Regrets, I've Had A Few...

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Very early on in my career, I went to meet a senior executive at one of the fastest growing entertainment companies in Asia.

At the time, I was a Marketing Executive in the Consumer Goods space and, while the work was interesting, I wanted to explore what else was out there, especially in this exciting new area that was taking Asia (I lived in Hong Kong at the time) by storm.

The meeting was, ostensibly, for me to discuss Marketing roles with the company, and explore whether there might be a fit for my skills and experience. But that wasn’t my real objective.

My real goal was to test the waters to see if I could make the switch into something completely different. I’d always been interested in creative endeavors and I really wanted to explore what I might be able to do on that side of the organization - whether it blended both business and creative or, if I dared to dream, was purely on the creative side.

The thing is, as I told myself at the time, I didn’t have any formal creative training, or experience. I was a business major, had business experience and credentials, and everything creative I’d ever done, was on my own time. Still, the goal gnawed at me, so I mustered up the courage and went to the meeting to see what I could find, to ask for my shot, if you will.

The meeting itself went positively. We had a great discussion, and the executive shared his vision of where the company was going and what he wanted to do. He shared with me what they were looking for in terms of values and objectives, and he was every bit the evangelist about their mission that I had been told he was.

After he shared the company’s story, he asked about my background and, specifically, what I wanted to do. This was my shot, my chance to say (and possibly do) what I really wanted. To tell him that while I had great business credentials (for a 21 year old), I could do so much more. That I wanted to try something entirely different, to be creative (in all its forms) and that I was willing to do what it took to make that shift.

But I didn’t.

Instead, I told him about my degree, my marketing qualifications, the impact I could make on the business side of things. But nothing about my creative goals, my creative ambitions, my desire for change.

I walked out of that meeting knowing I didn’t take my shot, that I didn’t do what I should’ve. I didn’t “ask for the order”.

Why? I had a plethora of reasons - some explicit in my head and others implicit. I was worried that I wasn’t a fit. That I didn’t have the credentials. That I might be laughed out of his office. But basically, I just didn’t have the confidence or self-belief to ask for it and then deal with the impact that any potential rejection might have on my ego and sense of self.

I know and believe we shouldn’t live with regrets, but I do regret that choice. (And I do recognize that it was clearly my choice. How he would’ve responded is anyone’s guess but it was my choice not to ask.)

To be clear, though, it’s not a regret because of what could have been - as it happens, things worked out fine for me. Rather, it’s a regret because, really, at that point in time, in that situation, I let myself down. I should have believed in myself way more and had the balls to at least try. I should have understood that if you don’t reach for what you define as the brass ring, you’re definitely not going to get it.

Of course, I was also all of 21, so I’ve learned to cut myself some slack. But I’ve also since taken away the learning that it’s not enough to dream up what we want, we need to do. We need to make the choice and take the chance. We need to ask for the order.

That’s not anyone else’s choice. It’s our own. We just need to stop making excuses.