Burn the Ships: How to Quit Your Job

So I hear a lot of advice on making decisions.  Most wise adults will tell you to set up sure-fire guarantees in your life:
  • Don’t leave a job until you have another offer
  • Don’t break up with a girl until you know you can find someone better
  • Don’t move abroad until you know what job you can take when you arrive

The common thread is this: have your next step locked up before taking the leap.  Guarantee that you’ll be moving to a better position.  Eliminate risk.

Now, I’m no expert.  I’ve not run a statistical analysis on decisions and their outcomes.  I’ve only lived life once, and then I’ve only done it for 25 years.

But I have some experience dealing with risk . . .

Back in 2010 I was living in Washington, DC and I hated it.  I wanted to be in NYC with my friends.  But I wouldn’t move until I had a job in NYC.  I couldn’t just quit.  I needed a paycheck.

Two years passed.  I couldn’t get a job in NYC.  It’s tough to build a new life when your time is so consumed with the business of maintaining your current one.

But after 2 years and 6 months, I FINALLY got to NYC.  What new job did I take?

None.  I didn’t have a new job.

I got to NYC when I decided I was going, come hell or high water.  With only a 6 foot slab of floor in Ben’s room waiting for me.  WITHOUT a job, a paycheck, or a risk-free plan.

I got to NYC when I stopped insisting that life guarantee me safe passage.

I went for the guaranteed safe route AGAIN in January 2012.

I dreamed of being a writer.  I even had a few posts up on Kickass Academy.  Nice posts though.  Posts without swear words, that didn’t deal with attracting women.

I also had a Google Drive full of racier blog posts.  Juicy ones on transforming your personality, having good sex, and general “Damn the Man, Save the Empire” type shit.  Stuff that might have made the right kind of dudes come to any classes I taught.

I shared none of those posts though.  I was terrified of what people might think.

Plus, I had a gig as a consultant.  It was a suit and tie, MBA, traditional family type place.  Steady paycheck.  Why rock the boat by posting swear words and advice on meeting girls online?

I didn’t publish.  Until the steady paycheck went up in flames, that is. Funds dried up and the project I was supposed to work on was shuttered.  I was out of a job.  My safety net was stolen. I had rent that needed to be paid, student loans that would follow me beyond the grave, and NO income.  Straight fucked by most people’s standards. That was on January 15th.  On January 17th, I published my first class on meeting women during the day.

What’s the point of those stories?

The point is that IN MY ANECDOTAL EXPERIENCE the best, gutsiest moves of my life happened when I eliminated the comfortable escape route (or it was eliminated for me).   My life took its BEST turns when I burned the ships.  When I had no choice but to make the thing I wanted most a reality. Wouldn’t it have been wiser to have a Plan B though?  That way if things hadn’t worked out at least I wouldn’t have starved to death.  I could have made the same choices and still had the comfort of a back up plan. Maybe.  But I don’t think so.  Repeated experimentation has proven to me that there is a psychological cost to having a Plan B. You see, guaranteeing a safe way out before making a move is a tacit admission that YOU CAN’T count on yourself.  That you can’t rely on your own resourcefulness to make things work.  That you need an escape plan. How are you supposed to succeed when YOU won’t even give yourself the vote of confidence!?  When you are basically saying, “I’m probably going to fail, so I’d better set up my retreat beforehand.” Monthly paychecks, the guaranteed affection of a significant other: these are escape plans.  Plan B’s when your entrepreneurial endeavor goes under or you are incapable of finding a new girl.  They’ll keep you content.  But you’ll never achieve your potential as long as you’ve got one eye on the fall back plan.

So set up plan B or burn the ships?

If you’re living your dreams with a risk-free Plan B, stick to it.  Be my guest.  Enjoy the safety net.  Don’t add risk into the equation. But if you’re like I was and you’re not making progress in the MOST IMPORTANT areas of your life after months or years of half-assing it with one foot in, one foot out . . . . then maybe it’s time for a change . . . Maybe it’s time to give yourself no option but to succeed (or die).  Maybe it’s time to burn the ships. Burning the ships sends a message.  You are all that is left.  You will make it on your own.  You are enough. Is it risky?  No doubt.  You’re relying only on your resourcefulness to make it.  And that’s why burning the ships is so awesome.  It is a massive bet on yourself.  It is the most self-affirming decision you can make. It also has these benefits:
  • It fires you up.  Sure, it’s hard to get a job at a mid-tier company you don’t care about.  But it is actually easier to start your own dream company.  Because you’ll bust your ass and pull out all the stops.
  • It gives you an insane amount of self-esteem.  Burning the ships is a vote of confidence in yourself.  It says that you are enough.  `
  • It forces you to push past fears.  You’ll have to do things that scare the piss out of you.  Things you would have avoided if total failure wasn’t a possibility.  Those terrifying things are precisely the things that you NEED to do to be successful.  (like posting the real stuff on KA)
  • It raises the stakes.  Dire circumstances are the mother of resourcefulness.  You will be shocked at what you come up with when your back is against the wall.  There is NO MOTIVATIONAL SUBSTITUTE for necessity.
  • It gives you focus.  Everything in your life gets run through the filter of your ultimate goal.  And you’ll find resources you totally would have overlooked.
Now just to be clear, burning the ships doesn’t mean going into some dangerous situation without a plan. It means making sure that you have ONE PLAN and it leads to what you desire most. So in my case, when I knew I was going to move to New York, I made a Google Doc of every soul I knew in New York.  I wrote down how they could help me.  I wrote down a long ass list of things I could do for money.  On there was play the guitar in subway stations.  Hypnotize people for tips in Union Square.  Weird, awesome shit. When I decided to share KA, I shared it on a bunch of subreddits (word to the wise: mods don’t like that).  I started Skillshare classes.  I wrote a book.  I reached out to other bloggers.  I told my friends and they told their friends. I poured myself into making one course of action work.  So far, it has.  And it’s been the most rewarding year of my life.


I don’t know you.  But I have suspicion.  Your career is a compromise.  You trade your time for money, stability, and approval. And you are capable of so much more. You could be spending your short time on this planet doing something that matters to you.  You don’t need to take what’s been given.  You can do better than where you are today. And if push came to shove, you would fucking push back.  You would make it work.  You’d find a way.  You wouldn’t die. So burning the ships vs. having a backup plan . . . what is my advice? Burn them.  Burn them to ashes. Pursue what you really want as if it were the only way.  Because once you’ve burned the ships, It IS the only way. So . . .
  • Quit your job
  • Buy a one way ticket abroad
  • Dump the significant other you are only content with
Put yourself in a position where you cannot afford to NOT realize your dreams. Does this mean I’ll get an email from some kid who became a crack addict because I told him to quit his consulting job? I hope not.  But it’s possible. I guess I’m just more concerned with the kids that will email me once they’ve transformed their lives.  Once they’ve beaten their way out of their mediocre lives and their mediocre prospects to live with zeal. I guess it all comes down to this. . . . what’s the bigger tragedy?  Gunning for your ideal and failing HARD or living mediocre?? You know my opinion.  What’s yours? Charlie P.S.  Still want a guarantee?  Here is my guarantee for you If you only chase decisions with a guaranteed positive outcome . . .

If you only make moves that are in the bag . . .

If you never face life-altering stakes . . .

Your life will be a shadow of it’s full potential. That is my guarantee.  

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2 Responses to “Burn the Ships: How to Quit Your Job”

  • I couldn’t agree more, Charlie. Here are four anecdotes from my life I think corroborate your point.

    1. I said “Fuck Investment Banking” and moved to LA to work for minimum wage

    After finishing my undergraduate studies at the Wharton School of Business, I had no idea what I wanted to do. Everybody (fraternity brothers, classmates, professors, and even career counselors!) urged me to go into Investment Banking in NYC for a couple years because “that’s what everyone does and the money is good.”

    Being from California, I couldn’t stand the idea of another winter, much less a grueling 100 hour/week job prettying-up excel spreadsheets. So I broke up with my girlfriend, said goodbye to all my friends, and moved to LA to take a minimum wage job in the mailroom at a Big 3 Talent Agency, hoping to one day make it big in the Entertainment Biz.

    At first, it felt great. I was living in Hollywood, soaking up rays at the beach, fielding phone calls from BIG movie stars everyday (it was exactly like Entourage), and moving up quickly at the agency. I was living an adventure.

    However, as time went on, I realized this wasn’t where I wanted to be. First, my girlfriend and I decided that we didn’t want to break up, so now we were stuck in a grueling long-distance relationship, paying more money than we could afford to visit one short weekend each month. Second, I desperately missed my friends from college (looking at you, Ben!) and was having trouble with irresponsible roommates in LA. Last, I began to hate my job – I was working 70 hours/week, making minimum wage ($1/hour raise for each promotion!), getting screamed at and downright abused, and feeling intellectually stunted. The weather still fucking ruled, though.

    2. After a year in LA, I quit my job and moved to NYC without a penny to my name

    All of my colleagues and LA friends told me urged me not to go. The agent I worked for told me “you’re making the biggest fucking mistake of your life,” but it sure didn’t feel like it. The moment I decided I was moving, and especially the moment I quit, felt like FREEDOM. All of the anxiety about the job I hated and uncertainty about the relationship I was in (and wanted to be in) blew away in the wind.

    I worked out a 2-month training/consulting agreement with the agency while I looked for a job in NYC and prepared to move. When Google reneged an offer after 8 interviews (FUCK YOU, GOOGLE!), I considered staying at the agency until I found a job in NYC.

    It took a couple months of networking (much longer than I anticipated) and dozens of meetings. It caused tremendous self-doubt and second guessing. Eventually, though, I landed a job at a hot NYC startup working directly under the co-founders.

    3. When the startup I worked at went under, I started my own

    With very little personal savings, I opted out of joining another startup with 6-figure pay in favor of joining my friend as co-founder of our very own.

    We built a prototype, we raised funding, we had a huge launch, we gave talks, we sat on panels, we became niche industry leaders, we networked (and networked), we hired, we fired, we hired again, we fired again, we built more product, we threw away product, we launched again, we crashed on our faces, we created financial models and business models and operating models but didn’t fuck any models, we pitched over and over again, we were told “no” over and over again until we were told “yes,” and we went up then down then up then down over and over again.

    We worked so hard, and it always felt like we were rolling a boulder up a hill just for it to roll back down… while blindfolded.

    4. I’m moving to Rio!

    After a year and a half grinding away at my startup, I’ve realized that I’ve lost the passion and that we’re just not receiving the amount of validation from the market that we need. As a result, I’m making the difficult decision to turn down substantial angel funding (thusly keeping it alive for another 18 months), and I’m moving to Brazil end of year.

    I have a few cool friends going, so it should be pretty fun.


    I don’t regret each bold decision I just listed for a minute. Here are some of the benefits that have completely shaped my kickass life:

    1. If I had just worked in finance instead of moving to LA, I might still be working a miserable job in finance – golden handcuffs, yo!

    2. Working in Entertainment was an incredibly cool experience, one that I wouldn’t trade. I have incredible stories, a great professional network, and it’s an industry that still fascinates me. There’s a great chance I do an Entertainment Tech startup one day.

    3. Being long-distance for a year with my girlfriend was difficult, but it only strengthened our relationship. I mean, how impressive is 1 year coast-to-coast? We’ve lived together very, very happily for 2 years since.

    4. I loved the one year break from the East Coast, and I plan to live in California after Brazil. The network I built there will be invaluable.

    5. When I had trouble getting a job in NYC while living in LA, I considered prolonging my move. If I had done that, I’m not sure how much longer my relationship with my g/f would have lasted. I’m not sure how much longer my soul would have lasted if I had stayed at that abusive, intellectually-stunting job at the agency.

    6. Today, I consider quitting the agency job cold-turkey the single bravest and most important decision I’ve made in my life. I was losing who I was as a person. I was losing my confidence. I was becoming bitter. I was honestly losing my fucking mind. But it was a decision I had to make completely on my own, with every external force (colleagues, boss, friends, finances) pushing me not to do it, and that’s fucking difficult.

    7. If I hadn’t gone to the agency and LA, I probably wouldn’t have fallen into tech startups & entrepreneurship, which has become my passion.

    8. While the startup I co-founded hasn’t had the success we hoped, I learned 10X more in that year than I could ever hope to learn while earning an MBA. AND, I paid myself to learn (actual money!) instead of paying a university.

    9. Doing my own tech startup provided validation to myself that I have the stomach to be an entrepreneur and that it’s my passion, something that excites me enough to get out of bed.

    10. It all led me to Rio. I’m going to become fluent in Portuguese, learn Brazilian Jiu Jitsu, live on the beach, pick up surfing again, explore jungles, hang glide and kite surf, immerse myself in a whole new culture, and discover opportunities and bring my experience to a huge emerging tech market. It’s going to be a big, bold, challenging adventure.

    11. My girlfriend is coming, too. She begged. Apparently, she has a thing for Brazilian girls 😉

    I truly believe that Fortune Favors the Bold, and that’s how I’ll continue living my life.

    PS – If you read to the bottom and your name is not Charlie or Ben, you’re a badass

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