How To Find Your Dream Job

Getting to travel all over Europe for a living sounds like a dream job. Waking up in new cities every week, having a leisurely coffee while walking to historic sites, and then getting to work writing about what inspired Da Vinci’s Mona Lisa, or how Amsterdam’s Tulips are cross-bred. Then ending the evening early to enjoy the city. This is what I naively pictured to be the life of a travel writer. 

Then recently I saw Rick Steves’ behind the scenes episode. Rick Steves has spent the last thirty years traveling through Europe writing guidebooks, filming TV episodes, and creating a tour company. This behind the scenes showed how he has turned his passion for traveling into a travel brand.

How he built his company is intense. His film crew is almost nothing. They travel light, with just Rick, his producer, and a cameraman. Each with just a carry-on backpack strapped to their shoulders and two suitcases of filming equipment. The crew is up even before the Parisian bread makers have had a chance to bake their morning batch, and they stay up long after the lights of the Eiffel Tower cease to shine to edit their script and determine what shots they still need.

They spend nine days writing/filming/editing each city, and then they move onto the next one. Blitzing through Europe, documenting everything that they deem valuable to their audience along the way. There are even countless hours of pre-work, researching the cities and what they should even begin to consider for the script before they ever board a plane.

All of that is far from how I pictured travel writers going through their job. I gained a new appreciation for their work and realized that I would never want to do this for a living. I am happy leaving my passion for travel as a hobby.

The Reason Why We Mess-Up “Dream Jobs”

Misconstruing what a “dream job” is and the realities of the profession are extremely common. During my research, I found a book called, Stumbling upon Happiness by Daniel Gilbert. The book explores many themes of human cognitive bias, most of which make us unhappy.

One cognitive bias that messes us up is our imagination. When lacking actual details of what we imagine something to be, we fill in the gaps of what we wish it to be, not what the accurate realities are. Using the travel writing example, I had no context for how a travel writer approached their day. I filled in the gaps in my knowledge of what I wish that job would look like, a relaxing day with a little writing. After watching the documentary, those imaginations were shattered with the realities of the situation – long days and constant re-writing, editing, and research filled those shattered gaps.

This is why so many people are unsatisfied when they finally reach their supposed dream job. They chase what they imagine that job to be, and then when the illusion falls away, they are left with the realities of the work.

A Better Way to Approach Finding a Dream Job

Questions like “what is my dream job?” or “what is my life passion?” are misleading. They put pressure on the job itself to hit every expectation. A little introspection and research are better ways to find a dream job.

This also helps by having a Growth Mindset that is willing to explore new possibilities and hear different perspectives.

Introspection | Better Questions Than “What is My Life Passion?”

For introspection, tie your career to a problem instead of a specific job title. Ask yourself questions like, “what problem do I want to solve over my career?”, “what would I like doing, even with all of the challenges, frustrations, and irritations”, “where do I want to have the most positive impact?” and/or “what would I do for free?” These questions help you focus on the tasks and challenges you want to tackle. Instead of being attached to any specific industry, title, or corporation.

Also, take stock of your skills and the tasks you like doing. Identifying your strengths can be a challenge. Ask close friends and colleagues what your superpowers are. Ask them what you seem to do better than most people. Also ask yourself, “what skills do I want to develop” and “what tasks do I enjoy doing?”

It is very possible to be good at a job you dislike but to find a dream job it has to be aligned with something that you deem meaningful, have the talent for, and enjoy doing the actual day to day work.

Research | Talk to the Experts

Daniel Gilbert, the author of Stumbling Upon Happiness, recommends the best way to prepare for the future is to go talk to people who are already doing the work or living the lifestyle that you want for yourself. Ask these people questions to get the full picture to fill in those gaps that your imagination can’t quite get right. Think of this as a scouting mission. It is better to do this research then spend years chasing a dream that you end up hating within a couple of months.

If you don’t have someone in your network already working the job you want, ask your friends for contacts. See if the “six degrees of Kevin Bacon” will lead you to someone who is living that life that you aspire to have. If that fails – reach out on your own.

Follow people on social media who are doing what you would like to do. See what their life entails, engage, and ask questions. Maybe you might even get some time to talk with them in An Ask Me Anything post or could even ask for a 15-minute phone call to talk about their career. Reaching out might seem scary, but most people are willing to take the time to help out someone who is genuine and respectful of their time.

You can also supplement this reaching out with some research. Find blogs, resources, videos, or documentaries that feature this kind of work that showcases your dream job and investigate it fully. See if it is for you, and if so, start building that for yourself. 

What to Ask the People Living Your Dream Job

Someone who is working your dream job offered 15 minutes to talk! But what do you ask them? It depends on your familiarity with them and if you already met. If you have never met them before, keep it professional. As you get to know people more, it can move to be a little more personal. To help you get started, think of using some of the prompts below.

• What is your favorite part of the job?
• What is your least favorite part of the job?
• Did you always want to do this job?
• What is something you wish you knew before starting this role?
• How did you get into this career?
• What skills do you use on an everyday basis?
• How can I develop those skills on my own to prepare for a role similar to yours?
• How did you learn the skills necessary for this role?
• What is one unexpected thing to come out of working in this job?
• What have you learned in this role?

“Dream job” is a convoluted phrase in the first place. That’s a lot of pressure on both yourself to find and then get the dream job. The job then has to live up to that expectation. It implies that this job should be your main source of happiness and naively implies that for the most part, every day will be smooth sailing.

When in reality, even the best jobs have bad times, stress, and challenges. The question then becomes finding a job that is fulfilling even with all the challenges and tribulations.

Main Take-Aways:

The best way to see what a dream job entails is by talking to others who are doing it. If you can’t get a hold of someone working in the profession to talk to them directly, there are resources available. Being creative can lead to some interesting insight into a great potential career!

Action items

What is your dream job? Research people who are already doing that for a living. Send out three emails today asking those people a question about the job. Start seeing if that dream job is right for you.