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 any 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 strangers
  • 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
  • Strangers: I don’t know exactly what I’ll say, but I want to find out what is awesome about them
  • 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 your charisma, it means honing social skills.  You develop interesting conversational habits.  You adjust your body language.  You practice wisely.

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
  • Strangers: Trust that they want you to be interesting and that 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 asking out someone you like, to not care if they shoot 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

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


Do you know the 4 emotions you need to make a great first impression every time?

If you create these 4 emotions in a SPECIFIC order, you are guaranteed to make an amazing first impression. Get the order wrong…and it won’t turn out so well. This explanatory video takes less than seven minutes to watch and is 100% free.

Click Here To Get The Video And Discover The 4 Emotions!

Leave A Comment

Your email address will not be published.

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

      • Feedback: I liked this because it was fresh, not a lot of people share their own ideas about how they think life should be planned… it wasn’t boring at all, and yes if you write more stuff like this, I would definitl LU still read it! Even if it’s not directly related to charisma skills it all ties in togetehr! It’s very important to accept and embrace failure of all sorts so thanks for the remineder!!

  • 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! 🙂

  • This article is brilliant. Your YouTube work is very interesting, but your written words are truly inspiring. Looking forward to more.

  • Thank you for your posts Charlie. The life of a 20 something with a strong sense of ambition can be confusing, challenging, and sometimes down right chaotic. Between your channel and news letters, you’ve inspired me to keep trudging along (and to do so without major expectation). You are truly a god send Charlie, thank you for everything!

  • This is a great article! It reminds me how in one of your videos, you told people to take advice from those you admire. With your honesty and insight, you’re definitely someone that I listen to for advice on a daily basis! And what you described in this post is a lot like a lot of ancient practices like Buddhism (as mentioned) or stoicism even. The idea always seems to show up among the brightest in history. ?

  • This is great shit man. Improv is so good for you. It allows for expression of the true self rather than just the planned/rational self. The greatest fact is that it gets easier and brings you even closer to yourself and others.

  • Hi Charlie! Thank you so much for the post! I am control freak and want to quit this `habit` ) Your post is so inspirational and cogent! All respect!

  • Hi Charlie,

    Thanks for this post. I think it will help a lot of people (including me) but I have sone concerns.

    “learn computer programming in case shit gets bad and you need work.” doesn’t work like that, does it?

    And I don’t understand why not putting the last video in this page instead of making a sales pitch and putting a gigantic button. I guess it is related to page views but then you can put the video as an ordinary hyperlink, can’t you? It looks fishy in this way.


  • Hehe this is true and somehow even my religioun is teaching this. Though they teach to hand everything you’re worying about over to god. He always will give you anything realy necesarry. And he will give you a fulfilling task when he decides to. So you always will be happy, whatever you end up with. because it’s never bad and you werent even tryharding. The last trip with friends that I took was planed at a minimum. We knew where we were going to sleep and which city we were going. But realy, it was the best trip i ever made even thought we hadn’t got any idea of what we wanted to watch there specificly. We just got on a boat spontainiously and had a great hour, sat down in a random pub and had some great hours(The barkeeper was a realy nice guy) and so on. So I am living this plan less, experience more livestyle to it’s fullest lately. It’s the best thing you can do, especialy if you still see some purpouse in it (Given by religion in my case). The next thing that just happens to be is the blog I am currently creating with a friend of mine about art and photography ( but the url is going to change soon) All in all, great article! Thanks!

  • Hey Charlie! Great post. I was wondering if you heard about the GTD system and if so: what do you think about it?
    I personally started using it recently and I feel it gives me that balance between organization and planning, and more diffuse and creative, being-in-the-present, thinking moments.

  • I enjoyed your article very much Charlie and would definitely want to see more like it. It’s very difficult for me to let go of planning because of my fear of failure and judgement but I’ll keep trying! Thank you for sharing your thoughts.

  • Agree with all the positive feedback– this was both helpful & highly relevant (at least for my present circumstances). Esp. the parts about being open to all possible outcomes and plans, even hopes or say, expectations totally being swapped with the unexpected. Encouraging! Thanks!

  • I loved your post and would love to see more on this topic because I would like to understand more fully your ideology.

    How would this apply to a professional musician?
    I can see how it applies to those scenarios you mentioned but as a professional musician the goal of perfection and the planning of every detail is what makes the beauty come out in the music.

    Or is your article less on the practicing of one’s performance and more related to the actual performance day?
    Or should it not be applied to musicians in the same way as to ordinary life?

  • Hi Charlie, This is a great article. Even though it’s not long a few great reminders and new things to think about.

    I’d like to give a little constructive input. I think Buddha / Buddhism is quite misunderstood (Even in India, even by some Guru’s etc.). I learnt from teachers like BKS Iyenger (Light on Life / Light on Yoga) and of course the Dalai Lama that:

    the point of practising buddhism / yoga / meditation etc. is not to avoid desire or avoid enjoying things.

    But rather it’s simply to cultivate mental awareness of the present and everything that is going on with our body and mind so that when we 1) enjoy things or 2) feel pain or whatever we know what is happening.

    So for example when we get hurt, rather than getting lost in the hurt we can step back and see it for what it is..

    And likewise if we get a shiny new car, we can enjoy it but we are not stuck in the cycle of always getting the next thing / experience to feel good..

    Not a criticism on your post, but I think the true teaching of buddha is very close to your own ideology / thinking.

    It’s more like live in the moment, be self aware, enjoy life, don’t get caught up in too much thinking! 🙂

  • Charlie, you’re amazing! Every single time I read one of your articles, I have the impression that your tips are exactly what I need at that moment.
    Thanks a lot and wish me luck that I can put your ideas into action 😉

  • Wow I think this text helped me a lot! I have a good feeling when I read that not everything has to turn out as I have planned it. This thought makes everything a lot easier! Thank you 🙂