Tactics for navigating uncertainty

We are all living through a very uncertain time, whether we like it or not.

At this point in a normal year, I would have had the majority of my summer planned out. Weekends away with friends at the beach, annual trip to Martha’s Vineyard, and bike rides on the calendar to Brooklyn Crab so I could spend all evening playing games outdoors. I’m sure like yours, my summer is a pile of open questions.

On your agenda for this summer, there might have been a wedding that you’ve had to postpone, a job search that now feels less tangible, or a big birthday celebration that now will likely take place over Zoom. There are many empty spots on all of our 2020 calendars. 

Before COVID, many of us had decided at a particular point in our lives to be uncertain on purpose!

What a novel concept! I did that myself back in 2017, when a startup I’d joined wasn’t panning out as planned. It was the first time in my career (since I was 19 years old?) that I quit something without another job lined up. Even though quitting was a conscious decision that I made, it was terrifying! Uncertainty was NOT something I wanted to welcome in my life.

My very good friend Julia on the other hand, took the same leap of faith with much more confidence a couple of years ago. After a long and vibrant run at Adobe, she decided that she needed a break, and took a full year away from her professional career. During that year, she enjoyed time in different locations around the world, learning new skills (she’s now my favorite yoga teacher), and away from her beloved San Francisco. She shared her journey recently on one of Power to Fly’s Live Q&A chats where she answered questions about how she made her decision to step into uncertainty, her time away, and ultimately how she moved forward to her awesome role now at Guru Technologies, where she runs go-to-market enablement (and remains one of my closest confidants).

Many of the lessons she shared can help us all wade through the deeply uncertain time we are each living through, including:

  1. Focus on your north star Looking inward and getting to know yourself more intimately can help you stay clear minded, so you come out on the other side with more clarity. For Julia, this means:

    • Detoxing from technology

    • Seeking a diverse set of perspectives - especially look to people outside of your norm

    • Asking yourself essential questions like What lights you up? What brings you joy? What drives you?

  2. Quell the voice of productivity by asking yourself, what am I producing with all of this productivity? Understanding the business of productivity and strategies for how to move away from it can help.

  3. Trust the process by taking one day at a time, asking for help when you need it, and remembering that people want to be helpful to you.

The recording of Julia’s full Q&A on Power to Fly can be found here. And BONUS, she’s sharing more tactical tips that you can access here.

Crabwalking to a Brooklyn Apartment (from Carly)

The end of the year can feel like a big sigh of relief. You’ve been breathing in everything that’s happening every single day.

Carly apartment 1

For me, 2019’s big breath included: piloting Crabwalk’s 5-Week Program for the first time, saying goodbye to and eulogizing my grandfather, coaching and meeting with hundreds of MIT student entrepreneurs, traveling back to Buenos Aires, starting this Crabwalk blog...oh wait, this all actually happened in the first quarter of 2019, so you get the idea and I won’t go on! 

I spent the last two weeks of 2019 trying to exhale all of the year’s happenings, out. One thing I sought to be better at in 2019 was leaning on and sharing with others. I’ve always been pretty good at sharing what’s happening for me professionally... accomplishments, struggles, interests. Sharing about what’s happening for me personally or emotionally has not been my thing. My parents and husband will back up this claim.

But, I co-founded a business that teaches others how to lean on the people that are in their lives. So, I decided I better get better at that habit - that I’ve so successfully employed throughout my professional life - to my personal life too.

In addition to shaming myself into this exercise because of the business I co-founded, I also know that this is vital because our personal lives are really not linear. “Life” comes at each of us, relentlessly, all of the time and I am no exception to that rule! 

Carly apartment 2

So, what changed for me in 2019 because of this new focus? A lot! Taking steps throughout the past year to figure out what was blocking me from reaching goals, identify what or who could help me get past whatever was blocking me, and asking the people in my life for help, allowed me to take small exhales throughout the year. Exhaling more frequently makes me feel less alone, like I can drop-kick my anxieties away, and it turns out, get the things I want, faster!

I’ll let you in on one personal example from my 2019. My husband and I bought an apartment(!) last summer. It took us 11 months of searching to finally have an offer accepted on a place that we loved. Over those 11 months, we both got a lot better at leaning on the people in our lives which absolutely contributed to us successfully acquiring our current home.

Our community shared their own harrowing apartment searching experiences (turns out, everyone goes through the same hellish experience - we weren’t alone!), convinced me to up our final bid by 5%, and once we won the bid, made the mortgage and moving process a bit less painful because I crowdsourced just about every vendor we used (there are so many options - how would you even pick otherwise!).

Carly Apartment 3

The 5-step Crabwalk framework will absolutely help you move forward in your career when you are looking to make a transition, even if the road isn’t clear. But, it’s also a handy tool to keep yourself supported and achieving in your personal life too.

Here’s to many mini exhales in 2020.

What does Laura do when she’s demoralized? Hiking. Both literally, and figuratively.

Have you hiked Breakneck Ridge? It’s an hour north of New York City. The first 90 minutes is a rock scramble and then it’s an easy breezy (sort of) 3 hour stroll downhill. Each time I hike it I think I might fall backwards and plummet to a bruised (at best) and broken (probably) mess at the bottom. But somehow, I haven’t yet - lots of credit to my mother and her Austrian blood!

My day-to-day experience of life is meaningfully better than it was 3 years ago as a result of things that help me manage my state of mind: therapy, coaching, conversations with friends, journaling, daydreaming, meditation, shower thoughts, exercise, etc. Anything where I’m reflecting, learning about myself, and processing what’s happening around and to me. I come out more clearheaded. Hiking is one of those things.

There’s always a moment in a long hike where I wish I wasn’t on the hike. I wish I was in the car. Or at the brewery. Or just coming out of the shower with a beer or Moscow Mule. But then I’m still on the trail with an hour or so to go. Sometimes it feels like I’ll never get there. Ever. SAD FACE.

But the silver lining is I’ve been here before and I know what happens. If I put one foot in front of the other, I will always get there. I will always get to the end, if I just keep moving. One (sometimes painful) step at a time. The only way through is through. 

If I freeze. If I stop. If I sit down. If I could somehow find a helicopter. I could sit down and journal about why I haven’t reached the end yet. I can spiral about what I should have done differently earlier on in the hike - taken a shorter route. Worn my real hiking boots. Brought more snacks. Picked a less clammy day to hike. I can noodle. As I do. Figure out why I ended here. Be depressed about it. 


But ultimately none of that gets me down the mountain. The only useful things I can do is move forward in the best possible way I can. 

  1. Put one foot in front of the other

  2. Optimize the journey w/ what I have - maybe drink some water? Have a snack. Put on some music. Stretch. Change my sweaty shirt…  Just take a minute to tune into my body, reflect on what has worked to energize me in the past, and adjust.

  3. Then I can make sure I’m still on the best possible path to where I want to go. I can pull out the map and get clear on where I ideally want to be - THE CAR. Am I on the right route? Is there a shorter one? 

  4. Once I’ve optimized - there’s only thing left to do: Take a step forward.


Are you feeling demoralized? Tired? A bit scared you won’t make it to that car? 

Maybe you can just sit on a rock. Take a deep breath. Drink some water. Confirm where you want to go. And then take a step. Keep moving. You’ll get there.


Carly's journey to Crabwalk

This is cliche but true. 15 years ago I would have never believed it if you told me I’d be running a startup accelerator, teaching at MIT, and building Crabwalk. 

It’s not that I wouldn’t have been psyched about that story, but I simply had a different idea of what my life would look like. What has led me to this place surprises me even more. 

My current life is almost 100% credited to the existing people in my life like the alumni of my college, friends of friends, family, clients, and former colleagues to name a few.

Here’s the story of how I crabwalked to where I am today.

My journey to Crabwalk

I sought independence at a very, very young age. Money was a prevalent subject in my house. My dad is an accountant and financial planner.

So in my world at the time, financial independence = true independence. I believed this so much that when 10 year old me was asked what I wanted to be when I grew up, my answer was a philanthropist.

My mission was set; I would work to earn money and be financially independent.

I grew up looking up to other working women - Katie Couric, Barbara Walters, Oprah and Madeleine Albright. Alright, I guess the ones I knew of were all on TV.

My mom was a speech pathologist and teacher; my dad an accountant and financial planner.  One grandfather was a radio talk show host and the other a pharmacist. My grandmother a reading teacher. Besides friends parents who were lawyers and doctors, that was about my total knowledge of job options.

I set out to work as early as I can remember.

At first, just being at my dad’s office, and then as soon as someone let me, at age 12, I was a mother’s helper and was quickly promoted to babysitter. At 15, completely out of the blue, I presented my parents with minor’s working papers for them to sign so I could work at a local florist.

As much as I loved growing up in my small town, I was eager to head to a city and be where the action was.  

My first steps forward.

As soon as I got to college, my dad started to seed me with instructions of how to explore potential career paths. He suggested utilizing the resources I already had available to me, such as alums from Skidmore, who would be willing to share their own experiences. I wasn’t the most outgoing of college students so I wasn’t quite sure how I felt about approaching complete strangers.

My dad reassured me, however, that “people love talking about themselves, so just let them talk.”  It worked like a charm at those first few coffee meetings and my confidence grew during those outings.

That’s when I learned a key part of Crabwalking: how to leverage people I was connected to already to help me move forward in my career.

I got in touch with a young alumni who helped me secure my first professional internship at Goldman Sachs in New York City. I was psyched! I was going to be a financial services professional at the most well regarded bank in the world, in the center of it all, NYC. I was going to be able to make enough money to not only enjoy my life, but also treat my family and friends occasionally and donate to nonprofits that I cared about. Career, figured out!

And then, September 2008 happened and everything started to change.

I was on the front lines of seeing many people’s careers get up-ended. So I started to think, perhaps it wasn’t going to be the same for me as it was for my parents. Industries can change in a day, employers aren’t as loyal as their employees are, and it wasn’t good enough to be a one-skill pony.  

I didn’t fully know what that meant or how that would show up in my life years down the road.  What I did know was that I wanted to learn what my other options were outside of financial services.

That’s when I started to really move sideways and walk like a crab through my career.

My first crabwalk move to the side.

The move out of Goldman Sachs wasn’t easy. I was making a great salary at a highly regarded brand. My parents were quite confused when I told them I wanted to leave. My friends were too, they had been hearing about my dream to be a star on Wall Street since my first day of freshman year.  

When I told my colleagues at Goldman that I was leaving to take a job in local, city government, their heads seemed to be spinning too…

“You’re not moving to a competitor, so this isn’t about compensation?” — my boss asked at the time.

“Nope”, I said. 

I had been a political junkie since I was 12 years old, so when an opportunity in the public sector became available, I jumped at it. I think I would have been excited to work in any aspect of government, but it was a bonus that I’d be working at an economic development agency where I was responsible for working with the private sector to strengthen NYC’s economy. That meant I’d be able to fulfill a goal of mine of getting a bird’s eye view of all of the sectors in NYC.

But, it also meant that I’d be taking a huge bet on myself, and a huge pay cut. And it paid off.

Since taking my leap out of finance, I’ve worked in government, startups, academia, and am now on a journey as a business founder. Crabwalking has unearthed so much for me: my entrepreneurial nature, more confidence in myself, and true independence.

Crabwalking can be an amazing thing.

I strongly believe that my generation’s paths are going to be less linear than our parents. That we are all going to have to take a few steps sideways as we move forward, and that we’ll be better for it.  

Forging a new path will be a bit painful for most. Sometimes we get stopped before we even have a chance to get started because on a non-linear path, there are no clear directions or a clear destination.

It can be confusing or shameful for some when we don’t have all of the answers. We live in a Google-centric world where answers are always at our fingertips, but this isn’t one of those questions with an easily defined answer.  

Answering friends and family’s questions about work becomes more difficult, it takes us a little bit longer to fill out the “what’s your occupation” question on a form, and just like that, our future is a bit more open to interpretation. We don’t know all of the answers to these pressing, societal questions.

I am here to tell you that it is OK. YOU ARE OK.

Why do I feel the need to shout this at you? 

Because I have been on a long, unplanned Crabwalk. At first, I couldn’t really articulate why I wanted to leave the company on Wall Street I had dreamed about and aspired to. I measured my self-worth according to how quickly I could acquire promotions, vacation days, and top reviews. I was all about moving up and forward.

Don’t get me wrong, I am still the same ambitious woman I have always been and I very much want to continue moving up and forward.  But I feel much more comfortable in the sideways. 

Crabwalk exists to help you navigate through the journey so that you can embrace the sideways in order to continue to move up and forward.

— Carly

Life isn’t always linear.