Unconventional Freedom

By November 21, 2014blog

Freedom-SkydiveIf I had to pick two of my favorite words they’d be Unconventional & Freedom. I’ve been told my whole life that I see things differently than what’s conventionally done. At times it’s gotten me into trouble because I tend to question everything. But, overall I’m really happy with the results. I feel like I’ve been able to live a life I dreamed. A life with great freedom.

The key for me is that it has nothing to do with what others around me have dreamed. I’m not happy because I have money, live in a cool place or because I own fancy things. I’m happy because I’ve gotten to live my life on MY own unique terms. I became an entrepreneur not to get rich but to feel the freedom of creating things that could be of real value to my customers. To feel the freedom of creating an organization in my own unique way. To have the flexibility to vacation when I wanted (or not in the early days).

Growing up, the conventional wisdom was to follow the rules in school, go to a good college, and get a job/profession that could pay the most. Then it was get married, buy a house, start a family, and work to retire one day. It all seemed rather boring and pressure filled with expectations that didn’t seem to inspire me. Each time I tried to follow the conventional path, I lost energy and felt more lost than before. On the flip side, each time I did what felt uniquely right for me, I gained energy and felt inspired. I call that unconventional freedom.

I also found that in business when I did the things no one else was doing, I had more success (and it was a lot more fun for me). And when I did things because I thought I should, they didn’t turn out as well.

An example of this was when we were deciding on what to do for holiday cards for our clients. In the past we sent out thousands of relatively generic “Happy Holidays” cards “from all of us to you.” When my marketing manager, Cindy, came to talk details about that season’s cards, I said “I want to puke, these cards are so predictable and boring. What can we do different?” She came back with an amazing idea to do a company cookbook, with each co-worker who wanted to could cook their favorite dish that we’d photograph at a potluck lunch and then share those pictures and the recipes in a pamphlet-like holiday cookbook. We said, why not, wouldn’t cost us that much more, and we’ll have fun with it. Well, it was a BIG hit with our customers AND we all had a lot of fun doing it. I’m still reminded of it as a half a dozen or more companies I know are doing their own unique versions of company cookbook holiday cards!

cookbook cover Click to see 2006 RegOnline Cookbook PDF


  • Gerald K Flagg says:

    Except for very common but limiting constraints, I think most people start out being unconventional because they don’t know what the word means.

    Just watch the devopment of your own young daughters.

    The the constraints I referred to are economic
    constraints, Marrige constraints, job constraints, and other interpersonal constraints..

    Having. awonderful spouse and family as you mature is a great enabler toward being unconventional. But so is having an ongoing education and earning your own way.

    Finally an important ingredient for being unconventional is being given the right to fail in even the smallest choices because you usually learn from them because you have only yourself to blame.

    Ending where I started I think every one starts being unconventional but by imitating what they experience about them they offen become more conventional unless first given the right to choose and fail.

    One then quickly learns that by far most failures are really not bad at all, are quickly traversed, and are usually not quickly repeated.

    I didn’t get my 36 merit badges when only 21 were required to become an Eagle Scout by always passing the badge requirements on my first or even second tries. I learned such failures were an important set of experiences toward achieving the unconventional result of becoming an Eagle Scout. (One out of 100,000 starting scouts did/do so). And I was somewhat successful in passing this fun quest onto my ubsequent Boy Scout troops I ran, pledge class I supervised in college, and may be even to most of our kids.

    As always. if you want to know what I really think, just ask me.

    • Bill Flagg says:

      Thanks Dad, you bring up a great point that taking an unconventional path can mean there’s more failures along the way. Those who succeed tend to fail more than those that don’t. I’ve bumped into plenty of walls along the way, but have felt it was well worth it.

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