Risk, Luck & Vulnerability

The Situation

Most of us like to attribute the success of any risks we take to skill. Made a growth hire that worked out? Prioritized a particular product launch over another? Made a personal investment with savings that made good? It feels great to say that we weighed the risks and potential rewards, and the brilliance of our analysis paid off. (Alternatively, it feels better to blame bad luck when things don’t go our way.) But what if it’s all more luck — and takes more trust — than we’d like to think?

The Plays

Try acknowledging that outcomes might be more based on luck than you think (this also might be uncomfortable – we want our successes, and our failures, to be knowable). And, try sharing your vulnerabilities a little more than you’re comfortable with.

At its core, allowing for the possibility of luck in whether a risk pays off or not is a form of vulnerability. And, vulnerability with ourselves and the people around us builds trust, which gives us a foundation from which to build stronger relationships and accept more serendipity.

Admitting the possibility of luck doesn’t mean that we throw our decisions to the wind and let random chance decide any more than prioritizing vulnerability and trust in relationships means committing to full and total transparency in our communications and relationships.

But, purposefully becoming more open to the idea of luck and leading with trust both increase your surface area — the likelihood that you’ll put yourself in situations where your skills and talents allow you to take advantage of fortuitous circumstances, and that the trust and vulnerabilities you share with the people around you will give jet fuel to your relationships.


“Vulnerability… is taking some risks with sharing the thing that's truly happening, truly on your mind. Sometimes that's business related, sometimes it's personal. But I think it's about risk taking. And you do have to do work. You can't just insert, ‘Hey, tell me something scary that you faced yesterday’... into a conversation. You have to build the relationship.”

Pod & Post: The Psychology of Luck with Morgan Housel

“Coming to terms with the fact that you are a product of your past, the majority of which has been dumb luck (particularly where and when you were born and whom you were born to) is a pretty powerful idea… And it impacts how people think about money in particular.”

Listen & subscribe on: Apple Podcasts, Spotify, YouTube

From Another Newsletter: Unqualified Opinions

On risk and Legos:

“Smarts. Patience. Painstaking research. Some luck. Price discipline. A willingness to look stupid. That’s how you do it.”

On sharing your failures:

“No one bats one thousand and anyone who represents nothing but success is hiding something. Moreover, failing is important. Not only is it how we learn, but if you haven’t failed yet, failure is coming because you haven’t yet pushed the boundaries of what’s possible. And if you haven’t done that, it may mean that you don’t have enough experience.”

Post: The Messy Wall

“Walls do things. And we all have them. Make sure you know what they’re doing – what they’re keeping in and keeping out – and when you should build doors and windows or tear them down entirely.”

Throwback: There Is No Medium Risk

“If you can minimize the cost and tilt the range up and to the right, you win. But if you cap your upside in a world where there is no medium risk, you will inevitably lose.”


Go Deep

Scaling People: Tactics for Management and Company Building (Claire Hughes Johnson)

+ The book is full of tactics, ideas, and stories — to foster relationships built on trust, in yourself and in your team: “If you’re not self-aware, how can others trust your feedback about their own abilities and behaviors?… And if you don’t maintain a foundation of consistency and stability, how will those around you know what to expect?”

Ideaflow: The Only Business Metric that Matters (Jeremy Utley and Klebahn)

+ How anyone (not just creatives) can harness risk and vulnerability and luck to find ideas that solve problems. “Tackling an unfamiliar problem — or seeking out a better solution for a familiar one — requires not just ingenuity but courage and vulnerability. A willingness to put things our there and make the occasional mistake. The irony of the creative process is that we limit our creativity just when we need it the most.”

The Role of Luck in Life Success Is Far Greater Than We Realized (Scientific American)

+ Scientists did the simulations — luck is important in individual success. “Even a great talent becomes useless against the fury of misfortune.” But there are also factors that up your ability to attract and capitalize on luck.

Luck and the Entrepreneur: The Four Kinds of Luck (Marc Andreesssen)

+ There’s a road map for getting luck on your side, and it’s getting away from relying on chance and instead having a wide and eccentric mix of interest, hobbies, and approaches — and the ability to synthesize them flexibly and aggressively. “If luck does indeed play such a huge role, then that seriously dents the image of the successful entrepreneur as an omniscient business genius.”

And, preorder Morgan Housel’s new book, Same As Ever: A Guide to What Never Changes. “History is filled with surprises no one could have seen coming. But if we learn to see what doesn’t change, we can be more confident in our choices, no matter what the future brings.”

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The Expectations Game: Aligning Brand with Reality and Values