Navigating the geography of a creative life requires a compass - not a map. It's something you design without any instructions to follow or boxes to check off. There are no prerequisites or roadmaps that get you from point A to B. You can't put an address into a GPS because your destination is only revealed through your journey.

There's no license, certification, or advanced degree that qualifies you or permits you to express your creative desires. You are voluntarily signing up for a life in which nothing is guaranteed, and anything is possible, a life in which impossible dreams might become a reality, and ambitious aspirations might never materialize. For this reason, building a career in the arts is in and of itself a form of art.

You have to be crazy, insane, or feel as if there's no other option if you want to go down this road. This is what I wish I'd known about building a career in the arts when I started mine 10 years ago.

1

You'll watch your friends cross off the checkboxes of society's life plan, doing everything when they're expected to do it on the timeline they're supposed to do it in. Kids, marriage, mortgage all by a certain age. At moments you'll wish you had a "normal" life. But the chapters of a creative life aren't linear, and the ship that's headed to the “Destination Normal” sailed the day you signed up for a career in the arts.

2

You will lose friends, be misunderstood, and fail to live up to people's expectations. Burnt bridges and friendships fractured beyond repair are often the collateral damage of a creative life. This is the fatal flaw of our humanity. Nothing will hurt more. I wish I could tell you this won't happen to you, or that you're beyond this. But it will happen. And you're not beyond this.

3

Even if you get what you want more than anything in the world, there will be an opportunity cost. You'll have to give up other people's definition of success, temporary financial security, entire chapters of your life, and more. You'll have to decide what you're willing to give up to be successful and if the juice is worth the squeeze.

4

There will be times when you are forced to choose between people who have helped you to get where you are and the next level of accomplishment. You will outgrow people, and they might even resent you for it. Sometimes it will mean the end of relationships. As Steven Pressfield says, "When we turn pro, we will be compelled to make painful choices. There will be people who in the past had been colleagues, associates, even friends who we will no longer be able to spend time with if our intention is to grow and evolve. We will have to choose between the life we want for the future and the life we have left behind."

5

There's a difference between friends and fans. Fans always expect you at your best. Your friends will always accept you at your worst.

6

There will be peaks, valleys, dips, messy middles, dead ends, and detours. You'll experience the heights of happiness and the depths of depression. As Donald Miller said to me in his interview on the Unmistakable Creative, "A fulfilling journey of doing something difficult demands that you go through dark valleys." If you remember that your circumstances give you colors to paint with, you will be ok.”

7

Success won't heal your wounds, alleviate your insecurities or dispel your self-doubt. It's one of the strange paradoxes of achievement that accomplishing goals doesn't lead to everlasting happiness. It's something every creative discovers when one of their dreams comes true.

Dax Shepard echoed this sentiment in his recent interview with Brene Brown. Being rich and famous or having millions of people watch your TED talk isn't going to fix everything you think is wrong with you.

In his beautiful book Reasons to Stay Alive, Matt Haig said, "For about six months, my lack of self-esteem had been artificially addressed. I would lie in bed and go to sleep smiling, thinking Wow I'm quite a big deal, I'm going to be published. But being published (or getting a great job or whatever) does not permanently alter your brain.”

For a brief moment, after I got my book deal, I felt vindicated for the bosses who fired me and the women who broke up with me. But that didn't last very long. Despite writing 2 books with a publisher, I've wrestled with a constant sense that I'm deficient in some way, feeling that I'm not good enough to make a relationship last or to do all things I should have done with my life by the age of 40. Overcoming this sense of deficiency and embracing what Brene Brown has called “the gifts of imperfection” has been the most important work of my own spiritual journey.

8

It's natural to seek validation from your peers, fans, friends and family. But as I said in my previous book:

Validation is a like a drug. The more we depend on it, the higher dosage we'll need for it to work. When it's gone, we'll experience everything we would with a drug withdrawal— darkness, loss pain, and and the unquenchable desire for more.

9

There will be artistic losses, what Julia Cameron calls the “miscarriages of a creative life.” It took me 5 years to build the community that made my first conference possible. It took 5 months to destroy it beyond repair. It was the greatest miscarriage of my creative career, and it was so painful that I can't bring myself to attempt it again. But, your artistic losses will often be followed by artistic gains. In every ending, there's potential for a blank page and a new beginning.

10

You will want to quit, at some point. You will question your faith and conviction. Other people (parents, peers, friends, lovers, partners) will question it as well. Some of them will even leave you. In those moments, particularly if you're a man, you might start to believe what Chris Rock said in his recent Netflix comedy special: "Only women, dogs, and children experience unconditional love." Hopefully, that's not true.

11

Sometimes you'll laugh until you're crying and other times you'll cry until you're laughing. Hopefully, with time, you do more of the former and less of the latter.

12

You'll dream of the day when your creative work reaches an audience of millions, but the work always begins with an audience of one. If you're serious about building a career in the arts, focus on mastery instead of metrics because the only viable long-term strategy is to be so good they can't ignore you.

13

There's no such thing as an “I've made it” moment. You'll never be able to stop doing the work that got you there in the first place. Moments in the spotlight are always fleeting and building a body of work while also becoming a master of your craft is the work of a lifetime. As Scott Belsky wrote "The creative pursuit never ends. Creativity is never finished."

14

People will often ask successful people, "What do you wish you would have done differently?" All of us have things we wish we would have done differently: people we wish we'd never dated, jobs we should have quit, etc., etc. But if we had, we wouldn't know all the things that we do. As Robert Greene once said to me " No experience in your life should be thought of as wasted."

15

Sometimes the worst chapters of your life will lead to the most powerful chapters of your creative work

16

Discipline, habits, focus, and consistency are essential ingredients for a career in the arts and for anyone who wants to build a lifelong creative practice. What you do each day is what plants the seeds for the person you want to become.

17

Unless you capture your ideas, you'll never capitalize on them. Always carry a notebook and get in the habit of writing things down. This simple practice will serve you well. Everything I've written, designed, produced or created can be traced back to the pages of my notebooks.

18

If you want to create great art, you have to consume great art. Read the most celebrated writers, listen to the most celebrated musicians. Let them be the wings that enable you to soar.

19

The business of comparing your insides to other people outsides is rarely productive or profitable. It will never lead to the most significant work of your life.

20

If you are fortunate enough to get picked, by a publisher, a record label, or a production company, you'll be forced to confront a harsh truth about art and commerce.

You are a product and an investment.

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Your value will be quantified in return on that investment. The so-called gatekeepers of the creative world are the equivalent of venture capitalists in the business world. Just because the primary product of a business is creative work that doesn't mean it operates by different rules than any other business. It still exists within the tenets of capitalism and has to make money to survive.

21

Even though you have to make money to survive, your best creative work will never be something you do just for the money. The work you do just for the money is a job. The work you do to grow as a person helps you build a career. But the greatest work of your life is the expression of your soul's calling.

22

You will have to accept that most outcomes are out of your control. You can't control how many people read your blog post, how many people buy your books, or what people think of your work. Control is an illusion that does little more than contribute to the misery of a creator. Focus on the process, not the prize.

23

Bad ideas are necessary for good ones. Sometimes the best ones are hiding in plain sight. A few nights ago, I was researching how NPR produces story driven podcasts. At that moment, a dozen dots connected for me in a way they never had before. I'd already created this kind of audio, but I'd overlooked something that was staring me in the face.

When we produced our animated series with Soulpancake, I was the one who developed the storylines, chose the audio segments, and the music. I closed my eyes and just listened, and I realized that these could just as easily be stand-alone audio pieces, and new series I'm working on called Unmistakable Nuggets was born.

24

Comparison is toxic to creativity, but it's also inevitable. If you're an author, you'll compare yourself to authors who have sold more books. If you're a musician, you'll compare yourself to musicians who have sold more albums. But we each have a creative dharma, a destiny that is uniquely ours. "Envy is human, yes, but also corrosive and powerful. It is our job to pursue our own dharma and covet no one else's."

25

How you measure your success will have a significant impact on your happiness. If you choose to measure it entirely by external measures, or what David Brooks calls “resume values", you'll suffer from the toxic impact of quantifying every aspect of your humanity. If you choose to measure it based on the contributions you've made, and the people whose hearts you've touched, what David Brooks calls “eulogy values”, you're likely to be a happier person. This, of course, is easier said than done.

26

The more well known or famous you become, the more you'll be idealized. People will craft idealized images of you based on your work. You will never live up to that image or their expectations. This is especially true when people develop a romantic interest in you based on your work.

As Nick Notas told me, "For better or worse, it's always going to be worse because it's different. People get a partial view into who you are, and then you show up a full person with flaws, vulnerabilities, and insecurities." And you have to be self-aware enough not to buy into this image or your ego will wreak havoc on your life. To my parents and my sister, I'm still the goofball who went to the grocery store on an errand to pick up cilantro, only to have my sister tell my parents, "I bet he's in the produce section staring at the tops of the carrots, thinking it's cilantro. I'll go get him”, (true story). Your family is always a good litmus test to keep your ego in check.

27

When you start, you'll crave fame, admiration, attention, and accolades. But as you progress, those desires will diminish, and you'll crave impact, resonance, and significance. Instead of asking yourself "How do I get noticed?", you'll ask yourself, "Have I made a difference?". If you've followed my work, hopefully, I have been able to make a difference in your life, and if we have never met, hopefully, we will get the opportunity to.

The voices of your critics will always seem louder than those of your fans. 

• One of my books has 300 5-star reviews, and yet the only one I can quote to you by memory is from the woman who wrote me a 2-star review and said, "I hope this guy is a better surfer than he is a writer.”

• By some accounts, the conference I planned was amazing and life-changing. But what I remember 5 years later are the emails from people filled with "deep disappointment and rage" and the person who responded to my apology in our Facebook group, which I wrote when I emerged from a deep depression, by saying "Fuck you Srini." On the one hand, the conference is one of the creative projects I'm most proud of, but on the other, I can't help but think it caused more harm than good.

28

If you are lucky, you'll have someone to share your big moments with. If not, you'll end up dedicating your books to strangers on the internet, fans, and people you've never met. There are few experiences over the last 10 years that have made me feel as lonely as writing the acknowledgments and dedications in my books. So I treat them like I'm ripping off a band-aid.

29

People will question the validity of your career because it looks nothing like a "real job." One of my relatives told a cousin of mine that what I was doing was a waste of my education. So I made a mental note to cross her off the list if my parents suggest her as a guest at my future wedding.

30

Some of your dreams won't come true. Others will come in the most unexpected of ways. Terrible things will happen. But as my friend CC Chapman says, “Amazing things will happen too.” You'll experience delightful surprises that you could never have predicted or planned for. That's the beauty of a creative life. It's an ongoing work in progress.

31

Anytime you make a decision that's out of alignment with your values; it will come back to bite you in the ass. At the start of 2014, one of my mentors said "if you want to build a media company, I'm all in. If you want to build a personal brand, I'm out.” I didn't want to lose my mentor, so I attempted to turn Unmistakable Creative into a massive venture funded media company. It was a complete disaster. I completely overlooked the fact that the whole I reason I started any of this was so I'd never have to set foot in an office again.

33

You have to take time to appreciate your accomplishments no matter how small they are or even when they don't live up to your expectations. If your books don't hit the New York Times Best Seller list, you have to appreciate the fact that you got to write a book in the first place. It's easy to forget that many people would give anything to have what we eventually take for granted. This is hard because it requires you to surrender to the circumstances of your life.

34

No much matter how often accomplished people talk about commitment, discipline and work ethic, we can't overlook the role that luck plays. Sometimes you're in the right place at the right time. Sometimes an editor stumbles upon your article on the internet. Remembering that luck played a role is an excellent way to keep your ego in check.

35

There will be questions you'll never have answers to, and mysteries of the universe that you can't explain or understand with reason and logic. That's what keeps things interesting.

36

You will have to learn to love yourself like your life depends on it, because it does. But this takes practice because we spend so much of or our lives trying to fix all the things we think are wrong with us.

37

When you build a creative career, your art is your obituary. It's what you leave behind and what people will hopefully remember about you.

38

You have to remember to have fun, and it's really easy to forget this when shit hits the fan, things don't go according to plan, and it feels like there's no light at the end of the tunnel.

39

A life in the arts ultimately comes down to the work. The only good reason to pursue a career in the arts is that you can't imagine doing anything else. Even the most successful artists will encourage you not to pursue a career in the arts. In an interview with Offcamera host Sam Jones, Matt Damon said the following:

"If I can talk you out of this in a conversation, you're not cut out for it."

40

In the last 10 years, I've had days when I couldn't get out of bed in the morning, shed an ocean of tears, rode perfect waves that put an ear to ear smile on my face, and and created things that lit my eyes up with a sparkle and made my heart race in a way I didn't know it could. In the movies, when people die, scenes from their life flash before their eyes. And I'm guessing I'll see flashes of waves and words when that moment comes in my life.

If you're insane enough to walk down this road, destination unknown, no map in hand, remember that you are the one that's going to live with the consequences of every choice you make: not your parents, peers or society. Not the advertisers who are perpetually trying to convince you to buy shit you don't need to impress people you don't like. Not the random people who on the internet who heart your pictures on Instagram or like your posts on Facebook.

And we need people to take this path because if they didn't, we'd never have books to read, music to listen to, movies to watch, or art to admire. And remember, by definition, you change the world when you create something that didn't exist before. So go make something, give people a reason to find you interesting, and change the world, or some small part of it, that in the words of Neil Gaiman is ‘different for having been here.’”