5 Dangerous Questions to Help You Move Forward


This is a guest post by Matt Gartland of NerdKicks, a podcast and community dedicated to the belief that nerdy skills are super powers to be understood, developed and unleashed for good via our own personal hero’s journeys. Sound fun? Join in on iTunes and on Twitter, for the win!

Mark Twain once said, “Whenever you find yourself on the side of the majority, it’s time to pause and reflect.” He was right then. He is right now.

Innovation doesn’t occur from thinking the same thoughts. New discoveries aren’t made by retracing your steps. Life doesn’t become better by living it the same mediocre way it has always been.

No, to seize opportunities and experience personal growth – whether in our personal finances, health, creative projects, or relationships – we must do as Twain counseled: “Pause and reflect.”

This, of course, is hard. Why? Because complacency is comfortable, as Baker and team’s I’m Fine, Thanks documentary shows us. Detachment from original thought, unbreakable convictions and necessary hard work is a new norm. Oh, the irony, that The Walking Dead is a popular TV series when it is us, the viewers, that often resemble that description.

There was a time, however, when the gravity of such complacency didn’t weigh us down like a lead vest. In our youth, we were innocent enough to be curious, ambitious, restless, resourceful and, above all else, persistent. Such innocence cannot be reclaimed, as a bell cannot be un-rung.

However, there is an alternate path that allows us adults to re-experience the magic of our childhood. Kim and Jason Kotecki call it escaping adulthood. Steve Kamb calls it leveling up your life. I call it embracing your inner nerd.

Nerds possess the nearly uncontrollable urge to make things good, and to make good things better. We ask questions and enjoy methods of discovery. We accept that failure is a healthy part of the process. We live to learn so that we can make better decisions. And we have a hoot doing it, because science is fun!

The nerd spirit is a gateway back to the powers of our youth. And questions are the keys. They can be dangerous. But who’s interested in playing it safe? The MythBusters aren’t. Baker isn’t. I doubt you are either.

It’s time to get dangerous. And to do that, you have to ask yourself…

1. Do I fully understand the problem?

Sherlock Holmes is one of my favorite characters. He exemplifies wit, resourcefulness, objectivity and cunning. To solve a crime, Holmes must fully understand the case. So he examines every clue and ponders every possibility without prejudice, as a good and dashing nerd does.

Why does he do this? Because, as Holmes says, “There’s nothing more elusive than an obvious fact.”

We seek the same in our lives, the “obvious facts” that show the way forward but that so often elude our grasp. Ignorance is to blame much of the time for our “blindness”. After all, how can you accurately solve a problem if you’re unwilling to accept the full measure of it?

To solve any problem – debt, poor health, bad product launches – you must recognize the fullness of the problem, then embrace it. For example, Holmes routinely tastes things himself to uncover otherwise unseen clues. You probably don’t need to put artifacts in your mouth – but you should calibrate your understanding of the circumstance by sharing your feelings with friends and family, creating some simple pros/cons lists, and defining worst-case and best-case scenarios.

2. Is my method honest?

Ever feel like you’re a square peg being forced into a round hole? I have, and I’m sure you have too. Conventional wisdom teaches us that in such situations we should adapt into round pegs. But that’s rather disingenuous, don’t you think?

There’s a better solution: Find a square hole.

This is all about method, the process you select and leverage to overcome complacency in your life. If the method you’re using isn’t working, kill it and begin anew with a different one.

Simon Sinek’s now iconic Golden Circle paradigm illustrates this beautifully. Sinek discovered that the individuals and companies that enjoy remarkable success all fundamentally flipped the conventional WHAT–HOW–WHY model. Instead of leading with WHAT, they lead with WHY.

3. Am I making what I feel needs making?

I adore Adam Savage, the stupendous special-effects expert and co-host of MythBusters. There is perhaps no singular nerd more animated, brilliant, hilarious, authentic and inspiring than Savage. Best of all, he’s a true “maker.”

My dear friend Mindy Holahan introduced me to the Maker Movement, which organizes into ridiculously popular Maker Faire conventions. This year’s keynote? Mr. Adam Savage.

You must watch Savage’s speech – titled Why We Make – because it addresses a most urgent and sensitive question, are you making what you feel needs making? Many don’t for one reason or another: job demands, conventional environment, lack of resources, lack of will power, submission to critics. That’s impossibly sad.

Savage’s talk is the antidote to such sadness. In refection upon being asked why he makes such violent things, he says, “[the] question presupposes that I have a choice. I don’t think that I do. I’m making the things that I feel I have to make. And I don’t get to choose what I feel I have to make.”

4. Am I chasing my happy?

You probably don’t know who Ze Frank is. I didn’t until very recently, when I was implored to watch one of his short shows, titled Chase That Happy. You should watch it. You’ll laugh, a lot, and hard.

Here’s the surprisingly serious kicker, in Frank’s own words: “To chase your happy, you kinda become a scientist that looks for clues to your happy right where you are.” Spoken like a true nerd.

Are you chasing your happy?

5. How will I use the results?

This may be the scariest and most dangerous question of them all. Why? Because as Sherlock Holmes says, “If you eliminate the impossible, whatever remains, however improbable, must be the truth.” And the real truth can be downright frightening, not out of dread, but responsibility.

If you come to fully understand the problem through an honest method, whereby you discover what you innately feel needs to be made or done, then what are you going to do about it? Are you going to act upon that truth and seize the opportunity, despite the likelihood of discomfort? Or will you not, choosing comfort over adventure, complacency over conviction?

I believe these are dangerous questions, but necessary – and, to he enlightened, unavoidable.


If you don’t challenge yourself, how will you move forward with your goals?

Are you asking yourself these dangerous questions – or others? And how are you using the answers?

Please let us know!

27 thoughts on “5 Dangerous Questions to Help You Move Forward”

  1. Matt!!
    Great post and as always with you – timely as it gets. Life can be a jumble sometimes – this is sage advice – (and you know I always listen to you) – for getting out of the rough and on one’s right path. I always feel like you and baker are talking directly to me. Thank you my friend!

    1. Matt Gartland

      Great to hear from you Jay. Your remarks are very kind. I’m thrilled you found the article useful and motivating. Keep moving forward on your own path!

      Best regards,
      Matt 🙂

  2. Complacency is something we should all strive to move away from. That’s why I think we all need “I’m Fine, Thanks”. There questions are very helpful and I love the “find your happy” video – very funny!


  3. Matt – This is an interesting breakdown… A process that sounds quiet effective. Thank you! My favorite – the very first sentence “Innovation doesn’t occur from thinking the same thoughts.” How often do people get stuck in this routine of sameness? Very often I’d venture to say… I know I have! Running new project ideas through old scenerios and then wonder why we encounter the same problems, setbacks, and failures as we’ve seen on previous projects. Time to think some new thoughts!

    1. Hi Jennifer. Thanks for commenting. I agree that many (myself included) have a tendency to get lost in old scenarios. Progress necessitates that we move out of those cushy positions into circumstances that keep us on edge. Time to think some new thoughts indeed 🙂


  4. Matt, Thanks. We can all embrace our inner nerd–anything to shake up our lives and get us thinking outside the box and maybe recycling that box altogether. Loved the inspiration and laughs in the videos–especially Ze Frank’s. A good reminder not to take ourselves too seriously and that the best innovations come from doing what makes you happy.

    1. Matt Gartland

      Hi Lori-

      The “not take yourself too seriously” point you raise is super important. We are all doing important work, but I wager that we lose our edge if we freak out over every little thing. Don’t be rigid; be fluid 🙂


  5. Hmmm, I’m in the process of applying for teaching jobs. My cover letter goes from the what to how and then why. I’m thinking I’ll switch it up and put the why first. As you said lead with the why! I like that.

    1. Matt Gartland

      Indeed Rachel. When you flip things up, that helps you stand out – a very good thing when interviewing. Good luck with the teacher job applications!!

      Matt 🙂

      1. Matt Gartland

        Nice catch Mike. Thanks 🙂

        We’re in the same boat Joan. I should have caught that.


  6. I love your post. Sherlock Holmes and Adam Savage, two of my faves! 🙂 And now ZeFrank. That was awesome. I think chasing happy more often would help all of us. We all need to chase more happy and laugh more. My daughter, who is 7 yrs old, just introduced me to a game called My Grandmother’s Underpants. One person asks another person a question, and that person always has to answer “my grandmother’s underpants”, without laughing or smiling. It’s nearly impossible not to laugh. Which is fun.

    And that part about eliminating the impossible, that’s so true. I’ve somewhat recently come to the realization that getting a new job/finding a new income stream is the only way we’re going to get to a better financial situation. It’s impossible that we’ll be able to pay off debt, help our kids with education, save for retirement, travel more, etc, if I stay in the job where I am now. And that’s kinda scary. I’ve been there over 12 years. It’s a big change. But it’s exactly what I need to do to break out of the rut and expand.

    1. Matt Gartland

      Well said, Leah. Yes, embracing what you know needs done can be scary. Like any adventure into unchartered waters, you’re confronted with uncertainty and doubt. But that’s okay. Those feelings heighten your senses and give you more to fight for.

      Lean forward and make magic happen 🙂

      Matt 🙂

  7. These are great questions to be asking ourselves. Complacency is a total creativity killer, and as makers, entrepreneurs, creatives, businesses, etc. we have to be constantly challenging ourselves to recognize and solve new problems, think in an innovative manner, so we can be providing true value to our audience. And do so in a way that’s compelling, interesting, and isn’t reinventing the wheel.

    1. Thanks for the kind comment Dana! Complacency is indeed a creativity killer. We need creative not only to produce the art we feel needs making (see Adam Savage) but also to get ourselves out of sticky situations (like financial debt).

      Glad this article helped you think in the right direction 🙂


  8. Probably the first question is what gets me into trouble. Well, not really, but what usually impedes my progress. I tend to be impulsive and act on intuition, and sometimes that works, and sometimes it doesn’t.

    1. That’s very common; we all struggle with that. Such is the big questions of life, right? The important thing, at least first, is to be aware that there are “unknown unknowns.” From that acceptance, we can explore the situations further, in nerdy fashion of course 🙂

      Thanks Emily!

  9. I really like the last question. If you’ve been honest with yourself, this will be the hardest step of all – yet the most important. And probably the one I avoid the most. It’s much easier to work backwards so you end up with a solution you want – but this means you don’t end up with one you really need. My answer looks confusing but hits home for me.

  10. Pingback: bookmarks, issue 22 | my name is not matt

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