Wanna Get Lucky?: Why You Should Stop Planning and Start Experimenting

[Quick note: As many of you know there were some….er...technical difficulties with the internet in the last week. I know many of you had trouble accessing the video bundle link for managing your online image, building a capsule wardrobe, and looking better on video chat that I sent out last week, but it should be working now. Here’s the link again for women and men — please let me know if you experience any issues!]

This week I want to talk about a topic I’m very passionate about and discuss in Startup Your LifeLuck. Or rather, what is often dismissed as “luck.” 

If you believe luck is something you’re simply born with (or, more likely, without), science is not on your side. Psychologist Richard Wiseman’s research found that people increase their “luck” by consciously following four basic principles: they notice chance opportunities, make decisions by listening to their intuition, project positive expectations that become self-fulfilling prophecies, and exercise resilience. So, in other words: so-called “lucky” people seize the moment, are decisive and positive, and always find a way to bounce back. Most importantly, these are all active choices, meaning “luck” is generally not something that happens to us but something we deliberately create. 

Do you think startups are successful merely because the founders have a “vision” and sit around thinking positive thoughts all day? Yes, positivity is important. Having a vision does matter. 

But a positive vision alone will not deliver results. I promise.

Instead of relying on luck, startups experiment. They formulate hypotheses and test them out. They understand that experimentation is the best path to clarity and sustainability. And experimentation isn’t about chance. Calculated experimentation yields far more valuable results than years of planning. It seems counterintuitive, but it’s true.

In other words: Science is better than luck.

And yet, we associate the very word “experimentation” with risk and recklessness. Planning seems like the sounder route. But while planning seems like the responsible choice, it will only get you so far— and can actually be counterproductive. Planning assumes that the variables aren’t changing, that the environment is controlled. 

But let’s face it: that isn’t my life and it very likely isn’t yours. 

So, though it may seem contradictory to the notion of success you’ve embraced until now: I want you to stop planning and start experimenting.

Our reluctance to experiment often stems from the fear of public humiliation. What if I make a wrong move? There’s a sense of security associated with maintaining the status quo, even if it isn’t serving you or has adverse effects (yes, this is the cliché- but- true “devil you know” default response). We all have skin in the game and plenty to lose. But everyone, no matter their stage in life, can experiment toward something better.

So start small and begin observing and testing now. Don’t get held up by over-thinking before you act (remember: plan less, experiment more). I’m not suggesting that you should move mindlessly through space, but remember that “lucky” people manufacture good fortune in part by acting on their intuition— not through inaction. 

No matter where you begin or what obstacles you encounter along the way, it’s the strategy you hone and deploy— not luck or expert foresight— that allows for radical self- transformation and perpetual self- optimization. It’s triumph through trial and error, not certainty. 

Your life is an ongoing experiment, but it need not be a constant gamble. So let’s get lucky through experimentation. 



Want more style and life upgrade advice? Take the Sociology of Style men’s and women’s quizzes, or check out the Success With Style series for men and women.