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Become the Hero of Your Story
Steal My Playbook To Crush The Inevitable "Tell Me About Yourself" Question

Happy Saturday Everyone! 👋
Welcome back to the UpEmployment newsletter.
We’ll help you get more dream job offers faster and with less stress each week.
Last week I asked LinkedIn which job-hunting skill they most wanted a step-by-step guide for.
The #1 skill you chose was crafting & telling your story.
This skill always comes up as one of the top 3 pain points whenever I survey job hunters.
I will give you my formula for crafting a compelling story using your background that will have your audience at the edge of their seats.
As with many things, the secret is not to develop a brand-new system from scratch.
But instead, to use tried and true methods and formulas.
In this case, a formula that has been refined and used for tens of thousands of years.
Why Care About Storytelling?

45k-year-old painting of a wild pig found in Indonesia. Photo by: Maxime Aubert
Storytelling is all about connection and communication.
It’s not something that came on the scene recently.
It’s an ancient and primal ability that sets humans apart from other animals.
The painting above is believed to be the oldest painting in history.
The painting depicts three warthogs, two fighting and one watching the fight.
It was discovered in a deep limestone cave in Indonesia and has been dated to be over 45,000 years old.
To put that into perspective, it’s believed that Neanderthals (our cousin species) went extinct 40,000 years ago.
That means they walked around for another 5,000 years after this painting was created.
The pyramids wouldn’t be built for another 40,000 years.
And the pyramids are over 4,500 years old today.
We have been storytelling for a long, long time.
The fact that we have been engaging in this behavior for such a long time means that it is tied somehow to our ability to survive.
It’s likely the way humans were able to collect into groups larger than 150 people.
How did homo sapiens manage to cross this critical threshold, eventually founding cities comprising thousands of inhabitants and empires ruling hundreds of millions? The secret was probably the appearance of fiction. Large numbers of strangers can cooperate successfully by believing common myths.
And like all human abilities, we have developed and honed this skill over tens of thousands of years.
The Art of Storytelling.
The 4 Benefits of Good Storytelling
Storytelling is engrained in our DNA, but what’s it good for, and how will it help you with your job hunt?
There are 4 major benefits of good storytelling.
Build Confidence In Yourself
Every interview starts with, “Tell be about yourself.”
Every networking conversation will eventually lead to, “So catch me up on what’s been going on with you and where you are.”
Your ability to paint a compelling but concise picture that tells the story of your journey, your past, present, and where you are going in the future is critical for these interactions.
It will build self-confidence if you tell a gripping, well-rehearsed story with you as the hero in the center.
Self-confidence is sexy.
Self-confidence gets you hired.
Builds Empathy And Connection
Everyone loves an underdog.
Why?
Because at some level we see their struggles as our own.
The more vividly you can paint the trials you overcame and how they allowed you to grow, the more empathy you will create in your listeners.
With empathy comes a deeper connection to you and your mission.
Connection builds relationships.
Relationships get you hired.
Leave A Lasting Impression
I have interviewed hundreds of people.
Most people suck at storytelling.
I sucked at storytelling.
You'll be forgettable if you don’t tell a good story about who you are.
Recruiters, interviewers, and hiring managers review hundreds of resumes and speak to dozens of candidates.
The ones that rattle off their resume point by point are easily forgotten.
The ones that bring you on a journey showing you how they have become the person they are today, their wins, losses, what they learned, and the compelling future that involves our company get remembered.
Forgetable candidates get automated rejection messages.
Memorable candidates get hired.
Let Your Personality Shine
As a hiring manager, all the candidates start to blur together at some point.
At Uber, I remember interviewing the same person over and over again.
Different faces, same person.
The people who really stood out showed their personality.
Identifying their values, what they cared about, what kind of energy they would bring, and who they were outside of work was easy.
Showing your uniqueness makes you stand out from the crowd.
Standing out from the crowd gets you hired.
Alright, we get the benefits but how do we actually tell the story?
The Hero’s Journey
In 1949 a man named Joseph Campbell wrote a book called “The Hero with a Thousand Faces”.
In the book, he described a theory he called, The Monomyth.
Joseph Campbell was a literature professor fascinated with myths and legend narratives from around the world.
After studying stories from all the ancient and modern traditions, he made a discovery.
Regardless of where the story came from, they all used the same pattern.
Campbell called this the Hero’s Journey, and it goes something like this…
The Hero’s Journey is the story of a woman or man who, through great suffering, reached an experience of the eternal source and returned with gifts powerful enough to set their society free.
Look closely at the story of your favorite Hollywood movies or bestselling books, and you’ll see the same pattern.
Neo, Luke Skywalker, Harry Potter, Katniss Everdeen, Wonder Woman, and You all have the same general story.
You can use the Hero’s Journey framework to help you answer, “Tell me about yourself.”
The 12 Stages Of The Hero’s Journey
The Hero’s Journey has 12 stages.
The Ordinary World
The Call of Adventure
Refusal of the Call
Meeting the Mentor
Crossing the First Threshold
Tests, Allies, and Enemies
Approach to the Inmost Cave
The Ordeal
Reward (Seizing the Sword)
The Road Back
Resurrection
Return with the Elixir
I’ll now walk you through a step-by-step exercise you can use to craft your long-form Hero’s journey.
By shortening that story to less than two minutes, you can create a compelling personal story for your interviews.
Your Hero’s Journey Exercise
Grab your phone, open your timer app, and set the timer to 2 minutes.
Open an epic playlist to listen to as you craft your story (you can use this one I created).
Spend two minutes applying your story to each of the stages.
Once you have finished all 12 stages, condense them into a version that lasts less than 2 minutes.
Here is my condensed version sub-2-minute version.
“My name is Kyle Thomas. I spent the last decade building hyper-growth startups. I was one of the earliest employees at Uber, and over the course of 7 years at the company, launched and grew new markets and new products from 0 to over $300M in ARR. I have used that real-world startup MBA experience to help the next generation of startups with their operations and growth strategy. I'm now building a startup of my own called UpEmployment. After seeing the lack of progress in the systems, tools, and advice given to job seekers despite a significantly changed landscape it's now my mission to eliminate the anxiety, disorientation, and loneliness of the job search and replace it with motivation, clarity, and connectedness. I'm building the company to help millions of job seekers build an easy-to-use playbook for career success.”
There you have it, my easy to execute formula to tell your story in a compelling way.
You can use my Telling Your Story playbook to fast-track you from storytelling rookie to confidence storytelling champion.
Let’s become career champions together 🏆
Kyle
P.S. Whenever you’re ready, there are 3 ways I can help you:
#1: Free Job Hunt Strategy Call: Request a free job hunt strategy call with Kyle to get closer to landing your dream role tomorrow. On our call, we will walk through your vision and how to make it a reality, cover the obstacles standing in your way, and help determine the best next step for you to take based on your short-term and long-term goals. Schedule a call today!
#2: Want the proven playbook to get more dream job offers in less time with less stress? Discover how to build a proven system to land your dream job in a matter of days.
#3: Follow me on LinkedIn for more job hunt systems, productivity tools, and networking templates.
💎 Job Op of the Week 💎
Each week I’ll highlight a different job opportunity I think is cool and give tips for how I would approach getting into the role.

This week we have the VP of Operations position @ brightwheel.
What the company does: brightwheel is a childcare management software. They empower daycares and pre-schools with the infrastructure they need to communicate with parents, their staff, and run their business.
Why is the role awesome: You’ll develop and refine the internal systems and metrics to run the company. You’ll also be in charge of providing an exceptional customer journey from initial interaction through the full lifecycle of the relationship. Finally, you’ll be the lead on creating operational goal-setting for the company which will dictate future company success.
Why is the company awesome: The company is the #1 software used by childcare facilities in the US. My kids’ daycare uses it and I don’t know what we would do without it. Plus the founder is awesome. He brought the company to Shark Tank and got a deal ($600k for 6.67%) from Chris Sacca and Mark Cuban. Since then, the company has been crushing it.
How would I approach getting in: I would watch videos (like these) and listen to podcasts (like these 1,2) to get as much information as possible I could about the company and the people that work there in their own words.
I’d then reach out to the Operations Team I would be joining as well as the other company VP’s with a personalized LinkedIn connection request message and email. From those conversations, I would look for areas of pain that I could alleviate immediately using my prior experience.
Ex: Go through the customer journey, interview existing customers, draw out pain points, put those into a presentation for the company and share it with the other VP’s as well as the executive leadership team at the company.
Apply for the job here and DM me on LinkedIn, mentioning this newsletter, send me your resume, and I’ll forward it to my connections there.
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