STOP! Don't You Dare Quit Your Job to Start a Business Without Reading This First

Don't you dare quit your job to start a business without reading this first, only on

Becoming an entrepreneur is routinely described as the single hardest, most stressful, most humbling experience one can willingly subject upon themselves.  

It can also make you a better version of the person you truly are while simultaneously being extremely gratifying.  There is truly no feeling like earning the first dollar on your own - that someone paid YOU for your time, talent, product or services.  

But none of that is reason to jump blindly into some fairytale version of entrepreneurship that focuses on taking the leap at the beginning, finding your way at the end and skipping over the very messy, very ugly middle.  Where you’re stressing about making your rent.  Where you’ve spent hours, days, months even creating something you believe in so deeply that the rest of the world could not be less moved by.  

For these reasons, I truly believe becoming an entrepreneur isn’t something you should jump into lightly.  So I’ve put together this handy Cubicle Hustler quiz to see if you’re really ready to take that leap


Start With a Side Hustle

  • Have you been doing what you want to do as a full time business on the side first?  

If you answered no to this question, you need to stop buggin.  Right now.  

You want to walk away from your full time job on a whim, a hunch?  Because that’s what you have right now.  You have no proof that your idea is viable, that people want it, or that people are willing to pay for it.  

Start working on it on the side and devote your free time to this idea for the next six months.  Not sure how to balance a side hustle with your day job?  Start here.  

I don’t care what it is.  You can start now and test the viability of your idea before you put all your eggs in that basket.  Any business or idea can be tested so don't tell me or yourself that the only way to know is to do it.  

Have a tech idea?  Build a prototype yourself.  If you can’t code, hire a programmer to mock something up for you.  

Want to open a restaurant?  Start catering.  Open a pop up stand at your local farmer’s market on weekends.  Take your signature dish and figure out how to package and sell it.  

Something else entirely?  At least start polling potential customers to understand what they want, need and are willing to pay for.  Emphasis so very intentional.  You need to know that you have something that someone will be willing to pay money for.  Maybe more importantly, you need to know that you’re up to the dirty, nitty gritty details of running a business.  You may find that you actually don’t like the reality and preferred to dream instead.  


Get Your Financial House in Order

  • Do you have a enough clients or customers lined up to cover your expenses for the first 6 months?
  • Do you have at least 6-9 months of living expenses already saved up?
  • Do you have a plan to drastically cut back on those expenses (i.e. downsizing or moving in with someone)?
  • Have you paid off high-interest revolving debt, like a credit card bill?
  • Have you made and can you stick to a real budget?

After the buzz of taking a big risk subsides, after people have stopped liking your big announcement on social media, after the thrill of waking up in the morning and having 100% control of your day wears off, the reality of the leap you just made will hit you.  

It might coincide with the next date that would have been a direct deposit hitting your account and you see no more money there than the night before.  Or it might come when the money you set aside to live off until “things get going” dwindles faster than you expected and things still haven’t got going.  Or it may come at the moment when you have to give up your apartment to move back in with your mom because it’s just so much cheaper and nothing is all you can afford.  

My point is we don’t talk about the money it takes to start a business enough and the hardships you face when you haven’t planned for it financially.  

Six to nine months expenses is the minimum you should have saved up.  If you’ve been side hustling, you should also have enough business, clients or orders lined up to cover your next projected six months before quitting your job.  You need to have both because clients will be late on paying you.  Some clients may even stiff you on their bills.  Steady clients will dry up if their budgets get cut or people change roles or if their internal priorities change.  

Have your money right.  It won’t protect you from the stress but it will at least let you keep going and keep working at what you believe in.  


Quit for the Right Reasons

  • Are you happy in your job and career?
  • Do you get along reasonably well with your coworkers and manager?
  • Would the announcement of your departure be met with support and enthusiasm and not a sigh of relief?

You get a manager you can’t stand or got put on this team you hate.  Maybe they moved you to the cubicle near the radiator that makes you sweat like whore a in church and now you feel like your bosses don’t respect you.  It’s a natural reaction to a shitty work situation to start thinking of other options.  And if you’ve ever had dreams of being your own boss, now starts to seem like as good a time as any. 

It’s not. 

There’s this myth that entrepreneurs only have to make themselves happy.  That’s total bullshit.  When you work for yourself, you kiss even more ass.  You need to keep your investors happy, your customers happy, your employees happy, your vendors happy.  Being an entrepreneur is not carte blanche to suddenly be an asshole or not have to care what other people say.  In many ways, it’s the opposite.  

If you were otherwise happy working at a job, don’t use one change as the impetus to jump out and work for yourself.  Figure out what would make your current work situation more bearable and see how to go about changing that.  If you can't, start looking for a new job - especially if you haven't already been working on your idea on the side and if your money is looking a little funny.


Check Your Motivations

  • Have you stopped taking your cues from Instagram meme (like this) and started talking to actual entrepreneurs about their experiences?
  • Have you accepted and embraced failure as a likely outcome?

Remember what I said at the beginning about entrepreneurship possibly being the single hardest thing you will ever willingly do to yourself.

If you have any negative reaction to that statement, you might not be ready.  I’m not trying to scare you or discourage you.  I actually think more people should start businesses and spend some part of every waking day working towards that aim.  

But I do want you to know the truth of what you’re getting into.  If the prospect of failing spectacularly scares you, you might not be ready.  You have accept and embrace failure as a likely outcome and be able to dust yourself off from it and keep going.  

Talk to any successful entrepreneur and they will have failure stories.  Maybe dozens of them.  Stories of losing it all, of sleeping on friend’s couches until they got back on their feet, on being so disappointed in themselves they couldn’t look in the mirror.  These are very likely outcomes.  Ask yourself honestly if you’re resilient enough and financially stable enough to bounce back from these things.  And understand that your bounce back may not include success in your business.  Can you put your all into everything, fail miserably, and then dust yourself off and get back out there to find a job?  Accept that may be a possible path for your future.  



Look back over the entire quiz.  If you answered “No” to any of these questions, STOP!

Do not pass Go, do not collect $200, do not quit your damn job!

Keep working on your dream.  Get your money right.  Get your mind right.  Do all of these things first, then take the big leap.  

This post is Part 2 in the Cubicle Hustler series on starting a business for National Entrepreneurship Month.  Check out Part 1 here!