How to quit your job and start a business you love

Do you dread Mondays?

Put simply, have you ever wanted to say, “f*ck it" and quit your job?  

Do you want to make more than just money?

If so keep reading to learn how to quit your job the right way and start a business you love.

This post is less about quitting your job and more about getting your life on the right track.  Discover your passion and feel fulfilled with your chosen profession.  Find meaning and purpose everyday, every email, everything you do at work. Yes, a lofty goal but one worth pursuing.

Do less 'work' and more 'mission'. 

After all, Job < Career < Passion < Mission

This post is for dreamer and idealist in you. This post is for the 10 year old you who collected matchbox cars and dreamed of being a professional baseball player or a fireman.  When you're 10 you probably didn't dream of working 8-5:30 everyday in a cubicle, did you?  I’m pretty sure you didn't think wearing khaki pants, black socks and shoes in 85 degree August weather was going to be awesome.

There is reason Office Space is a cult classic.  It's not just that Jennifer Aniston looks great or that the guy from The League is awesome in it. It's that we've all been there, we've all had a job like that and known a Lundberg (talking to you, David Chang, LA Cellular circa 1994. Worst boss ever).

Don’t even read the rest of this unless you're a little crazy and a little weird. You need to be a little rebellious and nuts to quit your job. Face it, it's easier to turn your brain off and coast through Corporate America for the next 30 years. If you're smart and easy to work with, a corporate job is a relative cakewalk. 

Here’s the thing, most likely you're on the upswing in your career.  You probably make good money and your job security is relatively intact. You don’t bank millions but you don't sweat going out for happy hour or buying a new bike when you want one. Your life probably has it's stresses but compared to the dudes in Russia waiting in line for 2 hours to pay $17 for a Big Mac, you're good.

But (this is a big 'but') if you cannot turn off that nagging feeling in your brain that there must be more to life, then you’re in trouble. If you're a little crazy and a little weird like me and think that your life (gasp!) should have purpose and meaning then you're just like me. And, my friend, once you turn on this part of your soul, it's impossible to turn it off.

It's like the roller coaster at the park.  Once you see it you have to ride it. You can't not go on. Not going on just isn't an option anymore. And everybody has seminal moments like this. For me it was when I was 10 years old and first visited California.  I saw the Pacific Ocean and knew that living anywhere else in the world when I was older just wasn’t going to be an option.

I will not insult your intelligence by listing the common benefits of quitting your job and going out on your own.  Plenty of other people will waste your time, I'm going to avoid that here. However there are some lesser known yet more impactful benefits to going out on your own, including:

  • Accountability: When you're successful, it's because of you.  When you fail, it's because of you.  You no longer have a corporate veil or someone else to blame.  That's both exhilarating and frightening.  Just like shopping for an engagement ring*

* I remember walking down a street downtown Los Angeles in 2001 with $12,000 cash in my pocket. I was on my way to buy a diamond from a Hassidic Jew in an unmarked storefront in the heart of the Diamond District. After going through 2 levels of security and haggling with the guy for 20 minutes I left with a diamond in a small velvet bag.  The entire process took abut an hour and I remember thinking that if I got robbed I would lose either most of my savings or a $12,000 rock. It was frightening, exhilarating and awesome all at once.

  • Peace of Mind: When you go out on your own, you have peace of mind because you're doing what you want to do. Yeah, it's stressful and can be really hard but it's totally worth it. You sleep great because you're not worrying about wasting your life away.  You're not tossing and turning thinking about a job you don't like but you're afraid to leave.
  • You're generally happier.  It's not easy but you're generally happier because you're fulfilling your life's purpose.  Your life has meaning and quite honestly that feels even better than it sounds.  It's like eating that first fish taco after surfing.  You're out of the water, you caught some fun waves and the sun is going down and you know that taco is going to be good. Then you take a bite and it's even better than you thought.  It's like that.
  • Limitless potential.  When you work at a 'job' you really can only make so much and be promoted so far.  When you're out on your own, money comes in waves and the potential for huge windfalls of cash is much greater. [See also founders of Facebook, see Goggle, see Under Armor who all skipped the corporate route to do their own thing]

With that all in mind let's get rolling and I sincerely hope you like scars...

Quitting your job requires a plan.   This is not something you should so hap-hazardly, like drafting a kicker too high in your fantasy league.  You need a plan.  Luckily I left the corporate world to go out on my own so I am going to give you the answers to the test.

First some background:

I moved to San Diego in 1997 from Los Angeles (where I had lived for 4 years) after moving out west from New York. I interviewed with Sprint in June of 1998 and Don McGuire (one of the best bosses of all time) offered me a job soon thereafter.  My friend Eric and I drove to Mexico from LA for 4th of July and stopped in San Diego.  Right about that time I had to decide whether to move to SD and take the Sprint job or stay in LA and try to work it out with my then girlfriend.

I was standing in the ocean in Pacific Beach, tons of people were around and I remember looking to the sky and asking God for some sign as to whether I should move to SD. Just then, a dollar bill floated right in front of me in the ocean. It seemed to just float there and stay in front of me even though waves were crashing all around.  I took it as SD was good place for me and I moved a week later. I still have that dollar bill too.

After working at Sprint for 18 months I really wanted to go out on my own.  I loved my team, made great money and Corporate loved me. Still, I had an itch to run my own gig.  So I got rolling and set the plan in motion to start my own company.


There is a simple four step plan to follow to quit your job and start your own gig.  The steps are:

  • Decide
  • Test
  • Plan
  • Go


Deciding to leave is the first and most important step.  This is the one you really can’t get wrong because you can’t ask for your job back after you quit in a blaze of glory:)

It takes a special type of crazy person to want to go out on their own, so ask yourself if this is you:

  1. Do you have the right mindset to be an entrepreneur?
  2. Are you comfortable being uncomfortable?
  3. Will you do the extra sit-ups?

You need to be really clear about your mindset* before you quit your job.  Are you mentally strong enough, determined and willing to work your ass off to make this successful?  Are you cool with dialing back your lifestyle and eating Mac & Cheese for a year to get everything rolling?  

When you go out on your own, you’ll be uncomfortable a lot of the time so figure out if you’ll be ok with that. Are you willing to put the time in and ‘do the extra sit-ups” and work hard for this?  Muhammad Ali once said that he never started counting sit-ups until they started hurting and only then did he keep track.  Sound like you? Do you finish the WOD strong or do you fade out at the end?

If you’re unsure, look to past events in your life.  Were there any times when you persevered and accomplished something you didn’t think you could?  Have you ever really wanted something so bad that you grinded it out until you had it? If so, good!  That’s a good indicator of future success.

*There is a great book about mindset, called (wait for it) Mindset book link  

Moving on...


Ok, so you have the mindset and you’re a young Jay Z in the making.Now let’s make sure you’re not thinking  In the Test phase you want to test your idea and see if it’s worth pursuing.  The worst thing you can do is feel completely inspired, ready to roll and take on the world and launch a business selling sweaters to German Shepherds

That’s just a bad idea all around.  

You need to make sure that whatever you’re doing has a reasonable chance for success.  The easiest way to do it is to see if there are competitors out there doing what you want to do.  If yes, then good; if no, then bad.

You also want to make sure your idea passes the common sense test.  Does your idea make sense to the typical person?

Consider these examples:

“I want to sell organic cat treats to teenage reality TV star celebrities” Bad idea-  no market, no competitors and really?

“I want to sell flip flops made out of recycled plastic bags to millennials” Great idea-  huge market, enough flip flop competitors to make it viable, sounds pretty cool too. I’ll buy a pair!


If you’ve ever seen any of the Mission Impossible movies you know that having a plan is a huge key to success. While it’s less dramatic than Tom Cruise crawling through an airshaft, you still need a plan to quit your job.  You need to plan out:

  1. Money: Saving enough money to live on while you get your business rolling.  Whatever you have budgeted for business expenses, double it.  And whatever you have planned for incoming revenue, reduce it by 50% and expect that it will take you twice as long to hit that number.  
  2. If you think you’ll make $30k selling flips over the next 6 months and it will cost you $10k; assume it will actually be $15k in a year and the costs will be $20k. I know that sucks but trust me, better to assume that now then get it wrong in 6 months.
  3. Set-up: Office, computer, business licenses, business cards, website, corporate entity determined and formed, these are the essentials to have in place before you launch.  
  4. Executive Summary: Write a quick 1 page Executive Summary to vet your idea.  Does the idea make sense? How will you make money? Who are your customers? How will you reach them?  Be crystal clear on these points before you move forward.

When I was leaving Sprint, I knew who my future customers were, had my vendor relationships set up, website set up, business cards done, office space leased, 1/2 my team recruited, business licenses in process, corporate entity in process. So when I told my boss on a Friday, I was literally ready to go to my new office the next morning.  Yes, I worked on Saturday, I was pumped to start and didn’t want to wait unit Monday (more on loving Mondays later).  I was as prepared as I could be and you should be too.

Think of being Batman. You wouldn’t go out and fight crime without putting your Bat Suit on, right?  Same thing here, get everything in order and then roll out.  


You’ve made the decision, done the planning and tested the idea.  You’ve gone over it in your head 1000 times and you’re ready to roll.  You’re like the Seals going after Osama Bin Laden, you’re packed and ready to roll.  If so, then this last step is easy.  You’re parachute is on so you need to jump out of the plane. Time to make your mark on the world and bring some meaning to your life.  Let’s go, man.

When you actually leave and tell your boss there is a good way and a bad way to do this.  Don’t pull a Bill Simmons, piss off ESPN and leave on bad terms.  Bad idea.  Leave on good terms and don’t leaving your boss hanging anymore than you need to.  

Have you seen the movie, “The  Way Way Back?”  Great coming of age story, takes place on Cape Cod in the summer, Steve Carrel is the bad dude. Highly recommend it.  The end scene is when the kid is leaving his mentor/hero and they are both genuinely bummed to be separating. You can feel the sadness and appreciate the bond that these two have.  That is exactly how you should feel when you tell your boss. Here’s how to avoid f*cking it up:

  1. Tell your boss only, don’t tell anyone else. Don’t let him/her get blindsided.
  2. Explain that it’s more about you pursuing a dream then the job sucking.
  3. Tell him/her on a Friday.  That gives them the whole weekend to figure out how to spin it to Corporate and everyone else in the office. 

Wrong way to quit (Monday, 9am): “Today is my last day.  I can’t stand this job and want to get the hell out of here.  Also I had sex with your intern on your desk.”

Right way to quit (Friday, 4pm): “I love you, you’ve been the best boss but today is my last day. I’ve always had the dream of running my own gig and I’m finally ready to take the leap.  Thanks for everything and if you need my help transitioning to a new person, just call me.”

See the difference?  Make it painless and smooth and it will go way better.


So now you’ve decided to leave and now you have a plan.  Right on! We could end right here and you’d be all set to roll but there’s more stuff for you to know.  I want you to give you a Lindsay Lohan-ish cautionary tale about mistakes I’ve made and how to avoid them.  Then we’ll get into some success stories and how to maximize your chances of getting it all right.


I have made more mistakes in business than you probably ever will. Just like Nicolas Cage has never said no to script, nor have I to a business mistake.  Here are some great examples of what NOT to do.  Please don’t tell my dog, he still thinks I’m perfect.

1. Not watching the money closely enough.  In my 1st business I got a big office, hired an admin and generally didn’t watch my operational costs closely.  I let my admin buy supplies and never really checked to see how she was spending the money.  Consequently we burned through cash and almost went out of business several times. LESSON: Watch what you spend like a hawk. 

2. Paying for advertising. I spent a ton of cash on ads, web ads, etc without ever seeing much of a return.  I learned quickly that paying for advertising is stupid as it is expensive as there is no barrier to entry.

Meaning that if my grandmother wanted to run a full page ad in the New York Times about her ability as a breakdance instructor, she could do it as long as she had the cash.  Never mind that she can’t breakdance. Advertising is not trustworthy anymore because anyone can buy an ad.  Better to use social media, speaking engagements, etc to build a tribe and trust with that tribe. LESSON: F*ck Advertising.

3. Hiring wrong. I’m good at hiring people now but I’ve made some major mistakes along the way. I’ve hired incompetent people, lazy people, people who interviewed awesome but sucked at the job.  LESSON: Interview right.  Make sure you hire right but asking a few simple questions, like:

  • “What in this person’s past leads me to believe they will excel at this job?”
  • “Can I trust them?”
  • “Are the above average intelligence/work ethic?’ 

If you can’t answer these questions with a resounding YES then don’t hire them.

4. Wasting time on bad deals/bad customers. I’ve pursued wrong deals with the wrong people and it ends up being a waste of time. LESSON: Make sure you like your customers and your vendors.  Whenever possible don’t work with a**holes.

5. Don’t chase money.  Almost every bad decision I’ve made in business was done chasing money.  I worked with a hellacious private equity group out of another country that gave me $15M to launch a division for them.  If I stuck it out 1 year I would have made a cool million.  I quit and returned their money in 120 days.  They sucked.  LESSON: Don’t chase the dollar.  Chase your passion and the money will follow.


1. Since 2002 I’ve been out on my own and been able to support our growing family.  When I started it was me & Kelly and 2 dogs.  Now it’s me, Kelly, our two daughters, two dogs and two cats. It’s like Noa’s Ark around here. Funny because Noa is my daughters name.

2. I’ve worked with some great people who’ve become lifelong friends.

3. We’ve made it through the tough times.  2008-2012 were brutal, just awful years.  Remember that scene in Lone Survivor where the guys are getting shot at and they tumble down a cliff?  The get all torn up, break some bones, etc and when they come together Axe says, “That sucked”.  That is exactly how I feel about 08-12.

4. I have never missed an important day/event/party/recital/gymnastics/musical/etc of my daughters.  I make my own schedule so I’ve never missed anything that they’ve done.  I feel very lucky to be able to say that because I have tons of friends who’ve missed birthdays, important events, etc due to their high powered job.  My most important high-powered job?  Being a dad.

5. I make my own schedule.  In any given work week I go surfing, play hoop, play football, play softball and go to crossfit.  Fitness and being active is crucial to keeping me somewhat sane so I schedule it in.  When I worked in the corporate world it was a miracle if I went to the gym 3 times a week.

6. This is from the shallow end of the pool but my office reflects my personality and what I like.  The walls are painted blue, there are surfboards, money tree plants, whiteboards, pictures of Buddha, prayer beads, family pics and a life size FatHead of Gronk in the back room.  I have Chili Peppers and Muhammad Ali posters up and a guitar 10 feet from my desk.  This is less an office and more a upscale man cave without the pizza boxes and beer lying around. (Beer, champagne and wine is all in the fridge).

So with all of this in mind, here’s some general advice in no particular order:

1. Quit gracefully with class

2. Save your money when you first start out and learn to love Mac & Cheese

3. Don’t stress the business plan but make sure your idea is strong

4. Make your brand personal to you

5. Be someone you can depend on.  Work your ass off and do what you say you’re going to do

6. Celebrate your early successes

7. Embrace your streaks.  When you get on a good streak (writing/marketing/sales) do everything to keep it going. Sleep at the office, forget to eat, whatever, keep it rolling!

8. Get a dog* if you don’t have one.  You need to be able to come home and see someone who loves you no matter what.  Plus, they’re fun to take to the office. 

*And for you single guys out there, there is no better way to meet an awesome girl than if you have a dog. I know this firsthand because I met my wife of 13 years through my dog.

9. Evolve*.  Respect that your business will evolve.  When NWA came out, Dr. Dre was a rapper.  Now he’s a media mogul producer with a line of Beats headphones. He discovered Snoop, Marshall, 50, Kendrick, etc. He evolved so don’t be afraid to evolve.

10. Know who your champions are. You need people around you who support you unequivocally.  Times can get tough so know who your support system is and lean on them.

11. Make it fun and make it awesome.  Start a softball team. Institute a weds night happy hour. Do some volunteer work together.  And if you’re working for yourself set this all up with other solo entrepreneurs.

12. Make some t-shirts you can wear around town.  We’ve had a few made including a Be Happy shirt and a Be Epic shirt. Everyone loves them and they really get us some nice brand recognition.  Plus they look cool as shit, if I do say so myself:)

13. Ge the right office supplies.  I’m a freak for the right pens and paper so get yourself something that you dig.  Yellow pads are everywhere in our office.

14. Adopt a meditation practice.  80% of the most successful people have some sort of meditation practice.  Who can argue with that?

15. Read a ton.  I read a ton of books (see below) usually about business, motivation/inspiration or fiction.  The more the better.  My college philosophy professor, Billy Jo Lucas said the best education you could have is if you read 10,000 books in your life.  He should know, he house was filled with books and he even had bookshelves in his bathroom.  He also had a great wife (who was super cool) and cooked a mean gumbo.


*Disclaimer: I’ve read all of these books and the links you see here are not affiliate links.  [I should probably set up affiliate links but am too busy/too lazy/too not tech savvy to do so.  Either way, enjoy.]

1. Think like a freak, Levitt & Dubner

2. Finding Inner Courage, Mark Nepo

3. The Magic of Thinking Big, David Schwartz

4. Mindset, Carol Dweck

5. Scar Tissue, Anthony Kiedis

6. Way of the Superior Man, David Deida

7. Sacred Hoops, Phil Jackson

8. 48 Laws of Power, Robert Greene

9. Paddle your own canoe, Nick Offerman

10. The Monk who sold his Ferrari, Robin Sharma

11. Thrive Fitness, Brendan Brazier

12. Rework, Jason Fried


Quitting your job isn’t easy, it can be nerve racking and anxiety provoking.  But it’s worse to stay in a job that you don’t like and doesn’t fulfill you. This isn’t Mad Men- you shouldn’t be so cynical and unhappy with your job that you dream of  drinking whiskey at 11 in the morning.

If you’re truly looking for purpose, fulfillment and direction in your life, I hope this post was helpful.  I know that when I quit the corporate world I was scared out of my mind. I was scared I was going to lose all of my savings, never be successful, etc. 


If you're ready to seek a life of fulfillment, purpose and passion then here are a few great ways to start:

  1. Email me directly with any questions. I'm here to help and I've probably gone through what you're going through right now. Email: jim at jimsimcoe dot com
  2. Send me your business ideas, no matter what they are and I'll give you my honest opinion of them. Email: jim at jimsimcoe dot com
  3. Find a mentor who can help you plan out your life with you.
  4. Start thinking about the ideals and values that you believe in and write them down.  Check them against your job, your friends, you life and see where you're in alignment and where you're off.

Luckily it all worked out for me.  I believe it will work out for you too. I strongly believe that if you’re committed to a specific ideal or specific vision you can manifest it in your life. 

You’ll have to work your ass off, grind all the time but you can do it. Along the way, you’ll get scarred up. You’ll go through hell, people will screw you over and you’ll make some big mistakes.  You’ll be wrong a lot and you’ll eat a ton of Mac & Cheese. You’ll have to check your ego at the door and be ok with sweeping the floor and getting copy paper at Staples.  Some people will love you, some won’t and some won’t care at all.

But after all of this, you’ll love your life.  You’ll love your place in the world and you’ll make more than money.  Your family will be proud of you, your friends will be stoked (and a tiny bit jealous) and your dog will think you’re a superhero.  Best of all on Sunday nights, when it’s really quiet and you’re lying in bed ready to fall asleep, you’ll think:

“Tomorrow is Monday, f*ck yeah