Act Two: From Store Owner to English Teacher

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Rebecca Stone
Editor in Chief of Female Investor Magazine Female Investor Magazine is dedicated to female investors success | #1 Source For Female Investors

In this series, we profile real women who have made later-in-life career changes. In Act 2, women share what they’ve learned from recent career reinventions.

WHO: Debbie Dalen, 55

WHERE: Calgary, AB

WHAT I DID BEFORE: Store owner, Pretty Little Things

“In 2008, I was working in the non-profit sector when I decided to open the store. It was something I’d always wanted to do. From the second I left non-profit to opening the doors took six months: I figured out the name, got a business license, got the merchandise, got the spot, and opened my store. All in six months.

It was a vintage clothing and housewares store called Pretty Little Things.”

WHAT I DO NOW: High school English teacher

“After running the store for about six years, I realized if I wanted to keep the business going, I needed to go big — as in launch a website and find a larger location. I found a bigger spot. But I was a single parent, so needed to think about financial stability and low risk, and I wasn’t sure (continuing with the store) was it.

I was just feeling sick about it one night, and woke up the next morning and thought, ‘Oh my gosh, I’m closing.’ And it felt like the right thing to do.

At the time, I was about to turn 50. I thought, ‘What is my long-term plan here?’ I hadn’t been losing money with the store but hadn’t been making enough to save for retirement.”


“I started looking at the core of what matters to me, plus what could provide the most stability. What did I see myself doing in what is likely the last iteration of my career? I had a master’s in English and a teaching certification from 30 years ago. So, I started the process of sending in all my credentials (to the ministry of education). It took two years.

It was a lot of navigating the system. And I just wouldn’t stop, I wouldn’t take no for an answer. Throughout this process, I told my advisor I wanted to teach high school English. She said, ‘You’re not going to get high school, most student teachers get junior high.’ So, I said, ‘Okay, thank you,’ and thought, ‘Nope, I’m not doing that.’

I found a high school teacher in the Catholic system and asked my advisor if I could do my practicum with her. She said no. Everything was no! I kept thinking, ‘I’m 54 now and I just don’t have time for all these No answers.’

So, I kept at it and got a practicum with that teacher, and it was amazing. I worked with great teachers. I was worried they wouldn’t accept me because I was older and a brand-new teacher. But actually, they looked at my life and work experiences, and treated me like a colleague.

I finished my practicum in May. Everyone told me I wouldn’t get hired in a high school; I got hired the very next school year. I’m now in my second year of teaching Grade 12 diploma courses.”


“I just went in without fear, and it surprised me how seamless the transition was for me.”


“Nothing. Maybe I’d have started sooner, but I’m choosing not to look at it that way. I could think, ‘If only I’d started this 10 years ago, I’d have 10 years’ experience under my belt.’ But nothing good can come from that thinking.”


“One of the best pieces of advice I got is, find people who are doing what they love. Go and talk to those people. Ask them questions about their work: What do they love about it, what works for them, what have let go of.

Talk to people you admire. Because you might find there’s something those people are doing you never even thought about.

And write stuff down — I think that’s huge. Just write stuff down every morning, or always keep a notebook with you and start noticing the things you love or really appeal to you. Start pulling all that together, and you might find you’re creating your own success story.”

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