On the Hot Seat at Pioneer Nation

//On the Hot Seat at Pioneer Nation
Photo courtesy of Chris Guillebeau

Photo courtesy of Chris Guillebeau

An entrepreneur exists along the fine line between impostor and badass.

Thankfully, at Pioneer Nation, I got to spend a few days with lots of other people on this fine line, too. (If you have not read about the Impostor Complex, go check it out. Come back to my blog later; compared to Tara Gentile’s work, I’m totally lame.)

And that is the point.

Compared to other web designers, other content creators, and other videographers, my work is crap. When someone wants to hire me for a website design, I can easily name ten other designers who are better than me.

But I don’t.

Instead, I calmly guide my future clients into working with me, ignoring the feeling that I’m a total fraud. I can do that, most of the time; and I can justify it, too. There are lots of clients that think I do great work. Some of my stuff is pretty good. But some of my stuff, it really sucks.

Accepting the Call to Adventure

Photo courtesy of Chris Guillebeau

Photo courtesy of Chris Guillebeau

I really like the WDS production team. They’ve got clever and adventurous ideas, and they are responsible for creating the community of independent entrepreneurs that give me a sense of belonging. When they asked me to get on the Hot Seat at Pioneer Nation, and describe a problem I was facing in my business so we could workshop it onstage in front of hundreds of people, I jumped at the chance. The problem I faced was simple and fundamental: my newsletter CTA (Call-to-Action) really sucks. Laptop-Living-landing-page This landing page is not my best work; it’s functional. I made it last year, and never got around to really fixing it. I can get away with this, in front of people who don’t know how to make websites, and don’t know what a CTA is for. But I was in a room full of digital professionals, showcasing my most unpolished, mediocre work as my introduction to everyone.


Photo courtesy of Chris Guillebeau

What have I done?

The criticism was polite, but it was swift and brutal. One of the perils of working solo is that there is nobody around to ask you the fundamental questions that stand out to even the most casual observer. I kind of knew that the logo for Laptop Living was not very good, but never really thought much about it, until hundreds of people were looking at it thinking, ‘Wow, that is one ugly logo.’ My CTAs weren’t good enough to workshop productively. I had fundamental problems that would take much longer to untangle. My photo even got called ‘creepy.’ Then, I missed the bit I worked out with Sean, where I would plug his Location Rebel community as a better place where people could learn about living from a laptop. Leaving the stage, I felt like a failure and a fraud.

Photo courtesy of Chris Guillebeau

Photo courtesy of Chris Guillebeau

Education By Failure

When I took the invitation to take the Hot Seat on the mainstage with Sean and Tyler, I knew full well that I may fail. Every time you step up to the microphone, you take the implicit risk of failure and embarrassment. Failure is something I do not fear. (Actually, I recently discovered I do not possess the capacity to fear failure. For better or for worse.) I am brave, and adventurous, and I have always believed that everything else being equal, if I fail faster than you, I win. So I said yes, because if I did not succeed, at least I knew it would be a fun way to fail. I invited this criticism, because without it, I could easily coast for another year using a bad logo and a bad photo, never realizing what people were actually thinking about it. Inviting the embarrassment and shame onstage in front of hundreds of people wasn’t easy, and it wasn’t fun, but I know how fast one can grow when taking a journey through the forge of failure.

Impostor or Badass?

Before I properly had time to process most of these lessons, on the morning after Pioneer Nation, all of my websites went down. All of them. At 9 am on a Saturday morning. My websites, my client websites, emails, everything went down. Bluehost sent an automatic scanning bot that shut my server down with no warning. I flew into action mode. (This was not the first time Bluehost had crashed on me.) I accessed my server backend, got tech support on live chat, and started rewriting database tables. Let me make a clear declaration: I don’t know anything about MySQL database tables. I don’t work with them on a daily basis. I only have a vague conception of how they work. The whole time I was working to repair this colossal error, I was thinking, “I’m such a fraud. I’m not even a decent web designer. I can’t even keep my websites online. I’m an impostor.” And then, after fifty minutes of downtime, everything was fixed. My websites were back online, and it is very possible that nobody ever even noticed.

A Badass Impostor

As little as I know about server administration, I acted quickly, and I fixed the problem. I didn’t call my clients and tell them all ‘sorry, I don’t know what’s going on.’ I fixed the problem – even though I didn’t know how. So yeah, I’m an impostor. A better web designer would have had a better server rack, and wouldn’t have to deal with a crash like I did. But the better web designers have all gone through what I went through. They learned like I did, by experience. will-rogers-quote So even though I’m an impostor, I’m a badass impostor, because I learn fast. I am willing to do things that I don’t know how to do, because that is the only way you gain enough experience points to level up.

The Forge of Failure

Image via Wikipedia

Image via Wikipedia

Iron is not forged in an easy place. It has to be heated, and beaten, and it hurts. When the forging process is complete, there is nothing left of the dross. The impure metals are forced out by the heat and the hammering. It is only by fire that we can effect massive change, and as I sat on the Hot Seat, I knew that was what was happening to me. Instead of waiting until next year to figure these lessons out gently, I learned them quickly, and it burned, and it worked. And I saw how this could be made so much easier, with Show and Tell.

The Solution: Show and Tell

Creatives need someone to whom they can show their work, talk a little about what they want it to do, and get a couple superficial comments that serve as authentic first impressions. We need a Show and Tell. To prevent mishaps like my Hot Seat experience, I’m going to host a weekly Show and Tell on Google Hangout. Six participants, first come, first served. Everyone gets 10 minutes: five to show what they’re working on, and five for feedback. If you want to join a Show and Tell circle, sign up here.

By | 2014-04-02T16:28:58+12:00 April 2nd, 2014|Introspection|

About the Author:

Father of 3. WordPress website designer. Creative director @ Stellar Platforms. Writer, multimedia producer, digital marketer, and retired superhero.


  1. Adam Dunlapa April 2, 2014 at 7:33 pm - Reply

    Fake it til’ you make it as they say.

    • Caelan Huntress April 3, 2014 at 10:37 am - Reply

      That saying always makes me think of this quote from Cary Grant: “I pretended to be somebody I wanted to be until finally I became that person. Or he became me.”

  2. erindonley74 April 3, 2014 at 4:41 pm - Reply


    This blog really pissed me off. It’s the problem I continually see with struggling entrepreneurs… we’re getting advice from each other, instead of gaining feedback from paying clients.

    Have any of your paying clients actually said, “your website is atrocious?” No, that’s because they were sold on your stellar communication skills and your genuine enthusiasm to do the work that’s needed. You’re a master at building trust and keeping a client engaged and informed through your entire process.

    Maybe your peers need 100,000 email subscribers, but maybe you don’t? Do your paying clients actually want to read a newsletter? Why not start there instead of accepting it as truth that the way our peers are marketing is the same standard we should hold too?

    I mentored with an executive coach whose clients were some of the top financial leaders in America. That coach had the worst website I’ve ever seen. Do you think he hangs out with his peers? No, he surrounds himself with those he serves to continually learn what they want and need.

    I, for one, and DONE with entrepreneurial networking groups. They keep me believing my efforts are never quite enough… and most importantly, I don’t get business from them! Peer coaching is crushing the momentum of millions of entrepreneurs.

    I hope this helps you remember your brilliance and expertise that is clearly evident to those who have worked with you.

    • Caelan Huntress April 5, 2014 at 7:50 am - Reply

      I’ve been doing pretty well at getting feedback from my clients, Erin. This was the first time I had asked for such candid feedback about my brand from other entrepreneurs, and I found the insight really valuable.

      I agree with you that we can’t rely on only peer-level feedback, and there is definitely a risk of getting drained if the feedback saps your enthusiasm and momentum.

      But isn’t it better to get challenging feedback, instead of remaining ignorant to the impressions that you make?

  3. kersylearns April 4, 2014 at 9:28 am - Reply

    Aw Caelan from someone who was there, let me tell you that you definitely did not come across as a fraud or incompetent person. I also came away just wishing my website was beautiful, and deleting half of it, and just feeling like “ARGHGH.” It’s good. It kicks us when we need it.

    Erin has a point, which is that it’s important to be aware whether your website works on your clients, not on us fellow pioneers. But especially as someone who isn’t the world’s most confident designer, you need to project “trust me, I’ve got this.” And consistent messages go a long way for that, apparently.

    Ultimately no one CARES if there are better designers than you. What matters is that there are no better designers who will also throw themselves at Bluehost, go out of their way for customer service, question themselves regularly and provide a friendlier smile out in your corner of the world. Your customer doesn’t want the best designer, they want the most YOU designer. Weird feeling, right?

    • Caelan Huntress April 5, 2014 at 7:53 am - Reply

      Thanks, Kersy. You’re right, keeping that mental confidence is essential.

  4. Rob McNelis April 9, 2014 at 6:06 pm - Reply

    Nice site dude! found you through a comment you made on BBT.

    Would love to hear more about your online goals. hit me up at @robmcnelis


  5. Saul April 12, 2014 at 4:07 pm - Reply

    Great post! your Show and Tell idea sounds awesome. I just sent you a e-mail about trying to get an in-person meetup along those lines (I tend not to remember/follow through with online hangouts!)

  6. […] I went to Pioneer Nation last month, there was a really inspirational story told by Laura Roeder. […]

  7. […] progression in my experiment of radical honesty. First I revealed my superheroic failure, then the onstage critique of my dysfunctional newsletter, and finally I revealed that I have been struggling with poverty, […]

  8. chuiso May 12, 2015 at 2:00 pm - Reply

    Hola! Gracias por esta información. Llevaba un rato buscando por internet sobre este tema hasta que he encontrado tu página web.
    Está realmente bien el artículo. Sigue de esta manera!

  9. […] For the past few years, my newsletter has been a mishmash of client highlights, digital marketing, and social media tips. I didn’t send it every week, or even every month. There were lots of sections, and lots of images, and since I included plenty of personal anecdotes about living abroad from your laptop, I called it ‘Laptop Living.’ It was very unwieldy, and then, I broke it on the hot seat at Pioneer Nation. […]

  10. marca personal consejos October 7, 2015 at 11:10 pm - Reply

    Pudimos percibir ponencias y reflexiones de gran nivel en relación a diferentes cawmpos áreas
    donde aplicar el personal branding.

  11. ultimate team October 21, 2015 at 10:16 am - Reply

    I like what you guys are up too. Such clever work and coverage!
    Keep up the wonderful works guys I’ve incorporated you guys to my blogroll.

  12. […] been to both Pioneer Nations (you can read about my experience at PN last year – and how I broke my newsletter on the Hot Seat) and I’ve been to the last three years […]

  13. […] (This advice was really useful for me after my experience on the Hot Seat.) […]

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