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The Start of Something

I think we solidified the beginnings of this idea while on a hike in Andes, NY. Or was it at the nutella coffee shop in Union Square? Or was it over a breakfast-date-mind-meld when we both were pivoting from consulting to HR? Or, was it years back when we first started sharing our girl-crush on Brené Brown? I think it started with Brené, let’s be real. We both read Daring Greatly at different parts of a year and it just happened that the topics out of that epic book orbited our conversations in every shape, form and medium. From colleagues, to the beginnings of a friendship, we became more and more vulnerable in our chats about life and work. Fast forward 2–3 years, we realized we talked about the same topics on the daily. It was time to do something about that; get out there, find out how others are finding and defining their own balance in life and work and bring them together to learn from each other.

It started with a list (doesn’t it always start with a list?), then it evolved into a google doc — what we call the ‘Elaine and Crystal brain’ type docs. A fine dance between the ‘what’ and the ‘how’ (that’s the core to our very own ying and yang as partners by the way). We didn’t know where this was heading but we netted at a high-level objective — create a community-inspired something to connect experiences and growth journeys. To craft this something, we wanted to hear from others on these topics:

To start, we listened:

We surveyed over 150 folks in our network (targeting a diverse and wide range of ages and experiences) with the focus of understanding the following problems:

  1. Purpose is ever evolving, and everyone is at a different stage of their self-discovery process. How might we offer a space for peers to share their experiences and learn from each other?
  2. With an undefined timeline of when face-to-face connections can take place again, how might we expand meaningful conversations virtually beyond a connection?
  3. With an overwhelming amount of sources for content on the topics of work-life journeys, how might we create a crowdsourced repository which also facilitates conversation?
Step 1: the survey!

Who we heard from:

  • 73% women, 24% men
  • 57% between 25–34 years old and 43% over 34
  • 82% live in city, while the rest split between rural and suburban areas
  • Average of 7.2 satisfaction (out of 10) with your job today. Driving force of satisfaction — purpose and people at the company.
  • Average of 8 (out of 10) when asked “how much do you invest yourself in what you do” and not surprisingly what’s stopping folks from giving their all is a lack of purpose.
  • Big theme validated by a question about what drives you: 92% of you said purpose. Money second and recognition third.
  • Most of you (61%) crave the shiny objects and make ad-hoc career decisions based on your passion while 27% of you look at your career like a ladder.
  • An overwhelming amount of you (93%) find clarity about your career through conversations, which is awesome because this is the space we want to play.
  • The top voted topics that interest you include leadership, career journeys, team dynamics, and promotions.

Not surprising that folks have had both positive and negative experiences with managers and team dynamics. The stand-out negative experiences include 64% of your struggling with work politics. Humans are tough to crack, am I right?

Where this lead us next:

Conversations. Not only because we’re hardwired to connect with others, but because these results elevated that conversations are where this population goes to get clarity about their work-life journey. This validated our objective — we want to create a safe space to connect and have these conversations about the top topics shared with us — and so we announced we were to pilot a few different approaches and would be back in touch with those interested in participating.

We were SO excited to experiment with different conversation styles to see what sticks. We dove right in and got to work. ‘Elaine and Crystal brain’ style.


What’s in it for me? It was important to start with this differentiating question up front. Why would you come to our pilots? What would you get out of them and perhaps what could you give?

We aligned fairly quickly on these three outcomes and they were the constant throughout each pilot:

  • Connect digitally with new humans
  • Learn about yourself through experiences of others
  • Find commonalities in struggles and superpowers to inspire

From there, we designed each pilot with intent to be diverse, conversation-inducing and thought provoking.


  • Pilot1: Bring humans together, don’t prep topics or share agenda prior
  • Pilot 2: Bring humans together and have them read an article before hand to discuss
  • Pilot 3: Pre-assign humans to meet 1:1 and then bring humans together to discuss the 1:1 meetings as well as debrief an article or topic shared prior


They were all scheduled for 1 hour and we facilitated them all in a similar flow:

  • 10min intro — Crystal + Elaine intro + context setting to explain career / Life moments
  • 20min icebreaker — Everyone goes around to share where they are in their life, their careers and share a recent growth moment from one or both
  • 20 mins Pilot specific action and activity — 
    + Pilot 1 + 3 had Pondering questions: What is on your mind right now that may have you feeling unsettled or you’re unsure of?
    + Pilot 2 focused on reacting to the article / video and respond to questions
  • 10 mins — Give / Get from this group — Asking what each human can give to this group and what is one thing they want to get from this group or someone in this group
  • Close — Host a mini, live review/retrospective and share next steps


What attendees liked and key themes across:

  1. The ease and natural flow of conversation.
  2. Getting inspired by other badass women.
  3. Taking time out of a busy day for what felt like a self-care practice, laughing and learning.
  4. The sharing of everyones background and stories and knowing the reality of how people deal with everyday struggles.
  5. The low pressure candid space to share and connect on common challenges
  6. Everyone reading a topic for discussion was great as well.

What attendees suggested we could do better:

  1. Pilot 1 attendees wished there was a common theme or article to prep and discuss throughout.
  2. Continue the conversation, maybe adding follow-ups to the calendar.

So where do we go from here?

We’re digging into what this something can become. We have been doing research about organizations that exist in this work-life journey conversation space, we have been talking to our power-squad of founders and thought-leaders and we’re continuing to learn from each other.

We’re excited to be on this journey together — building, experimenting and making magic. Thanks for coming along for the ride too!

We hope to find this something out by the end of the year, stay tuned.

Crystal Jeffs & Elaine Schwartz

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