Shedoesthecity turned 10 this November, and to mark the occasion, we’ve connected with contributors past and present to find out what they’ve been up to lately, how their careers have evolved, and what they are looking forward to in the future. 

Karen Cleveland is the Senior Manager of Communications at the CAMH Foundation. She has contributed to Huffington Post Canada, The Kit, National Post, FASHION and more.

For several of Shedoesthecity’s early years, Karen contributed a weekly “Etiquette School” column, where she addressed everyday manner quandaries with humour and tact. Beyond sharing her engaging writing, Karen reminded us all how to behave nicely. We’ve enjoyed following her illustrious career ever since. 

SDTC: How did your career begin? And where are you now?

KC: My career started in not-for-profit (shout out to Rethink Breast Cancer!) and brought me back to it, where I am now at the CAMH Foundation. In between, I worked for some great agencies, led the marketing/communications department at St. Joseph Media, started a travel magazine with some friends, freelanced and did a few more things.

How did writing help steer your path?

Writing stories that I wanted to write has always been, and continues to be, my fuel. It fills me up. Writing for other people – be it a client, a boss or anyone – takes a different kind of energy, and you need to find ways to replenish that energy. For me, that’s more (albeit different) writing. When I look back at my editorial writing in the past ten years, it brings me back to where I was at that time and always makes me nostalgic.

When you reflect on the past ten years, what are the biggest career lessons that come to mind?

I have a theory that life serves you up the same lessons over and over again until we get it. I needed to learn the lesson that professionally, your gut will never serve you wrong. It’s so easy to get distracted by shiny things that are louder, but your gut will never steer you wrong.

What has been a more recent discovery, a life lesson that has really impacted you?

Having cancer threw me for a spiral in a way that I never could have expected. It prompted me to take stock in what was going on in my life and get really quiet about what was serving me and what was okay to let go of.

In your opinion, what are the biggest challenges in the media industry today?

Facebook. No seriously, people allocate their budgets in different ways and it is simply a different business than it was ten years ago. I get nervous when I hear people saying, “I have this all figured out, just trust me.” The leaders that I’ve seen really persevere in media are the ones that know how unpredictable and wild things are, and they’re humble about learning.

What do you love most about what you do?

I feel like I have the mix: I go to bed on Sunday nights genuinely stoked to go to work the next day. But when I have time off from work or hours stuck on planes, I just write. I write stories that will maybe get placed one day, or I just let them sit and collect dust. But these things never compete and they always feel good and right.

If you could go back in time and give your younger self some advice, what would it be?

Take it easy. I was so, so hard on myself and put enormous pressure on myself (it didn’t come from anywhere else) to get the title, the role, the blah blah. It is never about those things.

What piece of advice, or tip from a mentor, do you think about often that has helped you make decisions about your professional life?

Find really great mentors. Do work that you’re proud of with people you really respect and admire working with. Don’t hope for a wishbone when you need a backbone. Don’t confuse feminism for careerism.

What are your hopes or predictions for the media industry at large in the next decade?

My hope is that people will still really honour and seek out great journalism: the hard, messy, critical important stuff that is often devalued for the sake of click bait.

When you think back to 2007 and compare to now, how do you think you’ve changed the most?

Oh gosh, this is what happens when you get older: you look in the mirror and notice big changes but still feel like the same person. I go to bed way earlier now and am not going out eight nights a week, but I’m still super curious and energetic. The biggest change, besides a few hard-earned laugh lines, is I’m way more comfortable with being uncomfortable now. Ten years ago, the idea of going freelance would have terrified me, but once you do it, it’s really reassuring to see just how far outside of your comfort zone you can go.

Anything else you want to share right now?

I really hope Jen isn’t too humble and edits this out, but I want to say how beloved and admired she is. I keep in touch with friends, readers and writers that I met through SDTC ten years ago and it’s a testament to the community that SDTC is. Ten years ago, there was nothing like it. Today, it’s still totally its own thing. Jen McNeely, you’re a legend and you’ve made an indelible mark on this city and this country.