When to bail water, and when to bail out

Never give up, never surrender; 3 feet from gold; blah, blah, blah. There are so many cliches and so much advice on why you only fail if you give up, but that’s simply not true. There is a razor-thin line between finding success from the “never give up” mantra and being imprisoned by it. Knowing when to give up is as important as persistence.

Galaxy Quest GIF that says "never give up, never surrender"

In some cases, every day a driven individual doesn’t give up is another day they dig down into a deeper, darker hole. I know because I’m that very kind of personality that would be bailing water out of a sinking ship stuck at the bottom of the ocean. Knowing when to bail water and when to bail out is vital to your health and future success.

One key on the keychain of success is knowing when to give up. For every success story where someone didn’t give up, there are dozens more of others who worked harder, longer, and still failed. I’ve heard people who “never gave up” for a year, thinking that was long, finding massive success, and high-IQ individuals with amazing products, take a beating for decades. Why do people punish themselves?

Hard-working, well-intentioned people punish themselves because there is this ugly belief that giving up is surrendering to failure—that giving up is never acceptable. But true failure is not learning from your screw up. If you don’t actually give up, you don’t learn a damn thing.

When to give up. 5 things to look for.

So, how do you know when to give up? According to my many podcast interviews, and my own failure-ridden journey, there are actual signs it’s time to bail out, rather than bail water.

1. When The Passion Is Gone

When you’ve lost the passion and belief in the end game. When your heart isn’t in it, get out. If your passion is still there and you still believe in the end game, then you’re just in the messy middle, says Scott Belsky, CPO of Adobe.

If the passion is gone, and you’ve lost the vision, that’s when to give up.

2. When You Aren’t Good At It

I pushed my graphic design business to the limit. I had some great clients, but the truth was I wasn’t naturally good at graphic design. Sure, I did well by my clients, but only because I outworked other designers. But I couldn’t keep up, it was exhausting and I didn’t have natural skill.

If you’re not naturally good at something or can’t get there with hard work, that’s when to give up.

3. When There Isn’t A Market Need

I’ve worked with some amazing companies, and have heard their nightmare stories of products that were too early. Steve Jobs was one such leader that buried projects he considered were ahead of their time. The fact is just because you’re passionate about it, doesn’t mean the market is.

If there’s no market need and you can’t make a living, that’s when to give up.

4. When Your Relationships Are Eroding

Putting relationships on hold to find success is a stupid decision 100% of the time. The founder of Best Buy, Richard Schulze explained to a group of us in 2006 he made that mistake. He justified time away from his wife to make a better life for themselves. She died of cancer and he never got that time back. He said if he’d done it all over again, he would have never started Best Buy. CEOs like Toby Lutke of Shopify are proof that you can spend plenty of time with family and still grow a business.

When your relationship with family, friends, and God are compromised, that’s when to give up.

5. When Your Health Is Dwindling

I’ll openly admit some of my early struggles as an entrepreneur have caused some irreversible emotional damage. Some of the things I put myself through were simply not worth it. Period. I see entrepreneurs gain unhealthy amounts of weight and slide into depression. This is NOT acceptable and never worth it.

If your emotional or physical health are sliding and you can’t fix it, that’s when to give up.

Giving Up, Is Moving Forward

Sometimes, giving up, embracing the failure, and learning from it, is the only way you can move forward and be successful. So if you need permission to give up right now, I’ll give it to you on one condition: Commit to learning from your failure. Knowing when to give up, provides clarity in how to move forward.


This piece was inspired by an earlier LinkedIn Post.

Hi, I’m Justin. I’m a writer, podcaster and entrepreneur. I cultivate & amplify emerging tech companies’ stories, reaching millions of people.

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