The real-world system to uncover your dream job

Recently I spent some time with a friend who told me he was feeling stressed out at work.  He felt stuck in his job doing work that was uninteresting, with long hours and a small paycheck.  Maybe you can sympathize with all or part of his situation.

“I just can’t win!” he told me.

After a few minutes of talking about how much he disliked his current job, I stopped him to ask what he would rather be doing instead?  Had he thought about what industry he’d like to be in?  What kind of people would he like to be around?  What would he like to be paid?

So many of us say we want a better job.  When it comes down to it, though, we rarely get specific about what that means and what it will take to get there.

Specific goals require a specific strategy, and the sooner you establish an end goal for your job search, the easier it will be to build backwards a plan to get from here to there.

Most people are not specific when they enter the job hunt.  They’ll take whatever they can get and make it work.  They say things like, “In this economy I can’t afford to be picky.”  And then they wonder why they’ve had jobs that are stressful, underfulfilling, and unimpactful.

In this post, I want to show you why narrowing down your job options is an important part of the roadmap to your dream job.  Then, I’ll show you how to find what your dream job is – even if you have no idea yet.

This exact strategy will help you be paid what you’re worth, and the strategies you’ll begin in this post can snowball into further career moves down the line.  It’ll show you how to land jobs faster and find jobs that aren’t advertised.  I’ve even had friends use this technique to have a job title created to match their qualifications.

Interested?  Let’s get started.

Top mistakes when searching for your dream job

Before we get to the strategy, I want to cover some mistakes that most people make when searching for a job they’ll love.  Once you learn these mistakes, and why they’re counterproductive, you’ll already be ahead of the competition.  You’ll stand out just from the fact that you’re taking a different route than the herd.

For the majority of people, the job search begins and ends on job boards like Indeed, Monster, and Idealist.  It’s an easy way to look for jobs, and I don’t necessarily think you should totally ignore job boards.  Most people rely on them, though, and that starts to get problematic.

If you limit yourself to just the jobs you see on job boards, you’re missing a huge portion of the job market – the hidden job market.  These are jobs that are never posted.  They’re filled by hiring managers asking colleagues to recommend somebody for the job.  So how do we begin to tap this job market?

Well, the first mistake many people make is they don’t ask around.  They don’t talk to people inside and outside of their industry to get advice and intel on what kind of positions they might be hired for.  Below, I’ll show you how to ask experts about the job market and find out about jobs you didn’t even know existed.

The second mistake involves building your network.  When thinking about a new job – a dream job – ask yourself, “Who would I like to meet? What kinds of people do I want to work with day-to-day?”  It’s not just about the professional network.  It’s also about what kind of person you’d like to become and what personality you have.  Below, I’ll walk you through some steps to think about what people you’d like to work with and what industries to find them in.

The third mistake is about pay.  Your dream job has to pay you well.  For some people, that means making $150k.  For others they’d be happy with $60k.  There’s no judgement here, but you will need to research salary and look for a job in an industry that can pay you what you want.  Careful, this cuts both ways.  In industries where everybody makes a lot of money you end up with your fair share of assholes.

I want to congratulate you on getting this far into this post.  It turns out the biggest mistake most people make is that they don’t think about their dream job at all.  They spend a career bouncing from unfulfilling to stressful to meaningless work all in the name of a paycheck.  Just by reading this far, you’ve put more thought into your dream job than a lot of people.

So let’s get down to it and start narrowing down your dream job!

Imagining your ideal career

What is your dream job?

That’s a big question, and it’s one that will change over the course of your career.  As I mentioned earlier, you’re already ahead of the game just by asking it.  Answering it is a little bit tougher.

The first step is to start by getting creative with it.  Do a little bit of what I call Open Roads Brainstorming.  What kind of life do you see for yourself in the next 10-20 years?  Are you a powerful executive?  A beach bum?  Do you hike Everest?  Maybe you’d like a big house and a fancy car.  I’m not here to judge your dreams, just to make you think about them.

Start to get a specific picture in your mind.  Where do you live?  What is your family like (if you have one)?  How do you get to work everyday?  What do you do for work everyday?

Maybe at this point you don’t know the answer to the last question, but I want you to stop, take a few minutes, and imagine what your life could be.  Write the answers to these questions down on paper.  Commit to them.  It might seem like I’m leading you on some woo-woo “follow your passion” exercise.  I assure you that’s not the case.  By the end of this Open Roads Brainstorming session, you’ll have at least 20 potential jobs to start investigating.

Let’s really start to drill into what kind of job could make this lifestyle possible.  Consider the industry you’re currently in.  Could you make it work there or will you need to change industries? Will you be in finance? Nonprofits? Tech? Law? Make a list of industries that interest you – have at least 5.

Consider the type of job you have now.  Are you in research? Sales? Marketing? Product development?  Think long and hard about whether or not you want to stay in this role.  Make a list of jobs you could be good at, from manual labor all the way to executive leadership.  What kinds of work could you see yourself doing?  Make a list of these potential job titles – be sure to have at least 5.

Now things start to get interesting.  We’re going to cross multiply the list of industries by the list of job titles.  Just with our sample list above, we now have:

  • Finance research
  • Nonprofit research
  • Tech research
  • Law research
  • Finance sales
  • Nonprofit sales
  • Tech sales
  • Law sales

OK.  We’ve wrapped up our Open Roads Brainstorming.  What did you notice?  Did you learn something?  The point of this exercise was not to get a definitive list of every job possible.  It was to open your mind up to things you could be good at.  Often on this list you’ll see a type of job you never considered before.

That’s all great, but what do we do with this list?  Well, read on…

Actually talk to real people

Now, for the important part.  You have to go talk to people who actually work in those industries.  Start with people you know.  Ask them for introductions to other people.  You can also approach professionals in other industries directly.  We’ll get into talking to successful people more in part 2.

The key when talking with people in the jobs/industries that interest you is to ask questions about their background, the industry, and possible paths you could take.  It’s easy to want to unload your current problems – don’t.  Instead, focus on being interested and engaged with their story and what they’re knowledgeable about.

Keeping up conversations can be hard.  Here’s the technique I use to talk to people.

First, mindset.  Be interested, curious, and looking for ways to help.  Make the person you’re talking with feel like the conversation is all about them.  Be positive and enthusiastic.

Second, questions.  Open-ended questions that show your curiosity are the best way to keep a conversation going. You should feel like the other person is doing most of the talking.  Use questions to ask about background, what they’re currently doing, and what they plan to do in the future.  Actually working my way through past, present, future in my head helps me a lot with thinking of new questions to ask a person.

Third, restatement.  If you only ask questions it’s going to feel a bit like an interrogation.  Use restating the other person’s points is an opportunity.  Like this, “It must be challenging to travel so much with your family at home.”  Most people will respond with, “Oh yeah, it’s really tough…” and the conversation goes from there.  Statements buy you time and breathing room between questions.

Fourth, compliments.  Everyone likes to be complimented.  Starting a sentence with, “I really admire the way you…” or “That’s so cool that you…” show genuine care for the person you’re talking with and it will endear you to them.  Of course, don’t give a compliment if you don’t mean it.

You should spend 80% of your time asking about the other person’s life, experience, and projects.  Only in the last 20% of the conversation should you ask for advice.

Give a brief overview of yourself, what you’ve done and some of the things you hope to do.  Then, ask for specific advice.  Don’t expect the person to do all the work for you.  Instead, show you’ve done your homework by asking for advice like this:

I’m trying to change jobs and build a more interesting career.  I’ve already done y and z.  Now, I’m thinking of trying a, b, or c next.  What do you think? Am I approaching this in a productive way?

Asking for help in this manner dramatically increases the quality of the advice you’ll receive.  Instead of platitudes, you’ll get specific, actionable advice.  That’s exactly what you want at this point.

At the end of the meeting you’ll want to ask if there’s 1 or 2 other people they think you should speak with.  Chances are you’ll get some recommendations.  Actually talk with those people, too.  Use the same strategies over again.  Then, follow up with the original person to let them know how it went.

You’re simultaneously building your network and learning about your job prospects in different industries.

Talk to at least 5 people to get a good picture of your potential career options.

Next steps

Now that you have brainstormed and spoken with people who can help you narrow down you options, let’s talk about actually getting that job!

In Part 2, we’ll dig into who are the influential and admired players in your industry, and how to practice targeted networking.  We’ll see how to establish relationships with people who have the ability to hire you for the job you want.

Take me to Part 2! – How to Meet Successful People


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