“People may spend their whole lives climbing the ladder of success only to find, once they reach the top, that the ladder is leaning against the wrong wall.” — Thomas Merton

It’s Monday morning. Are you climbing the wrong ladder? Or worse – are you standing in your own way?

Last week I had the pleasure of speaking to a successful entrepreneur for whom I have great respect, after he kindly reached out to wish me well after my first year in business. He always tells it like it is and cuts to the chase which I love. He said, “good for you – you stepped away from a boring but stable corporate job – what will you do for the next five years now that you have overcome that obstacle?” I offered that I was looking over the summer to get smart about my focus over the next year and that I would love his advice as I respected his opinion and wisdom.

He laughed and reminded me that many of my colleagues at RIM (he was a BlackBerry business partner which is how we met) had many “words of wisdom” for him over the years. They took time and effort to tell him how to run his business more successfully at great length. Generally once they wrapped up the list of things that he should do, they immediately started complaining about how much they hated their job and their day to day life, but that they “had” to do things in their life a certain way. A personal mindset of limitation. But a complete lack of self awareness professionally seeing as they had never walked in his shoes to understand the challenges of entrepreneurship but were more than happy to educate him.

His advice to me was that I already did the hardest part – by taking the leap of faith in myself. I now needed to look inward. He had no advice. After 20 years of success at a number of diverse ventures he said he’d learned a few things but was undergoing the same desire to change and pivot. His answer was basically, “It’s hard. It’s hard for everyone. There is no silver bullet or right answer. So when you struggle know that everyone struggles in the same way if they are being honest. I don’t have the answer for you. No one has the answer for you.”

It was heartfelt, honest and true and he put himself out there. It made me feel better that even he, someone who I thought really had it figured out, found these sorts of questions challenging.

The one thing that I know to be true is that when you give of yourself without precondition or expectation you are headed in the right direction. Throw yourself out there 110%. Fully commit. If you fall flat on your face it’s okay. Anyone witness to this act of bravery will cheer (and not laugh). It’s the embarrassment (or perceived fear of failure) that keeps people chained to their jobs, or mind set, or way “it’s always been done”

There is no right or wrong way. Rather, it’s about doing things your way. It’s the only way really. You learn mostly to aim for the “right” answer and as you get older this mind frame get harder to shake. School reinforces this for 20 years and the workplace also attaches a lot of merit to the idea that there is a right answer. Plus you’ve been putting in time towards a direction. This is why taking the leap into doing anything different is so challenging. You are railing against in many ways what you have been taught to be true for decades. The over riding message is: there is a way, if I learn it or copy it, I too will find success and happiness. You set your ladder (likely) up against a wall and now you are climbing. It seems sacrilegious to admit that perhaps you are climbing up the wrong ladder (especially if you are fairly high up your climb).

For me the realization that I was on the wrong ladder took hold when I was absolutely certain I had no desire to get the “next” promotion at IBM. I was quite certain I’d dislike the next job more than my current one for all the reasons of the culture of bureaucracy and conformity that caused me to question whether I was on the right ladder in the first place. But it was hard because many people were impressed at the job and title and it seemed on paper like the “right” job.

But some early lessons stick out as transformative many years later. I had the great fortune to have Eric McCormick as a professor at the University of Waterloo. He taught me in a 3rd year English Literature class 20 years ago. He was a character who had office hours at 7:30am because according to him, those students who cared for his time would come no matter when his hours were, and if he was too accessible students would waste his precious time, and moreover he liked to run at 9am – so decision made. I think that he was getting exasperated with the credentialing of students at the University even back then, as he was a true creative writing fiction while he taught at the school.

He issued an assignment to my class where the use of any citations or footnotes would result from the paper being marked with a C being the best outcome. The class immediately revolted. Asking all kinds of questions to challenge this assignment’s merit. Increasingly agitated, he bellowed, “If at this juncture of your education you are so insecure about your ability to come up with an original idea that the thought of not relying on the work of others makes you nervous, you should immediately re-evaluate whether you belong at this institution!!” and that was that. Assignment issued. Per his conditions.

Once the paranoia of a well worn method to churn out a paper was dispensed with – it was awesome. I could just write whatever. No constraints. No bibliography. Just come up with some ideas and argue the point. Freeing. And he was right – in 3rd year for the love of god one should be able to think and say something intelligent and original.

I was reminded of this episode at UofW during my conversation with my entrepreneur friend. These wise folks have no advice. There is no right answer. There is only the effort and the creativity that you apply to the problem that you are trying to solve. Be interesting and memorable, dammit. The world is vanilla enough. No one will laugh at you, I can almost certainly promise you that. And you have a much greater chance of success if you start early, finish late and do something unique that makes you stand out from everyone else creeping toward the “right” answer.

Figure out if you are on the right ladder and then immediately get the hell out of your own way.

Written By Anna Foat