Farm girl to ad executive: Trish Wheaton thrived in world of ‘mad men’

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Trish Wheaton spent three decades as a successful advertising executive in an industry notorious for its “mad men.”

She was global managing partner at Young & Rubicam in New York. Then, over a 30-year marketing career at WPP, the world’s largest communications holding company, she held a variety of C-suite and global positions at two of its largest agencies, Wunderman and Y&R Advertising. She has received honors and marketing awards in three countries, and she has served on corporate boards.

Originally from Minnesota, Wheaton moved to Montreal when her husband accepted a faculty position at McGill University. It was there that she began a career in marketing with the Canadian office of Wunderman. In 1985, Wunderman moved its Canadian office to Toronto, where she currently resides. With Toronto as a home base, Wheaton assumed leadership roles in Wunderman’s UK office as well as global roles out of the New York City headquarters.

She is also the founder of Leaning Out, an executive consultancy that prepares senior professional women for post-career success and purpose. When she retired at 65, she was surprised at how unprepared she felt. How do you transition from a high-octane career to your next act? She realized many women were in the same situation, then she pounced on the gap in the marketplace.

In terms of personal investing, Wheaton prefers value investing and is currently taking a more conservative approach. Her investment portfolio holds a broad mix of real estate, equities and bonds.

Fun fact: She knows how to speak Swahili from her time in the U.S. Peace Corps!

Where were you born and where did you grow up?

I was born in northwest Minnesota and grew up on a farm that is still operating as a fifth-generation business. I am the youngest of nine, and I have six older brothers. My mother had been a teacher but she became a housewife when she started having so many children.

My father was a farmer who had an illustrious career in agricultural leadership politics at a national level. Dad was on several boards, including the world’s largest grain marketing cooperative. He created his own involvement in a much larger world.

All four of my grandparents immigrated from Norway, and Norwegian was the first language spoken in my home. My parents actually spoke the preserved “Old Norsk” language that was brought over a century earlier. If you get me in the right mood I will happily speak some Old Norsk!

Did your parents talk with you about money or success when you were a kid? What did you absorb either implicitly or explicitly?

Money was always talked about in the context of the business. Family farms are family affairs, and everyone gets involved. I could always tell you what a bushel of wheat was selling for – this was front and centre in our lives. My mom had her own entrepreneurial business raising chickens. This provided her with “egg money” that she salted away and spent whenever she felt like it. She advised my sisters and I to always have our own (metaphorical) egg money.

The environment I grew up in didn’t distinguish between age or gender; we were all part of this enterprise. All my older siblings were very successful, and it wasn’t an option for me not to be a success. It was expected. We all went along with these expectations and we all learned how to make money.

Another huge influence on my approach to business was my Norwegian heritage. That Scandinavian ethos of social responsibility and collectivism really informed how my parents conducted their business as a community, and these values carried over to my siblings and me.

I figured how to be competitive without it seeming like that wasn’t the nice thing to do.

Trish Wheaton

How did you manage to move to the top in the male-dominated world of advertising?

By being quick-witted. In my mind, we were all equal and the expectations were the same for everyone. I figured how to be competitive without it seeming like that wasn’t the nice thing to do. I learned how to have an opinion and be okay with having it challenged. Sometimes I needed to vocally support that opinion and at times these discussions reached high decibel levels.

In retrospect I think it helped that as a teenage girl I had brothers who were all older than I was. I learned how to listen, and that was a very important lesson.
Interestingly, studies have shown that a disproportionate number of women who make it to the C-suite had farming in their background. Farming teaches you how to be responsible, and you gain a realistic sense of what is required to see successful outcomes.

Another big thing? I made sure to remember that in any business you are measured by your contribution to the bottom line. At the end of the day, just like with the farm, it’s about making money. There will always be challenges along the way, whether there is a recession or COVID-19. A pivotal moment for me was when I took over Wunderman’s [an agency within the WPP group] Canadian operation.

At the time we were moving into a data-focused digital world, and these weren’t capabilities we were known for – we were a direct marketing firm. I knew I had to take bold steps, and it was tough getting people onside with that change in direction, especially since we were still a highly successful direct marketing firm and success can be very seductive. But that wasn’t where the future lay.

Not everyone agreed, but it turned out to be a great business decision, and in two years’ time we would have been out of business if we hadn’t pivoted.

What is Leaning Out, and how did you come up with the idea for the platform?

Throughout my lengthy corporate career, I had operated in an entrepreneurial way but always within a massive global company, and there was a lot of support and resources around me. When I left that career, I was searching for resources to help me transition to what would come next, but there were none available.

The genesis of Leaning Out is to provide professional women (and men, too) with resources and a community – a conduit into opportunities that will help them make the next phase of their lives both purposeful and rewarding. The idea for the platform came out of my personal need. Doing my own research, I discovered there was a big gap in the marketplace in terms of resources.

Our mission is to prepare and inspire professional women for post-career success and authentic purpose.

How has Leaning Out evolved along the way?

We have had so much learning over the past five years. Since its launch in 2018, Leaning Out has partnered with premier women’s professional advancement organizations in both the U.S. and Canada. Hundreds of women have participated in and benefited from Leaning Out’s salons, workshops, coaching and online engagement.

COVID was a huge challenge, of course. We had to do a big pivot away from live events, and this caused a major reassessment of our business model. While our target market continued to be women ages 55+ leaving a professional career, we found out there was a secondary market of equal size. This was a big “aha” moment.

Our secondary market consists of people ages 40 to 55 who are looking to pivot their careers. They are likely to have less financial flexibility, and often they still have kids to educate, but they have similar needs as our original target market. Today we attract people who have been “aged out” and left a professional career involuntarily, and we also attract many voluntary leavers. Our model has shifted more toward thought leadership pieces and one-on-one coaching; this is what people in transition are looking for.

What’s in your investment portfolio and why?

It’s been a broad mix of real estate, equities and bonds, with the percentages of each varying over the years.

Real estate has been a high-yield/high-enjoyment investment for decades. In addition to my primary properties in Toronto (which anyone familiar with the Toronto real estate market knows have been a great investment), I’ve owned properties in Manhattan (recently sold) and a current vacation property in Vail, Colorado. All real estate has had the added benefit of supporting my lifestyle as well as producing excellent returns both for rental income and capital gains at the time of sale.

As I get older, I’ve reduced the equity portion of my portfolio to take out some of the exposure. The equities I own tend toward value investing based on performance over time and dividend returns. While some of the sexier equities always look tempting, at my life stage, I lean toward less risky investments.

What advice would you pass along to the next generation of entrepreneurs?

It is hard to overcome inertia when you’ve come out of a career in the corporate world. You are “mistake averse”: there is lots of exposure. I’ll share the advice I was given, and that is to just do it! Just get started. Write a business plan. And don’t wait for 100 per cent certainty if you are 80 per cent of the way there.

I’ll add that you have to be passionate about what you are doing and what your product is. You have to really believe to get you through those times when it can all seem a bit overwhelming. You will end up doing lots of hard work and on stuff that you might have never done before. For example, troubleshooting your computer – I have no IT department!

What do you do for fun?

Perhaps most importantly I have learned how to play as an adult. Playing is something that can be lost along the way adulting.

I have so many passions. I do a lot of physical activity – I golf, I ski, and I swim. I also love to garden and I love to cook. All of these activities keep me sane mentally.

Reponses have been lightly edited for clarity and length.

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