How to know when it’s time to quit ~ four questions to answer honestly.

It is so much easier to start something than it is to finish, AMIRIGHT?!

I’ve come up with business ideas on a Saturday, been all in by Sunday, and have fully given up by Friday.  I have been the college drop out.  I’ve quit jobs before I really gave them a fair shake.  I’ve experienced my fair share of quitting but looking back I don’t have regrets.  I am convinced that quitting the things that are wrong for us can actually be the most productive use of our time. 

My Dad once told me a parable about a man who places his ladder against the tallest wall and begins to climb.  As he’s climbing, he is met with great resistance. People constantly shout up to him, “there is nothing behind that wall” but he keeps going.  For years he climbs, and when he reaches the top he is a very old man.  He looks over the top of the wall and sees emptiness. To his left and right he sees other much smaller walls that lead to lush gardens and green pastures, but his wall has led him to nothing and now he is too old to climb another.   

We live in a society that praises the endless hustle.  We revere the people who are so dialed in on their dream that they keep pushing to great levels of success even when everyone seems to be screaming “you’re going to poop the bed.”  But these people are the lucky ones.  Most of us don’t have the luxury of knowing exactly what we want to do when we grow up. Even when we’re 35 many of us are still left scratching our heads and waiting for that thing to click on like a light bulb. Guys, there’s probably never going to be a light bulb.  It’s OK to change our mind about things and it’s OK to take a few swings before we hit that home run, but eventually, we’ve got to choose what we want and go all in for it.   

In truth, most successful entrepreneurs never have that moment where the sky parts and angels float down singing “you’ve found the thing you are supposed to do.”  Many great success stories involve a lot of pushing through resistance, overcoming imposter syndrome, and wanting to quit but forging ahead regardless. 

Going all in on a dream without any promise that it’s going to work out can feel terrifying, but if you have chosen the path of the entrepreneur, you’re already braver than most.  You know a little healthy fear never killed anyone, and you give yourself permission to feel the fear and do it anyways.

So how do you know that your ladder is against the right wall?  You can start by taking imperfect action and opening yourself to the growth that comes in the process. You should be willing to pivot wherever necessary and also, when the time comes, willing to quit.  You don’t want to spend your whole life pursuing emptiness.  Quitting the wrong things will free up your time to go all in on the right things and you absolutely should quit that wrong thing asap. 

If you are currently in a point of resistance and considering throwing in the towel, here are some questions you can ask yourself. (Spoiler alert: chances are you probably shouldn’t quit.)

Would you still do this if you knew it wasn’t going to make you rich?

Money is a great motivator but it should never be the only motivator.  If you knew your business would keep a roof over your head and food in your belly, but probably not help you afford the dream home in Maui, would you still do it? If you knew your business was going to help others, or solve a problem in the world but only provide you a modest income would that be enough to keep you going?   All entrepreneurs should have a ‘why’ and this ‘why’ should be enough to keep them going when they are inevitably met with resistance. There is nothing wrong with having lofty money goals and wanting all the freedom that comes with a fat bank account but if the money is the ONLY reason you keep climbing, you might be climbing the wrong wall.  Still, this doesn’t mean you should quit. It means you need to find a ‘why’ that is bigger than your bank balance.  Pivot your business into something where the real reward is filling a hole in the world and embrace the money that comes as a bonus.

Have you REALLY given this thing a fair shake?

There’s a distinction between quitting the moment you feel the least bit of discomfort and pursuing the wrong thing for way too long.  You are going to have to get very comfortable with hearing ‘no’ if you are going to be an entrepreneur. Hearing ‘no’ is a good thing, it means you are narrowing down on your messaging so the customers who aren’t for you can fall away.  Hearing no is not a reason to quit as long as you are also hearing yes.  If there are people who are picking up what you’re putting down you are on the right path.  JK Rowling took 6 years to write the Philosophers Stone, and was rejected by multiple publishers, but her kid LOVED the book so she kept pushing.  If you have been at it for six months and are wondering why you are not a famous billionaire yet, you’ve got to give your head a shake.  I know we sometimes hear stories of entrepreneurs who launch a product and within a year are a household name, but they are NOT the norm.  The normal path to success is marked with ample failure, pivots, and persistence.  So if you haven’t yet given it a fair shake, you are definitely not ready to quit. You are probably just getting warmed up. 

Are you seeing progress?

Slow progress is still progress but if you have been at this for a while and are more or less in the same place that you were in five years ago, the universe might be trying to tell you something.  Some ideas may need some tweaking and some might just need to be flushed down the toilet.  Just as you should never be in business solely for the money, you should also never be pouring yourself into a business that gives you nothing in return.  If you are not seeing progress but see others in your same realm making huge strides, take a good look at what they are doing better.  Be honest with yourself and be willing to give up the things that aren’t really working.  Look around; if you are a total pioneer in your pursuit, you are either on to something completely genius or absolutely terrible.  If it’s been years of no progress, chances are it’s the latter, but that still doesn’t mean you need to quit. Use the points of resistance to pivot yourself into a position where things start to flow.  You could be headed in the right direction but just need to be moving towards it from ten paces to the left. 

Do you love it?

This circles back to ‘would you do this thing even if you knew it wouldn’t make you rich.  Loving something doesn’t mean you never have moments where you hate it.  When you pass from this earth will you be able to look back on your life and see that your days were filled more with joy than despair?  All you really have is the now, so if you are currently pursuing something that fills you with dread on a daily basis, tread carefully.  If you are miserably slogging along to one day reach some arbitrary financial goal or gain some sort of notoriety, you have chosen the wrong wall to climb and you should most definitely quit, GTFO and don’t look back. Keep on pushing till you find that thing that makes you want to jump out of bed (almost) every day. It’s out there and chances are it’s right behind the wall that was right in front of you all along. 

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