Kelsey Ramsden



University of Victoria - Bachelor of Economics

Richard Ivey School of Business - MBA

Kelsey Ramdsen has some advice for herself at 21: “Don’t try and look too far down the path. And don’t be concerned when the path changes.” Working jobs from legal assistant to coffee shop manager to fish monger, Kelsey’s path has had its fair share of bends. After an MBA and a post-college consulting job that she confesses made her want to “veer into oncoming traffic every work day,” Kelsey left the corporate world to start her own construction business.

A pretty scary decision at the time, Kelsey was bit by the bug of entrepreneurship. Developing one successful business after another, her path changed again following three kids and a bout with cancer. Following her latest venture, a site helping others challenge the status quo, Kelsey spends much of her time educating budding entrepreneurs via speaking engagements and her own business services firm. She’s even been named Canada’s top female entrepreneur by Profit Magazine two years in a row­—credentials that are far from the every day.

I always say, “Don’t ‘should on’ yourself.” The truth is that if you want something bad enough, you will make way for it. To do this takes uncomfortable trade-offs … We can’t have it all, but we can have what we’re willing to sacrifice for.

How did you go from working for someone else to working for yourself?

There are more people than we know who have decent jobs. We perceive these people to have great lives from the outside, but inside, there’s a chance they’re dissatisfied and simply not fulfilled in their job or career. I’d like these people to know that I get it. It’s a scary place to be; to step out of what’s supposed to be the ‘good life’ and into something very unknown. That said, it will make your life the ‘good life’ you’re searching for.

When I quit my corporate job, I had an instant wave of relief — immediately followed by panic about how I’d maintain this lifestyle. I saved a little and decided I needed a six-month burn rate savings (to cover rent and eating macaroni and cheese to survive for three months). I cancelled all unnecessary services like cable, magazine subscriptions and trips to the spa. I became lean financially so I could be career nimble. Then, I started to cultivate relationships I might need in starting my own thing from within my current career at the time. Otherwise, I figured I might not have access to these relationships after I left my job.

Finally, I wrote a near and dear letter to those closest to me whom I knew I would need to lean on for support during the hard days when I would question my decision. I sincerely told my support network why I was doing what I was doing from both an emotional level, while also being sure to quell their concerns about things like me paying rent. And then, when I was sufficiently fed up and felt like I didn’t want to wake up to go in to work for one more day, I quit.

I wouldn’t be anywhere near this feeling I have of personal success if I hadn’t done the thing that was nagging at me day in and day out. I’m absolutely certain I would not be as financially successful or accomplished. It’s the best decision I’ve made — outside of picking my husband.

What does your typical day look like? How do you prioritize your schedule?

I really don’t have a typical day. That said, I always wake up at 5:30 a.m. and head to bed at 10 p.m. Somewhere in the middle of that, I run our five-person household, feed children, wipe bums, book speaking gigs, develop new content, build relationships, and yes, eat a jar of pickles!

My priorities are family, self-care, service to my clients and then any other requests come after these three things. How people prioritize is a difficult subject to tackle, because truthfully I think too many people let the ‘shoulds’ override the ‘have-tos’ for long term success.

I always say, “Don’t ‘should on’ yourself.” The truth is that if you want something bad enough, you will make way for it. To do this takes uncomfortable trade-offs, but that’s reality. We can’t have it all, but we can have what we’re willing to sacrifice for. If this aligns with your priorities, then you have as much as one ever can. If it doesn’t, that’s when you feel a want for more.

What is it about the life of an entrepreneur that makes you feel it’s the right fit for you?

I love the freedom and possibility of the entrepreneurial life. I can’t breathe whenever I feel like there are too many rules. Also, people think entrepreneurship is easy street, but this is the greatest fallacy someone can believe when entering this space. The truth is this: being an entrepreneur is not for everyone, but it’s right for people who are willing to give up working 40 hours a week for someone else’s dream to instead work 80 hours a week for their own dream.

What challenges keep you awake at night?

It depends on the night. Some nights, I worry about my kids. Other nights, I’m worrying about whether or not I’ve made the best decision that day. But on most nights, I don’t worry anymore. I’ve developed many coping mechanisms that I explore in my book, Is This My Life?

As an entrepreneur, is work/life balance ever a problem with you? If so, what is one no-fail tactic you use to create balance?

I don’t feel there’s such a thing as work/life balance. You can only create balance for yourself so that you can approach your life — which includes work and a host of other things — from a balanced perspective. I have a list of things that I know get me off balance, so when they happen, I’m aware of the situation and can change it. Treat time as the most important currency. It’s more important than money.

My one no-fail tactic for feeling balanced takes three steps. First, I identify what I need to feel physically and mentally at the top of my day, and I communicate that need clearly to those in my life who might want my time to be spent in other ways. I then do those things I need to do to operate at the top of my game.

Next, make sure you have a Plan B for those days you need nothing to come off of the rails. In other words, make sure you pre-plan. If I have to give a talk to 3,000 people tomorrow, I will have someone lined up (mother in-law, friend, pay service phone number at the ready) to step up in the unlikely event that one of my kids fall ill or breaks his/her leg at school. Then, if something does come up, I am covered for long enough to do the thing I cannot waiver from.

Finally, play. Live your obituary. I have a great blog post on this subject. The truth is that life is short and without giving myself permission to live, then it’s no wonder sometimes I feel like I am dying.

What is your personal mantra?

Optimism can take you anywhere.

What qualities does it take for someone to be a successful entrepreneur?

1 / Willpower

2 / Determination

3 / Focus

4 / Humility

5 / A clear sense of self

6 / Willingness to change

7 / Capacity to endure unreasonable levels of pressure

8 / Capacity to not take for granted the tremendous opportunity afforded to us

9 / Be nimble

10 / A lack of rule following

What do you feel it takes to stand out among other entrepreneurs?

Truth-telling. The only real competitive advantage is self. A thousand people know how to develop a website like Facebook, but only one guy did it, and it’s based on his openness to ideas. It’s based on his list of attributes. In order to truly stand out, you can’t try to copycat anyone. It’s about living your life as truthful to yourself as you can and living it open and courageously.

What one piece of advice do you wish you could tell a 21-year-old version of yourself?

Don’t try and look too far down the path. Don’t try to predict something you can’t see. And don’t be concerned when the path changes. And most importantly, stop looking at what everyone else is doing while trying to keep up or ‘beat’ them. Do what you are doing as well as you can do it, and in the end you will be at the peak of the right mountain for you. You don’t want to end up on top of someone else’s mountain. Live your life, not the prescribed one.