How to Create a Bad Ending (For Your Business, Your Marriage, Anything, Everything)

This week we had a chance to spend time with a group of local entrepreneurs from New Ventures

Each founder has made huge strides to accomplish their mission. They’ve collaborated with a cofounder. They’ve hired. They’ve brought their products to market. They’ve branded themselves. They’re pitching to investors. 

Beginnings: They come with excitement, momentum, and hope. 

And yet, we couldn’t have a conversation about startup culture without talking about the statistics:

Only 10-20% of startups survive past the first year. That’s a well-documented reality in the world of entrepreneurship. Many startups fail due to insufficient funding and/or finding out too late the market doesn’t really want to buy what they have to sell. 

But there’s another reason.

“It’s unfortunate but true: If entrepreneurship is a battle, most casualties stem from friendly fire or self-inflicted wounds.” 

This quote comes from Noam Wasserman (Harvard Business School professor of entrepreneurship), in his book The Founder’s Dilemmas. Wasserman offers another statistic: Venture capitalist research attributes “65% of failures within their portfolio companies to problems within the startup’s management team.” 

In other words: Businesses are falling apart because of less studied but “all-important people problems.”

Maybe you’re not in business. Consider another statistic: 

50% of all marriages end in divorce. That percentage has decreased in recent years and has become a more nuanced statistic, but the core, human issues remain.

No one sets out to create a bad ending. Not for business, and not for marriage. 

But there might be something for us to learn here, through a bit of ‘reverse engineering.’ Whether it’s your business or your marriage at stake, imagine your worst-case failure.  

If you set out to create that bad ending, what would you need to do?

Here are a few suggestions.

  1. Pretend it won’t happen to you. 

Get caught up in the excitement of starting, and don’t consider the worst-case ending. 

Maybe become superstitious: Operate under the fear that if you talk about potential conflict, it may actually happen. 

Or stick to naivete: You’re not like other people. Nothing could make you embittered or passive aggressive toward your partner. Conflict won’t be an issue for you.

This is one of the surest ways to fail in any relationship. Assume that conflict is an exception, and so are you. Rather than the alternative assumption...

Conflict is normal and necessary—so long as we’re humans living (or working) together, in relationship.

If you want to fail, don’t adapt the above mindset.

Don’t re-calibrate your expectations and plan for conflict.

Don’t think about conflict at all. 

2. Create a story, then never explore it. 

When something happens, like a disappointment, an unmet expectation, or a confusing interaction, create a story about the person (or people) involved. And make sure that story includes a negative judgment about the intentions of the other person.

Run scenarios and talk with others about it. Just never actually bring it up to the person. 

Do that, and then do the same thing for subsequent events of the same nature. Reinforce your story over time, until it’s ‘final straw’ day. Then have a major break-up conversation.

If you’d wanted your work or home relationship to survive, you would have stopped to self-reflect:

The stories you create in your head are often good. But no, they aren’t perfect.

You would have made room in your story for a few question marks. 

You would have engaged in a tough conversation with empathy, curiosity, and positive assumptions about character and motive. 

You would have actually had the conversation months ago. Except, you didn’t.

3. Let weirdness build up over time. 

As alluded to earlier, when something weird happens—anything that doesn’t match your expectations—consider it a minor offense and add it to the tally.

Let your minor offenses build over time. Keep track or don’t—the outcome will be the same. Big endeavors sink every day as the result of a dozen small punctures.

Lastly, don’t examine the nature of this cumulative toll. Don’t talk about what’s really happening as weirdness persists over time: the deterioration of trust.


Still looking to fail? 

Read the above statement. Disregard. And return to point number one. 


In all seriousness, thanks for reading. Thanks for considering tough topics like broken trust and cumulative toll. The positive sides of these practices are crucial for thriving relationships and thriving workplace cultures. 

To learn more about how to build a healthy workplace culture, keep reading.

Local to Winston-Salem? On September 6, 60+ startups (including the New Ventures folks) will come together for “Demo Day” at Biotech place. Mark your calendar if you’re looking to get plugged in with the startup community. 

And for more ideas on how to fail, call us.


Counterstories is a blog collaboration between conflict resolution specialist Steve Beck and writer/editor Rachael Schmid. If you have a powerful story of forgiveness or peacemaking (or just want to share your thoughts on this post), we’d love to hear from you. Reach out at admin@cstevebeck.com.