Growing up, there was one driving expectation my parents – like all other Traditionalists and Boomers at the time – placed on me: Go to university, graduate, and become a successful, well-paid professional. There was no discussion or consideration of not going to a post-secondary institution or of becoming a tradesman or of not making millions of dollars. Anything less than a well-paid professional (E.g. doctor, psychiatrist, lawyer, etc.) was simply not an option and would be considered “failure.”

I was given every opportunity to achieve those expectations and I truly wanted to be a lawyer when in high school but shifted to Political Science when I entered University because of my experiences on student government and my city’s Mayor’s Youth Advisory Council.

However, before I could do anything with that education, I fell into a retail career when I was offered – and accepted – a franchise of a retail store I was working part-time at since the age of 15 years old.

I was a failure. I did not achieve the academic or personal expectations my parents, and in turn, I placed on me.

Some 12 years later, I was married and had a son, which changed my perspective on entrepreneurship and the time required to run a successful business.  I walked away from the chain of stores I built and took a senior management position at a Big Box retail chain.

Within a year, I realized I was bored and needed more so I moved to another chain but focused on building their e-commerce sales as the Internet was becoming a powerful tool for businesses.

A few years later, I was convinced by one of the technology firms that I hired to build those e-commerce websites to take on a sales and marketing position with them. And so I was now a VP of Sales and Marketing for a technology firm.

32 Years Old, A Father, And Still Figuring It Out

I went from wanting to be lawyer, then a civil servant, to running my own retail chain. I moved from that to managing a Big Box retail chain to marketing an e-commerce technology platform.

By the age of 32 my career changed a few times and I still didn’t know what I was going be when I grew up.

Another few years passed, I was unexpectedly headhunted a customer experience consulting firm, thanks to my years building customer-facing businesses. A few years after that I was invited to join a marketing agency – that I had previously hired to do work for my firm – as an executive in charge of marketing technology solutions.

Some 10 years later I shifted again and joined a niche marketing start up here in Toronto – Sensei Marketing Inc. –   as Partner and CMO, where my experiences allowed me to co-author a marketing book and become a keynote speaker. That, in turn, led to an invitation to become of Professor of Marketing at Seneca College, where I teach a curriculum based on the book I wrote.

During this time, I’ve also managed to invest in a hospitality business in Canada’s East Coast where my partner and I run a 3-bedroom B ‘n B.

And finally, as of two years ago – due to the loss of my son to depression – I’m now also the Co-Founder and Managing Director of a national not-for-profit corporation focused on reducing the suicide rate among Canadian students.

50 Years Old And Still Figuring It Out

The point of me sharing my life’s story is to let students out there know that it’s OK to not have it all figured out and it’s OK to fail to meet the high expectations imposed on you by society, your parents or those you impose on yourself.

Setting high expectations is a practice we’re taught from an early age, and especially in school.

We’re expected to achieve high grade point averages as acceptance at universities has become amazingly competitive.

We’re expected to earn high marks while in university to compete for the best co-op jobs.

We’re expected to go on to post-graduate programs because a Bachelor of Arts isn’t enough when competing with the growing number of graduates.

We expect to earn six-figures upon graduating because the cost of housing is rising faster than ever before.

We’re expected to have thousands of followers on social media, always be connected, and share positivity, even when we’re not feeling particularly positive or our social ranking may drop.

It’s OK To Fail Expectations

Setting high expectations isn’t a bad thing; we often need high benchmarks to help motivate us and to keep us focused. The problem is that we’re often not taught to manage those expectations or taught how to deal with failing to achieve.  In fact, in our highly competitive society, we’re not allowed to fail or made to feel “it’s OK” if we don’t meet those high expectations. And that’s a problem.

So to you students I say: Take heed of my story. At 50 years, I’ve had a half dozen successful careers and I’m still figuring it out.  It’s OK to if you don’t meet initial expectations; failing to meet the benchmarks you or others may have set for you is an opportunity to find what’s truly right for you. You have an entire lifetime to experiment, grow, and do new things.

To you parents I say: Make it OK for your kids to fail. Teach them the value in failing. Allow them to fail.  Some of the greatest business and personal successes have come from failures. We learn from those and they challenge us and motivate us to do more if we’re not made to be afraid of failing.

Failure is not defined as “failing to meet expectations.” Each experience – achieving or failing to achieve expectations – is a step in our life’s journey, not the endpoint. If kids are not taught this valuable life lesson, we’ll continue to lose more kids to depression.