It never hurts


When I recorded a podcast with Peter DeWolf a couple months ago, one of the questions he asked me was about The “Lucky” Ones interview series. He asked, “Who would be some of your dream interviewees?” This was a fair question. I should’ve been able to think of at least half a dozen people on the spot. Instead, I hemmed and hawed—long enough that, thankfully, my seemingly endless umm’s and uhh’s were edited out of the recording—before blurting, “Oprah! Because she’s interviewed everybody!” Not the most original response ever, but of course I’d pee my pants if I ever got that opportunity.

Later, though, I thought about the question some more and wondered why in the hell I had such a hard time answering it. I’M A WRITER, I thought to myself. THAT SHOULD BE THE EASIEST QUESTION TO ANSWER. But of course, I didn’t have a hard time coming up with a whole long list of dream interviewees once I wasn’t on the spot and being recorded.

Who are some of the people I idolize? I can think of countless writers, musicians, and other creatives: Cheryl Strayed, John Green, Patti Smith, and, if we’re going the dead or alive route, Frank Zappa and Sylvia Plath—just to name a few. Naturally, in coming up with this list, my mind went to several of the bloggers I admire and look up to. You know, the ones who have reached rock star status and do it for a living. My most recent interviewee, The Art of Non-Conformity blogger and New York Times bestselling author Chris Guillebeau, was one such blogger that popped into my mind. I’d love to interview him, I thought.

And then I had a not-incredibly-brilliant, but actually very common-sense idea: Ask him.

So I did. Simple as that. Why in the hell hadn’t I thought of it sooner? His site has a page very conspicuously labeled “CONTACT.” I am very good at conducting short, polite, and (I think) endearing emails. The worst that could happen was that he didn’t respond, which I wouldn’t have blamed him for. He’s a popular guy and is probably swimming in emails. The next best possibility was that he would say sorry, but no. That would’ve been fine, too—cool, even. Hey, at least he took the time to say no! Instead? He responded within two hours: “Sounds fun. Let’s do it. :)”

OH. OKAY. LOL. That was easy.

So before he could change his mind or jet off to another country (and after thanking him profusely), I sent him over some questions, making doubly sure there were no errant typos. And, as you can see, the result was a thoughtful and insightful Q&A session with a New York Times bestselling author. NBD. Oh, and this—this made my day:


THIS IS NOT AN EVERYDAY EMAIL, FOLKS. Not yet, anyway. But it got me wondering… who else could I ask to do a favor for my relatively modest (but growing!) blog? Who else might surprise me by saying “yes?

That remains to be seen, but it sure taught me a good lesson, which comes back to my post from last week: ask. You know, as in ask and ye shall receive? Again, common sense—and yet, too often we assume that someone is too busy, too popular, too important for our time, so we don’t even bother trying. It may be the case that we don’t get what we ask for—in which case we should be gracious and understanding—but we might also be pleasantly surprised.

You know what that means: Look out, Oprah. I’m coming for you.

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  1. I just love this post! I loved seeing Chris here and his answers too, but this really rang a bell with me. I’ve tried some pretty ambitious stuff at certain points in my life, and even if I wasn’t always very successful with them, I still have the wonderful experiences I can build my life upon. I so happy for you and your courage to ask, and now I really need to get around to do some more asking myself.

    • Glad you liked it! So true about the experiences you collect. Even if they don’t go the way you hoped, there’s always something to be gleaned from them.

  2. Great job, Cassie. And you really are a rockstar! The honor was all mine.

  3. You are so right – it can be so hard to ask for what you want, but in most cases the worst that could happen is that you won’t get what you want – which you’ll already be getting if you don’t ask.

    • Exactly. I know I need reminding of that every now and then. It applies to everything—INCLUDING discounts at Jiffy Lube. (True story.)

  4. Ah, this is so great. I have trouble even asking people I know for help/services/advice so the thought of asking strangers I admire kinda terrifies me. So excited to see/read about how your willingness to ask is working out for you though!

  5. This is so exciting and perfect! I’ve also been on a path that seems to be ultimately leading in the direction of “why CAN’T I do that?” I had that thought after daydreaming about moving to a different country and it all seems really crazy, but really what’s the worst that can happen (I mean, besides homelessness in my case, but I see that as a temporary setback if it does happen)! I’m very excited to see where you take this. John Green and Patti Smith would also be on my list. As well as maybe Emma Watson (I think she’s really cool because her life is kind of crazy but she seems relatively normal). And Oprah for sure because why not and she HAS met everyone ever. Who knows, you could be on the path to becoming the next big journalistic superstar, and one day you will be famous following your career of in-depth interviews with the famous (so meta!).

    • Homelessness? Pah! Temporary, indeed. I am totally ready to accept the possibility that I might be homeless in a couple of months, so we can commiserate together if that happens to us both. (But it probably won’t, so YAY!)

  6. Excellent – and dude, so true. Asking for favors, asking for help, just reaching out and ASKING in general, does amazing things. I’ve been emailing and emailing and emailing lately, trying to get a job (or multiple jobs), and the response has been pretty great. And again, that was an awesome interview.

    • I said it on your blog, but I’m sending lots of lucky vibes your way! Sounds like you’re already on your way to getting what you need, though. Sometimes, it quite literally pays off to ask for help.

      Oh, and if you’re already set with a job but see something part-time that might work for me… um, hi. 😀

  7. First, I hope the dinos are yours & going with you to California. Second, you never know until you ask. The worst someone will say is no. And, actually, except for someone I interviewed recently, nobody’s ever told me no. She didn’t so much as tell me no as she did ask a million questions (and then asked for a piece of the money pie when the piece got published). When I told her no, she told me I was rude. You win some, you lose some.

    • The dinos belong to my sisters, and therefore they are not mine to take. But maybe the girls wouldn’t notice if I took just a couple on the road trip…? I could use a velociraptor in my life.

      I’m surprised someone expected you to pay them! I mean, compensation should be discussed early on if that’s what’s expected. But interviews in general aren’t, like, paid. (Unless you’re a major media outlet that can afford to and is eager for the story… but otherwise, it’s a form of promotion.) You win some, you lose some is right.

  8. It’s funny how much gets accomplished when you stick your neck out and stop worrying about the negative what ifs. Not blog related for me, but I’m going through a lot of the same discoveries you are right now in other aspects of my life. Thank you for always putting yourself out there and sharing it. It really is inspiring.

    I’m so happy for you and proud of you!

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