VENTURE OUT
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Recalibrate Your Why
Understand Your Personal North Star and Make Sure Youâre On the Right Course
I recently consumed Simon Sinekâs Start With Why and Infinite Mindset. Considered must-reads and a god-like figure in the productivity community, I finally got around to it. Donât get me wrong, Iâve watched his infamous TED Talk (15 million views!) over 10 years ago, so Iâm quite familiar with his Golden Circle and have discovered my Why.

It got me thinking about my own Why – how do you make a change if Iâve fallen off course, and what are some techniques/excuses that we make about it? Follow me on the journey to see if weâre on course to our personal North Star.
Prove To Me Your âWhyâ
One nugget I found interesting in his book was the idea of donât confuse our Why with the proof of our Why. For example, Iâm currently sitting in my local Starbucks (with a mask) at 630AM writing this. The fact that I got my butt up before sunrise and am here cranking out another one (DJ Khalid!) is the proof of my Why. In other words, my Why is not this newsletter or the morning routine that successfully got me here.

My personal Why is:
Thatâs a Why statement that a professional coach helped me to discover through a series of sessions. Two years later, reading it again, I find that it still resonates with me.
TAKEAWAY â Use the evidence in your life to help identify and reinforce your Why. And if you happen to realize thereâs something you do that does not match, well, just stop it. Whatâs the worst that could happen. đ
Why an âExistential Flexâ
Digging deeper in Simon Sinekâs Infinite Mindset, there was one concept in it that I wanted to spend some time exploring.
Existential Flex: âProfound strategic shift in order to better advance your cause and failure to do so may ultimately result in the demise of your organization.â â Simon Sinek
For most of us, here we are climbing the professional career ladder, doing our best to be a good family member, and diving into our passion projects with every free minute. But is it all really contributing to what our purpose in life is? Are our achievements directly related to our Why? Or have we been sucked into the rat race?
During the pandemic, Simon Sinek found himself having to practice what he preached.
So, Simon sat his team down, gave them an action to come back in 48 hours to the next meeting with at least 15 ideas on what they could do. The trick is that these canât be just any idea to make money, they had to be ideas that matched their Why.
But first, he did something that we should all remind ourselves of.
Previously I challenged you to identify your Why. Did you do that? If you did, great, but if you didnât then you must like driving blind. Recall, in order to do an existential flex, which is:
The keywords are, âso preoccupied with protecting the status quo.â
It wasnât by choice per se, but my career path took a tangent a few years back when I didnât get a promotion that I applied for. Looking back on that moment, I can recognize that I didnât get it because I was exuding and living my personal Why. I had lost my North Star and because of that, I came across as probably fake. The existential flex happened to me but only now am I really trying to lean into it.
TAKEAWAY is I doubt any of us ever live 100% true to our Why, so take this moment to reflect and then flex. As for Sinek, his team says, âwe have a more diverse, robust business. Thatâs rad.â
Break Through Thinking to Your Why
I want you to reimagine WHO you are. In every situation.
The purpose here is not to be the next Meryl Streep or Daniel Day-Lewis. No, the purpose here is to be able to rethink, reimagine what you are capable of doing.
For example, letâs say youâre in a big meeting full of people and you have something to contribute to the conversation. If you think youâre just another worker, you might be hesitant to speak up. But, if you can imagine yourself as one of the decision-makers, then I bet youâd speak up and be heard. Even then, thatâs not the entire point.
Challenge long-held orthodoxies.
The real benefit from reimagining our role is not only being able to accomplish something we didnât think possible, but really the ability to expand our mind past what we thought were barriers.
Love âem or hate âem, social media influencers are brilliant at this. Awkward teenagers transform themselves into Tik-Tokkers (did I spell that right?!) with a million followers. YouTubers build an entire brand empire, complete with employees and everything. On Instagram, people can become traveling, food, and fashion experts.
TAKEAWAY is at any age, in any stage of your life, you can reimagine your role in life and challenge who you thought you could be.
Excuses & Shame of Your Why

I know the topic of shame is much too big to cover in just one email. But in our current conversation about focusing on our North Star, making a change if weâre not on track, and doing things like reimagining what weâre capable of, I think itâs important to acknowledge the excuses we make. And sometimes theyâre rooted in a construct called shame.
For example, a study was conducted to understand the views of employees in a law firm and why they did not apply for a promotion.
The shame here is that people believe that in order to be professional, they need to sacrifice their personal life and at the expense of their family. Yet, deep down, they know to be happy there needs to be a balance outside of work.
So, letâs bring this home and wrap up this series with the final TAKEAWAY, which is, please stop making excuses for yourself. You have a North Star so sail towards it. If you find youâre off course, then itâs ok to do an existential flex to get back on your path. And donât let the imaginary barriers we make for ourselves hold us back. Do what I do and tell yourself every morning in front of the mirror, âPeople do like you and gosh darn it, youâre gonna crush it today!â
References
Existential Flexibility | THE 5 PRACTICES
Prepare for Existential Flexibility: A Magical Meeting Story from Stephen Shedletzky, Head of Brand of Experience at Simon Sinek, Inc. By Douglas Ferguson
Simon Sinek: To Succeed in Business, You Must Understand the Game By Greg Thomas
Getting Your Team to Buy into a Big Change by Namrata Malhotra and Charlene Zietsma
The Ways Big Cities Think About Large-Scale Change by Ben Hecht
Big Technology Change Without Big Risk by Brad Power
Break Down Change Management into Small Steps by Jeff Kavanaugh and Rafee Tarafdar
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