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Steve Tripoli: Lots of small businesses struggle, and their owners often have emotional as well as financial stakes. So how do they judge with a clear head when's it time to "pull the plug" and shut down for good? Let's let some business-owning Marketplace listeners give us their take on making that tough call.

The spray guns are busy these days at Mike Shipstead's business. His shop in Santa Clara, Calif., specializes in spray-on plastic coatings for pickup truck beds.

Things are good now, but for a couple of years, Shipstead operated closer to the edge.

Mike Shipstead: You know, people asking for payment and not enough customers coming in, and you're wondering why the phone's not ringing.

He says deciding whether to go on when times are tough is like "flying through fog." His test in those times was to ask himself three questions:

Shipstead: Is there an opportunity to grow? Can we get there as a business — do we have the people and the resources? And then I guess thirdly, do I want to go there?

As long as he answered "yes" to all three, he kept going.

A couple of towns away, lawyer Kristie Prinz is an entrepreneur by necessity. The law firm where she was nearing partner status collapsed. Launching her own practice has been rough-going.

Her test of whether it's time to pull the plug has more to do with stress levels. She's seen other struggling entrepreneurs feeling so desperate they were falling apart.

Kristie Prinz: And I think if I had ever gotten to that point for more than a day, then at that point I would have perhaps decided to throw in the towel.

In Dundee, Mich., listener Paul Purdue's Internet-based business has folded. A load of debt and a long scramble for new cash ended with a potential investor's verdict.

Paul Purdue: His words to me the second before I turned to my wife and said, "We're gonna have to close this," were we had dug too deep of a hole.

So, three people whose businesses cover the range from failed to hanging on to thriving. But Paul Purdue, Kristie Prinz and Mike Shipstead draw startlingly similar lessons about avoiding that "pull-the-plug" decision.

Purdue, whose business went under, speaks first:

Purdue: Watch costs, and understand what you could not be spending.

Prinz: Tighten up the capital, tighten up the collections. In the end of the day, there's no business unless you have the money.

Shipstead: I think what I've learned is start with as little overhead as possible.

So getting and handling start-up money really matters.

Entrepreneurs tend to be optimists who have a hard time pulling the plug. That's why our small-business expert, Patti Greene, says someone they trust should monitor decision-making.

Patti Greene: Whether it's a spouse or a partner or a parent or a business partner, whatever it might be — but for them to remind you that, this is the bottom line on what you can actually afford to lose.

It's not just about money — it's about what you can take emotionally, and even how the business is affecting relationships.

So Greene really likes Mike Shipstead's three questions: Is there an opportunity to grow, can we get there, and do I want to go there?

Greene: Because they include, not just about the business, but about him personally.

Greene says your three questions don't have to be the same. Just be sure to have your personal "pull-the-plug" measuring stick.

I'm Steve Tripoli for Marketplace.