.

In the case of the arts, this means practicing.  Take writing.  You prepare resourcefulness in writing by reading.  By writing more.  By writing dialogue and then descriptions and then action scenes.

For leaving your job, you save money, literally accumulating resources.  You brainstorm your skill sets, brush up on the ones that need work, and learn computer programming in case shit gets bad and you need work.

For improving with women, it means honing social skills.  You develop interesting conversational habits.  You adjust your body language.  You practice wisely.

An absolutely critical key to resourcefulness in all areas of life is Kickassery.  Charisma, social courage, high self-esteem, daring.  These aren’t just for meeting girls in bars.  They are tools that will open up the less obvious paths.  Like the time my buddy got into law school because he happened to chat up the dean of admissions.  Zillions of opportunities are hiding out there.  And kickassery blows the lid off them.

Trust in yourself (and in the universe)

There isn’t always a clear way out.

Authors write themselves into scenarios they don’t know how to handle . . .

Improv sketches take turns you weren’t prepared for . . .

You don’t have a 100% sure thing lined up when you quit your job . . .

You have to realize: your imagination sucks.  You cannot possibly account for all the ways a new route will have opened up because you forged onward.  You cannot conceive of all the random occurrences that will change a desperate situation into a windfall.

Trust that the universe will provide you with the raw materials you need.  Trust that you’ve practiced enough to turn those raw materials into success.


  • Authoring: Trust that your skill and the characters you’ve created will help you find a killer way to end a story
  • Improv: Trust your partner to give you a theme to work with and your practice to provide a funny response
  • Women: Trust that she wants you to do well and that your practice will provide you with the ability to convey your best self
  • Travel: Trust that there is something awesome about everywhere you go and that all you have to do is meet the right people

You’ve developed resourcefulness.  Trust yourself.  You’ll find a way.

Accept all outcomes

This is huge.  Massive.  It enables you to do anything.

You need to allow for the possibility that everything will blow up in your face.  You have to accept as a possible outcome . . .

  • that the audience will HATE your show
  • that your bank account will run out
  • that the girl in the bar will think you stupid and boring

Basically, allow for abject failure.

Most people see these outcomes as unacceptable.  If they cannot completely control for them, they won’t dare expose themselves   So they don’t quit their jobs, they don’t talk to girls, and they don’t try improv classes.

Realize this:

Life goes on.  You will be okay.

When you realize you will be okay no matter what, you no longer need to control the world.  You can loosen up and just be.  And surprise, surprise, not NEEDING things to turn out the way you want makes them so much more likely to turn out the way you want.  You know this is true from your own life.  Think of all the times your NEEDED the girl to like you and she didn’t.  Versus all the times you didn’t have to force it and she did.

Have goals.  For sure.  But you need to accept that all outcomes are possible and all outcomes are acceptable.  Nothing is off-limits.  If you can get there, you’ll have full freedom to access your uncontrolled, unconscious genius.

I don’t think the goal is Buddha.  To live without desire.  But I do think the goal is to approach that state sometimes.  To not need anything.  To forfeit control over what happens next.

I’ll put it concretely

  • when you talk to girls, to not care if she shoots you down
  • when doing improv, to not need to be interesting or funny
  • when writing, to just let shit pour out of you while you warm up
  • when travelling, to not need every minute to be filled with a “must see” monument
  • when training Muay Thai, to not need to hit the fastest or the hardest
  • when having sex, to not need to make her cum; to not need to be good at all

Relinquish control.  Forget planning every detail.  Prepare yourself, trust yourself, and develop the strength to let come what may.


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14 Responses to “How to Plan Your Life So It Doesn’t Suck”

  • I appreciate this so much bro thanks.
    I have this OCD thing that I have to plan every single detail til perfection before I execute something, and I am unable to do anything before I imagine every tiny aspect of what will happen in my mind. This post sort of freed me from that.

  • Definitely one of the best posts – not just from you, but in everything I’ve read. This is definitely a great topic to write more about since it’s so universal. As T. S Eliot said, “The moment foreseen may be unexpected when it arrives.”

  • As someone who’s just recently jumped into the personal development field professionally, I scour the online world – deciphering good from bad – and learning along the way.

    I share that to preface to give context to the following…

    (drum roll pleeeeaaaseeee)

    Your content absolutely crushes (in a hellluva good way 😉

    Keep on keepin on.

    You’re offering the world a ton of value in a space that I believe desperately needs it in this 21st century tech crazy world..


    • That’s super kind of you man! Appreciate that a ton. It’s been a while since we’ve written on the blog because of all the work we’ve been doing on YouTube, but you’re making me want to get back into it 🙂

  • Hey Charlie,

    Great post man, thanks for sharing!

    I was a little skeptical in the first few paragraphs – as someone that likes to plan and see’s the huge benefit in it – but your summary was right on the money.

    It reminded me of a quote that I tend to forget but when I hear it, it always resonates with me – “He who cares less, wins”.

    I often care too much. To the extent, I’m wondering what you’ll think of this comment. Thanks for reminding me not to give a shit what you think! 🙂

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