Carly Chase

PODCAST: Be in the driver's seat of your own career

What a dream car…

What a dream car…

I co-founded Crabwalk because I believe that every professional needs to be in the driver’s seat of their career. I say this will such vigor because I KNOW it to be true—from personal experience.

20-year-old Carly sincerely believed that if she checked all of the right boxes early on in life—great grades, academic accolades, “right” internship, head down and do what you’re told—the road ahead would become very clear and she’d coast along in autopilot. Job in finance or government. Apartment in NYC or DC. And the rest would take care of itself.

It turns out that a lot of that came true, except the part about being on autopilot. The longest autopilot I think I’ve felt in my 15-year career lasted 6 months?

Turns out being in the driver’s seat and having to actively steer my career was the better choice for me. I’ve now crisscrossed my way through not only finance and government but also discovered the wonder of entrepreneurship and startups as well as academia.

The one mental model that’s helped me most? An entrepreneurial mindset. When faced with a big challenge in a chaotic and ambiguous environment, I push myself into offense mode instead of defaulting to defense mode. I try to find the opportunities to keep me moving forward.

I shared a lot about this cross-over effect in my work, and a whole lot about my own career path and history on the Boston Speaks Up podcast, hosted by Zach Servideo last month.

If you’re curious to hear more about how we think behind the scenes at Crabwalk and how an entrepreneurial mindset can support you, regardless of the career path that you’re on, then tune in!

Top Accountability Program Questions Answered

We all get by with a little help from our friends.

We all get by with a little help from our friends.

The simplest way for me to stay motivated is to find others to be accountable alongside. Having prompts from others forces me to get out 0f my head and take action.

That’s why we decided to launch our Accountability Program  - to help ourselves and our Crabwalk community stay motivated amongst all that’s happening in the background for each of us.

Each Friday of the program we’ve been holding Live Q&A sessions. Motivation, lack of focus, and uncertainty has come up each week, so below are tips + frameworks for how to tackle each of those feelings.

How can I get conviction about what I want next?

Many of us want to make the “right” next move, adding additional stress to the process of a job transition. Reframe this to relieve some pressure: Life is a series of chapters. The next step you take simply leads you to the next chapter. 

To help determine what that next chapter is, reflect on the current one you’re in:

  • What is it about this chapter that I love? 

  • That I don't love? 

  • What can I change for the next chapter?

How can I stay motivated to find a new job while currently working at a demanding job?

A big, hairy open-ended goal like finding a new job on its face can be overwhelming and this super unpleasant cycle starts:

 
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When we get overwhelmed, we get stressed, and when we’re stressed we become unmotivated. Our minds are powerful - just not always in the way we want!

To combat this cycle, break that big beast into micro goals with this framework:

Step #1: Where do I want to be in my job search 6 weeks from now?

Step #2: Fast forward 3 weeks. What would I need to have accomplished to be on track to achieve my 6-week goal??

Step #3: What do I need to do this week to put me on track for my 3-week goal?

Step #4: What’s one action I can do today to move me towards my 1-week goal?

Step #5: What will prevent me from getting step #3 done this week?

Achieving micro goals like this will keep you motivated, and propel you forward.

What if I’m having trouble achieving micro goals given competing life elements (COVID, kids, noisy house)?

Yep - even when we’ve got our to-do lists, giant cup of coffee, and 8 hours of sleep our day can still go sideways really quick.

The trick is to forgive the day and give yourself credit for what you were still able to get done (I bet it’s a lot whether it’s responding to emails, getting in that 15 minute run, or spending an extra 10 minutes with your kid). You’ll get another chance tomorrow!

If this is happening constantly, you can also plan for it and reset your expectations given what’s out of your control. Use this quick framework:

Step#1: Take 15-30 minutes to map out everything on your plate (it's worth it) Go through your list, highlight the ones you need to finish today. Create a clean to do list on a new piece of paper in order of what you'll get done. After this step, you should have a full view of everything you owe to someone else.  

Step#2: Scan your calendar and gut check time. Is it realistic? Can you realistically get your to do list done in the space you have with some buffer time for unexpected things? If not, keep reading! 

Step #3: Take 15 minutes to renegotiate - how can I make it all fit? Do I have too much to do today or too little time to do it that day? Can I take something off my calendar or make something on my calendar shorter (e.g., turn a meeting into an email)? Can I delegate tasks?

Step #4: At the end of each day, scan and reset expectations. Scan your to-do list. If you didn’t get something done that was promised (implicitly or explicitly), reset expectations with that person.

How do I find opportunities in a field I’m trying to pivot into, and therefore new to?

Finding passion in a new industry, field or role is exciting! To understand the opportunities, become an expert in this new area. Let’s say you’re looking to make a transition from the financial services industry to a fin-tech startup. Here is an example for what becoming an expert looks like:

Step #1: What do I already know about the industry? List all of the existing data points you know about the industry you want to enter into:

  • I have a list of 10 fin-tech companies that are interesting to me

  • I know that being a VP at JPMorgan is not the same as being a VP at a startup

Step #2: What don’t I know about the industry that I want to know?

  • What does a typical startup org chart look like?

  • How do my current skills translate to to jobs in fin-tech companies

  • How does recruiting/hiring work?

Step #3: How can I answer these questions? I could…

  • Audit what I know about the industry I’m currently in so I have something to compare it to

  • Contact + ask questions to alums from my school who work at 3 of the fin-tech companies I’m interested in

Step #4: Who do I already know that could help me?

  • Oh ya, my friend Alex’s friend from college works at Robinhood which I just read about in the news and seems to be growing. 

Step #5: How and when will I contact Alex?

  • We text all of the time, so sending that text right now...

How do I know if the goals I’ve set are big enough, yet achievable?

To understand the usefulness of your goals, you first need to know what overall direction you want to head towards. We refer to this as our ⭐️ north star ⭐️. To really understand your vision, ask yourself, where do I see myself when I’m 80 years old?

  • First, picture it: Where am I living? Who am I with?

  • Second, what’s got me smiling? What am I proud of? What stories do I have on repeat?

Now, back to today and moving towards that vision of your future self. Let’s start with a short term vision, and figure out if it’s achievable:

  • Step #1: What do I want to be doing 6 months from now? What’s my ideal world?

  • Step #2: What do I need to have accomplished in 3 months to be on track to achieve my 6-month goal?

  • Step #3: Specifically, what do I need to accomplish over the next 6 weeks to help ensure I make my 3-month goal?

  • Step #4: How and when will I do the tasks required for my 6-week goal? 

  • Step #5: If you cannot answer #4, then you need to renegotiate your 6-week goal to ensure it is achievable.

 

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.

How to set a goal when the road's not clear

How to set a goal when the road's not clear

At Crabwalk, we aim to help successful professionals move forward. In order to move forward towards something, we have to set a direction for where we want to go.

Without a specific direction, we wouldn’t have anything to measure our progress against and know if we’re actually getting anywhere. The consequence of this is that you’ll likely waste energy, resources, and time flailing in place.

But what if the road’s not clear?

14 ways to virtually nurture your connections, stay motivated, and make any job transition easier

14 ways to virtually nurture your connections, stay motivated, and make any job transition easier

There’s now a big opportunity for more Crabwalking. There’s more time and emphasis being put on connecting with the people that matter most to you. These connections can keep you motivated while also helping with anything happening in your work. Seize the opportunity and nurture your existing relationships, while social-distancing. Here are 14 ideas to get you started, from the comfort of wherever you are quarantining.

How To Keep Moving Forward In Ambiguous Times

How To Keep Moving Forward In Ambiguous Times

Chaotic, ambiguous, and unsure are three of the many ways I’ve heard the current environment, we’re all now operating in, described. Unknowns are all around us and leaving no part of life - health, economic, social - unscathed. We’re each left to sort through the rubble of our individual and collective paths with little data, historical precedent, and more distance between us. We’re all being forced to figure it all out, really fast.

I LOVE to solve jigsaw puzzles, and one of the things I stare at, about every 10 seconds, while solving them is the box because the final picture of the puzzle I’m solving is there to guide me. We don’t yet know what the end of COVID-19 looks like, and trying to predict what the world will look like on the other side of this is likely a waste of time. So, how can we keep moving forward when the path is so unclear because everything is changing all of the time?

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.

Tactical Tips: How to Nurture More Relationships, Faster.

As we’ve shared with you in an earlier blog post, you probably know more people than you think. After spending just a few minutes building your Crabwalk roster, you’ll quickly prove this to yourself. 

What do you do after identifying all of these awesome people in your life? Build and maintain strong relationships with your roster. We call this NURTURING! 

Nurturing everyone on your roster, all the time might feel overwhelming if you are thinking about nurturing each relationship, one at a time. But, what if you could reach 50 people on your roster with a single (not obnoxious) email? Enter the low-tech, super-efficient listserv!

I had the privilege of working under Mayor Michael Bloomberg at the New York City Economic Development Corporation (NYCEDC). In my experience, the public sector is one of the most fun environments to work within because you’re all there for a common cause and mission, as opposed to just a paycheck. My two years there resulted in some of the deepest professional relationships that I have, many of which have blossomed into great friendships too.

Like any organization you move on from, over time you get to watch your ex-colleagues take on new and exciting challenges, and route for each other in a very different capacity than you do while you’re colleagues.

My ex NYCEDC colleagues have gone onto do unbelievable things including working within large tech companies, political campaigns, venture capital funds, policy organizations, nonprofits and, even founding their own startups. They also are no longer all located in NYC, and now I have contacts in places across the country, including Boston, Ohio, Michigan and San Francisco.

Of course, each of us is pretty busy, and even though we have the best intentions, it can be difficult to stay in touch. Becoming frustrated with the amount of effort it was taking to keep track of everyone - my former colleague Matt and I started our very own listserv recently!

In just a week, we have a Google Group of 75 (and growing) former EDCer’s (as we affectionately call ourselves). The goal of our group is to connect, and keep connected, our diverse and talented community. We intend to use the group email forum to post-professional opportunities, cool events (we like happy hours!) and hangouts, political events, and fundraisers, ask for advice, or just say hi and share what we're up to.

Want to set up your own? Here’s how we created ours:

  • Go to the Google Groups homepage here.

  • Click the “Create a group” button

  • Enter the group details:

    • Group Name: “NYCEDC-alumni”

    • Group email address: I won’t tell you ours, but I will tell you that this is a crucial field because this is the email address your entire group will write in the “TO” field of every email they write to the group. So, don’t make it too complicated!

    • Group Description: This listserv was established to foster community and share professional and social opportunities for NYCEDC alumni. Although the group was started by alumni, our community is meant to be inclusive of current NYCEDCer’s plus all the current & former partners who help ensure NYCEDC's success.

    • Group Language: Ours is English

    • Topic types: Ours is just for discussion

    • Posting Option: We allow our Members to post wherever it’s easier for them - by email or on the group website

  • Next, you’ll want to go to “Manage Group” to check your settings and adjust as necessary. We’re starting out in a more watchful way than we intend to be in the future. This means that we’re moderating all messages to the group (i.e., we get to approve each message before it gets sent to the group). You will also want to look through the permissions section and maybe assign a co-owner or manager of the group in “Roles” to share some of the responsibility of managing the group.

  • Then, you’re ready to invite your Roster (!) under “Members” → “Invite Members”.

  • We decided that we wanted to let people request to join (we knew there were people we had missed) but also wanted to control who was joining. You can do this under “Permissions” → “Basic Permissions” → “Join the group” → “Select who can join”. We now are notified when someone requests to join, do a quick cross-check on LinkedIn to verify their identity, and then approve their request to join.

We just sent our first invitation to a group happy hour to celebrate the holidays together. In addition to sending out a note to the listserv, we also sent through a calendar invite so we could track RSVPs. I’m thrilled that I’ll get to see so many of my favorite people in one night!

-Carly