When To Give Up And When To Keep Pushing

Most people say deciding to start is the hardest decision you’ll make when it comes to running a business, but I actually think that’s wrong.

The hardest decision you’ll make is when to give up and when to keep pushing, especially if you don’t knock it out of the park within the first few months like you hoped you would.

I’ve probably started 25 companies in the last 15 years. 5 of them worked. Most failed. So that’s 20 times I’ve had to make the decision to give up. To lose a huge amount of money. To fire amazing people. To tell my wife “this one didn’t work out as I’d hoped”.

Most people associate giving up with failure, but I believe the opposite is true. When you give up, you’re not “weak”, you haven’t “quit”. Instead, you’ve eliminated opportunity cost on something that wasn’t working, so you’re free (time + mental energy) to pursue something else that has a possibility of knocking it out of the park.

It’s either a home run or time to move on.

So what should you ask yourself when trying to make the decision to push forward or move on? Here are some questions that have helped me over the years:

  • Is this a market size problem or an approach problem?
  • Do we have the wrong strategy or are we applying the wrong tactics (especially when it comes to sales & marketing)?
  • Do our existing customers LOVE us, like us or tolerate us? Why?
  • If we keep doing what we’ve been doing, will we get the same, a better or a worse result in 12 months? Why?
  • Are our metrics (CAC:LTV) improving as we move forward, staying the same or going backwards? Why?
  • Do I have the patience to stick with this and right the ship?
  • Do I have the belief that we can win if we get through this?
  • Are we going to run out of money? If we do, when will it be and will our numbers be good enough to raise money to keep going?
  • What does my gut say I should do?

As you can see, these questions aren’t rocket science. But they do blend important aspects of metrics, founder psychology, patience and customer feedback. They’ve acted as a great guardrail for me over the years and I hope they’ll help you out if you’re unsure of what to do next.

At the end of the day, my gut has always proven correct. Whether that meant staying focused on BigCommerce for 6 years and building it from nothing to almost $100M in annual recurring revenue, or shutting down a bunch of companies that were generating millions in revenue so I could eliminate opportunity cost and go all-in on something that I ultimately felt had a bigger chance to help more people. My gut has always been my guide.

As we end 2016, it could be the right time to spend a few hours thinking about the questions above and being honest with yourself. Quitting sucks and fucks with your head, but if it means you have a clean slate in 2017 to pursue something much bigger, I say it’s worth dealing with a few weeks of discomfort to get on the path you were meant to be on.

Good luck on your journey.

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About Mitchell Harper

Mitch is a 7x company founder, advisor and investor. He is best known as the co-founder of BigCommerce. His companies have generated over $200,000,000 in total revenue and he is currently building an online education company and a SaaS company.

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