Betting On Yourself

If you’re an artist or an entrepreneur, your working life is by definition about risk. You’re already rolling the dice or you wouldn’t be doing what you’re doing. But beyond the inherent hazards of the artist/entrepreneur’s life, how should you manage risk?


No, we're not "swinging to the sweet sounds of Risk Management"

(I’m not referring, by the way, to the Seinfeld episode featuring George Costanza and his protégée.)

My theory is to bet on yourself.

If I have $10,000, should I put it in the stock market? Or should I use that cash to back my own dream?

My stuff has crashed and burned 90% of the time. But always when I find myself with money, I use it to buy time—time for me to work.

I bet on myself.

Why does the chef who has opened three restaurants, all of which have gone belly-up … why does he leave his safe, lucrative, prestigious job running someone else’s four-star kitchen to take another flyer on another new eatery? Is he crazy? Yes. But he knows his own heart. Is he driven by a dream of fame, money, recognition? No doubt. But in his deepest soul he is impelled by his own vision. At night after work, snuggled up with his sweetie, our chef sees new menus scrolling before his eyes; he sketches designs for stunning entryways and scribbles rosters of all-star staffs; he envisions the entirely new cuisine he will invent and elevate to perfection. He can’t help himself. Should he splurge his bankroll to take his squeeze to St. Bart’s? Okay. But the lion’s share must go to a seed account for the Next Big Try. It has to. His only alternative is to hang himself.

When I worked in advertising in New York, I would sock away my paychecks, then quit and move someplace cheap where I would write a novel. When I couldn’t sell that novel, I crawled back to NY, got out the knee pads, then did the same drill over again. When I made money in Hollywood, I used it to buy more time and did the same thing.

One frozen February Friday in New York, I caught a ride up to the country with my ad boss (who was a superstar creative director and a good guy, who had taken me off the street when my “portfolio” was literally scribbled on the backs of cocktail napkins). As his BMW was cruising north on the Saw Mill River Parkway we happened to pass what was probably the dirtiest, scurviest freakazoid hippie no-hoper, shivering in the frozen slush along the roadside. “Yeah, Steve,” my boss said, indicating the gentleman in question, “that’ll  be you in a couple of months.” I gulped. Of course I was thinking the exact same thing. My boss knew my history. He had once described me as “the man who has written more words for less money than anyone in literary history.” But he knew, and I knew, that I was going to roll the dice again—and probably in the aforementioned two months.

In Hollywood, writers and directors have an axiom: “One for love and one for money.” What they mean is that the crafting of a career in the real world sometimes requires a canny to-and-fro-ing between art and commerce. Take one job on Track #2, the commercial track, but make sure the next one is on Track #1, the track from your heart.

Bet on yourself.


Steve shows you the predictable Resistance points that every writer hits in a work-in-progress and then shows you how to deal with each one of these sticking points. This book shows you how to keep going with your work.

do the work book banner 1


A short book about the writing of a first novel: for Steve, The Legend of Bagger Vance. Having failed with three earlier attempts at novels, here's how Steve finally succeeded.



Steve shares his "lessons learned" from the trenches of the five different writing careers—advertising, screenwriting, fiction, nonfiction, and self-help. This is tradecraft. An MFA in Writing in 197 pages.



Amateurs have amateur habits. Pros have pro habits. When we turn pro, we give up the comfortable life but we find our power. Steve answers the question, "How do we overcome Resistance?"



  1. Julian Summerhayes on March 28, 2012 at 3:35 am

    *gulp* – i am sure every budding writer can relate to this. it sort of freaked me out because it feels like the space i find myself in. i am not yet willing to give up on the dream of doing something worthwhile with my life, but trying to balance the creative act with commerce has to be the hardest thing i have ever faced. i don’t know how to stop. my muse or subconscious won’t allow me to work in an environment where i cannot do my art or express myself in a meaningful and life-sustaining way. i know it sounds melodramatic, but as long as i have the will, strength and life left in me i will keep going. i love writing but more than that i love the idea of creating something that perhaps, just maybe, has the ability to connect with people and make a slight difference to their lives.

  2. skip on March 28, 2012 at 4:31 am

    i took that bet almost 40 yrs ago and never regretted doing so. either live your passion or die wondering if you should have.

  3. FredInChina on March 28, 2012 at 5:43 am

    “Life should not be a journey to the grave with the intention of arriving safely in a pretty and well preserved body, but rather to skid in broadside in a cloud of smoke, thoroughly used up, totally worn out, and loudly proclaiming “Wow! What a Ride!”
    ~Hunter South. Thomson

    When my eldest was 22, he visited me in China and we had the following discussion:
    I: Say we are both lost in a foreign city, we don’t speak the language and we have zero money, what would you do?
    He: I would find a job, maybe unloading trucks, just so we can eat and find a shelter…
    I: Okay, I hire you!
    He: (stupefied) but, but… you don’t have money…
    I: It’s okay, I only need to pay you tonight… now, about finding work to do, let’s get busy!

    The message went through, he is now altering back and forth between jobs for the local TV station, and the making of his own reportages.

    Thanks for this good article Mr Pressfield.

  4. Jeremy on March 28, 2012 at 6:38 am

    Steve, once again you show the ability to get things rolling on both tracks for me (and I’m guessing many who read this series).

    “Bet on yourself” gets my muse ready to run through a wall, and it’s tempered with “One for love and one for money.”

    Spear in one hand, shield in the other.

    Thanks again.

  5. Warren J. Duffey on March 28, 2012 at 7:52 am


  6. David YB Kaufmann on March 28, 2012 at 8:16 am

    If you’re alone, with no responsibilities for others, it’s easy enough to slip-slide in and out, off and on the two tracks. But if there’s a wife or children – they better be willing to not only go along for the ride, but to apply the defibrillator to the artist’s heart. (And yes, my wife’s got the cables ready.)

  7. Jason on March 28, 2012 at 8:21 am

    “Bet on yourself.” Just what I needed to read.

    Thank you, sir!

  8. Sarah Mae on March 28, 2012 at 8:21 am

    Love this. Thank you!

  9. tolladay on March 28, 2012 at 8:28 am

    Such good advice.

    Back in March of 89 I leveraged my pitiful salary (at an exorbitant interest rate) to buy a computer. It was a Mac SE. It cost me $3k when I was making less than $24k/year. That computer, plus a lot of skull sweat, lead me to a better paying job within 6 months. In short, it paid for itself in the first year alone.

    Though I have a BA in History (with a minor in Attic Greek of all things) I make a very good living in graphics because I bet on myself very early on. Short of a therapist (which is another type of self-investment) that computer was the best investment I ever made, and has paid for itself year after year.

  10. Jason Keough on March 28, 2012 at 9:57 am

    Wise words. You hit the 10k hour rule you’ve written on in the past, many times over because of your belief in yourself.

  11. ruth kozak on March 28, 2012 at 11:01 am

    Thanks for the inspiration. I’ve just invested a lot of money in the final editing of my novel but it’s an investment, years of work, and it’s worth it.

  12. Jerry Ellis on March 28, 2012 at 11:50 am

    I thank the gods for you, Steven. You always hit the nail on the golden head as far as I am concerned. I hope you will be kind enough to allow me to post the following?

    My two hour live radio interview is this Sat, March 31, 10-12, EST. It will focus on my time of desperation in Hollywood when no one would even glance at my script about the Cherokee Trail of Tears, where 4,000 of my ancestors died when forced to walk 900 miles from their homes in the SE to Oklahoma. So I decided to sell all I owned to walk the route myself and tell the world of their plight. My book, Walking the Trail, written on spec, sold at auction in two weeks and was nominated for a Pulitzer. We can be viewed on the internet at if the listeners will set up an account they can chat with me on the site Saturday. Listeners can also go to the website and sign up for I accounts for I phones.

    Call in number is 423-614-5553
    Welcome to the World Wide Woop! – Streaming Radio, Video, Bluegrass, Talk Radio
    Like · · Share

  13. Rod Roth on March 28, 2012 at 12:03 pm

    I am, Steve, I am, for eleven years , now. And I won’t ever quit. Thanks for the post. It is having a bracing effect for me this afternoon. Semper Fi

  14. Chad Darwin on March 28, 2012 at 1:59 pm

    A-W-E-S-O-M-E…as usual…thanks for the inspiration!

  15. Andrea Lavin on March 28, 2012 at 2:07 pm

    Thank you Steven Pressfield, for the this post and for every word you write! You inspire me beyond measure! xo

  16. Dr. Susan Biali, M.D. on March 28, 2012 at 5:27 pm

    This is breathtakingly awesome. You’ve just given me permission to do what I long to do at this juncture. Not that I needed permission from anyone other than myself, but it’s still so fantastic to hear it from you. I bought myself four years in Mexico from 2005-2008 to focus on dancing flamenco and writing. That choice has paid for itself many times over. My book emerged out of that time, as did my professional speaking career and my life coaching work as well.
    My time in Mexico was the best investment I ever made in myself and my life and my art, yet I have always explained my results as being the inevitable benefits of following one’s heart and instinct.I love the idea that I was actually betting on myself. And I won!

  17. Consuelo on March 29, 2012 at 12:05 am

    Love your blog. Shared it with two friends tonight. Solid. Wonderful advise to all with a dream.

  18. basilis on March 29, 2012 at 1:33 am

    The future belongs to those who believe in the beauty of their dreams, I bet.

  19. Hamilton Wende on March 29, 2012 at 7:08 am

    As always Steve you are an amazing inspiration!

  20. Ian on March 29, 2012 at 7:11 am

    Not disagreeing, but when you have a wife, three kids, a mortgage, and a steady wage, it can be a difficult decision.

  21. Matt Brennan on March 29, 2012 at 10:55 am

    I love this. You have to have some confidence, and you have to go in at 110 percent!

  22. Amanda Sowards on March 29, 2012 at 10:57 am

    Okay, so…. the money I’ve invested (and the debt I’ve incurred) getting those college degrees WILL pay off in the end, then.

    Good to know. Because, sometimes, when you get to the end of a long road, hoping for something better, only to find another long road, it gets really, really discouraging.


  23. Zeph! on April 3, 2012 at 7:45 pm

    “Bet on yourself.” That would be a great bumper sticker.

  24. Mike Laughlin on April 5, 2012 at 8:13 am

    … until one reaches retirement age. By then, one should know how to live with means and still get something done. There is some obligation to go out under own steam, without having become a burden on others.

  25. Turndog Millionaire on April 6, 2012 at 11:36 am

    Very inspiring. As someone who’s about to venture into a rather scary new world, this is exactly the thing i needed to read

    Thanks you very much

    Matt (Turndog Millionaire)

  26. Bob Holmes on April 8, 2012 at 10:45 am

    Man, Such courage and encouragement. Thanks Stephen! I needed that.

  27. Jim on April 12, 2012 at 9:58 am

    Steve,thanks. I need to depend on myself more and not make excuses. Excuses are garbage and a waste of time.

  28. Julie Tallard Johnson on April 16, 2012 at 6:53 am

    I just came off a 5 month sabbatical to write my first fiction (first draft). And did! It feels great, even if I am a bit poorer financially, to have fulfilled the first draft of this dream.

    Thank you Steve.

  29. Casey on May 9, 2012 at 3:58 pm

    “One for the reel, one for the meal.”

  30. Georgina Shamon on September 26, 2012 at 10:04 pm

    this is the balance I’m trying to find in my life right now — between track 1 & track 2. Thank you for sharing!

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