How to Create a Portfolio Career You Love

Maureen McCann has a pragmatic and fearless approach to her unique career. Currently living in Victoria, BC, Canada, she has a career consulting boutique business called Promotion Career Solutions, owns and operates a vacation rental property with her husband and is a landlord for a property she owns in Ottawa. Her wise management of money, and her understanding of real estate has helped Maureen design a work life that she enjoys.  “Learn what works for you and play to your strengths,” she says as we converse over the phone about her portfolio career.

In her 20’s, Maureen started to read financial books about money management and property. “I read on my 20 minute commute to work. What I was reading made me realize that managing money better could make a huge difference in people’s lives. I considered becoming a financial advisor but changed my mind. I didn’t want to be someone who sold mutual funds."  Maureen developed a motto “run the numbers” and it has helped her create her work life. “I genuinely love what I do and I want other people to love what they do. When people run the numbers, they find out what they really need to live on. Then, they can make career decisions based on their true financial situation."

At this point in our conversations, we veer off slightly and discuss wise money management and Maureen shares a tip. Drive a beat up car. "“With the income from our cottage, we could’ve bought new stuff like a new car, but we didn’t.  We made sacrifices and drove an old 1998 Chevy Celebrity and we put our rental income back down on the mortgage to pay it off faster.” Now, her vacation rental property has almost become a passive income. "I have created systems that help me manage the emails and bookings, and the people who rent from us clean it themselves and do a really good job.”

Wise money management skills are essential skills for everyone and portfolio careerists managing multiple income streams need to learn how to manage their money wisely but it is not a skill that everyone innately develops. Maureen believes we have to be taught and she has spent hours combing over books trying to understand how to manage her money well. "When people don’t understand money," she says, "They often live in fear. You have to run the numbers in order to address the fear of not having enough because running your numbers helps you to see what is and isn’t enough." We discuss how fear often paralyses people and prevents them from changing careers.  "It’s a cop out to say I can’t change careers because of financial security. People have this underlying fear of how much they think they need so they don’t change anything. They stagnate and don't make any changes out of a fear of not having enough.”

Money, fear and careers. Maureen has made a career consulting business out of understanding some of our deepest fears around money and our jobs. She has also made some tough career choices herself. Three years after she and her husband bought their cottage in 2001, she got laid off from her job and it was a lesson in change and transition. “I started to volunteer in the career development field and shortly after, got offered my first paid job as a career professional.” Simultaneously, she got pregnant which was also a lesson in having tough conversations with a new boss. “It was a very hard conversation to have with a new employer and now that I understand that piece about our careers, I can help my clients with their tough conversations. Somehow, I felt like I had dishonoured my employer's trust because they had just hired me. But, from my experience, your boss will totally understand."

In 2005, she had her first child and went back to work six months later.  Then, in 2007, she decided to go in a different direction with her career as a career professional. "I officially walked away to start my second business. I always knew I wanted to work for myself. I thought I would be able to help more people if I could go out and do it on my own." As well, because Maureen’s husband works for the military, she knew he would eventually get posted somewhere else so entrepreneurship hit all of the criteria she needed for her career.  “I created a business plan and I showed a guy that worked at the entrepreneurship centre. He said my business plan was all good, gave me the thumbs up and it was like, 'Away you go’.”

She broke the news to her husband with a power point presentation when he was on a home leave from Afghanistan.  “I sat him down and I was at slide number two which was to run a business and stay home to take care of our daughter.” He stopped me and told me to go ahead and do it.” Maureen adds, “We have to have these conversations with our spouses.  A lot of couples don’t have these conversations and they stay in their jobs and aren’t happy.” It is often hard for people to break out of the work they are doing even when they are unhappy. Maureen adds, ”I firmly believe we are raised to think that we have to have a steady income but I think we are doing a disservice to ourselves. People approach their careers out of fear, fear of not having, and they sign up for misery, and in some cases, it's becomes like jail time. I’ve decided I’m going to make my own jail time and privately fund my pension.”

For Maureen, a portfolio career that allows her to income stream from different directions helps her create a work life she loves. "If someone asks me to do something and its fun, I'll do it. But if it isn’t fun, I won’t do it. When I first started my business, I said yes to everything but now I have built my life so that it wraps around my family life. When we lived in Europe, I worked enough but I was also able to travel. I can adjust my work life to match what I want. If I invest, I want a good outcome."

I ask her what advice she would give to someone thinking about a portfolio career. " They need to ask themselves what do they really need to make?” Maureen continues.  “Then, work for yourself. You are handing out the keys of your destiny to an employer and you don’t have to do it.  But, if you choose to work for someone else, either way, you don't have to hand them the keys. Your employer is not responsible for your happiness. If you are unhappy, do something about it. The next step is scary. However, we have to first work for ourselves by being wise with our money." 

How to Become a Serial Entrepreneur like Ryan Corry

Ryan’s entrepreneurial portfolio career began while he was playing NCAA hockey for Plattsburgh State University in New York State. As a project during his senior year in university, he had to create an event to generate income. “I organized a large American Pie style party and hosted it at an open-air pub with about 700 people in attendance. I made a profit and crushed everyone in my class!” He said with a smile. This was the beginning of Ryan’s entrepreneurial juggling act.

I met Ryan at a Career Development Mix and Mingle hosted by our mutual connection, Joy Ulrich. Ryan was at the mix and mingle to pitch his second startup business called Skillpics, an online platform that visually connects job seekers and employers. Ryan had hit the pavement with his concept and was actively connecting with different organizations in Calgary. I later ran into him again at a conference in Edmonton where he was marketing his platform to career coaches from across Alberta. I was impressed with the product and curious about Ryan’s entrepreneurial portfolio career. Ryan was kind enough to later meet me in a café in Bridgeland in Calgary where I sipped a latte and quickly tapped notes on my laptop as the story of his career effortlessly poured out.

After playing for Plattsburgh State University, Ryan moved to Pensacola, Florida to play hockey in the Southern Professional Hockey League with the Ice Flyers and continued juggling hockey and event planning. He planned the same American Pie style event again, had a successful return and realized he could make a profit in the industry. His hockey career then took him to Europe where he played with the Lyon Lions in Lyon, France. He again juggled hockey and events planning, organizing another event called Fall Fest, but this time across continents in New York State. “I learned that playing hockey and coordinating events from another continent was definitely challenging. But I made it happen because I loved working with performers and discovering talent.”

While playing in France, Ryan decided to hang up his skates and return to Canada. He had achieved his goals of playing hockey in the U.S. and Europe and he wanted to get back into the community and try out different things. Prior to returning to Canada, he decided to take a detour and travelled to Thailand. He said, “I needed to reset and gain perspective. I wanted a clear head for the decisions that were to come.”

A career change is never easy and for professional athletes, it can be an adjustment. Upon returning to Calgary, he said reality kicked in and he started to look for a "real" job. He had a good work ethic, had graduated at the top of his class and didn’t think it would be hard to find work. But, it was. “I had to try different ways to get noticed. I created my first cover letter, which was a storyboard of my travels and volunteer work. It was a visual representation of my skills designed to capture the attention of employers,” he explains. “I did all this work but it didn’t match up with how employers were looking for talent. I had been away from Calgary for six years and I was finding it challenging to connect with employers.”

His Skillpics concept was evolving in his efforts to connect with employers. However, while continuing to find work, Ryan decided to use his skills to help in the community. “I took over responsibility for and re-incorporated a non-profit organization that executed a charity formal event. The event preceded a Christmas Classic hockey game with friends who were just starting to play, right up to professionals. I used my hockey background and event planning experience to help raise money. I wasn’t paying myself with this, but I needed to create work for myself. It was rewarding to be doing something worthwhile."

He continued planning charity events while simultaneously looking for paid work. In addition, he had also been on the lookout for a well-made onesie for his girlfriend. The adult onesie craze had hit both Europe and Canada, and Ryan’s former Swedish roommate had purchased a high quality, European-made onesie for 250 Euros. While in Calgary, Ryan couldn’t find a product with the same quality, so he decided to get one made, “In the spring of 2014, I actually got my first onesie sample and spent about $300 for three rather than ordering one for 250 Euros from Europe.”

Ryan had an interest in fashion and creating a brand. “When I created the onesie, I chose the name UNI which was slang for uniform in the hockey world. By chance, UNI also means one in Spanish. I built on the name with UNI chillwear.” He ordered three and wore a sample onesie to the bar to show his friends. It was a well-made product so he decided to make 50 more. “I took out a loan, made more, sold them all and started to realize this might be a business opportunity.”

Ryan’s former teammate, Jeff, who was doing his MBA, thought he could apply his learning directly to this new potential startup. This helped Ryan get motivated to complete the business. He adds, “We went from 3 units to 50 to 125 then 250 to 400 and we are now at 650 units and getting better margins. We completed our second winter and we have done $140,000 in gross revenue. We wanted to create a brand so we branched out to sweaters, t-shirts, hats and sunglasses. We have mostly done word of mouth marketing and through good customer service, we have built client relationships on-line. We also market at trade shows, festivals and events.”

While building UNI chillwear, Ryan networked with graphic designers, models, and photographers and found that finding talent was inefficient. “I was wasting time going through Facebook and Kijiji, asking for coffee meetings to see portfolios of work. If they weren’t the right fit, I would start looking for someone else. It was a waste of my time to try to hire someone this way, so I started conceptualizing an online platform where I could easily go to a portfolio of work. I drew my first platform for the on-line concept Skillpics. I thought the platform would help jobseekers connect to companies that needed people.”

While working on both startups, Ryan landed a job with Bust Loose managing events, travel experiences and basic operations of the business.  He worked with Bust Loose for a period of time before he decided to quit to focus on UNI.  Once the business started to grow, Ryan reentered the workforce and with his event planning background, he landed a job with the Alberta Ballet. “They hired me to do their biggest event.  Shortly after the event was pulled, my boss was laid off and I found myself doing a plethora of jobs around the office. My title was changed to Project Specialist. I did anything from writing RFPs to connecting with key people in Calgary. It was a great learning opportunity, but I ended up getting laid off in the recession. I then turned my attention back to Skillpics.”

Ryan knows how to adapt, and juggle multiple ventures, key skill sets for entrepreneurs and portfolio careerists.  Skillpics had sat on the back burner while he was working with the Alberta Ballet.  Ironically, once laid off, he had time to work on the platform that was to easily connect job seekers and employers. “I strategized, invested from UNI chillwear and hired Vog Calgary App Developers, a solid mix of people with an energetic, honest work ethic.” Skillpics had started from a cover letter he had created years before as a job seeker. He further refined his idea as he became an employer frustrated with trying to find talent for UNI chillwear. Ryan had started his portfolio career as a hockey player/event planner and was quickly becoming an entrepreneur/business owner juggling a growing business and a new startup.

Ryan’s career has met some challenges since he returned to Calgary.  However, he seems to have an innate determination to succeed and a will to keep working towards his goals regardless of setbacks.  When I asked him if he could pinpoint some advantages of currently being an entrepreneurial portfolio careerist, he didn’t hesitate when he answered, “I like to be able to make money and be successful, but I want to make money doing what I love.  The amount of money I make helps me keep track of how successful I am.  Whether it is for myself or for a charity.  It is a measure of success because if you are creative, efficient and strategic and you do these things well, then you’ll have a large degree of financial reward. The fruits of your labor will be reciprocated. Money can be like a trophy.”

When it comes to disadvantages, Ryan believes time management, the energy that goes into a startup and the lack of capital are the tough parts of starting a business. “I had to mix in two professional jobs because we aren’t going to make money overnight.” He continued, “At times, skepticism creeps in. I wonder whether or not all of this work will pay off in the end. However, I counter skepticism with the idea that I’m making an investment. I’m investing into a business and taking a risk like every person who pours money into getting an education. When they come out of university, they have to find a job and pay their investment back.” He then added, “We are all investing into our future in a different way.”

Although the road ahead may be challenging, I believe Ryan’s tireless work ethic, his ability to see gaps in markets and his determination to solve problems will continue to turn his investments into a successful entrepreneurial future.

For more information on Ryan's businesses, go to unichillwear.com and skillpics.com.

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I would love to connect with you if you are thinking of starting a portfolio career or already have one and want to OPTIMIZE.

What are the Benefits and Challenges of Being Entrepreneurial?

Self-employment seems to be in the air! I have recently been meeting former portfolio careerists who became solopreneurs or entrepreneurs, income streaming from various entrepreneurial ventures. I am so intrigued by their work lives that I have decided to spend the next few months covering self-employed solopreneurs like Kym Keith (recent June article) and Brad Hussey (future August article) who work on their own providing a service or selling a product without hiring staff. They are flying solo in their business and are streaming income from multiple directions.

Others like Ryan Corry (this month's July article) are entrepreneurs; the term used for self-employed individuals who hire staff to help them with their business. Entrepreneurs, like Ryan, who are also portfolio careerists may stream income from more than one entrepreneurial venture or they may run a business and possibly work in a salaried job or do contract work.

Whether they are flying solo or hiring staff, there are definite benefits to operating a branch on our portfolio tree that is completely donated to self-employment. Portfolio careerists who are opting for self-employment tend to like the freedom to create, innovate and control the work being done. They like the ability to take charge of marketing, networking and the growth of their venture. Their entrepreneurial project gives them an outlet for their creativity and business savvy, and also provides them with a sense of pride and ownership.

There are certainly advantages to having a self-employment branch to our portfolio tree. However, as I've said before nothing is perfect. The ability to start a small business that will make and not lose money is a difficult endeavour. It requires doing our homework, learning how to write a business plan and coming up with an idea that will be marketable. As mentioned by Kym Keith, she went through an intense business planning course to come up with a marketable plan.

A good business plan is just the beginning. Just like hard work without a plan can lead to business failure, a well-done business plan won't be executed without hard work. Launching and running a business is exceedingly time consuming and most business owners work long hours, which for some people may be a disadvantage. Another disadvantage is that many businesses don't make money right away and, hence, streaming income from other directions will be necessary. This is the juggling act that can become tiresome because there are only so many hours in a day.

However, I enjoy being a self-employed solopreneur who primarily works on contract. I have an incorporated career services business as part of my portfolio career and I like the freedom self-employment gives me to create my own work life. There are downsides. If I don't work, I don't get paid. I don't have paid vacation or benefits. I have to come up with my own retirement plan and I often have no idea how much money I will make in a month.

When I read the above paragraph, I realize self-employment is not for the faint of heart. I tend to have a higher than average risk and uncertainty tolerance, but being comfortable with risk isn't the key ingredient of a self-employed person. I have met people who have a lower tolerance for risk, yet they choose self-employment because they prefer to be in control of their work life rather than leave it up to someone else who has the power to lay them off, leaving them with no income at all. I have learned through meeting various entrepreneurial portfolio careerists that everyone is different. No two are alike in their approach and their level of risk.

In the articles to come, I will feature some of the inspiring people I have met who are streaming income from various self-employed ventures and are, in a sense, paving some interesting pathways that may change the way we all work in the future.

The following link solopreneurs has more information on the differences between the two self-employment approaches.