Prototyping a new OS for 2019

Sara Kalick
9 min readDec 26, 2018


I recently gave a talk on storytelling in South Africa that started with a story about my life in three chapters.

Chapter 1: Chaos
My 20s were spent going where the wind blew me. After a three-month jaunt backpacking across Asia after college, I took a job managing a drum & bass sushi bar nightclub in Washington, D.C. Next, with no design experience, I hustled my way into becoming an assistant designer for a clothing line in New York. Guided in part by a wild-haired, short-lived belief that I should marry an Italian (long story for another time), I almost moved to Italy at 24 — because that’s where Italians live. Instead, however, this led to the decision to go to business school as a way to kill two proverbial birds with one student loan-financed stone. Of course, instead of Italy, I ended up in Spain… Okay, so you get the picture.

Chapter 2: Control
I left business school with a deep belief that I needed to get to Director, a title that would signify the kind of career growth and CV pedigree that would easily open doors. So I buckled down. I learned a craft. Became an expert generalist. Built my brand and my reputation. Rose through the ranks. Got the big title and the big responsibilities. Launched a start-up. Spoke at conferences. You know, the things one does.

Chapter 3: Controlled Chaos
Sitting at a crossroads almost exactly this time last year, my amazing coach Whitney Birdwell suggested I do a vision exercise to paint a picture of the life I wanted to lead. Although I love a good mood-board or collage assignment, I found myself resisting.

Ultimately, I felt like I didn’t have any new inputs in which to envision a new world, without which, the output might look an awful lot like my existing life, only on a new continent.

In a very SYPartners way, I designed a seeing tour to open my aperture and challenge my assumptions about what’s possible. This was the genesis of my global curiosity tour, of which many of you are following. And a few months in, I can easily say that I’ve been living my best life. I feel lighter, more full of possibility, and more creative. (Cue eye rolling.)

Now, looking toward 2019, I find myself wanting to design this journey less as a moment and more as a new way of being that combines the best of chapter one and two: a life fueled by unreasonable curiosity and based on a steady stream of (somewhat) thoughtful experimentation.

As such, I’ve been thinking a lot lately about design principles for this new operating system. They’re admittedly a work in progress, which is the point. I’m drawing from, wholesale stealing, and occasionally bastardizing what I’m learning from the muses and spirit animals that make up my imaginary board of directors.

And, since it’s that reflective time of year, I thought I’d share them with you. As I see it, the first two principles below provide the vector, the second act as the thrust.

Start with your values.

If you’ve never articulated your values, do it now. Like, right now. While you’re at it, write a personal purpose statement, or at least a rough draft. These tools are the filters that help you understand what sparks joy in you, what lights you up, and where ultimately you should be focusing your energy.

You didn’t ask, but…

My values are love, freedom, curiosity, and admiration. This last one, oof, I struggle with it. But I’ve got to be honest, I seek out people I admire and in turn like to be admired. I’ve always liked to do cool things and I’ve just got to own that (did you see the gorilla photo in the last post?).

The shorthand for my purpose, not yet beautifully annotated: To help people and organizations envision and activate their place in the universe.

Based on the recommendations of a bunch of people, here’s what else I’m reading to help me with this practice: Ikigai: The Japanese Secret to a Long and Happy Life and Designing Your Life: How to Build a Well-Lived, Joyful Life.

Optimize for compound interest on learning, impact, and finances.

The first six or seven years I was at SYPartners, my brain was on fire. I was learning so much all the time, such that quite literally almost nothing else mattered. I didn’t mind the late nights or weekends that can come with consulting. I ate greatness (SYPartners’ purpose) for breakfast, lunch, and dinner.

But after getting sick a few years ago, I realized how out of whack my life had become. This was especially true when the learning curve slowed down.

So now, as I hit a massive reset button on my life — and with greater clarity on who I am — I want to make sure that I am optimizing for what matters most to me. But as a grown-up with real world financial responsibilities, I want to do that while making the money part work for me as well.

This part is a constant experiment, but here’s some directional support:

Align who you are with what you do.
You know that electrifying feeling you get when that light inside you is totally luminous because your gifts are fully activated in the work you do? Just do more of that. (To read more about this check out Elle Luna’s The Crossroads of Should and Must.)

For me, right now, that looks like anything and everything I can do to help social impact entrepreneurs tell their story and fund their futures, as well as designing programs and platforms that help activate the best in individuals and teams.

Use “Hell Yeah” as your compass.
Jonas Altman turned me on Derek Sivers who says, if you’re not saying “Hell Yeah” then say “no.” So as new projects come my way, I’m listening to my gut to filter for what I can give an emphatic “hell yeah” — and filter out what I might take on for the wrong reasons.

Chase pleasure.
A new friend in London introduced me to the idea of jouissance — a sort of excess of life or enjoyment beyond the pleasure principle. According to the psychoanalyst Jacques Lacan, jouissance “begins with a tickle and ends with blaze of petrol.” Sounds like something worth chasing.

So when I say pleasure, I don’t just mean this in the hedonistic sense of the word (though maybe it’s an AND). But as it relates to a life of unreasonable curiosity, I am practicing saying “yes,” particularly as it comes to new challenges that will stretch me.

Align your money with your values.
Khe Hy, once called the Oprah for millennials, writes a lot about how many of us are sitting around telling ourselves stories about all the ways there is not enough and connecting our net-worth to our self-worth. Letting our fears of loss of status and money guide our choices, rather than our values.

But this is scarcity thinking, and you’ve got to combat that. Having taken a leap of faith himself, his blog RadReads is packed with useful insights. He also offers 1:1 coaching programs for those who want to align their money with their values.

For me, right now, I am not throwing caution and my retirement to the wind, but doing the not so hard math of looking at how I want my life to work — and backing out the real numbers on how I need to work to live that life.

My mental model and massive experiment is: How might I work nine months of the year, four days a week? It sounds more luxurious than it is, and I plan on working plenty, and frankly, making money (thoughts are things). But what it means is creating time for the projects and initiatives that offer something other than a financial return. Which brings me to my next point.

Bend time to your will.

Those who know me well, know that I’m someone who’s often optimized for high-frequency. For the last 11 years, my calendar was defined by chock-a-block programming. As a result, dinners were canceled. Whole Sundays were lost to recharging on the couch. Life was deferred.

Today, I am trying to completely reimagine my relationship with time. While by no means a perfected science, here are a four things I’m experimenting with that you can try too.

Slow down.
The past few months, I’ve been actively trying not to rush. To literally and figuratively walk, not run or Uber to my next appointment. Now, I’m about to take my slow-down game to the next level.

Productivity and creativity maven, Jocelyn Glei, just launched a four-week course called Reset to give you the practical tools and advice to work in a way that is intentional, energizing, and inspiring. If you’re curious, also check out her amazing podcast, Hurry Slowly.

Protect priorities.
At SYPartners, we had a team practice of establishing protected time for personal commitments. Each person would block their calendar, and the team would work together to ensure that everyone took the time they needed. This is called Golden Time.

Of course, right now, I’m the only one mucking around with my calendar. But as I take on more work, I’m preemptively blocking my agenda with things I am prioritizing like Portuguese classes and yoga. It might sound silly, but simply having it on the calendar makes me more likely to protect it.

Create white space.
Meanwhile, as I protect things that must be scheduled, I am holding space for the things that can’t. This looks like making sure that my days aren’t overloaded with pre-programmed calls and appointments, using three as the magic number and four as the upper bound. The point is to create breathing room to allow for the unexpected.

Time box.
Multi-tasking is a myth that too many of us buy into. Reading emails while on the video call. Toggling between different open to-do items. Our attention gets frayed. Our output and outcomes suffer.

So, when I do need to do work, I’m trying to be hyper-focused, blocking time for specific activities and giving them my fullest attention for a defined period of time.

This takes building new muscle memory, but with practice, I am able to make progress on one thing before turning my attention to the next. Here are a few tips in case you want to give it a try.

Activate the collective.

Fundamentally, relationships and networks are the currency that will fuel my flywheel. They are the key to new lines of inquiry, ideas, worlds, and, therefore, possibilities. Therefore, connections need to be nurtured, never taken for granted.

Luckily, I’ve always been a bit of a relationship making machine. Authenticity and empathy are two key ingredients. Here are two others that are a big part of my practice.

Julia Middelton, the CEO and founder of Common Purpose, signs her emails, “Love, Julia.” While I’ll admit that the first time I saw this, even the Berkeley hippie in me felt awkward. But leading with love is an invitation for those around you to show up 100% themselves. It opens doors and creates space for new possibilities.

I’m trying to do this by being more vulnerable and less controlling — expressing myself and my emotions more, owning my feelings, and sharing my gratitude.

Too often, people see networking as transactional. Something you only do when you need something — rather than relationship-making for the long-term.

As I meet people, whether they’re an old friend or a new acquaintance, I try to make sure they don’t leave empty handed. Whether that’s impromptu coaching, sharing knowledge and ideas, or fostering new connections for someone else. I want to make sure that everyone I meet feels like it was worth their time.

Now, I realize that some of this comes naturally to me as an extrovert. But for the introverts and other phobics out there, Karen Wickre has taken the work out of networking. Frankly, her new book is a must read.


With that, I will say goodbye until 2019. Until then, may you all design the year and the life you want to lead.