5 Simple Questions To Find Creative Work You Love

December 7, 2015

There is a crippling problem facing many of the most talented, creative and innovative people alive today.

We have too many awesome ideas.

How can you blame us? Thanks to the internet, there are more possibilities for our life than ever before. Not interested in a typical career? You could start your own business, travel the world, start a blog about that thing you love, work on an organic farm, write a book, work with a charity you believe in, become an artist, or maybe all of the above.

That’s the problem. There are so many options that we can’t choose just one.

What’s a passionate person to do? How do we know which ideas are worth running with and which are better kept in the someday/maybe folder?

As someone who struggles with this myself, I’ve discovered a few questions that have helped me get to work on the ideas that actually matters to me.

Question 1: Are you romantic about the shitty parts?

This is inspired by one of my favorite bloggers, Mark Manson. What are the shitty parts of the project you’re considering? Do they seem terrible or slightly romantic?

For example, blog writing is something I love, and the crappy parts of it like spending all day in my office, painfully editing 700 words, posting every week and learning web design actually seem romantic to me, so it works out.

You want to be like the girl who wants to get married so much she dreams about having petty arguments with her spouse.

When I wanted to be a touring musician I used to fantasize about living out of my car. I remember a time when I thought the most exciting thing I could do with my life was tour 364 days a year, with one day off for Christmas (I have an old blog post to prove it).

If you’re a driven entrepreneur that wants a fast-growing start up, do you dream of sleeping in your office and working 18 hour days? If you want to write a book do you love the idea of lamenting over the fact that “your muse” didn’t show up today?

Not to say that the shitty parts will be enjoyable, but they will be a lot less painful if you’re really in love with what you’re doing.

Question 2: What would you be willing to devote the next 10 years to?

I thought I loved copywriting. On one hand I do, since marketing and writing are two things I really enjoy, but as I started to look into it as a career I realized something important.

I didn’t want to grow old with it.

Turns out, I was only in it as a way to make some money in the short term, and as those things go, it was going to take longer than I expected, and I quit.

This question “am I willing to put in 10 years” challenges the notion that I’ll be able to get results quickly and easily. While sometimes that does happen, often I find myself excited about projects for the instant gratification, and the reality is that gratification takes far longer than I anticipated.

If I really want to do something, I’ll be willing to put in the time it takes to make it a reality. A project that’s actually aligned with my desires will feel like something I want to grow old with.

Question 3: What would you do if you never had to worry about money?

When I was in the Navy I stood a lot of watch. During the down time I loved striking up conversations with my co-workers.

I was curious about what their passions were, but not wanting to sound pretentious by asking “what are you passionate about?!?” I tried out a thought experiment as a way to discover what they would love to do with their time if money weren’t a factor.

Here is the situation I would run them through, I called it “The Ultimate Severance Package”.

Imagine you are at work and your boss calls you into her office.

(For the purpose of this exercise, if you don’t have a job, imagine yourself at a typical job with good benefits and a salary that gives you plenty of money to live comfortably. If the paycheck isn’t enough to live comfortably, bump the number up to at least $80,000/year.)

She asks you to sit down then says,

“I have good news and bad news. The bad news is we have to let you go. This is your last day, so pack up and head home.

The good news is I’ve negotiated the ultimate severance package for you, and you will be receiving 100% of your pay, with all your benefits, including health care, for the rest of your life.”

You walk out of her office stunned, but also excited by this new opportunity. You think to yourself “I never have to work again…” and it’s almost too much to comprehend. You pack up and head home, sharing the news with a few friends as you drive back to your house. They all ask you the same question.

“So, what are you gonna do?”

“I don’t know yet”, you respond honestly.

You get home and sit on your couch. The thought keeps playing over and over in your head, “I never have to work again.” It’s so simple and yet hard to grasp, since you had assumed making money would be one of the primary objectives of your life.

You decide that since you don’t have to make money, you might as well do things you enjoy, and you have a few ideas.

You pull out a notebook and at the top of the page write “My Bucket List”, then begin writing.

You look at the list and it’s exciting. Maybe you’ve written down places you’d love to travel to, activities you’d love to do, or simple things like taking a week off and just doing nothing. You’ve got some great ideas, and the next day you begin your new life, excited to embark on these new activities.

A week passes, a month, even a year, maybe two years and you’ve gotten to do everything on your list. You’ve traveled, you’ve wined, dined and checked off everything on your bucket list. You arrive back on your couch and look at your list. It’s complete, but you have a strange feeling of “now what?”

This is the important part.

You consider the fact that you have many years left in your life. Where before you pursued activities, now you look for something deeper, something that you can’t do in a weekend. Some might call this a sense of purpose, or a calling, but it doesn’t have to be grandiose. It’s a discovery of your uniqueness and how you can express that in the world. Again, it doesn’t have to be big, and often it’s something simple that gives you a full sense of satisfaction.

“How do you want to use your life”?

When money is no longer a factor, we can be free to pursue the things we really love, and often it doesn’t take a miracle severance package for us to be able to do those things, just a little imagination and some creativity.

Question 4: What would you do if you were really selfish?

10-year olds don’t have a problem discovering what they love because they don’t have an internal board of directors trying to agree on the next move. When you’re a kid it’s really simple, you just do what you want.

Let’s pretend that this board of directors doesn’t exist. As adults we have more to consider than just our desires in the moment, so the board of directors can serve a purpose, but just for a few minutes let’s set them aside.

What would you do with your life if it were purely selfish?

What would you do if you didn’t consider your family, your kids, your friends, your college, your spouse, or anyone else but yourself?

Maybe what you come up with isn’t possible, like wanting to quit your steady job that supports your family to join the circus. That’s ok, because it’s not the result we’re after, it’s the desire.

Maybe you notice a desire to be in the circus that translates to getting into acrobatics. Maybe you get your kids involved with being a circus performer and it turns into something the whole family is interested in.

Either way, the key here is to start by letting yourself want what you want. If you can’t get that far, you’ll never make it to actually doing what you want.

Question 5: Does it feel like playing with Legos?

Several years ago I visited Legoland near my house in Carlsbad, California and I was shocked.

You couldn’t build anything!

There were a bunch of rides, just like Disney World, but most of the decorations were made of legos. Glued together. I was expecting a huge room full of lego pieces where I could build to my heart’s content.

(As it turns out, Legoland’s target demographic isn’t 30-year old men trying to relive their childhood, so having lego pieces available for kids to steal, throw at each other and/or eat isn’t the best move from a liability standpoint.)

When I was a kid, I loved Legos more than anything. I could (and would) sit in my bedroom and build with Legos for days. My Dad even bought me a drawer designed for nails and hardware, so I could use it to organize Lego pieces.

What could you do with your life that would be as fun as building with Legos?

For me recently, I noticed that I love arranging my poetry into hanging art pieces. Who would have thought? I spend hours in photoshop getting everything just right and it feels like I’m playing with Legos.

Bingo, I found something I love.

What You Really Love Is Already Inside of You

The one thing all these questions have in common is they are designed to uncover what’s already true.

If we simply slowed our life down enough to listen to our desires, we would find it much easier to stay true to ourselves, instead of being led astray following other people’s agenda for our life.

If you relax into the knowing that the answers you seek about what you should do with your life are already inside you, the search won’t be so desperate and you may find it easier to discover your own truth.


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