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How to find the courage to execute on big bold plans

In my latest blog post, I argued that most entrepreneurs are optimizing for productivity when they should be optimizing for courage.

It turns out that how you spend your time – hour to hour – does not determine your success. The only thing that matters is how willing you are to act courageously on extraordinary, BIG ideas.

Bill Gates isn’t worth 80 billion because he’s 800,000 times more productive than you – but he did have an extraordinary vision for the future and the courage to execute on it.

So how DO we optimize for courage? What mental weights can we lift to build the muscles that help us pursue risky, hugely rewarding opportunities?

This article will show you five strategies to do exactly that… 

1. Share an opinion of yours that most people don’t agree with

It’s become trendy for everyone to have a blog. People stay stuff like “It’s never too early to start building your personal brand”.

Being a thought leader definitely makes entrepreneurship easier, but there’s another – subtle, but no less powerful – benefit to building your platform and finding your voice: It gives you an opportunity to tell the world how you see things differently.

What do you believe in that no one else does?

The above is Peter Thiel’s favorite question to ask budding entrepreneurs, and it requires ENORMOUS courage to answer publicly.

While a lot of bloggers are publishing inane list-posts, guides to social media and other noise, you can build your courage muscle by bravely publishing your most unconventional thoughts, beliefs and opinions.

You’ll get bolder by default while also learning first hand that anytime someone violently disagrees with you, someone else vehemently agrees.

2. Eliminate the enemies of Courage

One way we can build our courage is by removing the obstacles to it flourishing. Neuroscience has confirmed a link between Anxiety (the antithesis of Courage), stress and depression. By focusing on eliminating the latter two, we can remove anxiety from our lives and significantly increase our capacity for courageous action as entrepreneurs.

The best way to do it is to ritualize both exercise and meditation into our every day life. My most risk tolerate and successful clients – those two aren’t conflated by accident – all have some form of the above as a part of their routine.

The human nervous system can’t keep up with the fast paced decisiveness (in the face of relentless uncertainty) that entrepreneurship demands of us… without a regular neurological flushing of the happy chemicals brought on by intense exercise.

Likewise, it gets hard for us to see the best, courageous path forward when we’re manic and stressed. Finding the mental space to see the truth, though some form of mindfulness, is a game changer.

3. Go Social Skydiving to grow your own thick skin

“Social Skydiving” is my new favorite concept. I believe it was originally pioneered by the geeks-trying-to-learn-how-to-talk-to-girls crowd, but we shouldn’t let that stop us appreciating a brilliant idea.

At it’s core, Social Skydiving is the act of leaping into social situations where you HAVE to interact with others in uncomfortable, but ultimately fulfilling ways.

The classic example is to simply introduce yourself to a group of people at a bar. Do so and you’ve leapt from the plane and now have to build your own parachute. What do you say next? How do you navigate the corner you’ve just painted yourself into? How do you keep this bold thing going without coming across as a total weirdo?

If that sounds like the most horrifying thing you’ve ever heard of, then you’re getting it.

Social Skydiving forces you to confront the part of your brain that is TERRIFIED of being rejected or ostracized from the tribe. It’s jumping into your fear of strangers and forcing yourself through it, to the joy of spontaneous social interaction on the other side.

Though you can’t imagine it, after the initial failures and inevitable learning curve… winning at social skydiving actually starts to feel phenomenally rewarding. If that isn’t a metaphor for entrepreneurship, I don’t know what is.

4. Find Courage buddies

Your income is supposed to be the average of the five people you spend the most time with. Your ability to do courageous things in business is the same.

This is perhaps the most important distinction in this article: When you’re assembling an entrepreneurial mastermind, dinner party or coffee date it’s worth re-evaluating who you really want to spend time networking with.

The intuitive approach is to simply aim to connect with as successful person as you possibly can. This can have mixed results – especially when you’re starting out – because people who appear successful won’t always be the courageous ones. A lot of people create small amounts of success by pursuing mediocre and non-risky business ideas.

Early in the game the courageous people are busy FAILING – which means shortsighted people will look over them as an opportunity to network and connect. (Side note: The courageous ones are also the people who NEED that connection.)

When you move up the entrepreneur learning curve and get to meet the titans of business, you’ll realize only the courageous people have remained. The “me-too” uninspired entrepreneurs with unoriginal businesses have all ended up doing something else.

Hang with courageous people and they’ll rub off on you.

5. Read about Courage

I saved this one for last, because it’s the most accessible in that it requires the least courage to get started. Most people will jump on this and ignore the preceding four tactics. You shouldn’t be one of them, because while reading about courage WILL build yours… it’s long and incrementally slow process. For best results, combine this with one or more of the above suggestions.

Reading is the ultimate brain washing because words put images, thoughts and feelings in your head. Symbols on paper and screens cause you to hallucinate different realities.

When you pick up a biography of a courageous individual, reading puts you in their shoes and literally activates the same neurological pathways and connections they used to do the courageous thing you’re reading about.

Vicarious courage is still courage.

I’ve written extensively about the masturbatory nature of most self help material, but when seeking to inspire courage… inspiration really does work. Pro tip: Stick to real world based material (biographies and first hand accounts) for the really powerful stuff and skip the abstract personal development.

This is by no means an exhaustive list. What do you do that builds your courage? Share your thoughts in a comment below this article.


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  1. This was sooooo good Peter! I loved what you said about courageous people rubbing off on you. I have to actively make decisions not to spend time with negative, stressed people. I’m in the process of joining a mastermind too. All the best! Your work is amazing!

    1. Hey Susie!

      Our social circle is one of the biggest psychological influences in our lives, so it’s something we need to definitely be intentional about. Thanks for stopping by 🙂

  2. This is great Peter. I exercise my idea muscle every morning so hearing you talk about the courage muscle made complete sense! I’m certainly going to incorporate these five strategies and try to think of a few more to build up that courage muscle. Thanks again!

  3. Thanks Peter for the insightful post.

    I wonder how did you miss adventure sports !
    its one of the best ways to face one’s fears…

  4. I love your strategies for building courage here. I’ve been consciously making sure to do at least one thing that make me feel uncomfortable for years now and it’s awesome. These ideas take it to another level. Heading to a networking event tonight so will definitely give ‘Social Skydiving’ a test run.

  5. Well courage certainly works but at a cost. However the higher the cost the greater the lesson learned. After failing plenty I’ve learned a lot with a build up of thicker skin and mental strength but physically tired at moment. Just experienced the jump off the deep end and guess what…. it’s going to workout. So all that stressing for nothing but…. mental toughness. Just watch those people who look like they can handle anything and act like that… Thanks Peter perfectly timed lesson for me.

  6. This is an interesting article that perfectly touches on the essential ingredients needed to brew courage. Reading autobiographies and first hand accounts of those who courageous definitely instills that same sense within the reader. One of my tricks, which may or may not work for others is to always think about the time or times when I was most courageous and find a way to apply that moment or feeling to my current situation. It seems to work but the more I can fit under my wing in this area, the better, so thanks so much for your insight!

    1. Heya Kiz, thanks for stopping by. Remembering past acts of courage is a GREAT strategy and a fitting number 6 for this list. A lot of the time, we already have all the resources we need within us…. thanks for the reminder!

  7. I try to pre-arrange opportunities for courageous action. For example, scheduling difficult calls so that the actual courageous act becomes just taking action on something that I have set out in advance. This seems to work kind of like ‘deadlines for courage’ and I find it’s easier if I separate the ‘deciding which actions to take’ from the actual ‘taking action’.

    Another awesome post. I’ve already made a lot of progress using suggestions from your previous post as well. Thanks a lot!

  8. I give myself permission to be afraid and to do it anyway. I make lists and prioritize tasks and break the MOST important task into the smallest next step so I always know what the ONE most important, bite-sized thing I need to do this moment is. Then I put my blinders on and just do that one thing.And then the next one thing. And then the next one thing.

  9. I find that knowledge wipes out the fear of the unknown for me, so I usually seek to understand new tasks or opportunities that create a bit of apprehension.
    Fortunately, my sense of adventure and exploration is strong; stronger than my anxieties, so I tend to live in a manner that my friends call ‘courageous.’ (which always sounded weird to me, heh)

    I’m currently learning and researching how to become a very successful entrepreneur…and I am very excited about the message that I soon will be sharing, in a BIG way.
    2015 will be a great year, a new adventure! 🙂

    Thanks for your insight and postings, Peter, and for sharing your message also!

  10. Greetings Peter
    Great info…it’s so great I would like to share it with my readers and followers. If this is something you are willing to allow me to do, please let me know what attribution I need to provide the reader with so the know you are the source and get full credit for your genius. Please keep me posted.

  11. Very insightful post Peter…I really resonated with #2 and #5 and have spent the past few years eliminating my own enemies of courage (notably my chronic worrying!) through daily meditation and exercise.

    Slowly down and creating mental space has definitely helped and I would like to add perfectionism to your list of enemies to slay. Many otherwise courageous people are defeated before they even start by thoughts that they/their work is not good enough.

    Thanks for the great strategies!


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