Did I mention I have no clue what I’m doing?

Did I mention I have no clue what I’m doing?

Question Mark Man

As of Sunday, May 1st, I’m now in Chicago. This was part of my original plan.

And yet, as I sat on the grass looking out at Lake Michigan, I wondered “what the hell am I doing?” I didn’t even have anywhere to stay yet! I had just left my mother’s house, where I knew where I was sleeping, there was food in the house, and it was a safe and comfortable environment.

So I’m in Chicago…what exactly happens now?

Luckily, here’s the thought that came into my head next:

Even though I don’t know what’s ahead, I’m doing this anyway.

So I don’t know where I’m staying, what I’m eating, or what I’ll do when it rains – big deal! If those are my biggest challenges (and they’re all pretty easily solved), then it’ll be just fine. Yes, I know the scoop when I’m staying with family, but by definition – it’s comfortable! Not exactly easy for me to step out of my comfort zone, which is something I’m committed to right now.

So where does that leave me. Well, here are the things I DO know:

  1. I will travel
  2. I will meet and talk to people
  3. I will practice my daily fundamentals

Yup, that’s pretty much it right now.

Does it scare me? Yeah, a little.

Do I have a regular source of income to support my lifestyle? Not yet, and I’m working on that.

Do I have absolute freedom in where I go and what I’m doing each day? Absolutely.

That last scenario is too important for me to give up; I need to keep following my dreams and my heart, even when I have no idea what’s around the corner. Besides, that’s what keeps life interesting and me guessing. I’m someone that really enjoys solving puzzles, and what better way to do that than to put myself in a new environment and situation every day! It seems to have worked out so far.

So what’s all that going to require:

Courage, and lots of it. I still deal with fears, anxieties, worries, and self-doubt; the point is whether I move through all that stuff and get to the goodness on the other side.

Nathan in Chicago


Yes, it takes courage, along with…

One of the perks of taking a train is that you have more of an opportunity to meet people. I took the Amtrak from Boston to Chicago over the weekend. In the dinner car on Saturday night, I sat with a tall Texan, who introduced himself as “Maverick” (Tom Cruise and “Top Gun” aside, a possible red-flag right there).

It turns out Maverick has been all around the world, served for his country, and now sees the US  by driving RV’s and commercial vehicles wherever they need to go.

I told him about what I’m up to and where I’m headed. When he found out how old I am (30), he remarked “Oh, I had dreams at 30, too.” He was even a bit dismissive that someone my age could be a consultant. (I can’t imagine the heart-attack he might have if he learned what people younger than me charge.)

I replied that my ideas aren’t going to stay as dreams.

While he seemed to accept that, he did say that most people don’t fulfill their dreams because they’re lazy. I disagree. I’m realizing that almost everyone (myself included) need two things to succeed: structure and support.

Structure: a way to measure or track our progress; accountability to get things done; a clear road-map of how this is all going to happen

Support: cheerleaders, coaches, mentors, friends, family, positivity, affirmations – people (including yourself) believing that you can do it

Without those elements, I think it is difficult to reach our goals. This may be self-generated and/or it may come from external sources. I’m actually looking into how I can find a way to offer those two things as I continue in my fun pursuit of facilitating awesomeness. :-)

No one does anything alone. Not even Maverick.


I’d love to hear how you’re pursuing your goals – what works or has worked for you?

Feel free to let me know the answer to that and any other comments you have.

Until next time,


Former life: actor/office worker/virtual assistant; lived in Los Angeles for 11 years. Since then: sold nearly everything, took a $5 flight to Hawaii, lived there for 3 months, wrote an eGuide about all of it, and still traveling. Currently: digital nomad - looking to improve myself, have fun and serve others.

5 comments on “Did I mention I have no clue what I’m doing?
  1. Awesome Nathan! You sir, are truly living. You might be able to make more money by settling down…but you’d be half as happy if you were lucky. You’re an inspiration to me. I don’t know if I’ll be a genuine nomad like you are, but I would like to travel a great deal in my lifetime.

    • Nathan says:

      stephen! thank you so much for the kind words! i checked out your deep experience, and enjoying what i saw over there! i seriously appreciate the support and the way you’ve jumped onboard nonstop awesomeness – means a great deal to connect with like-minded individuals who are committed to living to their potential – it’s the only way to be, right? :-)

      based on what you’ve already done, if you want to travel lots – i definitely see that happening! keep on rockin it!

    • Nathan says:

      by the way – what part of the world are you in? perhaps we’ll cross paths on our travel adventures!

  2. Thanks Nathan! Yeah, I love that not only do you travel, but you reach out and connect with strangers. I think that’s a huge part of what makes travel so rewarding!

    I’ve actually thought that would be cool to cross paths with you sometime. I’m currently in Charlottesville, VA. I’ll be moving in with the parents in Mooresville, NC soon.

    I tend to favor international travel over domestic, but I still really want to see the USA. My goal is to make a living online somehow to untether myself from any one location.

    • Nathan says:

      awesome stuff stephen! if i’m ever in your part of the world, i’ll let you know. thanks again for reading & reaching out!

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