How to Write Your Own Dream Job Description

Happy Saturday y’all 👋

This newsletter is designed to land you more dream job offers in less time and with less stress.

I hope this week treated you well. It has been a whirlwind for me and my family. But I’ll share more about that at the end.

Before I dive in, I wanted to share one thing with you.

I’m running a masterclass next Thursday, 2/23, at 7:30 pm ET, 4:30 pm PT.

I’ll dig into the first critical phase of your Dream Job Hunt and provide actionable exercises to cut through your uncertainty and anxiety and catapult you toward your dream job.

This phase led me from unemployment to a 6-figure raise and an executive role at a well funded Y-Combinator startup.

It’s also led students in my UpEmployment Program to get laser-focused and land dream jobs in as little as 30 days of starting these exercises.

I’ll also be sharing the UpEmployment Playbook (a $149 value in itself), so make sure to attend live! >>>CLICK HERE TO REGISTER<<<

It’s All About The Clarity Baby

In case you missed last week’s newsletter (you can read it here), I gave a high-level overview of the 5 phases of a successful job hunt that will all but guarantee you land a dream role.

Those phases are:

Phase 1 - Clarity

Phase 2 - Confidence

Phase 3 - Connection

Phase 4 - Creation

Phase 5 - Competition

But, while there are 5 phases in the process, the first and most critical phase is Clarity.

Why?

Let’s say you were stuck in the middle of the woods, and you knew there were lions, tigers, bears (oh my!), quicksand, and mirages all around you.

But you also knew that somewhere in that forest, there was a magical city with a magic lamp that could make all your dreams come true.

As your first step, which option would you choose?

OPTION 1: Run straight into the woods and zig-zag in different directions.

OPTION 2: Pull out your satellite GPS and get pinpoint precision accuracy on where you are, where you are going, and the turn-by-turn path to get there."

“I’m not crazy Kyle! The right option is clearly Option 2.”

You’re right!

Now, why doesn’t your job hunt reflect that obvious decision?

The key to any job hunt that results in a dream role is the hunter’s ability to do these things:

1. Identify where you have been

2. Identify where you are now

3. Define where you want to go

4. Identify the gaps between where you want to be and where you are now to create a Dream Job Description

5. Hunt for jobs that will check off most, if not all, of the boxes that would eliminate that gap.

We covered steps 1 - 3 last week so we’ll dive into creating your Dream Job Description now.

But before we do, I’ll tell you how I figured this out the hard way.

Finding Out The Hard Way

In college, I bounced from major to major as I tried to figure out who I wanted to be when I grew up.

From pre-med to international studies to business, and finally ending with economics I switched every year or multiple times per year.

The truth is, I didn’t know what I wanted to do.

Mid-way through my senior year, all my friends in the business school had jobs at the big four consulting firms.

I had nothing but a pile of rejected online applications.

But, through a networking technique I developed as the President of my fraternity, I was able to snag an internship in Washington, DC, in the United States Senate.

I would be working for Senator Richard G Lugar from Indiana.

He was one of the most tenured Senators in the government and a guy that worked hand-in-hand with people from both parties, including then-Senator Barack Obama on denuclearizing Russia.

Safe to say, Senator Lugar was an incredible leader to be around and a certified grade-A badass.

My living setup in Washington, DC was like something out of reality TV.

A girl from Alabama, a guy from Connecticut, a girl from Ohio, a guy from New York, and me, a guy from Washington state, all packed under the same roof and working for different politicians from different parties.

My days at work were just as surreal.

I was given full access to the belly of the Senate offices and the US Capitol building.

I walked through the halls and underground corridors, running into political legends that were regulars on the news or imitated weekly on Saturday Night Live.

It was like a US history Disneyland.

But, as the summer came to a close, I realized I didn’t like my work in the Senate office.

There wasn’t any formal sit-down where I looked over what I did and didn’t like about DC and the job.

I was doing a lot of informational research and briefs that didn’t result in any immediate action and realized that if I stayed in DC, there would be much talking about doing things and no actual doing.

I wanted to be the one executing and building the future.

So, after 3 months in the Virginia summer heat, I packed my bags and headed back to Seattle.

I knew I wanted to be in business but didn’t take the time to figure out what that meant.

The result…

The NEXT Job

I took the first job opportunity I was offered.

I joined a large global freight forwarding company.

It sounded sexy… to me at least.

Offices around the globe moving products from the world’s biggest companies by land, sea, and air.

The reality was far less inspiring.

I would be a Customs Brokerage Representative.

That meant I would sit in a cubicle in a gray office outside the airport in a suit and tie and manually enter data from a piece of paper from the shipping company into an old computer system.

The company didn’t inspire me, the environment was old school, and I didn’t see myself wanting to be like anyone above me.

All of those are terrible signs.

I stuck it out for two years, trying to make the most of the opportunity, but after being rejected from the management trainee program for the third time, I told myself enough was enough.

I was so unhappy with my job and the lack of progress I saw in my life that I committed to making a change.

Lots happened over the course of the next year but in the end, I quit my job in Seattle and moved across the country to live with my long distance girlfriend in New York City.

Arriving in New York City, I better understood what I DIDN’T want but hadn’t figured out what I DID want.

My list of things that I wanted to avoid was:

• Working in a cubicle

• Wearing a suit and tie to work every day

• Doing data entry

• Working in an old-school, slow-moving industry

That narrowed my focus ever so slightly but didn’t provide the direction I needed to have a quick and successful search.

If you look at the list above, thousands of jobs and professions fit into those categories.

As I navigated my new environment, I interviewed for roles in hospitality, marketing, recruiting, and sales, just to name a few.

All of these things were so different, scattered, and unfocused that I couldn’t create a clear picture of the value I would bring to them or why I wanted to work for them in the first place.

After three months, it felt like I hadn’t made any progress because I was moving in a million different directions.

That’s because I didn’t have the playbook I’m giving you now.

How To Identify The BEST Job

What happened next opened my eyes to the right way to job hunt.

I was running out of money and about to take a job selling domain names (a decision that almost cost me millions of dollars).

While I waited for the company to complete my background check and give me an official start date, I got a text from a guy I went to grade school with.

He had an hourly gig that would pay me $25/hr if I was interested.

The Temporary Work: Filling a backpack with marketing palm cards and walking up and down the aisles of the airport taxi lots selling to taxi drivers.

That doesn’t sound too exciting, right?

In fact, my roommate was looking for a job and I asked him if he wanted to come with me.

He said no.

He wasn’t willing or interested in walking up and down the baking concrete outside the airport.

I was, but there’s a reason why.

The Company: Uber

Seattle had been one of the first markets Uber had launched and it fundamentally changed how I got around my city.

I fell in love with the product and was a die-hard evangelist from day one.

So when presented with the opportunity to do anything for the company, I jumped.

I would have shoveled shit if it meant a slight chance I could get my foot in the door.

I didn’t know it then but that attitude is the difference in landing the BEST job and not just the NEXT job.

The only way you can feel the willingness to do whatever it takes to get a job and enjoy the process is to be passionate about the company, the industry, the mission, the people, and where that role will take you in your career.

That’s why I was willing to take that gig without question.

I was passionate about the product.

It was clear that they had a need.

I was quickly and willingly able to fill that need.

I had the hunger and hustle to grow, evident in every interaction I had with people at the company.

Taking that temporary hourly gig landed me a job as Uber’s 250th employee in less than a week.

A Better Way

Focusing on what I didn’t want landed me a job at Uber.

But there’s a better way.

The better way is to understand what you don’t want but optimize for what you do want.

What you do want is a role that will accelerate you toward the person you want to be in 2 to 5 years.

You want to be able to laser focus on the companies, roles, skills, and experiences to target in your next position.

If you’re able to do that, it will do two things.

1. Allows you to build a compelling story about your background, knowledge, and ability to impact a specific set of companies, industries, or roles. This will help you focus your job hunt.

2. It gives you a specific description of what you’re looking for when you’re networking, allowing more people to help you.

Back to my story quickly…

Fast forward 7 years of growing the Uber business.

The world was in the early stages of the COVID-19 pandemic, and Uber’s e-bike business that I was working on didn’t make sense for the company’s overall finances.

They sold the division, and everyone was let go.

Once again, I was on the job hunt, determining what I would do next.

This time, however, the student had become the master.

I went through the exercise of laying out what I liked about the roles I had in the past and what I didn’t like.

I looked deeply at when I was the most effective at Uber and when I enjoyed the work the most.

I took stock of what I had done in the past and who those skills and experiences could best serve.

This allowed me to get very specific.

What I landed on:

• I’m looking for a company that is… a Series-A to Series-B consumer-based business with a heavy operational component in the physical world looking to scale rapidly due to increasing demand and whose mission I’m passionate about.

• I’m looking for a role that is… the Head, Director, or VP of Operations.

• I’m looking for an experience that… will allow me to drive the strategy of the operations department, report to the founders, and give me a seat at the table with the overall company strategy and exposure to fundraising.

• I’m looking for pay that… is $200,000 salary with relevant equity.

• I’m looking for a work environment that… doesn’t require me to be in the office all the time.

   

• I’m looking for a team that… is full of A players and founders with a track record of excellence.

Why were the above items vital to me?

I had identified that my ideal self in 2 to 5 years was the COO or founder/co-founder of a company.

When I compared the future version of myself with who I was today I identified specific gaps.

Future me had:

• Experience managing an entire operations department.

• Experience hiring people and designing an organizational structure to scale.

• Experience building the operational infrastructure necessary to scale the business.

• Experience with the venture capital fundraising process.

• Learned from founders who had started the company from scratch and raised millions of dollars.

• Built a strong network of founders, entrepreneurs, and startup executives.

• A salary over $200k.

I had gone from knowing what I didn’t want to having a crystal clear image of the role I wanted and where that role would take me.

Within less than 3 months of job hunting, a former manager and mentor connected me to an opportunity that checked my top priority boxes.

I took the job and started scaling their operations through the pandemic.

To be clear, the role didn’t check every box, and a role rarely checks off every desired box.

That is why it is essential to write down what you want and rank each aspect of the role.

Do you value remote work and are more flexible on pay or title?

Do you value the company’s mission and contributing to that more than the scope of your role at the company?

Each person has different priorities at different times in life and at different points in their career.

Knowing what you want and where each item you want ranks will allow you to focus your job search and make it far easier to decide when you receive an offer.

If, in a discovery call or phone screen, it comes to light that none of your top three categories are met.

Move on.

Suppose one company can offer you three of your top four priorities and another can offer 5 of your top priorities.

In that case, you will already have a framework to make your decision.

How To Craft Your Dream Job Description

We’ve arrived at the fun part.

The part where you get to take action and start your job hunt on the right foot.

Using this Dream Job Description you can sprint towards a role that will have you waking up each day on fire and saying, “I can’t believe I get to do this.”

Pull out your prior role analysis and your no-BS self-assessment (you can find those exercises here).

Grab a sheet of paper or open up a document.

On the blank page, write down the following:

• Job Type

• On-site/Remote/Hybrid

• Location

• Industry

• Job Function

• Title

• Company Stage

• Salary

• Benefits

• Company Mission

• Experiences Provided

• Skills Provided

• Teachers Provided

• Network Provided

• Other

• Ideal Companies

Now do the following.

Future You + No-BS Self Assessment: Use the description of the future version of yourself and your no-BS self-assessment to identify the gaps in skills, experiences, teachers, and network you’ll need to fill to become that person.

Prior Role Analysis: Use your prior role analysis to identify the type of environment you work best in.

Write out the details for each of the Dream Job Description Categories that correspond to the role that will fill the gaps between you now and you in 2 to 5 years.

Job Type: Full time, part time, contract, temporary, internship.

On-Site/Remote/Hybrid: Which type of work would be most ideal to your working style and the person you want to become?

Location: Where do you want the company to be located? Is there anywhere you don't want the company to be located?

Industry: What is the industry you want to work in? You can include up to 3-5 but we'll want to get as focused as possible to make your targeting easier.

Job Function: Management, IT, Product Management, Product Management, Marketing, Manufacturing, Sales, Strategy/Planning, Consulting, Operations, Customer Support, Growth, etc. What sandbox do you want to play in?

Title: What’s the ideal title you’re shooting for?

Company Stage: At what stage is your ideal company or a company that will give you your ideal opportunity? Seed, Series-A, Series-B, Series-C, Series-D+, Publicly traded, well-established but privately held.

Company Size: How many people work at your ideal company? 1-10, 10-50, 50-100, 100-250, 250-1k, 1k-2k, 2k+. Remember, typically, the smaller the company the more exposure to more skills and the closer you get to the executive leadership.

Salary: What number would make you say, “hell yeah!”.

Benefits: What type of benefits would your ideal company and role provide? These can be cash or non-cash benefits.

Company Mission: Is there a company mission you want to work on (ex: environmental sustainability)? What mission are you most passionate about solving? What will you not shut up about when talking to your friends?

Experiences Provided: What is your “future self” experience gap? What have they done that you need to have experience doing?

Skills Provided: What is your “future self” skills gap? What can they do that you need reps in and an understanding of?

Teachers Provided: Who is the best teacher to take you to where you want to go? Who or what type of person has been there, done that, and can show you how?

Network Provided: What is your “future self” network gap? Who do they know? In what industries and at what levels?

Other: Add anything else that would be part of your dream role that isn’t mentioned in the categories above.

Ideal Companies: Use all the details above to create a list of 10-15 dream companies that match the criteria of the company-specific characteristics above.

Prioritizing

Now that you have your list of characteristics prioritize them.

Why?

You’ll have multiple weekly or possibly daily offers when you do this process right.

You don’t want to be judging those opportunities on the fly.

Instead, prioritize each of the different characteristics from 1 to 5 (1 being most important and 5 being least important).

Different people will prioritize different things and that’s ok.

If you’re about to have a baby you’ll likely want to prioritize health benefits and some sort of parental leave.

If you want to learn everything you can and are financially stable maybe teachers and skills are number 1 and salary and title drop down the list.

However you want to prioritize the characteristics is up to your discretion and your stage in life but be thoughtful about it.

This will act as your grading checklist for any offer you hunt for, find, or are presented with.

The Final Output

When done correctly your Dream Job Description will go from…

To…

See the difference?

I cannot overstate the power this clarifying Dream Job Description will have on your job hunt and how critical it is to land a dream job.

What Comes Next?

Getting the first phase right is critically important to land more dream job offers faster and with less stress, so don’t skip it.

The next phase is taking this Dream Job Description and using it to get rock solid confidence in who you are and where you’re going.

That means knowing your salary, crafting a killer story, and optimizing your digital reputation on LinkedIn.

For those, you’ll have to come back next week!

We could go even deeper into the Dream Job Description (and I do in my UpEmployment Program) because of how important it is to set up your job hunt for success, but we’ll stop there for today.

In the coming weeks, we’ll dive deeper into each of the 5 C’s and the systems, tools, templates, and case studies that will lead to more dream job offers in less time with less stress.

I’m excited to share everything I have learned over the last 12 years and go on this journey with you!

Let’s become career champions together 🏆

Kyle

P.S. Whenever you’re ready, there are 3 ways I can help you:

#1: FREE Creating Crystal Clarity Masterclass: I’m hosting a free masterclass to dive deep into creating dream job clarity and starting your 90-Day Dream Job Hunt the right way. Save your spot today!

#2: Want 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 here.

#3: Follow me on LinkedIn and Twitter 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 awesome and give tips for how I would approach getting into the role.

As I said at the start of this newsletter, this week has been a whirlwind. On Wednesday, I took on a new Job Opportunity as Dad of three as my wife and I welcomed our third child into the world.

What the company does: The boss pees and poops in his pants and screams at you.

Why is the role awesome: You’re responsible for the life of another human. The most rewarding job you can ever have.

How would I approach getting in: So when a man loves a woman they… I’ll spare you the details.

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