A Conversation With My 20-Year-Old Self: When Starting A Business, Prepare for War

What I would have told myself almost five years ago

Recently I was asked, “What advice would you give yourself before you started your business?”

It is this:

“It is said that if you know your enemies and you know yourself, you will not be imperiled in a hundred battles; if you do not know your enemies but do know yourself, you will win one and lose one; if you do not know your enemies nor yourself, you will be imperiled in every single battle.” — from Sun Tzu, The Art of War

Young Jackie, if you want to succeed in business and also life, you must study war. No one told you this. No one prepared you for this. But I will.

(Also, just for some context into my brain, I am a female and my favorite movies are: The Godfather trilogy, 300, and Gladiator. So, this post is not from a place of “The Secret”/self-love/vision boards/etc. My inner mentor is much closer to Vito Corleone instead of Deepak Chopra.)

No classes or books could have prepared you for the battle ahead. There is a reason that people quit on this journey, but this the strategy for how you can win.

So, let’s get into it.

Your two biggest enemies will become:
1. The people closest to you.
2. The strongest enemy of all: Yourself.

The most common things you will hear from the people closest to you:
“Shouldn’t you get a real job?”
“You work too hard.”
“You don’t work hard enough.”
“Well you have the time to do x, y, z.”
“You’re so lucky.”
“You’re not technically at work, so come with me to do this.”
They will support you… in the beginning. Then around the six month mark they will wonder why you haven’t gotten this “thing” out of your system then go back to the 9-to-5 grind. They will then call you “lucky” a few years into it, somehow completely forgetting the years prior.

Don’t worry though, because as you press forward, your troops will come. You can’t plan this step, but as you push through the pain and the doubt the people who will join your army come out of nowhere to assist you. To get to that point you have to go through the lonely times of continuing to make your art even when it doesn’t seem to be going anywhere.

In those lonely times, you will encounter the hardest enemy. The one that takes down even the strongest. The smartest. The geniuses. The visionaries.

Steven Pressfield famously calls this the Resistance.

The Resistance doesn’t just want to suppress your art, it wants to murder it. You must meet it with all the strength you can gather because if you underestimate the enemy, the Resistance, it will kill your work and make you so fearful that you might not ever recover.

I have seen far too many artists stop simply because they refuse to hit Publish. To share their art. To expose themselves. To stab Resistance while it sleeps. The more you win in the private, lonely battles, the more you grow to understand your enemy and the easier it is to defeat.

The amount of things you will abandon due to Resistance are nothing short of embarassing.

I underestimated the enemy throughout the years. I thought if I just visualized myself successful, if I woke up earlier, if I worked harder, if I bought a new notebook, if I wrote a manifesto, that these would somehow help me when the clock struck midnight and I was staring down the raw doubt inside my brain telling me to stop.

No one will warn you about this enemy. It is one that plagues all people who dare to do creative work. You can’t simply approach it with hope, you have to approach it with the intent to annihilate.

So my work sat in the drafts. It sat in my email. It died a slow and haunting death there, never to be released.

When it comes to sharing your art, you must. The things you have experienced and learned could help endless people, but if you don’t share them, it helps no one. Resistance wins, and your confidence takes a punch to the gut.

Young Jackie, be prepared for these doubts. Be prepared and stick the path. Stop messing around and stick your nose to the grind. Don’t celebrate until your work is DONE. Not “close”, done.

Take these tips to heart, young one, they will help:

  1. Get comfortable being uncomfortable.
    The only constant in life is that things will change. No matter how much you try and force life into your submission, the more things will fall apart. Make the best of every single situation you find yourself in and remember that you have yourself and your battle skills.
  2. You only have to slay Resistance once.
    In 300, before the soldiers are heading off to war, Queen Gorgo looks at her husband and says, “Come back with your shield, or on it.”
    Go to your working station. Grab your pen. Do not leave your office until you are finished with your work for the day, even if you die in there. Anything less than full sacrifice will not do. Once you have won, even once, you must keep going. Every single day you lose, the battle gets harder and harder to win. Every single day you win, you become stronger and the enemy goes from a giant to a faint whisper.
  3. Your art is about who you become, not what you get.
    If you are looking for success and fame, those are elements outside of your control. Focus only on winning the battles. Who you become by publishing your art on a consistent basis is far more important than what you achieve. You will become internally stronger. Maybe you will need that strength for another creative mission in life. If your article/book/ebook doesn’t get the rave reviews you were hoping for, who cares? You are now a stronger person by creating the thing. The finished items are your trophies, your badges of honor. Many creative people aren’t celebrated until long after they’re gone. Be prepared to make this sacrifice. Make your art anyway.
  4. When you feel Resistance sneaking up on you, PUBLISH.
    This one took me a long time to learn. I would leave my work in “drafts” telling myself that I just needed to edit it later, then I would publish. They were never published. Never, ever let something die in your drafts if it is coming from a place of true passion. Hit publish before Resistance has a chance to kill your work. Publish before you’re ready. Win the war, even if it is messy. Yes, people will criticize you for spelling or grammar errors, but forget those people. They are only criticizing you because they are losing their own battles against Resistance. If your work has a chance to die before the world can see it, PUBLISH.
  5. Remember you’re going to die.
    You’re so young and you feel like you have eternity stretched out before you but the years start speeding up before you even realize it. Publish more, publish faster, never ever stop publishing. You will leave behind a body of work. Once you’re gone, you can’t go back and write that one thing. I can’t possibly go back to the age you are at now, no matter how much I try. At this point, maybe I have 70 years left, maybe I have two. With death on your heels, you will feel the pressing matter of creating your art. Your art will immortalize you. They say you die twice: Once when you actually die, and the second time when someone mentions your name for the last time. Choose to live forever.
    “What we do in life echoes in eternity.” — Gladiator
  6. Study the metaphor of the eagle and the Phoenix.
    From my understanding, baby eagles are thrown out of the nest before they learn to fly. They have those few fleeting moments to either learn how to fly, or die. Stop hesitating with all of those things you want to do, throw yourself to the wind and learn to fucking fly. GO. Travel. Create. Meet people. Do interesting things. If it doesn’t work out, you can always go back, but nothing is worse than wondering what if? Don’t be one of those hollow people who never even tried. As for the Phoenix, set everything ablaze if you have to. Jackie, you and I know that if you have the chance to hesitate and stay in safety, you will. So throw yourself off the cliff or set everything in your life and rise from the ashes; either way, do the fucking thing.
  7. Along those lines, study the Hero’s Journey.
    This is the single greatest piece of work that school never taught you. School taught you to be safe, to stay in your lane, to get a job and grow up. There is a story you won’t learn until you’re 24 that I wish I could have told you right at this moment of 20. You will hear a calling to pursue things and you must go because your life depends on it. You know that same calling that told you to pack all your stuff from Michigan, get in a car, and go to Colorado even though you had never been there before? Yeah, that voice will keep coming back. Stop suppressing it. You know the things you love and the things you need to create and do in life.
  8. Read Steven Pressfield.
    Resistance will kill more writers than understanding alliteration and metaphors. Win the war inside your head, then win the one on paper. Not the other way around.
  9. Understand the basis of your personality.
    I know you cherish freedom more than anyone else. You have so many ideas that you are terrified to execute on because you think you must follow some path that has been laid out before you. It takes you three more years to start a venture of your own, and by the time you hit this point you will have already worked 21 different jobs. Stop kidding yourself. Put in the hard work and the effort into your own ventures. You excel when you have full creative control and whither when you don’t. You excel when you can dictate your own schedule. Come back with your shield, or on it. Do or die. Life is too short for anything less.
  10. Your army is coming.
    Like I said before, some people cannot come with you. They love you so much, but they cannot follow you on this path. Trying to drag them with you will only do more damage than it is worth. There is this great song that won’t come out for a few years by Florence + The Machine but the lyrics go:
    “Leave all your love and your longing behind
    You can’t carry it with you if you want to survive”
    All those things you didn’t accomplish, all those people who can’t come with you, all of the relationships you loved and lost… Stop mourning over them. The better people are coming, but if you leave one foot in the past and one foot in the present, you can’t move forward. Put both of your feet in the present and start running.
  11. Your life choices will not make sense to anyone.
    You are a little rebellious one. This doesn’t fade just because the world claims you are an adult. Don’t lose touch with those instincts inside of you. They will always guide you. Between 22 and 24, you will suppress your instincts. You’ll tell yourself to grow up. You’ll try to conform, fit in, and bow your head to the demands of the world. Stop that. Keep making those impulsive decisions because you know exactly who you are and exactly what you want out of life. At 24 you’ll decide on a new life career outside of the business you will create. It will require you to throw yourself once again out of the nest and fly on the way down. You never thought you’d be moving to California, but you will be. Everyone in your life will constantly look at you like you are crazy, except for the fellow crazy people who join your army. They understand, they get you, and will happily throw you out of the nest if you don’t do it yourself. They will cheer and encourage the new path. Trust.
  12. The world will always change.
    You might not know that you can create an entire life and career through means of the internet. Sure, you’ve heard rumors about it, but it’s true. Start now, don’t wait. You were lucky enough to be born into the golden age of opportunity and all you need is a camera and an internet connection. Don’t set your life course to one rigid idea. Technology will change everything and take advantage of every opportunity. When you hit my age, you will be able to wear a computer on your face. They will be called Google Glasses. Yeah, so think about that one for awhile.
  13. No one cares about your failures.
    Fail at as many things as fast as possible. You think that if you fail at something, the whole world will laugh at you and talk about it. The truth is they are all so focused on themselves, they will never notice what you start and stop doing. Publish, publish, publish.
  14. Just show up.
    At this point in your life, you are super unhealthy. Actually, you’re about to get your first ulcer at 21. I can’t lecture you about your life choices, but going to the gym wouldn’t be such a bad idea. When you’re 24 you will finally learn how to actually stick to a gym habit, and the secret is to show up no matter what. Even if you just go to sit on the floor and stretch, get there. You will always eventually feel like working out. The same can be applied to your writing and video making. Just start filming. Just sit down to write. Start playing around, then create.
  15. You must do the thing to have the power.
    You won’t discover the genius mind of Elliott Hulse until you are 23, but I would even tattoo this quote on you if I could. You will constantly think that you must be granted the power, then you can do the thing. You’ll think you can’t write until you are more “qualified”, you’ll think you can’t make videos until you “know the right people” or “have better jokes.” You won’t be granted the power first. The power only comes through the doing of the thing. Do the thing. Have the power.
  16. Create more than you know what to do with.
    Create so much art, work, writing, content, videos, posts, etc., than you know what to do with. Make so much that you forget what you have even done. Make something every single day. It will never be perfect and you can’t calculate what will help your career or what will resonate with people, but you will never know until you try. Assume that you have to write 1,000 pieces before a single one resonates with people. Assume you have to make 1,000 videos before anyone cares. Keep doing the work and don’t even look at the metrics for five years. You will abandon projects because they aren’t going as well as you thought they would. Just remember, you’ll be my age in 4 years and 10 months. Right now I could have thousands of pieces of content out there under my belt. Think of me when you are hesitating. Give me those gifts because it will only benefit the both of us. Now, I have to publish even more so our 30-year-old self can have massive amounts of content in five years.
  17. Market or die.
    You must be brave enough to share your work. Getting your degree in writing is not something to shrink or be ashamed of. It is not somehow less valuable to the world simply because it is a Liberal Arts degree. At the end of your degree you’ll have written a grant, proposal, articles, been published in a paper, work as an editor, do tons of school newspaper articles, get your first paycheck as a writer, write tons of poetry, write a technical manual, and tons of other experiences you wouldn’t have had otherwise. However, the degree is just for the experiences, you could also just skip it and get straight to work if you wanted to.
  18. Get your hands dirty.
    Stop trying to think things through. Roll up your sleeves, stick your hands in the mud, and figure it out. Let life, experiences, and your intuition be your ultimate guide.
  19. Every single person is important.
    You never know which person will ultimately be a benefit and which ones will be a hinderance. Some of the best people will come out of the most unexpected places. Help every single person who comes across your path.
  20. The meaning of life is the climb.
    Every single time you accomplish a goal it will not be as exciting as the journey it took to get there. When you graduate with your degree, you won’t even want to celebrate because the climb is over. Eventually, you get insanely bored with conquering the goals you set out, so start setting much higher goals because the joy is in the climb.
  21. Always do more than you can handle.
    Forget work/life balance. That’s for people who hate their jobs or people who have children. You and I can have that discussion when we hit 40, until then, you are going to hustle like your life depends on it. Sacrifice some time when you have the energy to operate on Ramen and no sleep. But, of course, have a margarita every once in awhile with some friends. Then get back to work. Load more on your plate than you think you can handle. It will stress you out but then you will stretch beyond what you thought was possible in your life.
  22. Capitalize on your strengths.
    You and I know that there are certain things you excel at. Talking to people, making people laugh, and any athletic endeavors. All that time you will waste trying to be serious or follow careers that don’t fit your personality will just be a waste of time. Stick to the things you do the best, and once in awhile improve your weaknesses. Don’t flip that equation.
  23. Continue to stare down the enemy.
    You will be on the brink of failure repeatedly. You will be ready to close up shop. You will be ready to throw in the towel. Everything will fall apart. Keep creating things. These will be your final battles and your defining moments. It is you versus the devil. Gladiator and Commodus. King Leonidas and Xerxes. Don’t you dare pack up and go home. You slay the enemy. Don’t let the fear get to you. Know that if you keep creating you will come out on the other side. Sell everything you own if you have to, just keep going. Do not quit on your art just because things are hard.

That is all you need to know. Prepare for war. Know your enemy. Win.

“At my signal, unleash hell.” — Maximus
One clap, two clap, three clap, forty?

By clapping more or less, you can signal to us which stories really stand out.