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Choosing a Career: 2 “weird” (but extremely effective) tips

Forget advice like “follow your passion.” There’s two techniques you can use to find the career that’s right for you. Even though they’re deceptively simple, almost nobody uses them.

Ramit Sethi

Q: How do most people approach choosing 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.

Of course, if you ask for tips on choosing a new or better career, you don’t get much help:

  • “Follow your passions!”
  • “Network with people.”
  • “You’re lucky to have ANY job in this economy — so just take what you can get.”

There is a better way. You can explore all your interests to see what you really like, then find career paths built on those interests.

Sound like a pipe dream? For the people who take the random approach, it definitely is.

But for the thousands of people I’ve helped do this over the last 12 years, it’s a reality.

(To hear directly from one of these students, listen to Tim’s story here.)

There are two techniques you can use to choose the career that’s right for you. Even though they’re deceptively simple, almost nobody uses them. Applying just one means you’ll be ahead of 99% of job seekers.

Bonus: Need help getting started?


Technique #1: 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 career 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 technique. 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.

Technique #2: Choosing a career by “Window Shopping”

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

choosing a career

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.

But how do you test them?

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.

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.

I recorded this short video to explain exactly how this process works. Watch the video and find out:

  • How to learn about a company (or even an entire industry) without having to spend 5 years working there (1:52)
  • How to find and approach people that can give you inside info on a career choice — including the specific questions to ask (2:16)
  • A quick but powerful mental framework to make your job search more productive than 99% of job seekers would (3:05)

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?”

choosing a career

This is how you 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 into how this works.

Window shopping: The step-by-step breakdown

Here’s a few nitty-gritty details you should research about each job you listed with the Cloud Technique:

  • 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?”

Then, the “secret sauce” of the technique 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 about 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.

The Top 7 mistakes to avoid when choosing a career

What do you do once you’ve found the ideal career for you? In their excitement to apply, many job seekers end up killing their chances by committing one of the Top 7 Career Mistakes.

You could do everything above correctly and still wind up with a job you HATE — or no job at all — if you commit one of these common mistakes.

To make sure that doesn’t happen, I put together a free video to show you which mistakes to avoid. Plus, tips for how you can stay on the fast-track to career success.

Just enter your information here for instant access.

Avoid these “Top 7 Career Mistakes” so you can land your Dream Job quickly

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