Sowing, reaping and harvesting – it’s not just for farmers.

My Dad was a farmer. He had an eighth grade education. And he was one of the smartest people I’ll ever know. He also managed a multi-path career, although he never called it that.

Know that you want to have a multi-path career but can’t quite wrap your head around it?

Think like a farmer.

I grew up in rural Saskatchewan outside of a village named Eyebrow, which is on MSN’s recent list of “50 Canadian Towns With Quirky Names”. It’s named after a parabola-shaped hill above Eyebrow Lake, not a random body part as you may suspect. But I digress …

Life on the farm was glorious. I had an amazing childhood. During summer school breaks I would load up my wicker bicycle basket with writing and art supplies and head out onto the paths in-between the crops and then spend countless hours capturing my musings on paper. At that time, I didn’t think about whether the crop to my left was wheat or oats and the crop to my right was barley or durum. I was just soaking in all of that incredible prairie air and expansiveness.

When I’d return home sun-kissed and inspired, my sister and I would head out into our huge vegetable garden to weed out that nasty portulaca that crept like a prairie wildfire into everything else. As we weeded, I gave little thought to whether I was caring for a row of cucumbers or wax beans, potatoes or carrots.

Sometimes potato bugs or cutworms damaged vegetables. And in the fields, hail, drought, grasshoppers, or geese would often take their toll.

What did I learn from all of this as it relates to a multi-path career?

A multi-path career is exactly like a farm or a garden.

My childhood farm in rural Saskatchewan

Sow multiple career paths. Tend to everything equally to give it a fighting chance. Pay attention to what’s thriving and put more focus there. And if something isn’t yielding good results, cut your losses and try something else. Don’t waste your time continuing to invest in something that you’re never going to harvest no matter how much energy (or fertilizer!) you put in.

Maybe you have your head wrapped around that concept, but you’re standing in the gardening aisle at the store and don’t have a clue which seed packets to buy (or what will make up your multi-path career).

I found myself in exactly that position when I attended a Schulich Executive Education Centre (SEEC) Alumni Breakfast at York University. The facilitator, Stephen Friedman, was speaking about developing a career vision and the thinking about the extent to which the things that motivate us (e.g. lifestyle, progressive advancement, personal development, social interactions) map onto the career choices we make.

When Stephen said this, it felt as if all of the cherries had lined up on my career slot machine …

“I’m a novelty seeker. I need to do a lot of different things. I like to do this, then I’m going to teach an undergraduate lecture, then I’m going to do some coaching. I need that. I need to do lots of different things all the time. My schedule changes every week. It’s different all of the time. I like novelty. Do you? Is your current career path giving you the top motivators in your career? If not, what can you do to get those things?”

When the session ended, I couldn’t get to the front of the room quickly enough to speak with Stephen. I was excited, but at the same time overwhelmed and consumed with anxiety. And I had a burning question.

His answer? Start with one.

You don’t need to have it all figured out – just the first one. The rest will come.

I’ve included an illustration of my career canvas, which shows exactly how that can happen. It will be different for you. It’s different for everyone. But the point is that one thing will organically lead to another and to another.

You can see by the illustration that I didn’t have it all figured out at once. I couldn’t have. There was no possible way that I could have known that meeting Murray would have led to my work in film and television or that meeting Darren would ultimately lead to our prebiotic soda company, because neither of them were actively engaged on their next ‘career path’ when we met. Instead, it came to be as organically as a garden or a crop.

I’m still tending to four of my five simultaneous career paths because they’re all yielding good results in different ways and I’m not prepared to cut any of them loose in favour of another. The only one that’s on the backburner is film and television, and that’s strictly for practical reasons. The opportunities are there if I choose to pursue them. The skills and experience I can bring to the industry are only increasing through my other work. It feeds my creative spirit and it’s where I feel at home. I just don’t have the time to invest in this too without the quality of everything else and my own well-being suffering. But while that land rests, I continue to cultivate my relationships in the industry so that I can pick it up again in future if I choose.

What’s your first career path? Like me, it may be your current career, because you enjoy it, because it pays the bills, because you’re gaining skills, experience and knowledge that will help you in your second, third and fourth careers, even if you don’t know what those are. Whether or not you love it or you need to love it is a topic for the next blog.

Whatever the reason, extract from that opportunity everything you can think of. Be strategic. Know what you’re looking to gain and take full advantage of every opportunity that maps back to that. Not everything will directly relate to what you’re trying to achieve (otherwise you’d be working for yourself and not someone else!). Just don’t get so distracted by the day-to-day of your current role that you lose sight of the key skills and experiences you’re looking to build and the opportunities that are right in front of you to do that.

Having trouble figuring out the first one or the next one?

First, make sure you’re running toward what you want to do instead of away from what you don’t want to do. Look before you leap. It’s much easier and less stressful to pursue that next career path while you’re gainfully employed. Many incredibly successful entrepreneurs got the kick-start they needed when they were booted from their current jobs, and if you’re unemployed this may be the perfect time to find out exactly what you were meant to do. Wherever you find yourself …

Think about this and jot it down. We’ll make sense of it later.

• What do other people struggle with?
• What do your friends say you’re great at?
• What do you think you’re great at?
• What skills have you developed?
• What knowledge have you acquired?
• What challenges have you overcome?
• What would you do if you had a free afternoon?
• What idea do you have?
• What problem do you have to solve?

Be honest and take time for this part, because it’s fundamental to everything that will follow. And if after reading this, you decide that a multi-path career isn’t for you, then that’s okay too. Just make sure that it’s because it doesn’t appeal to you, not because you’re afraid or because there are obstacles in your path. Because we can deal with the pains and fears, and we can kick those obstacles to the curb.

I’m not passionate about everything that I’m working on.

There, I’ve said it.

One of the most difficult things about becoming super passionate about something is that it can have the opposite effect on other things, including work you used to love.

When I became involved with The Cocksure Lads Movie, I felt like I was “home” – that I should have been working in the film industry all of my life. Everything else I had been working on suddenly paled in comparison to my new true calling. And that threw me for a loop.

It was as if I had opened my eyes for the first time and been exposed to an entirely new bright and shiny world. I felt energized outside of my day job. I had a new lease on life. And I couldn’t get enough of it. I had energy enough for two people. I felt younger, and more capable, motivated, focused, and creative. I also felt appreciated and respected for all of the skills and experience that I brought to my new role. It was amazing.

Credit: misgafasdepasta.com

At my day job, however, I began to feel the opposite. In an instant it seemed less meaningful and fulfilling. I felt less motivated, unsettled, and not fully fexted to outcomes and the future. The emotional contrast was jarring. And I was left in a very uneasy state, because I’ve never invested unless I could fully commit – never been one foot in.

I’ve heard this from others, and it can be a very conflicting, confusing, and uncomfortable place to be. Until it either settles or it doesn’t. 

I think there are only two directions to go when you find yourself in that position, but beore you go either way, you may need to force yourself to get comfortable with the discomfort for a little while.

Why wait it out? There are a few reasons.

First, like many other things in life, it may level out if you give it a little time. It did with me. If you always put your best foot forward and your mantra is to perform such that you’ll be front of mind for opportunities, you may falter a little, but ultimately you can’t help but pull yourself up by the bootstraps and get back to your high performance level. You still may not feel fully passionate about your work, but even if your heart isn’t in it, you’ll likely find that your head is.

Second, unless you have a lot of disposable income, you may want to consider how your day job can give you the freedom and additional income to help build other elements of your multi-path career. My corporate job has provided me with the stability that I need to pursue my other passions. Having a steady income affords you more risks in other pursuits and can also fund those other pursuits. So don’t look a gift horse in the mouth. If you give up that income, it can either generate some positive pressure to make a go of your other pursuits. Or it can have the opposite effect, introducing stress and anxiety that zaps all of your creative energy. Under stress, some of us become Jekyl, others become Hyde. Choose wisely.

Third, there may be skills and experience that you still have an opportunity to build in your day job that can help in other elements of your multi-path career. As I’ve mentioned in a previous blog, the skills that I continue to build at KPMG contribute to every other aspect of my career.

Finally, you may find that there’s a way to integrate other elements of your multi-path career with your day job in a way that will benefit both. Years ago, I worked for a sporting goods company in need of a product catalogue. I pitched my art and photography skills, and created a separate but complementary and non-competing business producing the catalogue.

But I’ll add a caution here. It may not settle, and you may find yourself chronically demotivated in your day job, constantly counting down to the end of the day when you can bolt for what you really want to do. That’s not sustainable. It doesn’t do justice for either you for your employer. And that’s when it’s time to make a change.

Will you now the right choice? Yeah, I think so.

Let’s start to break down your multi-path career, focusing on my career coach Dev’s advice – “Do what you need so that you can do what you want until you can do what you were meant to do.”

• What do you need to do? I call that the potboiler job. For me, that’s my corporate gig.

• What do you want to do? For me, those are my special interest jobs – Connectiv Innovation, Crazy D’s and Lonny’s Smile. These roles produce surprising moments or nuggets of experience and learning and development that buid versatility and competence.

• What were you meant to do? That’s your dream job. For me, it’s this blog and all that I imagine it becoming in terms of giving back and pulling all of my experience and skills together to help others and create something that’s my very own.

Still have some blanks to fill out? No worries. We’ll tackle that in the next four blogs … and beyond, if by the end of it you’re still not there.

Why a Multi-Path Career?

I was a permanent, full-time employee for industry icon KPMG for more than twenty years. For many of those years, I never contemplated any other option. Corporate life was stable, comfortable, and rewarding. Why introduce risk?

To put all your eggs in one basket is to risk everything.

My role was eliminated due to restructuring. It surprised me, but it didn’t devastate me, because it was only one career path in a portfolio that I had already diversified. I had options. They weren’t all profitable at that point. But I had jumped at the chance to try new things and explore new opportunities. I had built a strong network in multiple industries. And I always performed so that I would be “front of mind” for new opportunities.

Security alone is a compelling reason for building a multi-path career. If you have multiple career paths, if one takes a sideways turn you can turn down a different path. If not this then that … or that.

Divergent Paths

Credit: Garen M.

Why choose one career path?

I remember the pressure to choose a career path in high school, and have seen the same pressure with my own kids. 

I don’t believe it’s realistic for high school students to choose what they want to do for the rest of their life. Many of us at middle age or beyond are still trying to figure that out.

Why do you have to choose?

A multi-path career allows you to organically pursue multiple interests at the same time, enabling you to play to your analytical skills in one role, your artistic abilities in another, and your leadership capability in yet another.

Pursuing multiple interests simultaneously allows you to embrace your whole self and can lead to a great sense of fulfillment and eliminate the frustration that can sometimes grow as a result of pushing an area of passion to the sideline in favour of a career that pays the bills.

As my career coach Dev says, “Do what you need so that you can do what you want until you can do what you were meant to do”.

Switching your brain adds energy

For some of us, it’s not just about having multiple interests; it’s about how it makes us feel to pursue them.

In any given week, I’m moving my children’s charity forward, chasing funding for my prebiotic soda company, working on research projects for the technology innovation consultancy, and yes, still managing KPMG’s largest business-sponsored portfolio.

It energizes and challenges me to move between multiple career paths. And each career path is enriched because of the others.

Leverage helps you go further, faster

When I’m researching funding options for the soda company, I learn about opportunities that can benefit my children’s charity, in addition to the innovation consultancy and our clients.

I leverage my non-profit experience and passion when I’m designing and executing the corporate social responsibility strategy for the soda company.

My experience launching multiple start-ups positions me well to coach new entrepreneurs, and to speak and advocate from a place of first-hand knowledge on the challenges facing small businesses.

At most networking events, I establish contacts for multiple career paths.

Working as an Executive Producer in the film industry has built an entirely new network and set of skills, including how to build a recoupment model for private investors and even structure a winning Dragons’ Den pitch, which is now coming back into play as we pitch the Dragons for the soda company.

My KPMG experience provides me with leadership, management, coaching, mentoring, portfolio and project management expertise built on best practices, which benefits everything.

And I can go on and on. The number of leverage points between the multiple career paths has probably been one of the most surprising outcomes of my multi-path career journey.

Like-minded people

When you pursue a multi-path career, you will be amazed and inspired by the network of incredible individuals you meet who are also pursuing this career path. I wouldn’t be writing this blog if wasn’t certain that there were so many of you looking for a more fulfilling, flexible and rewarding career option.

I meet new people every day and although within our individual portfolio careers we are pursuing diverse interests for different reasons, overall we are pursing the same thing.

Individuals with multi-path careers are by their nature positive, driven, achievers. And energy and ideas are amplified when you bring these like-minded individuals together. Accountability is also increased. I meet with one of my multi-path career friends once a week for dedicated working time on our respective projects, and we both meet with two others weekly to talk about our progress and challenges and to talk through our challenges and opportunities. We have a set agenda and takeaways from each meeting. And you can be assured that I make sure that I can report progress at each meeting.

As with any relationship, if you focus on making these relationships mutually beneficial, you’ll give and gain much more than you could have imagined.

Flexibility

I can’t imagine going back to a permanent, full-time job now. Even the thought of it constrains my brain. Right now I’m in Niagara Falls overlooking this spectacular view while my family is asleep in our room upstairs. I’m happy as a clam because I’m doing what I want when I want. When they finally wake up and find me here, I’ll head for a nice leisurely breakfast with them. Yesterday before they woke up I met my business partner Darren just five minutes away from the hotel and we auditioned to pitch our soda company on the upcoming Dragons’ Den season. Today on our drive home I’ll work on another blog. And tomorrow, I’ll meet with two incredible organizations Crazy D’s is looking to sponsor, start promoting our next Lonny’s Smile fundraiser, and have what I know will be an amazing dinner meeting for our innovation consultancy with a business partner and one of our visiting team members from Atlanta. It’s not an unusual week. It’s my multi-path career.

What About You?

 

 

Does this kind of career, this life appeal to you? If it kind of terrifies or overwhelms you, that’s okay too. It certainly did when I first set out on this journey. I wanted to do it; I just didn’t know where to start.

 

The first step is to identify if it’s for you. Think about how I’ve described the benefits of having a multi-path career. The details, the stories aren’t as important as what they represent. Your portfolio career may be vastly different from mine.

 

Does the ‘why’ of a multi-path career ring true to you? If so, what about it appeals to you the most? Write down your hopes and dreams. Be specific. I want to …

 

• Invest energy into doing something for myself.
• Take advantage of a business opportunity.
• Make my ideas happen.
• Apply my skills and experience to something I love.
• Build a better quality of life for my family.
• Restructure my life in a way that will give me greater freedom and fulfillment.
• Figure out how my personal passions can make me money.
• Wake up every day and feel excited about what I do for a living.

 

Be honest and take time for this part, because it’s fundamental to everything that will follow. And if after reading this, you decide that a multi-path career isn’t for you, then that’s okay too. Just make sure that it’s because it doesn’t appeal to you, not because you’re afraid or because there are obstacles in your path. Because we can deal with the pains and fears, and we can kick those obstacles to the curb.

How I
Stumbled into
Entrepreneurship

What’s my story? Why this blog?

For some people, entrepreneurship is a calling – a strong inner impulse that pushes them to pursue exciting and often risky career opportunities.

But for many of us, it just happens.

Let me tell you how I stumbled into entrepreneurship.

In 2012, I had a stable career that I was happy with – or at least, I thought I was happy with it. I had been climbing the corporate ladder for over twenty years, looking for the next rung as soon as I landed on the current one. Around that time, my Mum’s failing health meant that my parents needed to downsize. Part of that downsizing exercise led me to discover the tricycle of my little brother Lonny, who had passed away decades before after corrective surgery for congenital heart disease. That tricycle had helped Lonny feel ‘normal’ – he couldn’t run like the other kids, but with the trike, he could keep up with them. Inspired by the trike and the memory of my little brother, I decided to start Lonny’s Smile Foundation, a charity to give kids with special hearts the chance to experience what other kids do, such as going to summer camp. Did I set out to start a charity? Absolutely not – and yet that’s what I did, in 2012.

With Dr. Joel Kirsh, Paediatric Cardiologist & Founder and Medical Director of Camp Oki.

Photograph by Isaac Peiris

With this charity as my ‘side hustle’ and my passion, I kept climbing the ladder in a big corporate job, until one day I met Murray Foster from the band Great Big Sea and asked him if he’d host the annual fundraising Gala for Lonny’s Smile. I didn’t know much about him – just that he was a talented musician from my favourite Canadian band, and that he had a good heart, because he signed on to host the event without any hesitation. And so our connection began. The day after Murray hosted our second Gala, he reached out to me. “I’m doing a feature film. Would you like to work with me on it?” After falling off my chair, I said yes, without any hesitation or clue what it meant. I just knew with every cell of my being that I could NOT pass it up. As I’ve said to many people since, “You never know who’s watching you and what they’re observing.” Turns out, Murray was watching what I was doing for Lonny’s Smile – how I built relationships, how I raised funds, how I presented myself. And he wanted my skill set to be a part of his movie. After a quick trip the next morning to The World’s Biggest Book Store to buy a couple of books on fundraising for films, I mustered up all of the courage that I could for a role I was convinced I was ill-equipped for (classic Imposter Syndrome) and brought everything I knew and had experienced to the new job at hand. Less than two years later, I had raised the funds we needed through private investors, delivered unforgettable flash mob events, successfully pitched CBC’s Dragons’ Den (gaining exposure to over 2 million viewers), and landed an Executive Producer credit on my first feature film, “The Cocksure Lads Movie.” Most importantly, I had built a lifelong friendship and collaboration with Murray.

As luck would have it (but luck, I’ve found, is just an expression), the Producer of the film was watching me too. After the film wrapped up, he asked me to join his production company, Spiral Entertainment Ltd., as Executive Director of Business Development.

Did I set out to start a ‘side hustle’ in the entertainment industry? Heck no! I had always wanted to be part of the industry, but it wasn’t one of the rungs on my ladder. Guess I hadn’t looked around to realize that there was more than one ladder.

Then one day, SMACK! Someone pulled my ladder right out from under me. Almost twenty-five years into my comfortable corporate career, I found out that the ladder rung I was standing on wasn’t as solid as I thought it was, and my role was eliminated through restructuring.

Truth be told, I had talked to Murray for a long time about making an exit. The chair (paycheque, benefits, routine) was just too comfy, the handcuffs too golden.

So when I met up with Murray right after I got the news, he said exactly what I needed to hear: “That’s amazing! You’ve been wanting this to happen for a long time – and whether you get pushed or you jump, you land in the same place!” He was right. I had been imagining myself somewhere else, usually walking on the boardwalk at the Beach in my jeans (translation – doing what I wanted, when I wanted, how I wanted) ever since I started working with him on his film. I felt like I was “home”– where I was always meant to be.

Since then, my life has continued to take twists and turns, to the point that frankly I can’t see it being any other way now. I still work at that corporate job part-time. I’m also Partner in Crazy D’s, a prebiotic soda company that’s created a whole new category in the beverage industry, leading our Corporate Social Responsibility Strategy – the perfect fit for my “heart” and the skills and experience I’ve gained through Lonny’s Smile and my work with other non-profits. And during all this, I’ve been pulled onboard an innovation consulting company, which leverages many aspects of my skill set – my corporate experience, my deep entrepreneurial spirit (which I didn’t know I had) and my experience in and love for the non-profit sector (we’re establishing an advocacy arm focused on improving the lives of Canadians), something I’m deeply committed to. So, why this blog? A lot of us look around and say, “Must be nice for people who know exactly where they’re headed – to have that clear vision and focus.” But I only know literally one person who did that – the rest of us are from that unsettling and confusing club that just finds their way as they move along. I’m still finding my way, and I’ve now come to the realization that I probably won’t ever arrive there – I’m now content that this is truly how it’s supposed to be, at least for me. I’m looking forward to taking this journey with you and sharing some of what I’ve learned along the way. I hope I can offer something that’s relevant for you, and that you can tweak it until it helps you move forward down your own path. Maybe it will spark something in you. Hopefully you’ll find something you can take tangible action on. But I also know that I will learn as much from you (and probably much more than I’m even imagining now). Because that’s exactly how I got here in the first place, and if I took the time to credit everyone who’s had a part in that, well … I’d never get around to writing a blog! So, let’s do this. As my pal and side hustle co-conspirator Isaac says, “I GOT YOU”.