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Since quitting my job to build a startup, I’m asked the same question almost on a daily basis. No, it’s not, “Would you like to pay extra for guacamole” from my Chipotle burrito barista. It’s the harmless, courteous query, “So, how’re things going with Treatings?”

My answer varies, depending not just on the week but on the time of day, my mood, and who I’m addressing. It spawns from good intentions, though varying degrees of interest. On the light side, my co-founder Paul and I share a core group of friends. They ask about Treatings, but it’s more out of consideration than a burning curiosity. On the other side of the interest spectrum are my girlfriend and family. They have real reasons for asking for status updates. My Mom wouldn’t mind seeing her son back on a real health insurance plan, and my girlfriend would love to date someone with his own bedroom. There’s an even more practical basis for wondering: They’re asked the same question. And neither wants to say, “You know, I’m not sure,” because it could make them sound out of the loop or even unsupportive.

Providing updates to friends and family isn’t just about appeasing them. As we search for product/market fit, there’s an ever-present headwind we must lean into. Technical and social-based issues arise every day. Given that there are no natural forces that promise to carry us to success, the emotional support of those close to us provides a crucial tailwind. Conversely, any doubt, whether perceived or real, that those close to us might harbor in the sustainability of Treatings, is more menacing than any product hurdle.

Outside of our conversations, friends and family judge our success based on the status of the website, which can appear stagnant for periods of time. Much of the work we are doing isn’t public-facing. Whether conducting customer interviews, building out the back-end of our website or manually sending out emails that appear to be automated, we don’t always look like we’re making progress.

I’ve been able to cross off a few unsuccessful strategies in answering the “How’s everything going” question. Initially, my go-to response was an effusive burst of positivity. “It’s going great!” coupled with a demonstrative, hand-waving motion and a “look how happy I am” grin. A few unsatisfied seconds later, the listener, after dodging my thumbs-up windmill, would ask for more detail. If inspired, I might dig up a stat or two like, “We actually grew 300 percent last week!” keeping to myself the small number of users that represents that unseemly percentage growth.

This bravado didn’t help anyone. If things weren’t going well, it only made me feel worse. I missed out on opportunities for help or feedback by not letting people see past my smiley faced veneer. After many conversations about Treatings with my Mom, when I talked without actually saying anything, she emailed me asking, “You know, what I would really appreciate is if you could write down a summary of Treatings, and where you are with it right now. Then, next time someone asks me about it, I’ll have something to tell them.”

So, I tried another futile strategy. I figured, they want details? I’ll give them details. When asked about Treatings, I’d dive into our latest data point, “Only 10 percent of our members have gone on a coffee meeting, but people are three times more likely to schedule a meeting if someone has first reached out to them.” I’d go on to explain how that was shaping our strategy going forward. Cue eyes glazing over.

There isn’t a silver bullet. No one wants to see a founder become unhinged and offload their problems all because of a polite question. In general, I try to separate the people looking for a cursory status update from those actually interested in our progress and plans. When I’m asked how things are going, if there hasn’t been a big event lately I’ll  focus on what I’m learning – both from mistakes and the occasional successes. This often takes the form of stories about how people are (or aren’t) using Treatings, which helps me crystallize takeaways and others to understand where we are.

I guess we could always just make the product speak for itself. But stories are good, too.

This is the 13th installment of a PandoDaily weekly series that chronicles the experiences of a young entrepreneur as he bootstraps his startup.

Part 1, “The less-than-glamorous life of a young entrepreneur.”

Part 2, “How to survive co-founding a company with a friend.”

Part 3, “Starting a company and having a girlfriend isn’t easy.”

Part 4, “Customer validation: from lean startup to craigslist.”

Part 5, “Dealing with competitors without turning your product into Mr. Tumnus.” 

Part 6, “Why I gave up a cushy career as an investment banker to launch a startup.”

Part 7, “The best way to take feedback: Keep quiet.

Part 8, “The embarrassment of premature VC-infatuation.

Part 9, “Don’t ask me about money! I’m a startup founder.”

Part 10, “How a summer job selling knives helped me with my startup.”

Part 11, “When social norms interfere with your startup.”

Part 12, “It’s hard to tell which startups are simply spinning their wheels.”

Come back next Sunday to read the next installment.

[Image via Wikimedia/Daniel Johnston]