Quitters never win, except when they do.

Quitters never win is stupid advice. I know lots of quitters who win. Maybe not that day. Maybe not at that particular thing. But a person who quits once doesn’t stay a quitter forever. A person who knows when to quit and move on to the next thing feels like someone who has a clear idea of what they’re capable of or not capable of.

There are ample stories (and subsequent movies made) about people who didn’t quit and ended up winning. Imagine if Jeff Bezos never quit his Wall Street job to start Amazon. The world is filled with people in the wrong place at the wrong time under the wrong circumstances and what the world tells these people is to stick with it because everyone hates a quitter.

Different types of quitters

Like everything in life there is no black and white here. Quitting is a vast scale of grey that we all skate across throughout our lives. One day we’re steadfast and loyal to our careers and jobs and then next we think we can be YouTube stars or insta-famous if we release a sex tape like KimK did.

When you start something it may be for the right reason, it may be for the wrong reason but there is always a reason. When you quit it’s usually the same and it’s in the reason that I find meaning.

If you’re quitting something because it’s too hard then you’re tending towards the bad kind of quitting. If you’re quitting because someone was critical of your work, again you’re in the bad quitting world. Intent is everything.

When I hire people I always ask them to give me one full year of the effort, time and attention. If they get to the end of their first year working with me and they have learned all the can learn then they’re moving on for the right reasons and quitting is the right move. If they hate me and have learned nothing then it’s a good idea to leave. There really isn’t any right answer here.

When I was much younger I was fearful of becoming known as a “job hopper” because I was constantly starting a new business and finding a job to pay for my salary while I built the latest idea on the side. I’d quit when things became too complex at work, or if the boss was an asshole or if I was bored or if the job felt wrong for me. Really any reason to tip me over the edge and I bailed. Socially that was unacceptable and I recall my parents have a good sit down chat with me about this. I scoffed and carried on quitting.

How do you know when to quit?

Every time I talk to an entrepreneur the conversation will swing towards quitting. Starting a business is hard work and it’s pretty standard for entrepreneurs to discuss “the other side” when we talk about our businesses. The other side is full time employment.

The question everyone wants answered is:

How do you know when to quit?

My answer is always, frustratingly, the same: It’s different for every entrepreneur.

There are some pretty clear things that you can look at when considering if you should stop working on the your business. I’m going to list a few of them but please keep in mind, these things are not the same for everyone, this is not a definitive list and if they don’t resonate with you, that’s great too.

Are you giving up?

Oftentimes a business is started because it’s what you happen to have found yourself doing. You may have just fallen into this business because your mother left it to you and you’ve now taken over. But more likely you saw a gap and took to building a solution to fill that gap.

Is the thing you’re doing now still filling that gap? Have you realised that you can’t accomplish the goal you set out to achieve? Is there nothing that you can do to make it happen?

Or, are you just giving up?

Both are perfectly OK but accepting the reason you stop working on the thing you’re working is key to helping you cope with the fallout. The fallout is always going to be dark and difficult. There’s guilt attached to it and embarrassment much of the time. Fear of judgement from your family, friends and ex-colleagues plays on your mind.

If you quit because you know it’s the right thing to do and the only way forward then you can leave without fear. If deep down you know you can do more then you’re really just giving up despite the options available to you.

You have to deal with either reason; giving up or quitting. For me, that’s how I know when I should stop. When I know I can cope with the fallout, I’m happy to quit or give up.

There are two more very specific things to look to when you’re thinking of quitting:

Traction. Traction. Traction.

Are you gaining any traction?

Has it been 5 years without a single sale? Have you made any money at all doing this thing that you love so much?

If your focus isn’t financial, then are there any other signs of traction? If not, perhaps it’s time to walk away or try a different tactic one last time.

Are you happy? Even a little?

Suffering is not cool.

Grinding it out with no end in sight is not cool.

Hating your day to day work every day is not cool.

I don’t care if you are creating the cure for cancer in the pinky toe while working in your basement. If you hate going down into that basement everyday and working towards the cure for cancer of the pinky toe then you should stop.

Your work is the thing that you will do the most in your life. You work more than you sleep. You work more than you see your kids. You work more than you play (some of us). You work a lot in your lifetime.

If you are unhappy for 10 hours a day (work), then you’re happy when you see your kids and partner for 6 hours a day (if you’re lucky) and then you sleep for 8 hours a day, you’ve successfully closed out your day being mostly asleep or unhappy.

That’s not a life I want. Fuck that life.

I want to be mostly happy and awake.

If you wake up every day and think that being unhappy is an integral part of building your business then let me be the first to tell you that you’re wrong.

You should enjoy building your business. Not all the time, but most of the time. If the unhappiness outweighs the happiness then stop and reconsider your choices, business and life.

And before you berate me for oversimplifying let preempt a response:

Yes, it is that simple.

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Photo by Kristopher Roller on Unsplash