How I (Your Classic Overthinker) Found The Easy Way To Choose A Career

What do you want to be when you grow up?

**Cue the sarcastic eye roll***

I’ve been on that merry-go-round. You know the merry-go-round called what career should I choose? The ride that has you feeling on top of the world one moment and the bottom of the ice cream pint aptly named self-loathing the next.

Yeah, that ride.

Hell, I’ve even cleaned up throw up from a cotton candy stuffed 12 year old on that ride.

It was blue too.

But that’s the nature of the merry-go-round: it spins you around until you’re sick, desperately seeking a way off the ride.

Look, I know it’s not fun feeling lost, constantly searching for career clarity in a spinning, tell-me-your-life-plans world. It’s downright nauseating… but the silver lining is this: once you get off the ride your path in inherently straighter.

I wrote this guide in hopes it can help you get off the merry-go-round. Please enjoy.

Puzzle Piece One: Write Down What You Don’t Want To Do

While it can be overwhelming to initially figure out what you do want to do, it’s often crystal clear to figure out what you don’t want to do. So ask yourself, have you ever had a job that made you want to become a pencil and dive headfirst into a pencil sharpener? Or better yet, do thinking of certain jobs make you question “I don’t know how anyone likes doing that, they’re insane!” Yeah? Well, It’s probably a good idea to avoid jobs like that. When you thin the heard of possible career choices, that automatically makes the remaining choices stand out. It’s addition by subtraction, and this is a great thing for tired eyes. Simply put: if you know what you don’t like to do, then don’t do those things; you’ll be happier that way.

Puzzle Piece Two: Find Careers or Jobs That Interest You / Write Down Your Version of The Perfect Job

Let’s pretend for a moment that you’re the captain of a pirate ship. You’ve got a peg leg, no dental insurance, and a joke-telling parrot named Mr. Squawky that has your crew in literal stitches. However, there is one problem. You sold the crew on finding buried treasure but you don’t have a map. So how in the Hell are you going to find the buried treasure if you don’t know where to look? In pirates ships and in life, you need to have a map of where you want to go. I think the best way to “find your map” is to do two things. #1) Write down all the jobs that you would want to apply for. #2) Write down your dream career. Ask yourself: What do you want to be known for? What does your perfect day look like? What are you curious about? What do you envy? What jobs would you gladly do for free? Who would you trade places with and why? The key to this exercise is to be honest even if your answer isn’t popular. If you can’t be honest with yourself you already lost. When you make your list, you make your road map… oh… and Mr. Squawky the joke-telling parrot would be proud of you too.

Puzzle Piece Three: Ask Yourself What You Are Good At? & What Do You Have Potential In?

Let’s have some fun, answer these questions in 3 seconds. What in the Hell are you good at? What things do you do, that you can smugly say with your pinky out sipping tea, “Eh, I could probably do that better than him” What do people typically compliment you for doing? What do you think you have the potential to be good at? Ready, set go. 1-2-3. Ok. Good. Everyone (even you) is good at something and everyone has potential in something. It’s time for you to be honest with what you’re good at. In other words, start seeing yourself for you are. A few constructive ideas are to trust your intuition, pay attention to when people say you’re good at something, and pay attention to the things that come easy to you. Usually when something comes easy for someone, many people typically don’t notice it because they’ve never thought about it… (because it was so damn easy) I’m not Oprah but I’ll steal her thunder. You have a gift that is uniquely yours and it’s your job to discover what it is & share it with the world. Fittingly, you can only discover your gift if you look for it so start paying attention to your gift as if your life was a Where’s Waldo Game, and this time, you were the hipster douche wearing stripes. (No offense hipster douche bags) Waldo aside, the beauty is once you’re in tune with your gift, you will have a chance to make some serious impact on the world and you’ll be working from a place of strength opposed to weakness. That alone is worth the trouble of finding it.

Puzzle Piece Four – What Work Environments Do You Enjoy Best?

I was shocked when my best friend in the world and I had different ideas about what was the best work environment. I enjoy working from home, he prefers the office. What is now clear to my naive eye is apparently everyone has a different idea of what their best working environment really is. Considering that you’re going to be working most of your life, doesn’t it make sense to try to work in the environment you like being in? To find the answer, all you need to do is more good, old-fashioned self-questioning. Ask yourself, at work what do you value? Is it freedom? Is it comradery? Is it the mission? Is it the lunch break? Is it the empowerment to make your own decisions? Is it the corner office? Is it the outdoors? Is it the bathroom? Really be honest, what is your ideal work environment? Common sense says you’re going to spend a lot of time at work, so do yourself a favor and choose the environment you like being in. Try to think of the place where you feel most comfortable and most productive. We are products of our environments so choose yours wisely.

Piece The Puzzle Together

At long last, we have the four pieces of the puzzle- now it’s your job to connect them. We know what you don’t want to do, we know what you might want to do, we know what you’re good at and we know what type of work environments you enjoy best. So what’s left is taking time to put this puzzle together. I’ll do mine. I don’t want to work in an office, I don’t want a job that doesn’t allow me to be creative. I admire writing, I admire people who write movies, write TV shows, who write blogs and articles. I have been told that I’m good at writing and I’ve been paid to write which confirms my suspicions. My ideal work environment is working from home, where I have the freedom to manage my time and express myself and sell my ideas. For me, it becomes crystal clear my ideal career is that of a writer. Now do yours, what did you find?

Start Experimenting

Now that you have put your puzzle together let’s try some mini-experiments, to test our career hypothesis. The truth is, if you really want to know what the right career is for you, you can’t rely on thinking your way into your career, you also need to get on the playing field and get your jersey dirty. So for example, if you want to be a landscaper, start cutting the grass, offer to cut your family and friends grass, and see how you like it. If you want to be a director start making movies and put them on the internet, see the results you get. If you want to be a barber, start taking classes and start trying to cut some of your “Brave” friend’s hair. You get the deal, find a way to start experimenting with your dream career. That way you can test if your hypothesis really is the right career option for you. Pay attention if you’re getting good results, and if doing the job feels more like play than work. Again, being honest is key.

Try Your Best

You’ll never regret your best effort and if there ever was a time to give your best effort, what better time than the present? Give it your all when your experimenting with your new potential career. Hell, just give it your all in anything you do. If you don’t try your best, you’ll never know if you could have made it and that feeling of not knowing is a regret sandwich that you don’t want to eat. (Even if you’re hungry)

Enjoy Your Career & Know You Can Change

That’s it my friends, you’ve done the work and now it’s time to enjoy the rewards. Enjoy your career based on who you are as a person and not how society wants you to be. And remember, you are in control of your life. If you fall out of love with your career you can change it. Nothing in life is easy, but very few things are impossible. If someone is making a living doing what you love to do, there’s room for you too. Be smart, be optimistic, and work hard. With time you can achieve more than you realize.

Please like, comment, share and tell me what you think. What is your ideal career? Did you find this helpful? Who do you know that this can help?

27 thoughts on “How I (Your Classic Overthinker) Found The Easy Way To Choose A Career

  1. 1960: Just out of the Army, I registered for a job with the US Civil Service Commission and was, a few days later, asked if I’d like to interview for one of both of these entry-level jobs: Personnel Specialist; or Computer Operator. So I asked, “What’s a computer?” Fifty-two years later I retired from my computer career, a hell of a lot richer than I’d have been hustling Personnel!

  2. I love this !! And I actually laughed out loud at “ have you ever had a job that made you want to become a pencil and dive headfirst into a pencil sharpener?” – yes I have!! 😂😂😂

      1. Thank you for sharing it, you write beautifully. Glad you’ve found your ideal career.. I’m still searching and this article is a really useful guide. 🙂

  3. I joined the army because I had no idea what to do. I thought it would give me a bit of time to think. It did. 28 years! Best thing I could have done. I never did get a parrot though.

  4. I have really enjoyed this article about career merry-go-round, it rings true to so many, certainly me. The best phrase I am taking is ‘try your best, you will never regret your best effort’.

    1. Thank you so much for the kind words! Yeah trying your best is certainly something that I have to remind myself to do but honestly if you give your best effort there is no second guessing

  5. That’s brilliant! I went through every single piece of this crazy puzzle. It took me some time – and so much struggle – to figure it out. I’m now in the “experimenting & try-your-best” phase. I hope to get to the “enjoy” one eventually. Thank you for sharing.

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