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Choosing Safe and Easy or Exciting and Difficult?

Posted by on Aug 27, 2013 | 5 Comments

My life came to a small crossroad over the last two weeks. Our three children went back to school after a too-long summer break (I pretended to be a stay-at-home-dad for a few months.) That brought me to a choice- do I take a full-time job at the company I’ve been working for since January, or do I focus on writing, starting a running class, and doing freelance social media consulting?

It’s a classic “traditional” versus “creative” career choice. It’s a choice many of us will face at least once in our lives. We can take the safer, more predictable traditional route, or we can throw caution to the wind and take the more adventurous creative route.

The smartest thing to do would be to do both. You know, the “don’t quit your day job” thing. I could work the traditional job for forty hours a week, then work the creative shit before and after work and a little on the weekends.

Unfortunately I’m a little bitch when t comes to creativity. I tried the “do both” route from January to about May. My writing during that time, quite frankly, sucked. In fact, it’s still nowhere as good as I’d like. The regular job robbed me of the time for introspection needed to mentally compose ideas. Unlike more talented writing friends, my thoughts don’t just flow like diarrhea during a rotovirus outbreak. I need time, damn it!

I weighed the pros and cons of each:

Pros of the traditional job:

  • Predictable hours, set schedule
  • Steady income
  • Health benefits, retirement plan, paid vacation
  • Excellent opportunity to move up the corporate ladder
  • Relatively easy work, can mentally “coast”
  • Be part of a team of pretty cool cats

Cons of traditional job:

  • Very little challenge
  • Unspectacular pay scale, doesn’t get too much better with advancement
  • Would involve working in a retail environment
  • Would cut into my mma training/ exercise routine
  • Getting kids to and from school will become a challenge
  • No schedule flexibility
  • Feel like a cog in a giant machine

Pros of creative job:

  • Excellent creative outlet and accompanying fulflment
  • Opportunity to help people on a personal level
  • Almost limitless flexibility to do as I please
  • No boss, ergo no busy work
  • No real limit to income potential
  • More time with Shelly and the kids
  • Location-independent

Cons of creative job

  • Lack of “guaranteed” income, benefits, or vacation
  • Greater risk
  • Less interaction with people
  • More difficult work
  • High cost for failure

After making the lists, the decision was obvious. I have to take the creative route.

It’s the same choice I made when Shelly and I decided to leave teaching to travel the country in an RV, and it led to an amazing adventure. To date, I’ve never regretted taking the unconventional route.

How about you? Have you ever been in a similar position? What was the outcome? If you haven’t been in a similar position, what would you do if you were?

Tell us in the comments section!


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  1. Barefoot TJ
    August 28, 2013

    When I was single, in my 20s, many years ago (ah-hem), I worked in a run of the mill office job for seven years. The pay supported me, it had good benefits, and I was secure in knowing I would “always” have a job there. I was comfortable.

    Then I got the opportunity to work at a major airline in IT, my passion. The money would be so much better, the benefits even greater, and the hours would be tremendous…if I wanted it. The job would be challenging. I would have to learn A LOT, which I love. Ultimately, I would be responsible for keeping asses in the air, THE major goal of every airline. A bit intimidating to say the least.

    But I was young, on my own, and I was scared of giving up a comfy job. I had never been responsible for anything that important before, and I didn’t want to find my ass out on the streets if I couldn’t cut the mustard, but I also knew I was really smart.

    I decided to get over my fears and go for it.

    That decision led me to a wonderful life, with a wonderful husband (met him at the new job) and two great kids, not to mention the confidence that came knowing I could do a job like that and do it well.

    I definitely made the right decision.

    Good luck in your decisions too, Jason & Shelly!

  2. Damien Tougas
    August 27, 2013

    One thing you have going for you in this situation is that you currently are not sitting comfortably in a safe/easy job – you already made the leap once. That makes the decision a lot easier, as you probably don’t feel you have as much to lose.

    For people who are currently stuck in the safe/easy/cog job, jumping ship for the creative/unpredictable can be a much tougher leap.

    • Jason
      August 27, 2013

      This is true. The risk/reward assessment is far different than the first time I took a similar leap. The new potential “traditional” job doesn’t have nearly as many perks as teaching did, which also makes it that much less desirable.

      The decision is a lot like taking the jump to ultras for a long-time 5k runner.

  3. Instant Law Of Attraction Success Review
    August 27, 2013

    Touche. Sound arguments. Keep up the good spirit.

  4. Stacey Lynn
    August 27, 2013

    You took the only sane route. The other would have left you frustrated, bitter and unpleasant. Your kids don’t need to grow up with that.