When to bail water, and when to bail out

Never give up, never surrender; 3 feet from gold; blah, blah, blah. Cliches and advice abound on why you only fail if you give up. It’s a lie. 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"

Every day a driven individual doesn’t give up could be another day they dig a deeper, darker hole. I would be the ship Captain still bailing water out of a ship stuck on the ocean’s floor.

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 watched people who “never gave up” for a year and found success, thinking that was long. I’ve watched intelligent individuals with amazing products, take a beating for decades. Only to still lose. Why do they do this?

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.

How do you know when to give up? According to my many podcast interviews, and my own failure-ridden journey, there are concrete 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 how you know 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, can’t hire, or can’t get there with hard work, that’s how you know 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 or too late. 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 how you know 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 this mistake in a big way. 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 how you know 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, slide into depression, and do permanent damage to their health. This is NOT acceptable and NEVER worth it.

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

Giving Up Is Moving Forward

In many cases, giving up, embracing the failure, and learning from it, is the only way you can move forward and be successful. If you need permission to give up right now, I’ll give it to you on one condition: Commit to learning from your failure and commit to move forward better than before. 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. Are you looking for the best business and communications podcast ever made? Look no further, you lucky dog. Listen to only 2 shows, and I guarantee you’ll be hooked.

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