Dreamin’ Man

Have you ever wanted to get out of bed each day and do exactly what you wanted to do? When motivation is linked to your passion in life? Write a book? Take cooking classes? Study economics? Work as a musician?

It’s been one month after leaving my radio career to pursue a lifelong dream of songwriting and making music. And what a motivating month it has been …

I’ve done more to invest in myself the past thirty days than in the past 2 years! I’ve made industry contacts, met with musicians, played gigs, booked gigs, been in the studio recording a new album, booked future recording sessions, been hired as a session player, rehearsals, updated social media, written press releases, written MORE songs and recorded MORE demos! It’s been busy, but time well spent.

Have I made any money? Nope. But right now that’s okay as I knew I wouldn’t be making any anyways. I’m planting seeds for a future and making plans for the present.

Honestly, making this life decision has been a swift kick in the pants. There is nothing more motivating than knowing this is the new path you’ve chosen (especially at 45 years old!!). It’s been a very moving experience and has charged my soul to plow ahead.


I often think about the future during this process. Will I be successful? How will things turn out? But I always come back to what my wife recently told me : that success is in the doing. By simply writing that book, or taking that cooking class or studying economics or being a musician, you’re already a success.

Who knows what the future holds? Who knows where we’ll all be in one year, one month or even tomorrow? So, let’s enjoy today and be motivated to be what we want.

Thanks for reading. See you next time.

Walk On

Ever have a dream to do something with your life? To pursue a passion? To fulfill a lifelong fantasy?

Ever have doubts about it? Afraid of the unknown? Fear of giving up your established life as you know it? Scared of what people might say?


This is the first post on my blog Expecting to Fly, where I will chronicle my journey into pursuing a lifelong dream. It was a choice I made, a choice we all can make. Choices that will create the life we want. After all, it is your life to create.

My name is Craig Robertson. I am 45 years old. I live in Toronto. I have a house, a great marriage, many friends and a loving family. I live in a nice neighbourhood, with parks and walking trails and all the amenities you could need at your fingertips. Like most of us, I have bills to pay, a mortgage to worry about, groceries to buy, a car to pay for and home repairs to save up for.

I also had great job – a successful radio morning host broadcasting to the Greater Toronto Area. I got up in the morning, spun some great music, had a few laughs. I got to meet many famous musicians, interviewed hundreds of celebrities, got free concert tickets, free this, free that.

Yet, I wasn’t fulfilled. I always knew something was missing. Something that had lingered in the back of my mind for years.

So, I finally did something about it.

In early December, 2012 I quit my job. It took a lot of thought and debate and worry and conversation and fear and doubt and decision to do it. It wasn’t a ‘snap’ call. I thought about it the better part of twenty years. And when the time came to actually do it, I was scared senseless.

There are so many things to ponder – giving up an established career, a gap in your resume, the unknown of well, the unknown, and of course money. But a good friend told me “you’ll always find a way, things will work themselves out”. I guess I’ll find out.

You see, my lifelong dream was to pursue a songwriting career. I’d been writing songs since I was 13 years old and the dream to write songs professionally never left me. The dream was there in my twenties when I was going to radio school. The dream was alive in my thirties when I was fast-tracking my radio career. The dream was still there in my forties when I was established in a radio career. The dream never died. And I surely didn’t want it to die with me.


So here I am writing the first post on my blog called Expecting to Fly, my leap into a new life path. I hope it will inspire and shed some light. I hope you enjoy the journey.