OS21: Cara Thomas – “Serenflipity” & How Choosing Adventure Can Change A Life

The only way to get to the other shore is to lose sight of the one you are on

~ Steven Tyler to Cara Thomas

Cara Thomas with one of the Serenflipity cards

The word serendipity is defined as “the occurrence and development of events by chance in a happy or beneficial way.”

This theme has played out dramatically in the life of Cara Thomas, and is undoubtedly the thread permeating virtually every development in the creation of her labor of love, Serenflipity.

There seem to be two types of entrepreneurial paths. One is front-loaded with meetings, presentations, “valuations” and endless number crunching, the search for investors and then, the launch.

The other is an organic “following” of a calling, as if something is making itself through you, one in which no foresight could have possibly predicted a business or product, and yet the universe – in its inimitable fashion – insists upon it.

Cara Thomas’ “Serenflipity” made its way into the world through the second path.

In 2013, feeling stuck in her job, her routines, and her life, Cara decided to take a three-month trip to Asia, booking a one-way ticket to Mumbai. Given her proclivity for adventure and spontaneity, she asked various friends, colleagues, and clients to craft her a set of unique challenges to undertake during her journey – 90 total, 1 per day – to unlock the world of her travels and open up all sorts of fascinating opportunities for exchange, connection and surprise.

These assigned adventures – written on a set of 90 flash cards – were actions such as paying it forward by buying the coffee for the person behind you in line, or asking a random person for a mantra (which led her to interact with none other than Aerosmith frontman Steven Tyler in a Bangkok hotel lobby).

At the end of her trip, she realized she was on to something and, at the behest of a friend, began to hatch a business concept. This idea has since grown into a full-blown business called Serenflipity, which features 30 cards, each with a different challenge centered around the themes of “spark”, “connect” and “explore”.



Serenflipity has also bloomed an interactive event series, where groups of people collectively embrace one specific challenge (e.g., find the secret of true love) and set out into the community in pairs, each endeavoring to complete the task, make a memory and build stronger connection with themselves and the world.

In other words, Serenflipity is a business that reflects Cara’s personality, values and excitement. Something that is uniquely hers, and her special gift to serve others and the world.

In this conversation, we talk about the creation of Serenflipity, the events that led her to take her epic trip, and the dynamic role the original cards played in the process. Plus, we discuss how these magical cards transformed Cara’s life, and help to open others up to adventure – including and especially in their everyday lives.

We also discuss:

  • Cara’s 90-day framework – how she experiments with new ways of living or being for time-limited periods, reducing pressure and amping up “play” to enabled desired change and exploration
  • The impact of travel on her life, and how it has helped her and many others experience dramatic life transformation by simply dropping everyday routine and embracing the unexpected
  • How fun and play have shaped her style of entrepreneurship, and how following this joyful approach has enabled Serenflipity to grow and evolve as a business
  • Her annual ritual for success, business planning for herself and mapping out her 90-day experiments
  • How her focus on serendipity has opened her up in all sorts of wonderful ways, causing her to pay attention to the specialness of how life unfolds around her
  • And, of course, the growth of the business, and how it has served as the perfect mirror to her own experience and the culmination of prior experiences with innovation, design, self-improvement and spirituality.

The underlying theme of our talk is that there is more to life than what initially meets the eye, and Cara Thomas with Serenflipity aims to remind us of just that.

We hope you enjoy this conversation with her!

Cara Thomas

Selected Links from this Episode
Cara’s Recommended Books

You may also like