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How my worst fears came true while pursuing entrepreneurship.

‘What the fuck are you doing on a sheep farm in Montana!?’

‘Well… currently… I’m sitting at a bon fire I built, drinking my favorite $10 red blend out of the bottle, and looking up at the fullest sky of stars I have ever seen. It’s… it’s amazing!’

What he really meant to ask me was how I got to this point in my life where I’m camping on a sheep farm in Montana. Which comes with a slightly longer answer…

I arrived at the farm sometime in the evening on Thursday, March 31st. The lady of the house greeted me, and the man of the house was soon to follow.

‘Your’e gonna freeze your ass off’, is the first thing he says to me.

‘Oh, don’t tell him that!’ she said.

But there was a high of 33 degrees that night, he had a point.

‘Well you can set up anywhere, but you might want to set your tent up here’ he said, as he was kicking up a pile of hay for some ground padding for me. The hay was right next to a wall of wood basically, which had a short roof on it and might protect me from wind from one direction.

He continued; ‘Yea 3 roosters and a stray cat claimed this though, so you might have some angry visitors’.

Stray cat and a gang of roosters?

Last year all I could seem to worry about was potentially losing my job. Even during 300% and 125% quota attaining quarters it’s all I thought about, a few times a week I would wake up in the middle of the night in a heart racing panic. All self-inflicted fear.

And now here I am, without that job, in the middle of nowhere Montana, and all I can seem to worry about currently is if I’m actually gonna to have to punch a rooster…

I couldn’t help but love the hilarity in it.

On this night, my heart would still race, but only with excitement as the next morning I’m going to wake up surrounded by mountains, attempt to make coffee over a bon fire, and then go ski Big Sky, a bucket list ski mountain.

 A few days later at a bar in a brewery in Whitefish Montana:

‘Wait, I searched for Lifestyle by Design and this one douche comes up’.

‘Who is that?’ I asked my new friend Jason.

‘He’s this guy that rents nice houses and cars and acts like he owns them, and tells people he can teach them how to be a successful entrepreneur…’ Jason, who I randomly met at The Great Northern Brewing Company, informs me of this while he was searching for my podcast and web series on YouTube.

‘What the fuck?’ I said back to him, in disgust.

Jason is in his mid twenties, an avid rock climber from Arkansas, and was also on a road trip adventure of his own. We spoke for a while before he asked me ‘what do you do?’ which lead to the above conversation.

I didn’t get the name of the guy from YouTube that he was talking about, because frankly, I didn’t even want to know it. I have no idea if he is really a hoax or not, but I could tell that that was the perception he gives off to guys like Jason.

It’s almost like we have a sense of smell online, and both desperation and bullshit REEK!

You know the smell, whenever you come across anyone online who is trying to teach you something that sounds way too good to be true, or trying to make it seem like their life is more glamorous than it probably is (think ‘view from my office today!’ pics). You can almost always smell the bullshit. And I do not want to be that guy. Even though the title of my podcast and web series (Lifestyle by Design – The Series) might place it amongst these smelly types, the content within it will not. I refuse.

So let me clear the air around me a bit so that it doesn’t smell of false entrepreneurial hopes.

My story isn’t all that glamorous, but it may spark some curiosity, which is my goal of the show. I document my entrepreneurial experience while also interviewing other entrepreneurs about their experiences, and as you can probably smell, it doesn’t make me much money. So a few months ago I had to pick up part time (non-glamorous) 1099 sales work to keep money coming in. Which is only part of the reason I was on a sheep farm in Montana, the main reason being the experience.

It’s funny because this was my biggest fear while starting this entrepreneurial pursuit, that I wouldn’t make enough money from my show and I would have to scrounge to pick up work. Thinking back, what a shitty thing to ask of a passion; “Not only must you inspire me and give me some of the best experiences of my life dear passion, but you must also provide for me a handsome living wage!”.

So, yes, my worst fear came true, I picked up a part time gig, but it actually looks like this:

Since I can do the part time job almost anywhere that there are potential clients (it has nothing to do with farming), I made a road trip out of it. While driving to Montana to catch the snow before the end of the season, I spent 4 days (Monday through Thursday) working through South Dakota and Montana from about 10am-3pm ish each day. I made around $2,500 in those four days, camped at sheep farm for a few nights, and took Friday off to ski Big Sky, not so bad. The following week I made beer with my uncle, spent time with my family in Whitefish that I haven’t seen in a while, mountain biked a little, had a picnic at Glacier National Park, and skied a few more times at Whitefish Resort (previously called Big Mountain). I worked far less that week and only brought in about $600.

I worked extra hard and smart while on the job so that I didn’t have to work long hours. The job itself is not glamorous at all and consists of a lot of cold calling (the details aren’t important here), but during this trip it allowed me to make some decent money while I had the time of my life. Money that I can invest in myself to help bring my other 2 business ideas to life (more on these in a few months).

Worst fear aren’t looking so bad after all.

What I’ve experienced from entrepreneurship so far -in my very brief encounter with it-.

The attempt at entrepreneurship is fun, it’s exciting and rewarding, but it’s also littered with self-doubt, failure, depression, and flat out confusion. But all of those valleys are learning experiences, same with the peaks.

What it’s really about is making the most out of the situation that you’ve created for yourself.

So while I would never tell you to quit your job to follow your passion, if you are in fear of losing your job like a friend of mine is, I would tell you what I told him ‘the worst part of it is the uncertainty you are experiencing now, once the bandaid has been ripped off, it’s not so bad’. And also, sometimes what you fear most turns out to be a blessing.

If you are unfulfilled at a job, I would tell you to invest in yourself a bit and try to learn how you might be able to start that idea of yours while at your job and while you still have income coming in. If you don’t have an idea, start thinking of some, the world is shifting towards a solo economy pretty quickly, better to be a bit prepared. I feel we’ve learned this backwards our whole lives, adults would ask us ‘what do you want to be when you are older’, instead of asking us ‘what do you want to create when you are older’. It should be the other way around, a job should be a nice back up to a failed creation. Find a need and figure out how to fix it, the world needs you.  

If you are just longing for an experience, or are simply bored, I would tell you to just walk until things get interesting. An adventure doesn’t have to be a huge ordeal, it really doesn’t take much to jump in your car, head across the country, buy a tent at a thrift store on the way, and have an experience you’ll remember forever. Or, you could just simply walk until things get interesting. Which is some of the best advice I’ve found, it’s  from the book ‘Vagabonding’ by Rolf Potts, and it’s meant to be taken literally. This advice bode well for me in many situations, one in particular was when I travelled to Brazil for a month. On one cloudy day while waiting for the swell to pick up, I walked… I walked until I saw a guy glide in from the sky, the fucking sky!, and land on the beach right before my very eyes, ‘well things just got interesting…’ I said out loud. 15 minutes later and with the sweatiest palms you’ve ever seen, I was hiking up a mountain to jump off of a cliff with a guy from Brazil I had just met and could only understand a few words from: ‘today, wind perfect, not tomorrow, must be today, safe, very safe, wind is peeeerfect my friend, tranquillo’.

To me, lifestyle design just means having the ability to go off on an adventure when you want, for a sufficient amount of time, and with no preconceived notions of what ‘adventure’ or ‘sufficient’ mean to you. It doesn’t mean a rich life of leisure, that doesn’t exist.

So even though my show is called Lifestyle by Design, you won’t be getting a webinar invite from me about a topic that I just thought of in order to have a webinar, I’d rather knock on doors to make money (which is what I’m doing now). I’m not trying to teach you anything, my knowledge is only as deep as my experiences, and I have not yet had enough experiences, so experiences are what I’m after.  You won’t see an ad from me on how you can do what I do, because frankly, I don’t know if it is the right path to take. I only started taking it because I felt certain that the lifestyle in the picture below, along with an unfulfilling 9 to 5, is how humans get the equivalent of a collapsed dorsal fin…

…Stay wild my friends.

Creator of 'Lifestyle by Design - The Series'. A Podcast and Webseries on how to bring ideas like yours to life.

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