Do you enjoy standing on the edge of a cliff, peering over the edge, pushing your fear aside and jumping? Just when a parachute helps you land safely, even at the last moment, you look up the mountain side and know what must be done.

Entrepreneurship is perpetual cliff jumping. Once you’ve done it the first time, you must do it over and over again. A smart entrepreneur jumps with a parachute, and only pulls the string at the moment its needed, and not a moment too soon.

I am a newly minted perpetual cliff jumper, also known as entrepreneur. I still laugh when I think about the rush it was for me when I took my first cliff jump, landed, and then got frightened at the prospect that I had to do it again, except next time the requirement was to wait a wee bit longer before pulling the ripcord.

How I got to this point

All my life I was raised to “be your own man“. Those are the exact words that were oft slipped to me by my late Grandpa Mac. He was a wise man, a wisecrack to some, and a cliff jumper at heart.

Sitting around the dinner table as a kid with Grandpa Mac meant listening to excited conversations about politics and the economy, with a few risque comments intermingled. It was common for him to challenge others to a healthy debate.

What I learned the most from him was to truly, be my own man. He was well versed in many things, from science and technology to fine art and photo journalism. His background as an early photo journalist in the 1930s and 40s always impressed me, and I lived vicariously as a kid in his history.

By being your own person you learn to be driven. What drives you might be different than what drives me. Being driven by something is key. Key to a life long pursuit of an array of things that may, or may not, bring you ultimate happiness.

Curiosity may have killed the cat, but it never killed me

I am driven by curiosity. In fact I believe so strongly in it that I put it on one revision of my resume. During an interview process, one of the interviewers, the VP of Marketing for an innovative technology company told me that my statement, driven by curiosity, be your own man, and putting it in my resume caught his attention. While I didn’t get the job, what I learned from that experience is that by being myself, listening to the inner self, it pays dividends, and gets noticed.

Having a curious nature is natural in children and youth. Society squashes this through various means, and I know a few others have captured this well through their writing. By nature I am an optimist. Because of this, I have hope. The hope that society, locally, nationally, and internationally can change this.

A curious society is one that involves some more dreaming, more art making, more productivity. Sitting as a cog and being complacent isn’t an idea of flourishing. Think of a vine plant. In my garden recently some of the pole bean vines began growing together because I neglected to put in a proper channel, simple mesh nets. After putting in the mesh net, I had to pick up the vines and separate them, albeit carefully, to put them back on to the right path and climbing up the mesh net. A week later and they are grasping firm, climbing like crazy, andflourishing.

Where I am headed

In the midst of a great transition, I knew I needed to write this lengthy post. If even not only for me, to look back and remind myself why I am doing, what I am doing.

Leaving full time employment to develop and grow a business that you create, bootstraps and all, isn’t the easyroute. But in my opinion, might just be the best route. From the past two years of moonlighting I’ve learned that anything worth pursuing must at least have your passion behind it. The passion forces you to learn just enough about business and the things that aren’t necessarily your forte, so that it will survive, and flourish.

On goes my journey to full time develop and grow my business, Keenpath, an inbound marketing and social media marketing company. What started out as a blog three years ago has grown into a company. My first clients got some free advice and free work for the taking, only because I was testing the market. Then they began turning in to paying customers. Through this I learned that my skills, having a knack for understanding how the web, technology and tools like social media work to help business do better business and ultimately drives sales, lead me to a critical point. I could continue milling along doing something that is profitable, yet, at least for me, at the time was losing meaning, or I could jump the cliff, and work hard, sweat, bleed and have victories doing something that felt right.

Being driven by curiosity, and being my own man, has gotten me to this point. Where I am headed from here is only a hop skip and jump away, and you better believe I will be working on my hopping skipping and jumping, while jumping those cliffs, sometimes on a daily basis.

Guest post by Brian Logsdon (author bio at end of post)

What do you want?

Have you ever had that thought? Hmmm. What do I want? Broad question but let me give you the favorite answer – survey says: Ding! Happiness! 97% said they just wanted to be happy. The other three percent wanted to be rich because they thought that would buy happiness….

What makes us happy? What do we want that would make us happy? Something from the world? Nah – that all wears out eventually – planned obsolescence, perhaps, so that we will actually quit looking for “stuff” and “get it”- the clue, the answer, the “One Thing” that Curly was talking about in City Slickers – the thing that we each have to figure out for ourselves. But once again, let’s go to the Board: “What One Thing do we want to make us happy?”– Survey says – Ding: A Great Relationship! Yes, we all want a great relationship with our world. That might include a certain someone in our world, but even then, we still want to be in a great relationship with our world, don’t we?

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Having the courage to step to the plate will take you far. The sky is the limit where you can go. But what if you are having a hard time mustering up the strength to step to the plate?

I will never forget it. As a kid I grew up skiing, and then in my teenage years decided to give snowboarding a shot.  I had some experienced snowboarder friends and told them about my interest. Of course they encouraged me, gave me all the tips on what gear to get and we arranged a time to head up to the mountain and they’d teach me.

We got up to the mountain, and I asked Joe what run we’d be trying out first. Mind you, I thought he’d say the bunny hill, or the beginner slope. Nope. I guessed wrong. He said the first run of the day was a black diamond. Now I had done a black diamond on skis, but translating that in to a snowboard is a wee bit different. I was sweating a bit, and thought well, I have skateboarded for a while so I should be able to do this, no problem.

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