Setting Challenges For Yourself

I’m someone who is very self-motivated.  That’s a double-edged sword because it means when I put my mind to something, then I’m persistent and relentless to the point of being considered stubborn at times.  On the other hand, I’m not really motivated well by other people or any kind of externality.

All the time growing up I would get people say to me, “You know Sean, if you just set your mind to doing X, you’d get Y in no time at all.”  I would hear what they were saying, politely nod and then go back to doing whatever the heck I wanted.

I remember this one time in particular when I was in Grade 10.  I went to a Catholic High School and my academic and personal guidance counsellor was one of the priests.  He was constantly badgering me about my general disinterest in most of my classes and the effort I put in.

I was one of those kids that didn’t have to study, could grab the textbook, read it in one sitting and ace an exam or do zero research and bang out a top shelf essay.  On the other hand, my attendance at school was a bit “meh” and homework or assignments were things that other people did on time.  I remember multiple instances where I’d calculate the score I’d get and how many days it could be late before my mark would fall below 80% – then I’d make sure I did it just in time to stay above that.

Not every class was like that.  I liked History, Economics, Latin and Accounting – I absolutely loved Accounting in high school, so random.  But even classes I enjoyed like Computers and English, I still did the absolute minimum and in those two classes, for example, I’d often just do my own thing instead of what class requirement was.

After a year and a half of this, my guidance counsellor had seen enough and decided he needed to bring my mother in so the three of us could talk about where things were at with me.  My mom had to take the day off work, “get dressed up” and make the hour-long trip (two buses and a subway) to get to the school for the meeting – she was not impressed.

The counsellor then explained everything to her: “Sean is very bright, but he seems to lack motivation.  We can see he’s not lazy, he just doesn’t seem particularly interested in doing anything more than the minimum unless he likes something.  You know, we can’t only do the things we enjoy doing.”

In his opinion, I lacked a challenge so I should accelerate my learning, take night school and summer school so that I could finish high school a year and a half earlier.  Then I could go on to University and do more challenging academic study.

He seemed pretty chuffed with himself.  My mother said to him, “You think he’s bored and your answer is to do more of the boring work?  Then you think it’s a good idea to graduate a 17-year-old boy so that he can go away to University with 19 year-olds who are legally allowed to drink and spend every waking hour partying.  You think that’s the answer?”

That conversation ended shortly thereafter and when I got home I was told over dinner that I needed to focus more and try harder so that the school would leave my mother alone.

The thing was, my guidance counsellor wasn’t too far off – I was bored and unwilling to challenge myself to do better work.  I just wasn’t interested.  I was smart enough to skate through with minimal effort, but it didn’t really interest me at all and my care factor was zero.

However, when I decide I’m going to challenge myself and actually commit to doing something, then I am usually very good at sticking with it.  Casual Marketer is an example of this – I made a decision in November/December that I was going to write daily emails for this business so that I could create content regularly.  I launched on February 1st and haven’t missed a single day having written and published over 200,000 words in that time.

My next challenge is going to start in July.  I’m going to challenge myself to work one hour per day on Casual Marketer aside from the daily emails and the time I spend writing the Monthly Newsletter.  To make that happen I may have to get up an hour earlier in the day or whatever, but if I can focus on putting in one extra work hour per day, that’s 30 hours per month of extra time for creating more value.  That’s not going to be time spent futzing around on Facebook or answering emails, it’s going to be time working on the business and creating new stuff.

What I’m talking about here is an actual challenge – doing something that isn’t easy and takes your out of your comfort zone.  Set the bar high enough that it will help you get an important and tangible outcome, but make sure that you keep it in reach so that you remain motivated to keep going when things get tough.

I’m probably going to have to get more specific about my challenge in July – it’s great to dedicate an hour, but maybe I need to be more specific about the outcomes I want to achieve.  I’ll work on that over the next couple of weeks and report back after I move house on June 20th.

What about you?  Do you set challenges for yourself?  When you do, are they achievable and do you stick to them?  Are you pushing yourself hard enough so that the outcomes are meaningful?

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