You Will Never Find Your Dream Job

By admin | Uncategorized

Aug 03


A dream job is hard to find but oh so worth it.

There are many misconceptions about dreams jobs. Same with passions. The biggest one is that yours is sitting out there, like a tranquil duck in a pond, waiting for you to find it.

You will never find your dream job. Here’s why: our dream jobs are an opportunity to use our greatest strengths to solve big, interesting problems that we find fulfilling and meaningful with teams that are supportive, open, and kind. FURTHER, any dream job should actually support the lifestyle that you aspire to, so all of the above must also accommodate your family, your time for reflection, and your time to live the hell out of your life.

Job descriptions are written to solve an existing problem within an organization, which means that many of the above items are decided well ahead of your arrival, and you’re already behind schedule in solving the problem, which is never good for creating space for the rest of your life.

The likelihood that the latter matches the former is improbable.

You know what? I’m feeling sassy today. It is straight up impossible.

So, does that mean that you will never have your dream job? No, absolutely not. However, it does mean that you need to change the way you think about searching for it.


Dream Job = Dream + Goals + Research + A Deeper Look + Ask

The equation could be much longer but for the sake of my typing fingers and your attention span, let’s keep this a bit more straightforward.


I know that this is going to sound crazy, but if you want to have your dream job, you have to dream of it. Moreover, though I acknowledge that all of us are different, most dreams should not sound like, “A product manager role that builds on my previous engineering experiences and will allow me ample opportunity for promotion and self-development over the next 3-5 years.”

Your dream job should sound much more like a company vision statement. Lofty. Far-reaching. Ambitious. Ethereal. “I want a job where I work with brilliant people, and every day I have the sense that I made real progress. I want to feel challenged. I want to have time and space to support and grow a team. I want to develop a brand new skill set.” When we divorce ourselves from our experiences to date and instead align ourselves with the activities and ideas that energize us, our career paths look very different.

It is not lost on me that specificity is valuable, particularly in setting goals, which we will cover. However, if you are overly specific or prescriptive, you are likely to miss out on many amazing opportunities because they do not fit your narrow criteria. If you give up your preconceptions about what your job should look like, and focus on what you want it to look like, your list of opportunities will start to change.


What do you want your life to look like? Just like your vision of work, you need an idea of how you want to spend your time every day including the time that you spend outside of work. If your dream job is perfect while you are in the office but leaves the rest of your life in shambles, it is not much of a dream, is it?

Where do you want to live? Do you want a family? How do you spend your time? Who are your closest friends? If we do not create an intention around the form and shape of our lives, we have a big problem: We have no idea if we are moving in the right direction.

How many people do you know who have a terrible work-life balance, but claim that it is for a better future? How many of them have any idea of what that future is?

Hard Work = Success — we all know that formula. However, if you do not define success, what the hell are you working toward?

When I say set goals, I mean set intentions to build the life that you want. The life of your dreams, if you want to stay on theme.

With me so far? Rad, you are half way to your dream job.


Now, we can get to work. Your dream job is a single data point, which means that it exists in space with no other benchmarks. However, by creating intentions for your life, too, now you have something to work off of as you shape your vision of what those dream jobs could be. You know that they need to provide you with the vision that you laid out and that they afford you the opportunity to live the life that makes you happy.

Now, this may seem like a good time to jump back into the world of job descriptions. You will be inclined to analyze hundreds of them and look for that which most closely matches your description.

Stop it. You stop that right now. Job boards are not your friend.

Instead, you need to seek out individuals who have managed to create the job, the life, or the combination of the two.


If you look for the closest approximation to what you want, you by definition have not found what you want. That defeats the whole purpose of this exercise.

Finding someone who is doing your dream job is incredibly helpful because she can tell you how she got there, what makes her successful in the role, why it is meaningful to her, and what her vision is for the future of her career. You will never find these answers, at least honest ones, in a job description. Even better, you have now introduced yourself to someone who is doing exactly what you want to and presented yourself as a capable, ambitious, and intelligent person who has some real clarity on where you want to go. That makes you SUPER memorable.

Similarly, finding someone who is living the life that you want will help you to understand the tradeoffs as well as the inputs necessary to make it happen. If you want to work out of Aspen for three months a year to ski, how does that affect your career trajectory? Or how much you earn? Talk to someone who is doing it. Find out what they know. Make it real.

Still with me?

Now you have a clear sense of your dream job and intentional life, as well as examples and role models for how to get there.

Now, for a dash of introspection.

A Deeper Look:

Where are you now relative to where you want to be? What are you missing? How can you get it? This stage is where a deeper look comes into play.

However, don’t make the common mistake–this is where too many people get stuck. The purpose of a more in-depth look is not to enter the infinite spiral of misery searching for your purpose or to ask why God put you on this earth. A deeper look is to evaluate what stands between you and having that dream job.

I will give you a hint: the first thing that you probably need to do is convince yourself that you are worthy of this dream job. We all have piles of hang-ups

from many, many experiences throughout our life. They shape how we perceive our abilities and our opportunities. You do not need to give them all up, at least not yet.

But if you want your dream job, you need to rewire every neural pathway that tells you that you cannot have it.

Write it down. Shout it out. Tell the world. Tell yourself. You will never convince anyone else that you are qualified for your dream job if you do not believe it.

If you want to be CEO of a Fortune 100 company, then no amount of wishing will make you magically ready for the role tomorrow. However, if all of the choices that you make from this day forward align you with the job you ultimately want and the life you ultimately want, I would be willing to bet that you will get there MUCH faster than you would if you just hope that the job pops up one day.

NOW, the last part of the puzzle is to:


I assure you, you have already done the hardest part of this work. You’ve done the introspection. You’ve done the research. You’ve put your idea out into the universe to see what’s out there.

We’ve all been in interviews, yes? We deftly deploy our litany of well-plotted stories and tales of our heroics and genius for the better part of an hour. So then, as a courtesy, the interviewer will ask, “Do you have any questions for me?”

Remember the vision? The dream job? Ask how much of those activities are available in the work that you are applying to do. The inspiring and capable leader? Ask who will be your manager and how would the person describe them. The challenging but mission-driven problem? Ask what types of challenges teams will face day to day. Ask. Get specific. Poke. Prod. Look under the hood of the damn car!

You cannot blame the interviewer for wanting to tell you things that make the job sound attractive. That is, to an extent, his or her job. However, if you ask particular questions that address your biggest needs, it will be much harder for them to blur the truth. “How do you think about work life balance?” Versus “I see that you offer flexible hours for parents with young children. How many people take advantage of that flexibility and what does it look like day to day?” No. Contest.

Further, it demonstrates how much you think about these things and how much clarity you have on your actual goals.

Dream Job = Dream + Goals + Research + A Deeper Look + Ask

Your dream job does not exist yet. There are many ponds in the world, and many ducks floating in them.

Change your perspective. Dig your lake. Fill it with dreams. Let the opportunities present themselves to you.


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Leave a Comment:

(1) comment

Cindy Bertram September 27, 2017

Wonderful insights and tips!

A Job board is just a “board” sans the human touch. Just like a resume won’t get you hired. Instead it’s the person sharing why he/ she is exceptional in that face to face meeting.

Thanks to this and having a chance to hear Drew do a presentation I’m completely focused on using new tactics in my intense search!

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