How To Get Work In The Field You Love!

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Baby Boomers to Millennials often ask me how to get work doing what they love.

First off, there has never been a magic bullet for me. My career has not been vertical. My accomplishments are not linear. More  lateral.  My wins zig. They zag. Even though I am a creative type, I think this will be the reality for more traditional careers too.

Big disruption is happening.  Jobs go, and industries are AWOL over night. Experts predict that by 2022, people will not hold a job for more than 5 years.

So that means people will have to adapt and focus in on what they want their work life to be.


It means most people will have to think more like self employed people. So here are a few tips for baby boomers and millennials who are approaching work these days.


Take a job that is in or close to the field you want to be in, even if its not the ideal position.  This is true for millennial or baby boomer. We often take many B jobs in sectors we hate. And my experience is you will work as hard at a job at you despise, as you like.

So get into the area where you want to be.  Even at the bottom you can learn something  People skills, team building and endurance.

Believe me endurance is needed even in a dream job.

When I was in radio I wrote copy. I didn’t want to do it. I wanted to be a super star DJ in Belleville Ontario.  but not only did I meet my best friend,  I learned how to market shows because of that job.

I started teaching at Second City, for cash. But I quickly learned how to communicate what I knew. And now I love teaching. All those years of conveying improvisation concepts turned into this speaking career I have, today.

Some questions I ask myself are:

1. Will there be hands on experience in my field in this experience?

2. Will this position me to be around people doing what I want to do?

3.Can I be self-supporting through my own contributions? (Aka get out of your parents basement. Or    your kids basement.) Some jobs just get you some cash to pay your way and that is fine.

If you take the job:

1.) Get in the middle of things.  People want to work with people who are all in. People who do their work on time, do what they are being paid for and people who don’t act like they are on the way to somewhere else.

2.) Assume nothing. Don’t wait to be discovered. No Prince is going to come and kiss you and make you a super star in the office. No one knows your secret dreams. Your goals.  I find that no one is thinking of me as much as I think about me.   So keep looking for opportunities to learn and contribute.

This is what I know.

Experience is a great teacher. Malcolm Gladwell said in his wonderful book, Outliers,  you need to log  your 10,000 hours to be a professional.

You need to put in the time. You need to bomb, to stink, to smell up the place, cry, forget what you knew and soar and then bomb again before you get your wings. 

So keep the job and on the side keep refining your passions so that if and when you do quit you are moving toward something better.


Ask People For Help ( Especially Those Ones You Make You Jealous)

Whether you want a job, or want to move up, you need help at times. Ask people for help. Especially ask people ( almost jealous of) for help. I used to ask people who were in the same boat as me. Don’t do that.  ( Refer to Blog on Asking For What You Want)

How to Ask for Help:

Tip # 1. Ask a person something they can say yes to . People are super busy.  One approach is this,  “I want to work at _______.  Can you give me one tip I could apply to getting that work, right here, right now?”

And let me tell you one other thing:  Learn everything you can about them before you meet.  Go to the person’s site and look up their credentials.

Be curious to what they have to offer and listen to what they say.

And thank them.  Not with a text.

There is a lot of power in a thank you note.

I remember every thank you note.

Then ACTUALLY do what they said to do. Try at least one thing. What is the point of ignoring people’s advice?  Really listen. Because, if you hear something more than once take heed.

I have a rule of thumb. If I hear the same message from 3 different people I take it a sign to pay attention.

Case in point: It was right after 911. I was doing comedy but there was no money and my teaching had dried up. And people ( more than 3) kept suggesting I turn my comedy act and improv skills into a keynote speech and I kept trying to get back to where I once once. “I don’t want to do that.”

But after about the 20th person in a row said it me ( and an unexpected tax bill came in the mail)

“Lets give it a try.”

Guess what? I discovered an income steam, I not only loved, those gigs helped fund my vision projects.

So lastly is this. Applying for work that you love is not a one time deal.

There is a gap between what you want to do, and what is being offered.

Instead of looking at the gap as negative, think of it as a time to explore what you need to do to close the gap.

The gap is an exciting time. Its where the learning and leaning in is.. It feels uncertain and unsteady but its where the pulse of life lies.

Deborah Kimmett is a motivator, comic and keynote speaker.  She speaks and trains organizations all over North America on The Creative Power of Disruption. And  How Storytelling Can Help Your Leadership Skills. She appears regularly on CBC Debaters, and Winnipeg Comedy Festival. Get inspired and contact Aysun @ to book her for your next event.

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