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I’m a singer-songwriter-pianist touring about 100 shows a year. In my ‘former life’ though, I worked for a big marketing company. It was a good job, but when I listened to my heart, it wasn’t quite fulfilled. I was a trained musician and realized I really wanted to pursue music as a career but the switch seemed overwhelming.

I’d been performing some of my songs at open-mic nights as a hobbyist for a few years ‘dreaming’ of a full time music career when I was slapped in the face by a big dose of reality. I visited a great aunt in an old folks home and she had Alzheimer’s and I wondered, ‘what if that’s me in 60 years’? It was very real and was the kick-in-the-pants that caused me to talk to my boss the next day.

Instead of immediately quitting, he offered to keep me on 3 days a week. I found that the more time I put into music the more results I got. So after a year my morbid curiosity left me asking the only big question left to ask: ‘what if I put all my time into this?’ and I quit my job cold turkey. It was tough slugging at first, and I ate an awful lot of canned tuna and not very many t-bone steaks to make ends meet!

As I reflect on some of the lessons learned I can come up with a few that I’d like to share. Ultimately now I find myself putting in a lot of ‘time’ each week doing something I love but it doesn’t feel like ‘work’ at all. The possibility for boundless happiness exists.

Ask yourself: what makes you happy?

I knew what made me the happiest: Music. I chased that.

Surround yourself with like-minded people

I found other people who were already working at music, and some who were also trying to make the switch like me. Being around them as my community was crucial.

Initiate, don’t procrastinate

I really didn’t know what I was doing nor did I know what I was getting into. But the main thing was I didn’t wait to have it ‘all figured out’ before I started. I knew some things I’d try would be failures and others would be successes. I also knew that I’d likely learn more from the failures.

Build a plan but be ready for half of it to change

I drafted a business plan of sorts – something that captured everything I knew. It was my road map and I watched as half of it changed before I got through it. I’ve found that to be a constant as years have passed: Plans often change. You gain new knowledge all the time and to not use it would be crazy.

Partnerships and collaborations

Find partners and collaborators you get along with. Two heads are often better than one. I’ve seen this work in both touring and co-writing


You’ll run into 20 people who tell you ‘no you can’t do this’ for every one person who says ‘yes you can’. Perseverance is key.

Keep a ‘good stuff’ folder

Starting and maintaining any independent business is tough and you run into a heap of roadblocks so some days are really hard. One thing I do is maintain a folder of ‘good stuff’ that I can flip through as a reminder of some of my accomplishments. I highly recommend this!

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Singer-songwriter-pianist Jeffery Michael Straker performs over 100 shows per year across Canada. He’s recorded for CBC radio’s ‘Canada Live’, had a music video chart in the top 10 on Much More Music Canada and in 2012 toured in Africa.

His tour stops range from intimate house concerts to club & theatre shows and include a recent sold-out concert with the full Regina Symphony Orchestra. The review following his orchestral debut read: “Straker was simply spectacular...clearly one of the province’s best cultural exports”. Canadian Musician Magazine has said, “Very much an artist to watch” while the Chicago Free Press has written, “Rufus Wainwright, as well as k.d. lang are among the Canadians making essential and beautiful music. Add the name Jeffery Straker to that list”.

Straker has recently launched his latest collection of songs called Vagabond (Oct 2012). The release has been met with critical acclaim with the Toronto Star giving it 4 (out of 4) stars and calling it “one of the most faultlessly conceived and meticulously executed albums in any genre to come out of Canada in a long time”. “Vagabond” debuted in the top 20 on the iTunes singer-songwriter charts.

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