About a month ago I hit a lull – we had just launched our on-demand tutoring platform and things were growing the way we had hoped. Great. The decisions we had made were smart, calculated, planned and organized. There was this degree of certainty that had put my mind at ease.

I started wondering why, if everything was moving as planned, I was feeling uninspired. Things were stable. I was comfortable. I hated it. I realized that GradeSlam was being conservative. Probably not conservative by most other people’s standards, but conservative by my incredibly ambitious plans for the company.

I took a couple days to myself to think things over – reflection and introspection usually help me understand the problems (something I’ve learnt from my father). Conversely, I never come up with solutions to the problems when I am thinking about them, the solutions hit you when you least expect them. Understanding the problem is the first step. Once I have identified it, it will consume me until a solution presents itself when you least expect it. It took a couple of weeks but that vision eventually presented itself to me. It required a profound amount of creativity, but was attainable.

I can’t talk about the solution (or the problem) at this point, however that will make for a great post in the next month or so. Instead I realized the elements that I absolutely needed to do to put me out of my comfort zone.

Put Pressure on your Allies

The people you are aligned with benefit from your success, or at least they should. The reality is that they might be comfortable too. A little kick in the rear will often wake them up and together you will push past a barrier. Figure out how a few of the companies/people you work with can all collaborate in an initiative that has an unknown outcome. If (when) it succeeds, everyone will be happy and you will be worth more.

Invest Money You Don’t Have

The number one excuse I hear from people as to why they can’t do something is money. Money isn’t real – it only seems like it is. If you are feeling comfortable, you aren’t leveraged enough. Think about what money you have access to, and what opportunities would exist if you had more. Now take those risks. Obviously, I’m not saying to be reckless, well actually I am. Be a little reckless, if it is successful the return will be 10x - if it fails you will be even more fire under you.

Break An Industry Norm

Each industry has some customs that everyone follows. These are the generally accepted practices, usually put in place for a good reason. Break one. Or rather, disrupt one. By doing so you create two possibilities, each one positive in its own respect. If it is successful you are hailed as a pioneer. If it fails, you just told everyone that you’ll don't give a f***. This will get you on some other people’s radars.

Call People Out

I sit in meetings almost every day with people (not in my company because I won’t allow it) who think they can talk their way around the truth. Usually I will let them say their piece, knowing inside that what they are saying needs to be taken with a grain of salt. The next time you are in that situation, call the person out. I’m not talking about being rude, but if you have doubts, have them prove their statement to you. It might not make you any new friends, but if you are right it will shine a light on your strong business acumen – and will give you a little rush.

This post Feeling Comfortable? Here are 4 Tricks Push You To The Next Level first appeared on GradeSlam's blog.


Philip Cutler (@pacutler) is the Founder & CEO of GradeSlam. He is also the the Executive Director of Laurus Summer Camp and City Councillor in Westmount, QC

photo cred: http://www.claytonmooney.com/