My boss told me that I needed to land the plane.

He was referring to my career because I had yet to find something to settle on. Ugh, the word settle just makes me cringe. That’s probably a topic all by itself (aaannd, I just wrote it down to remind myself to write about it).

Craig was my real estate broker, so kind of my boss, but not really. I now consider him a friend, a very successful friend, who has landed his plane. He’s had a successful career in real estate for as long as I’ve known him, plus he loves what he does.

One day in the spring of 2010, we were sitting in his office on the 30th floor of a downtown Chicago high-rise overlooking North Michigan Avenue. He looks me squarely in the eyes and advises me with as much sternness and compassion as possible, “Chad, you’re going to have to land the plane someday!”

I looked at him with confidence on the outside, but insecurity on the inside, and said, “Craig, I’m landing the plane now, I promise.”

When I said that to him I was currently producing content-rich real estate videos for real estate agents to use in their marketing. A few months before that I was a mortgage banker. Six months before that I was a mortgage banker and real estate agent hybrid. A year before that I was just a real estate agent. Two years before that I was working for a home-builder in Cleveland. In a five-year span I was associated with 8 different companies. You can consider it 9 if you count the restaurant where I was bartending at the time.

There’s no doubt that Craig had a point and I’m sure that others were thinking the same thing but wouldn’t come out and tell me. I just couldn’t seem to land this so-called “career plane.”

The thing is, I do believe that we all must eventually “land the plane” in some capacity, but I couldn’t (and still can’t) justify landing it in a career that just makes me want to take off again…and again…and again.

That conversation very subtly got me to thinking. First off, I knew he was right; I needed to land the plane. Second, I knew that landing the plane wasn’t going to happen in the current situation I was in…which was now going on five years.

It was time to make a drastic change. That drastic change started when I sat down after that conversation and said to myself, “where in the hell am I going to land this stupid plane?!”.


Looking for a Place to Land

As you know, this blog is a documentation of our story as we try to reach our “really big freakin’ dream” of having a career as adventure travel TV hosts, so at that time of soul searching the travel world is where my thoughts began to focus. Over and over, my mind kept going back to the world of travel.

Maybe you’re like me, maybe you’re not, but as my thoughts kept going back to the travel world something in mind would intuitively shut down the thoughts at the same time.

It was if my mind was prevented me from actually believing that having a career in the world of travel, specifically as adventure travel TV hosts, was even possible.

This astonished me. I’m an out of the box thinker through and through. Anybody that knows me well, knows that I come up with the weirdest (I think coolest) ideas that I believe are absolutely accomplishable while others think I’m nuts. For some reason, though, my mind wouldn’t allow me to visualize landing the plane in a career like this.

What’s crazy is, when I was younger this wasn’t a problem. When I was younger I believed that I could be paid to complete adventures around the world, but for some reason that belief left me during college and into the first 4-5 years of being in the “real world”.

There is reason to believe that this was happening because I was led to believe that I needed to go to school, get a degree, find a good job, and yada yada yada, none one of which I believe now.

I eventually broke through the mental barrier and it’s been the most exhilarating, and sometimes scary, feeling!


Landing the Freakin’ Plane!

You see, for me I’ve finally decided to try and land the plane on something that I not only care deeply about but it’s something I am so passionate about that I’m willing to keep going at it year after year without seeing the light at the end of the tunnel.

Think about it. From 2005-2010 I worked for 9 different companies working the standard 8- hour day trying to make things work. Obvously, I was never satisfied with what I was doing. You couldn’t pay me enough to commit a year to a company, let alone commit to a company for the rest of my life.

Yes, currently I do work a job. I have to make money while we build our idea. I currently own a marketing company that helps companies convert more sales quickly and easily with their marketing efforts. It works perfectly with my non-committal mindset as I can work with multiple companies at one time.

I have to have some level of practicality even while dreaming big because being practical in this way is helping me position myself in a way that will enable me to reach my goals…especially when I’m the kind of person that hates being practical.

What’s different today versus 2005-2010 is that I know everything I’m doing in my paying job always revolves around the pursuit of my “really big freakin’ dream” career in some way.

Consider this. I’ve been working on Stampabout for over two years, and haven’t seen one cent in income. We’ve had a lot of frustrations to boot and don’t have any special circumstances, yet it’s the one place that I feel I can land this damn so-called plane that’s been haunting me for so long.

There are times that I do get discouraged, it’s inevitable, but the feeling of discouragement is much different when you land the plane in a career field you love than the feeling of discouragement in a career field you already hate.

Instead of hating your job more, you become more motivated to overcome the challenges, obstacles, failures, criticism, etc. It’s hard to explain, but I promise the feelings are very different.

Steve Jobs sums up that feeling for me in this video. Watch it before reading on.

Our dream pursuit is hard. It always has been hard and it will continue to be hard, but my passion for what we’re doing allows me to persevere and continue to push forward no matter the obstacle.

It’s safe to say that I’ve decided to, and I’m determined to, finally land the plane, even if the descent is full of uncertainty.


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Have you landed your plane in a career that you have passion for, the type of passion Steve Jobs speaks about in the video above? Tell me your story in the comments below.


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Chad is “Ready-Fire-Aim.” That means he prefers to try first, ask questions later. He lives by the idea of “failing forward” and believes it takes 10,000 hours (or 10 years) to master whatever it is one is currently doing. Chad doesn’t want to waste the rest of his life mastering somebody else’s dream, so he’s willing to keep trying any number of his thousands of ideas until one finally works. Chad is Stampabout’s ideaman, go-getter, and the “risk” in “calculated risk.” Chad is a sales and marketing professional that has sold and marketed everything from real estate, a healthy vending franchise system, payment processing systems, and beers to local bar patrons. He owns an ecommerce consulting company,, that helps his clients convert more visitors to paying customers.


  1. Hi Chad, I’ve been enjoying reading your posts and watching the clips. That restlessness is something I’ve felt quite a lot as well… I’m loving your Illustration here, and having spent 10 years in preparation to “land my plane,” literally, I would say that looking back at where I am now, the work and sacrifice to realize my dream has been worth it! I am looking forward to seeing where you and Jake go from here. And seriously dude, when you two make it to Africa look me up we’ll have some crazy adventure flying into the bush or go bungee jumping at Victoria falls. Peace and Love–Jonathan

  2. Dude! Sorry it took so long to reply, I know you had commented. I’m glad you’ve been enjoying the posts and the videos. Jake and I have been enjoying seeing you’re photos of Africa…and trust me we already started thinking about how we’re going to get out there to visit you. Hopefully, we’ll be able to make it out soon and we can do all those crazy things you speak of…AND find something of meaning to make others more aware about in you world. I’m jealous that you’re a pilot doing what you’re doing. Good stuff and keep it up. Send us any feedback and let us know if there is anything we can do here. I’ll chat with Jake and Paul (cameraman/editor/producer) about when we can make it out there.

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