How to Choose a Career that You’ll Love (The Dream Job Blueprint)

Q: How do most people choose a career?

A: They don’t. They stumble into a job after college, take whatever they can get, then follow one of the few paths available from that random job.

No wonder most people are frustrated in their careers.

There is a better way to choose a career. My Dream Job system lets you explore all your interests to see what you really like, then it helps you find career paths built on those interests.

The most important thing you can do to finally find your dream career is to get curious. I’ll explain what I mean by showing you my “window shopping method” below.

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How to choose a career: The “window shopping” method 

Try this: Google “Which career is right for me?” and you’ll probably get results like this:


Do you really think there is a magical test that can tell you exactly what career you should have? Three clicks and then, “Oh, I’m supposed to be an orchestra conductor!” Gimme a break.

The smarter approach is to explore ALL the careers you’re interested in, test each to see if you’d really enjoy doing them, and move on to other jobs if they’re not a good fit.

It’s kind of like window shopping at a mall. When you’re window shopping, a shirt or pair of jeans may catch your attention. You might even try them on, but you wouldn’t just pick any random thing off the rack and say “I guess I’ll wear this for the next 10 years.”

That would be insane!

Instead, you go through these steps:

  1. Get curious to know more (Try it on, feel the fabric, look at different colors, etc.)
  2. Research other options and read reviews online (Find other brands and look at Amazon reviews)
  3. Talk with your friends to see if you should buy this or not (“What do you think of this?”)

Then, AFTER you’ve gone through all these steps, you would make a decision and feel confident in your choice.

Maybe you wouldn’t go through all of those steps for a pair of jeans. But you would for a car or major appliance. The bigger the decision, the more “window shopping” you need to do.

See how this relates to choosing a career?

Turns out, it follows a very similar process:

  1. Get curious about potential jobs (whatever interests you or grabs your attention)
  2. Do deep research to see if you’re really interested in this (to make sure it’s something you’d enjoy)
  3. Talk to people who have worked in that field to get their advice and insights

This totally reframes the way most people search for a career. It also becomes a lot more FUN.

If you find that you love a career, great. If you don’t, you have a process in place to find what you do truly love.


The image above shows you how to turn the vague and confusing question of “What should I do with my life?” into a system that guarantees you do what you love. So let’s dive right in on how to choose a career.

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Step 1: Find your (potential) Dream Job using the Cloud Technique

One of the most daunting parts of choosing a career is picking just ONE job…that you’re supposed to do for the rest of your life.

  • “What if I decide that I hate doing X? Can I ever do something else?”
  • “What if I want to change careers in a few years? What do I do then?”
  • “What if I like to do LOTS of things and can’t decide where to focus?”

All of these “what ifs” make it tough to say yes to any career. You can skip past these doubts with this technique I’ve taught to thousands of my students. Just start by listing ALL the careers and job titles you might be interested in.

Anything you want to explore, just write it down.

  • Think copywriting sounds fun? Add it to your list.
  • You can imagine yourself as a marketing director? List it out.
  • Know someone that does inside sales and what they do sounds cool? Put it on the page.
  • Toyed with the idea of being a baker? Nothing is too left field. Write it down.

I call this the Cloud Technique because your options are as open as the sky.

This lets you say “Yes” to EVERYTHING you’re curious about instead of constantly saying “No, I can’t do that because…”

Where should your ideas come from? Here are a few career brainstorming tips:

  1. List any careers or job titles that caught your attention in the past.
  2. Go to LinkedIn or another job listing site and read job descriptions. If anything catches your eye or seems like it’d be fun to do, add that to your list of potential ideas.
  3. Think about the skills you already have or ones you’d like to develop. Then, search for jobs that involve those skills. For example, do you really like design and being creative? See what jobs require those skills by searching online. Put these options on your list of potential careers as well.

I’ll show you how to filter these ideas down in the next few steps. For now, it’s best to have a big list of potential careers to choose from. You can move on and start to refine your list once you have at least 10 job titles written down.

Step 2: How to know if a job is really right for you

Once you’ve tentatively selected a few job titles, it’s time to do some deep research. This is where you go from “Hmm…sounds interesting” to truly understanding what the job is about.

Remember: you don’t have to become 100% knowledgeable about these roles… just yet. You just want to learn as much as you need to see if a job is right for you.

Let’s use the job title of “engineer” as an example of what you’ll want to look for.

The first thing, you’ll want to do is get a bird’s eye view of the job:

  • What do engineers actually do?
  • What are the different types of engineers out there (petroleum, electrical, civil…)?
  • What kinds of companies do they work for?

You can find this info with a quick search through Wikipedia or Googling “introduction to [INSERT JOB].”

As you tackle those broad and sweeping questions, you may start to eliminate some options you originally listed. And that’s okay. In fact, that’s expected. Just because something sounds interesting in theory, doesn’t always mean it will be.

You actually want to narrow things down in this stage. If at any point, you run out of job titles on your list, simply go back to step one (with your new insights on what you want from a job) and start again.

Once you have a basic high-level understanding of the positions, you can dive deeper into the nitty-gritty details:

  • What does this job pay?
  • What type of educational experience is required?
  • What’s the trajectory?
  • What does the job look like on a day to day basis?
  • How many hours per week do they work?
  • Is there travel involved?
  • What makes a great engineer vs. simply a good one? Is it strategic vision? Creative ideas? Quantitative skills?
  • What blogs / books / websites do they read regularly in order to stay “in the know?”

The whole time you’re going through this process, ask yourself “Could I see myself doing this?” and “Is this something that still interests me?”

This process helps you discover what it is you truly enjoy. Once you’ve narrowed your list down again, you’re ready to hear from people who actually work in these roles. That’s how you guarantee this is the right career choice.

Here’s a video of me explaining the process further:

Step 3: Get the “inside” scoop on the job you choose

The key to learning what a career is really like is conducting informational interviews.

You may have heard about informational interviews before, but few people actually take this critical step. Three things you need to know:

  1. An informational interview is an opportunity to meet someone you’re curious about and learn from them. So if you’re curious what a Product Manager or engineer really does and want inside tips about the job, this is how you find that out.
  2. THIS IS NOT WEIRD. What’s weird is a bunch of people mindlessly submitting resumes to jobs they don’t know anything about and then wondering why they don’t do what they love.
  3. People want to meet with smart people who are curious in the same things. That means you, if you send a great email, have insightful questions, and are interesting. (I’ve provided the emails scripts for reaching out to people and how to prepare for these meetings here.)

During your interview, you can ask any lingering questions you had from the previous step (you can also find some ideas here). It’s not unusual to learn years of hidden insights in one interview. You’ll also start building relationships with people in that career field.

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This is the best way to choose a career:

  • Find potential careers with the Cloud Technique
  • Research to find if the job is right for you
  • Verify your findings and get the inside scoop with informational interviews

Almost every time my students have followed this process they’re the first ones to get a job offers when positions open up. It’s because they’ve shown interest and have taken the initiative to meet top-performers in the field.

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