If you have started a company, sooner or later you're going to get asked--or ask yourself--this question: "Would you do it again?" If your company happens to be among the 25 percent of venture-backed startups that succeed, it's an easy question to answer. But if your company is not successful--if it runs out of money, or fails to find a market, or plateaus too soon, or is sold at a loss, or comes to any other disappointing end--then this question will dog you for months, barking at you with regret and second guesses. And, if you're like me, you will do everything you can to not answer it forthrightly.

Note that this question is unlike "What would you do differently?" That one is too easy. We all have a list of decisions we'd change, or steps we'd take earlier, or employees we'd choose not to hire. Those are redos that hindsight makes obvious. But the question "Would you do it again?" requires more introspection and honesty. It requires you to ask yourself if the whole thing was a mistake, if you'd have been better off doing something else.

The question came up over martinis with my friend Chris Hogg, an entrepreneur who recently executed a successful exit as chief commercial officer of Propeller Health. At Propeller, Chris and colleagues built a terrific company that helps people manage their asthma or COPD. Recently, they sold it for $225 million. But this wasn't Chris's first rodeo. A few years ago, he founded 100Plus, a mobile app that helped people learn to adopt healthier habits. 100Plus was a nifty idea and got some buzz at SXSW, and Chris readily raised a seed round from some impressive investors. But consumers never showed up in the hoped-for numbers. The company didn't go bust, but it was acquired by a larger health care tech company. Chris left to join Propeller a year and a half later.

Would he do 100Plus again? "No way," he told me. "100Plus was a beautiful product in search of a problem. I built what I wanted, and what I thought users would want. But it did not solve a real problem that potential users were searching to fix, and I struggled to distribute and monetize it." Still, would he start another digital health company? In a heartbeat, he said. "Based on what I have learned? Absolutely. It's a completely addictive experience."

His conviction surprised me. All that sweating over investors saying "No!" to funding another round; all that fretting about paying employees. He'd given everything over two long years, with little to show for it. Yet with Propeller, Chris has been able to put that hard-won wisdom toward something successful. In my experience, few entrepreneurs are willing to be as honest with themselves as Chris. Sure, a lot people talk about how failure is good, but they do so without actually owning up to their own shortfalls.

As for my answer? Well, my startup, Iodine, did not transform health care as I had hoped. I spent nearly four years of my professional career on the effort, and I'll confess that I sometimes wonder what else I might have done with those years. Yet the outcome--a modest sale to GoodRx, a legitimately successful enterprise that helps millions of people--was decidedly a good one for me and my team. In the years since I took the leap, I have learned more than I might have ever imagined. And it got me to a place I never could have gone otherwise.

So I have my answer: Yes. Despite some stupid decisions and bad hires, sleepless nights, and spectacular missteps, I am glad that I took the plunge. Starting a company transformed how I think about business, and what I believe about myself. If I've learned anything, it's that there will be missteps and mistakes and misery ahead. And though nobody can promise success, you can bet you'll win some wisdom along the way.