How My Father’s Letter Changed My Life

Four years ago, I found myself struggling with the toughest career decision of my life. I was trying to choose between two very different options.

One was to stay in my corporate job, which provided lots of reliable income and benefits, but it wasn’t work I was unusually excited about doing.

The other option was to become a full-time writer and speaker, something I was truly passionate about, but that provided no long-term financial security and no steady salary.

I figure you’re never too old to benefit from someone older and wiser. So I wrote my then 80-year-old father a letter and asked him what I should do.

But instead of just giving me advice, he shared a story about himself as a young boy that I’d never heard before. His letter said:

“Son, when I was five or six years old I knew exactly what I wanted to do when I grew up. I wanted to be a singer – yeah a singer – like Bing Crosby, Frank Sinatra, or Tony Bennett. My mother always had the radio on listening to all the popular music of the day, and I listened. And I just knew that’s what I wanted to do.

By the time I started first grade I knew all the popular songs – words and music by heart.

By the second or third week of school, the teacher asked if anyone in the class had some talent like dancing or singing or doing magic tricks or things like that.

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Well, I put up my hand and said I could sing. So she asked if I would sing a song for the class. Despite the fact that I’d never sung in front of anyone except my mother, I said yes.

I picked my favourite song, and I did it. I sang the whole song – all the right words and melody. I still remember the song. It was I Don’t Want To Set The World on Fire by the Ink Spots.

When I was done, the teacher and students applauded. And that’s when I was certain, that’s what I was destined to do with my life.

Unfortunately, that turned out to not only be the first time I ever sang in front of an audience, it also turned out to be last time I ever sang in front of an audience. Life got in the way. But it really remained my dream for the rest of my life.

I just never had the courage to pursue it. That was 75 years ago, and there’s not a month that goes by that I don’t regret it. One day, son, you’ll wake up and be 80 years old like me, and it’ll be too late.”

And as if that story by itself wasn’t enough to motivate me, my father closed the letter with these words that literally took my breath away and changed my life.

He said: “I’d love to see you pursue your dream. But that doesn’t mean in your lifetime, son – that means in mine. Love, Dad”

Those words hit me like an unexpected kick in the head. Everything seemed to stop. I read his words again. (“Did he say what I think he just said?”). Yes, he did.

My father had laid down the gauntlet in front of me and challenged me to pick up. Not sometime in the future, many years down the road. But right now.

More importantly, my dream was no longer just my dream. It was now my father’s dream, too. At this point, he’ll probably never achieve his dream of being a professional singer. But through me, if I have the courage to go through with it, he can enjoy the closure he never had with his own dream.

I hope you get something out of my father’s letter, too. Many of us harbour a secret dream we’re too afraid to pursue. And as long as we are the only one we’re disappointing, I suppose that might be okay.

But we all probably have someone in our lives we care about who also wants to see us pursue our dreams. That might be a parent, sibling, spouse, friend, co-worker, or child.

Whoever that is for you, if you won’t pursue your dream for your own sake, do it for them. You’ll make two people happy in the process.

By the way, two days after reading my father’s letter, I walked into my office and resigned from my 20-year career to pursue my dream. And it’s been the best decision I have ever made.

Thanks, Dad.