When In Doubt, Trust Yourself To Do Hard Things And Take That Leap

Last week was a big one for my family.

My oldest son Lachlan graduated college and my youngest son Matthew graduated high school. Matt’s graduation was all the more special given that of the four graduations in our family over the last 12 months (another from high school and my PhD), his was the only one that was done in person.

Matt’s graduation was also very poignant for me given the huge disruption he’s had to navigate during his high school years. In particular, attending four high schools across three continents (with three separate curriculums) over the span of 14 months due to relocations with my husband’s (former) employer. Clearly not a recommendation in any ‘how to raise a teen’ handbook.

After relocating to Singapore from Australia, Matt pleaded with my husband and me to let him move 10,000 miles across the world to attend a military-style boarding school in California. Despite our reservations, we decided to trust that, while only 15, he had sufficient self-awareness to know what he needed to thrive – to develop his strengths and pursue his passions (and that it was not in the hyper academically-focused educational environment of Singapore.)

The hot August day I dropped him off Matt at his new school was a tough one on my heartstrings. As my was a fiercely independent youngest child waved me goodbye, I fought back tears until I was out of sight, then began my 10,000 trek back to Singapore.

The youthful wings he spread three year ago have only grown stronger and broader. As our family sprung to our feet to cheer wildly, I knew the decision to support him to fly so far, so young, had been the right one. Even despite the pandemic that left him semi-homeless when his school abruptly closed in March 2020 and Singapore close its borders to non-residents (including children of expats.)

Of course, our family situation is unique. Yet my reason for writing this column is because every one of us will arrive at decision points along our career, leadership and life journey that call upon us to do hard things; to trust that we have a larger capacity for rising to life’s challenges (and heart-tugging moments) than we may have given ourselves credit for.

Learning to ‘trust our wings’ can not only spare ourselves needless suffering and stress, but will embolden us to take the leap of faith in ourselves (and others) in those moments when it matters most. (If you haven’t had one lately, it’s coming.)

Psychologist William James once said, “Most people live in a highly restricted circle of their full potential.” It’s my hypothesis that the underlying reason for living smaller lives than we are capable of living is that we simply fear we lack what it takes to do what inspires us most deeply and blossom into the person (and leader) we have it within us to become.

In my work around the world, I often encounter people (including those in senior leadership roles) who tell me how they wish they were braver, more confident, and self-assured.

I get it. Me too.

Yet only when we dare to trust ourselves, not our doubts, can we discover how much we can actually do and build our capacity to do even more. Or to use the wings analogy, to discover the strength of our wings and how far they can carry us.

The last 12+ months have taught us that we human beings are more resilient and adaptable than we may often realize. Not only that, but that those situations that test us the most also teach us the most, building our ‘muscles for life’ to bounce forward from setbacks – better and braver – and find opportunity in the midst of our adversity.

Last month Matt’s application to attend the US Naval Academy was denied. I couldn’t help but feel disappointed for him. Yet if one thing is certain, wherever life takes him, he will succeed and make his mark. Not because things will always go to plan, but because he will always make a plan B (or C or D) and because, as his school President, Major General Bartell, told me in references to his leadership over this last incredibly challenging year, Matt will always find a way to make any situation better for himself and those around him. ‘People naturally follow Matt,’ he said.

Sure I’m a proud parent and clearly biased (thank you for indulging me.) But in today’s culture of fear and risk aversion, the world and workplaces desperately need more leaders like Matt – men and women, young and not-so-young – with the courage to trust their strengths and use them to serve others. It needs more people from every background willing to step up and do hard things, even when it requires breaking ranks with the comfortable and familiar.

Whatever challenge you are facing now, ask yourself this question:

What would you do right now if you trusted yourself that, whatever happens, you can handle it?

Just for today, decide to trust in your capacity to do hard things and choose self-trust over self-doubt and courage over comfort.

Then tomorrow, do the same.

Your wings are stronger than you know and will take you further than you think.


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