Last Sunday night, my daughter was moaning and rocking back and forth in her chair, wrestling with a question staring back at her from the computer screen. ‘What is the greatest challenge you’ve faced in your life?’, the college application pointedly inquired. As her Dad, I had some ideas. But her? She was stumped.
Looking at that question, I was torn between being terrified that I’d sheltered her from character-defining trials and grateful that I’d been able to provide her with a fairly carefree childhood. We ultimately uncovered something real and meaningful for her to write about, but in a world of possible obstacles and adversity it was clear that she has been living a very privileged life. That acknowledgement has provoked some real reflection for me too.
For years I’ve told myself a story. It starts with ‘no one ever handing me anything’ and ends with me in the position I am today. I didn’t come from a notable family, I never asked my parents for anything after I got married at the age of twenty-two. The opportunities that I’ve experienced and taken advantage of to bring me to today were a result of hustle, or something like that. When I graduated from college I started a company. As a young married family with one kid, and another on the way, we scraped by on $1,000 a month while we tried to get this new business off the ground. Taking that risk and coming out better on the other side laid the groundwork for all the other professional risks I’ve taken since. And look at where I am now.
I’ve revisited that narrative a lot over recent years and months, and the more I do so the more I realise that there are holes in that story that deserve acknowledgement.
I was raised in an upper middle class family. I never wanted for food or much of anything. My family owned a boat. The only jobs I worked as a kid were given to me by family or friends of family. And they paid me much better than my friends working summer jobs in fast food or at the Motel 6. I worked full time through undergrad and was able – with my parents’ help with tuition – to graduate with a degree from a well-regarded university with no student debt. When I married, we got a couple of old hand-me-down cars from our parents. And when I left a cushy job to go start a new company right out of school, my income was reduced to just $1,000 a month, so my parents offered to cover my rent for that first year. I could not have taken those risks or reaped the subsequent rewards had it not been for my family’s financial support.
So, the story that I’ve been telling myself all these years has big gaping holes that need filling. It has safety nets that require recognition, and privilege that deserves acknowledgement.
For those of us who are firmly convinced that anyone can do anything by working hard and pulling themselves up by the bootstraps, we need to recognise that most of us had additional hands helping us do the pulling, while many others had to fight hands that actively pushed them back down. We had resources avail- able to us that may not be available to those upon whom we heap our pearls of wisdom. We may, in fact, just happen to have been born into more favourable circumstances than those who we hope can learn from the path we’ve trodden.
This imbalance deserves to be countered. But before we start with the grandstanding, it’s a worthwhile experience to embark on some soul-searching. In acknowledging the privilege many of us have had, we can fill the holes in our own stories and move forward with a more honest, insightful, and impactful understanding than the conventional wisdom that anyone anywhere can achieve anything by just 'following their dreams'.
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