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

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!

Is waiting for your dream job worth sticking out a bad one? 3 steps to clear things up

I applied for a job that isn’t in my dream industry (wildlife / animal rights), but it would get me out of my current job. I honestly really hate the job I'm in now, but I'm unsure of whether I'd be able to laterally move out of this new job I'm applying for. The job I'm interviewing for is for accessibility at a nonprofit university. Timeline wise, if I got an offer it would be before I'd really had a chance to search for wildlife opportunities, so I guess my question is whether you have any advice on whether waiting is something advisable? — S.T., Utah

Carly and I got this question a couple weeks ago in one of our Accountability Group Q&As.

If you’ve already done the work to figure out what you definitely want to go in a certain direction — whether that’s industry, job title, city, etc. — and you hate your current job, do you hold out for a dream job or do you get something in the interim to get out of the job you hate?

On one hand, if you take the interim job, you’ll be out of the toxic place and have new energy to put towards a job search. A toxic job can leave you depleted in energy and with a bruised ego that makes it harder to job hunt with confidence. Plus, you might actually like the interim job and it could make your resume more appealing to your dream job.

On the other hand, you might think you’re sabotaging your chances of getting your dream job by looking uncommitted on your resume, or by going in a direction that's hard to explain. Plus, it can feel like settling for something not good again which is the very thing you’re trying to move away from.

In all cases, our biggest tip is to clarify where you’re trying to go, assess both options, and make a choice that’s in the right direction.

Here are 3 steps to take when deciding whether or not to take an interim job. Grab a piece of paper and a pen and try it out!

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Step 1: What have I learned about what I want in my work life next?

Write out your answers here. Keeping all the thoughts in your brain alone can make feel like you’re pinballing around. One minute you feel really sure you want something, and the next you find a reason why it might not matter. To help stop the pinballing, write out your criteria. You can do this in whatever form helps you get organized - that can be a journal, a spreadsheet, on visual board on your wall, etc.

• What do I know about what I want in a new job?

• What do I know I do NOT want in a new job (deal breakers)?

• What are still open-ended questions I have?

Step 2: How does taking this interim job align with what I want next?

If I take this job....

• Which of my criteria would it meet?

• Of the criteria it doesn’t meet, is there anything I can do to fill the gap? This could be asking for more responsibilities in the new job, or finding opportunities outside of work to meet that need (e.g. taking class or doing a side project)

• If I take it, how would that set me to get the job I actually want down the road? PRO-TIP: Fast forward one year from when you’re talking to a recruiter or potential employer at my dream job … what would my narrative be about who I am, and how this experience equipped me for the dream job?

• What would my job search process be 6-12 months from now if I wanted to make the move then? Would I be in a better position to search then either (e.g. mentally, financially, time-wise, location-wise)?

Step 3: How would not taking this job benefit me?

If I don't take this job…

• What does an ideal candidate look like for my dream job … what do I already have in place and what’s missing?

• What would I need to put in place to fill any gaps I have?

• What other job opportunities would I have that could be cool if my dream job wasn't immediately available or achievable?

Think about these questions to create some clarity around your two options. See what comes up, what your gut tells you, and what sounds most realistic.

I always think it’s better to caution around running away from a job versus running towards something, but that doesn't mean you have to wait around for the perfect job. Just make sure you're at least running mostly in the right direction.

Top Accountability Program Questions Answered

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:

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 use “weak ties” to get your next job

Basically me, going back and forth to NYC for job interviews in April 2012.

In April 2012, I (Laura) was yet again riding Amtrak back to DC after two straight days of exploratory chats and interviews in NYC. 

I checked my inbox and had gotten an offer for my first startup job: General Manager at HowAboutWe (a now defunct dating site).

My interview didn't come from a job board or my business school network. It came through a connection made by a high school friend I hadn't talked to in over 5 years.

Every job opportunity I've gotten has come from a connection, even if it wasn't a strong one. Turns out weak ties are the way to go.

Here are some tips for how to find your next job by nurturing weak ties in a way that feels authentic to you.

First, the start with the basics:

What’s a “weak tie”?

Weak ties are the people you’re loosely connected to through any activity in your work or personal life. Here’s how they’re described by Allie Volpe for the New York Times.

Think of the parents you see in the drop-off line at school. Your favorite bartender. The other dog owners at the park. The sociologist Mark Granovetter calls these low-stakes relationships “weak ties.” Not only can these connections affect our job prospects, they also can have a positive impact on our well-being by helping us feel more connected to other social groups.

Why are my weak ties important for finding my next job? Let’s talk about pie.

Imagine the jobs you know of only represent 2 pieces of the pie. If you don’t think your dream job exists, go looking in the other pieces of the pie.

Do you know exactly what you want to do for a living? Are you clear on the job you’re hunting for? If yes, congrats! That job search might be tedious but it’s helpful to know what you’re hunting for.

For so many people, the answer is a sheepish “no.”

If you haven’t been inspired by the jobs around you, chances are part of what’s holding you back is not having a model that resonates with you. Someone, doing something that seems realistic and inspiring to you.

If you’re only exposed to your immediate circle of friends, you’re only going to see the jobs that are in front of you. The ones your friends have, the ones that pop up on LinkedIn or get pushed to you by your career counselor.

Consider this your piece of the pie, combined with the piece of the pie your friends and co-workers know. The rest of the pie is unknown to you, for now.

If none of those jobs sound appealing, you have to broaden your view. Get a new perspective. See how the rest of the world works. What’s happening in all the other slices of the pie?

There are likely dozens of jobs out there that you know very little about, but that could bring you joy. That was the case for me.

When I started as a coach, all I knew was that I wanted to learn how to coach. I come from an operations background and love doing puzzles. Solving problems is my jam.  After 14 years of working to solve business/operations problems, I wanted to learn how to help individuals navigate their own challenges.

At the time, being a coach full-time seemed insufficient to make a living and totally out of left field in a way I couldn’t explain to people. No one in my immediate circle was a coach, or even had a coach. So I had to do some exploring. One of my first connections was through my CFO at my last startup, a wonderful friend and colleague named Chris. Over drinks, he mentioned our CEO who I had worked with for 2 years had recently hired a coach, paying him/her a not-cheap retainer. Both Chris and my former CEO, two people I respected, spoke highly of a successful coach. It put this whole coaching thing in a very appealing new light. This career became that much more realistic.

You can get exposed to new jobs by having conversations with people who run in different circles. Through your weak ties.

Where do I start to connect with my weak ties?

Start by identifying one thing you know you like (e.g. working for a particular cause like the environment or animal rights). Then look at all the people who you’ve ever been in contact with. Through sports teams, your alma mater, school programs, etc. Does anyone have a connection there? Could anyone make a connection for you?

What if I haven’t talked to these people in 5 years?

That’s A-OK. You can still reach out. Just acknowledge the passing of time and be earnest about it. One example:

“Hey Jon!

It’s been so long! Last time we talked you were in SF working for AirBnB. Still there? How are things?

I’m reaching out because I saw you’re connected to ASPCA. It’s an organization I’m really interested in getting involved with. I wanted to see if you had 20 minutes to spare to chat through your experience with them. If it’s not a good time, I totally get it. It would be good to hear updates either way.

Hope you’re well. — Laura”

In the meantime, start nurturing your connections with more intention to make these conversations even easier.

How can I nurture my connections with weak ties?

What is nurturing?
Nurturing is a series of touch points with someone. The goal is to know what's going with each other, e.g. where you are today and what you're looking to do next. Once you have the info, you'll be in a better position to help each other out in a mutually beneficial way.

Who should I be nurturing?
Anyone you've ever connected with could be worth nurturing if you think they could be helpful to you and you to them. You already know a ton of people, even if you don't believe us (yet). You know all of your current and past colleagues, friends you play soccer with (or whatever else), book club friends, neighbors you grew up with, friends of friends, your family friends ... you get the idea. All of these are fair game, even if you haven't talked to them in 10 years. 

How should I be nurturing?
Not all relationships are created equal. Your nurturing activities may be different by person. Think about "what type of activities do I already do to maintain relationships?" and "what types of activities do I hate doing?" "What feels most appropriate or natural for this person and for me?" Find a nurturing style that works for you (there are lots of ideas below).

Do I have to get coffee with everyone?
Nope. You might love to get coffee chats, or grab drinks, or have a Zoom catch-up over breakfast. These 1-on-1 connections can be meaningful and useful. However, they're not the only option. Let's check out group nurturing...

What is group nurturing?
It means a touch point that goes to many people, so you get the most bang for your buck. You likely already do this in your WhatsApp groups, text chains, when you’re throwing a dinner party, when you’re sharing an update on LinkedIn, when you play a game of soccer with your friends...etc.

Want to download our checklist on how to nurture connections with weak ties?

What are some of your favorite nurturing ideas?

Sometimes the hardest part of nurturing is deciding on how to nurture your connections in the most effective way. And often if we get stuck at this point, it can lead us to getting stopped altogether.

All you need is a touchpoint that works for both you and them. Here are some of mine and Carly’s favorite nurturing ideas:

Virtual Nurturing Ideas

• Send a postcard

  • Collect vintage or unusual postcards on your trips or in flea markets and send them whenever it strikes your fancy.

    • My sister regularly sends postcards, whether she’s traveling or not.

• Send a mass letter to celebrate around:

  • Holidays

  • Birthdays

  • Work anniversaries

• Send a mass email announcements because you:

  • Are graduating!

  • Had a life event - got married, had a child

  • Change of address - work or personal

  • New business card

  • Want to give a semi-annual update on your new business

• 1-on-1 “thinking of you” emails:

  • Share an article that you think is useful

  • Invite them to an event that you're going to

  • Send something relevant to them that made you think of them

  • Just saying hi

• Send a text:

  • A gif

  • TikTok Video (some good ones)

  • Medium article

  • A relevant tweet

Ways to nurture more than one person at once

• Organize an event:

  • Happy hour

  • Group activity

  • Game night

• Invite them to an existing event:

  • Work event that you're hosting

  • Webinar that might interest them

  • Virtual or real life trivia night

• Attend an industry event:

  • Conference

  • Party

  • Meetup

• Invite friends on social media, in online groups, or on your sports team to read a book alongside you, especially one that’s topical (e.g. How to be an Antiracist by Ibram X. Kendi)

1-on-1 (these can be virtual or in-person)

• Coffee

• Lunch

• Drinks

• Dinner

• Go for a walk

• Co-work together

• Do an activity together (e.g. exercise class, summer concert, museum)

Want another way to strengthen weak ties?

Join our 5-week career accountability group. You’ll meet others navigating their own career journey and get coaching from me and Carly. We’ll share proven tips to get you moving, feel clear-headed, accomplished, and energized. Join us!

Are we missing your favorite nurturing tip? Share!

Comment below or email us (hello@thecrabwalk.com) and tell us!

If you liked this blog, check out some of our others on the topic of nurturing:

• 14 Ways to Virtually Nurture your Connections 

• Tactical Tips: How to Nurture More Relationships, Faster

• Easy Ways to Nurture your Connections Over the Holidays

Want to download our checklist on how to nurture connections with weak ties?