Hack Your Dream Job (Here’s How I Did…Three Times)
August 30, 2014
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Life’s too short to have a boring job.
Life’s too short to have an underpaying job.
Life’s too short to have a job where you won’t grow.
Unfortunately, however, too many people have boring, underpaying, and low-potential jobs where they don’t grow.
I was going to be different.
I was going to get my “dream jobs”…the ones that other people my age couldn’t and wouldn’t get.
Was I smarter than everyone? Probably not. Did I have the same credentials? Hell no…I didn’t even have my high school degree when I got three of my dream jobs. And at the time, they were dream jobs for me…Now I have new ones. That’s OK.
How did I do it? How did I hack my dream jobs, and how can you hack yours?
Here’s a start…

Why are you even working? What things, experiences, securities do you want to have?…Once you know your dream lifestyle, now it’s a matter of getting from Point A (where you are now) to Point B (your dream lifestyle) as quickly and easily as possible.
What makes you wake up every morning? What do you do with friends if given the chance? What makes your heart sing? If money wasn’t an object and you were a trust fund baby, how would you spend your time. Dan Bilzerian spends his time shooting guns, playing poker, and hanging out with barely-dressed women since he doesn’t have to worry about money. But, seriously, what are your passions? Write them all down on a sheet of paper.
What do people compliment you on? What skills are you known for, or have been building for a long time? Email people you live with, people you work with, and people you respect, and ask them what skills they think you are really good with. Take tests like StrengthsFinders 2.0 and the Kolbe A Index. Then, flip that piece of paper over and write down everything you’re really good at.
Take your list of passions and your list of skills, and play OKCupid. If you are really passionate about basketball, and are not so athletic, but are really good at number-crunching, perhaps being a basketball statistician is your calling. For me, I found out that every single project or company I’d ever started or worked on had a community aspect to it, and I was really good with bringing people together, so my “Zone of Genius” became synergizing people to accomplish bigger societal goals. What do I do with that? Build communities like 2 Billion Under 20, help people take control of their own education, and consult for bestselling authors who help Fortune 500 companies get hard results through teaching soft skills like relationship-building. Figure out and articulate your “Zone of Genius” and watch your life change, now.
See F through I.
Invest in yourself. Learn how to code, or how to write, or how to sell, or how to chew gum and walk at the same time. Seriously, think of the skills you will need to not only get, but be successful in, the dream jobs that match your “Zone of Genius”. Go read subject-specific books. Take online courses or attend speaker series-type event. Do anything except watch TV (and if you are going to watch TV in your off-time, watch things pertinent to your dream job. Entrepreneurs should watch Undercover Boss, or Bloomberg TV. Basketball players should fill their DVRs with recorded basketball games. BE OBSESSSIVE!
This is key. Don’t be “that guy” who passes around business cards like sticks of gum to “friends” or cute girls in middle school thinking that everyone will like them more than they already did after 5 minutes. Make genuine, supportive, value-adding (for both people) connections with people in the field you want to work in. Want to author a book? Make friends with as many bestselling authors as possible. Go meet editors and agents. Make some friends. Also, make friends with people in other fields so you have a wide variety of people to ask for advice, opportunities, and perspectives from. You never know which person in your network will have the resources you’re looking for, so always continue building a supportive network of people that “have your back”. Most jobs come from your network, and your dream job most likely will, too.
Figure out which companies you actually want to work for. Look at what job openings are available that fit your “Zone of Genius”. When you find an epic company with an opening that matches your ZOG, write it down. Then, rinse and repeat. Get a short list of dream job opportunities that you can reach out to. This will save you a lot of time, and rather than shooting in the dark, you’ll have clear targets in your outreach efforts as you hack your dream job.
When you reach out to important people, you should know how to email them. Short emails, to the point, providing value to them up-front. Help them answer you back. If you’re calling, don’t ramble, and at least try to sound enthusiastic. Personalize emails to your short list instead of copying and pasting your ten page essay on why you deserve a job. You’re better off saying, “Hey, your company sucks at “X” (customer support, marketing, etc). I can help.” or “I want to learn under you, and am willing to work for free for two weeks. If I prove to be valuable after that, we can discuss wages.”
Don’t do what everyone else does. If it is a sales job, literally sell for the company without being employed. Then tell your future boss you just made him/her money. He/She will take notice. Get recommendations from people around the decision-makers. Befriend the gatekeepers, then have them recommend you. Go to the same events as people you want to work for. Make websites that say how much you want to work for “X” company. Point is…don’t just stand there. Do something!!! This is your DREAM JOB, right? Just how far would you go to get it? Go there.
Who’s going to turn down free work from a person who’s working in there “Zone of Genius” that is gushing passion for a certain line of work? Not many people. Work for a week to a month for free, and bust your butt to provide so much value that they simply can’t let you leave after your free “trial” period. It’s like getting a free piece of fudge at the chocolate store that is so good that you HAVE TO buy some. Work for free, make yourself invaluable, and suddenly you can not only get your dream job, but you’ll have a lot of leverage in determining salary, perks, etc.
If you can do eighty hours of work in forty, you’ll create more value and get more done in less time. Learn email hacks. Become a time management guru. Say “no” to distractions. There’s so many hacks to become more productive. Pick a few and try them out. Then, use them to get more done in your “free trial”, or even after your hired, and you’ll have your dream job or get promoted to it in no time.
Boss comes in and says, “I need someone to help with this project.” Unless you are in your dream job at the moment, be the first to volunteer for that project. Then kill it. Crush it, actually. Make your boss look so good that he decides to promote you and put you in charge of a new department or create a new job specifically for you and your “Zone of Genius”. My friend has done this at Google and has climbed the corporate ladder at blazing speeds at only 23. You should see the smile on his face. And the zeros on his deposit stubs.
Your definition of a dream job will change over time, and you’ll yearn for higher positions, fancier titles, and bigger paychecks. When this happens, fumble around the Internet for five minutes trying to remember my name or this article, and start at “A” again.
_ _ _
What do you do once you have your dream job?
I have no idea…Hack your dream body? Develop your dream relationship? Insert the word “dream” before any other meaningful word, and then go out and create that scenario in your life?
I’ll be here when you need me, but now it’s your turn.
Now go out and hack your dream job. Channel your inner Zuckerberg and take down the entire Harvard computer network that resembles job search frustrations in your life. You can do it (just don’t piss off the girl of your dream while doing it!).



About author

Jared Kleinert

Chief Test Subject at The Gap Year Experiment

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There are 2 comments

  • JJ says:

    Hey Jared I stumbled upon your blog after reading some of your articles on huffingtonpost about the lessons you’ve learnt about success. I respect and admire what you’ve done (especially your emphasis on “giving back”) and thank you for sharing this information! I really appreciate it.

    You mentioned in L) to “Become More Productive”. If you don’t mind sharing, what would the key (say top 3) of these “productivity hacks” be for you in your own life?

    If you’re ever in Toronto I’d love to take you out to coffee. I also see that you want to learn how to dance, I’m currently learning Cuban-style Salsa from an amazing instructor here with the emphasis is on musicality and “feeling” (in the Latin tradition), I’d love to connect you guys. Dancing is amazing.

    Enjoy your weekend!


    • Jared Kleinert says:

      Hey JJ! Thanks for your kind words and comments. I will definitely use your question regarding productivity as fodder for a future blog post, but in the meantime here’s a super quick answer:

      1) Work remotely as much as possible…No clocking in, less meetings, less office politics or distractions from bored co-workers, etc. You work where you want, and potentially when you want if you’re lucky, and are more productive for it if you are self-motivated….If you work in an office, there are some ways to negotiate “work-from-home” arrangements which I can send you a few links on or explain how I’d work that out.

      2) Your phone. When you work, put it on airplane mode and set a timer…Use the Pomodoro technique for timing work, and airplane mode restricts annoying email, text, etc notifications which kill productivity. When you’re in an email exchange that goes on too long, just call someone!

      3) Wake up early!!! I’m so much more productive on days I wake up at 5:30 or 6 then struggling to wake up at 9:30, 10, and so forth. Check out my last blog post for on this (

      That’s a good start! And please email me to say hi through the Contact page. 🙂

      Hope this was helpful.

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