The Break Issue #20: Cultivating Expertise



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​ ​Today’s Break is brought to you by . . .

Owntrail is a community embracing and empowering the windy career pathers. They have tools and support to help you make progress on your own terms. Co-Founder, Rebekah Bastian was recently on The Break Podcast to discuss how she left her high paying job to start Owntrail. Don't miss that conversation at the end of this email.


AND . . .


The Expand Conference 2022 featuring yours truly as a keynote speaker. This conference is put on by my friend Tareka Wheeler, and its packed with amazing speakers. The focus this year is "Leveraging the Power of Focus" and I will be specifically discussing how to use investing principles to Break Your Career. It is November 18 and I hope to see you there.


01 Expertise: The Foundational Source of Advantage



I have a tough time with expertise, I’m betting you do too.


Last week I did an overview of the Advantage Mapping Strategy. I view this exercise as fundamental to choosing what you do and how you spend your time for the greatest chance of success.


In short, Advantage Mapping is integral to designing your work-life.


Deeply understanding where your advantages lie, set you up for success and focus your energy on activities that have the highest odds of success.


This week I dive into the first source of advantage - your expertise.


Why most people struggle to define their expertise


I’ve struggled to define my expertise, and I still do. I’ve met with hundreds of people who feel the same way. Here’s what I’ve learned about why expertise is so elusive:

  1. We overlook our own skills. We tend to think more about what we struggle with than what comes easy to us. In our own head, it’s hard to imagine someone else struggling to understand something that seems obvious to us.

  2. We have imposter syndrome. We compare ourselves to others that seem more “expert” than us. Social media makes it easy to find experts and make a comparison to us and feel bad about our lack of progress. How can we be experts if we don’t have X, Y or Z? We can feel this in a work situation as well, where we question why we’re on this rockstar team full of top performers.

  3. We don’t like to promote ourselves. Try calling yourself an expert in public sometime. It doesn’t feel great because we assume someone out there will come along and poke holes in our “expertise”. Self promotion is very difficult especially for introverts (I am one - INTJ Meyers-Briggs).

  4. We don’t want to feel boxed in. Having expertise in one area can sometimes feel constraining. As a staunch “generalist” I feel this way. I don’t like the idea of being pigeonholed into one space or narrative. I’ve survived by being the exact opposite.

  5. We don’t like the “experts” we see on TV. We see blowhard experts on TV and they seem disingenuous sometimes. We don’t want to emulate them. Everything feels politicized and we don’t want to be “one of those” people.

A helpful description of Expertise that BREAKS these barriers


An Expert is just one step ahead of the people he or she serves.


Expertise is relative.


Expertise is dynamic, not static.


You currently ARE an Expert to someone, and you are simultaneously BECOMING an Expert to someone else.


Let’s not over think it.


If you can solve a problem that someone can’t - you are an expert, even if someone else is better than you at it.


If you have a job, or have ever had a job, then whatever you got paid to do, at a bare minimum, is your Expertise.


Let’s start there.


Your job is to uncover it, name it and own the process of aligning your Expertise with who you want to become.


This took me a long time to unpack with my coach. I had so much resistance to Expertise, and I had to BREAK that construct in order to unlock my natural advantages. It took a long time, and I hope I can shorten that time for you through this Advantage Mapping Process.


Why Expertise matters as an advantage


We live in a world where we can literally do almost anything we want. Our big problems are:

  1. figuring out what we actually want within infinite possibilities (choice overload)

  2. where start

These problems especially plague career changers


So we actually need CONSTRAINTS. The Advantage Map is designed to use our natural skills, abilities and aptitudes as constraints to funnel our creative energy into figuring out how to leverage our starting point to build the life we want.


Our current Expertise is a starting point, that we can leverage for advantage to start making progress.


Right now, you could use your expertise to get a client and become a freelancer.


Or showcase your Expertise to get a better job more aligned with your needs.


This is much easier than deciding to become an “expert” in some other area and starting from scratch. There is no advantage, with the time wasted, it’s actually a dis-advantage.


I'm not saying you should never choose an entirely different path. I’m only looking at this from an odds perspective - by starting from somewhere you have higher odds of finding advantage and leveraging that within your interests to find success.


How to uncover your Expertise when you don’t know it


For some this is an easy process. For others, like me, it’s more difficult. Here are some steps and questions that help:

  1. List the things you know (knowledge)

  2. Ask “What subject could I talk about for 30 minutes without notes?”

  3. Think about what problems or questions to people routinely come to you with.

  4. Mine data and responses from your performance reviews.

  5. Create a google form with questions about your expertise. Send to family, friends, coworkers, and peers, especially if you don’t have performance reviews.

For the last one, here’s the exact questions I used to get feedback from friends, co-workers, bosses and clients.

  1. What do you see as my 3-5 biggest strengths?

  2. What area do you consider me to be an expert in?

  3. What do you think I should be truly known for in my work?

  4. What is unique or refreshing about my approach?

  5. Is there a specific moment that sums up my strengths?

  6. What do you need to see more of out of me in the next 3-6 months?

How to apply Expertise in the Advantage Map


The expertise exercise is best done freeform. Take out a sheet of paper, or create a blank document that you can link inside of your Map. Use that white space to journal, or bullet point out your responses to the questions above.


Create a feedback form, and add the feedback to your page.


Then, once you feel like you have enough perspectives, start to notate or pull out common themes/responses.


Add those to the box in your Advantage Map, where we will start to combine those insights with your insights to the other sources of advantage in the coming weeks.


Whenever you're ready, 3 ways I can help you:


1. Get in the Breaking Work conversation on Linkedin. Messages are open. Follow me here.

2. Find your new job! I curate remote first tech jobs for you. Follow me on Pallet.

3. Promote your brand/business to 14k+ subscribers by sponsoring our newsletter contact partners@rejoinmedia.com (Booked out 4 weeks)


The Break Job Board


I teamed up with Pallet to create a curated job board for our community! These jobs are tech focused, remote first opportunities. I’d love it if you followed. Maybe, just maybe you’ll find your next big opportunity here.


Here are a few featured opportunities:

Also, If you’re looking to support the community and have a job to post, you can do so by clicking the ‘Post a Job’ button.


What’s happening on the pod?


Rebekah is a creator. She’s created a startup, a tech movement, a book, multiple written, visual and aerial art pieces, and two humans. She is the CEO & co-founder of OwnTrail and was previously vice president of product and vice president of community and culture at Zillow. Rebekah is the author of the award-winning book Blaze Your Own Trail, a board member of JPEG Morgan and Bellwether Housing, a contributor to Forbes and an investor and advisor to AuthenTech and Web3 companies.


Here's my Owntrail! Take a look at my windy career path and drop me a line.


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