How to Create a Portfolio Career - A growing career trend

More workers, who are able to work from a computer, are creating portfolio careers.

I was a portfolio Careerist before it was fashionable. For me, streaming income from different jobs or entrepreneurial ventures started as a survival tactic. I wasn’t trying to be trendy as I worked several jobs to put myself through university. I was attempting to pay bills and tuition. Five years later, when I graduated with my B.Ed. into a recession, my ability to juggle jobs became my strength. I pulled together substitute teaching jobs, a banking job and a job in a daycare to make ends meet and build experience. When I finally landed an interview, the school board was impressed with my ability to juggle multiple commitments. They believed my juggle act was a skill set much needed in a teaching position. As it turned out, they were right.  

Fast forward to today and I’m still a portfolio careerist streaming income from different directions. This style of work is nothing new. Creative types have been working this way for centuries.  Artists, musicians and writers have led the way, but streaming income was never the work style our parents promoted. They didn’t want us to end up poor like a “starving artist” so they told us to go out and get a “real” job.

But today, “real” jobs may be harder to find as some employers have shifted to hiring more independent workers. In addition, stagnant wages have changed the way we see the career ladder climb and has made streaming income from more than one source necessary. As well, it’s no longer as appealing as it once was to work in a 9 to 5 box that allows for little flexibility. Finally, the growth in remote work and technology innovations during the pandemic has made it easier for workers to juggle more than one income stream.

The trend towards portfolio careers is nothing new. In 2008, the Boston Globe wrote an article on the growing number of Portfolio Careerists in the U.S.  They interviewed Stephanie Creary, who at the time was a 31 year old speech pathologist, professional dancer, yoga instructor and Harvard Business School Researcher. She said she was a portfolio careerist because it was her strategy for dealing with multiple interests and she was glad someone finally put a name to something she had been doing for years.

One of the most intriguing aspect of the portfolio career movement is it’s no longer just attractive to creative types or people weathering recessions. Back in May of 2017, Harvard Business Review article, Michael Greenspan gives tips for executives who are thinking about making the leap from their full-time jobs to a portfolio style career. Greenspan admits “going plural” as he calls it is a challenge. Making the jump from full-time work to a portfolio career concept is not an easy feat, and requires mentorship as he explains in his article. And mentorship is beginning to happen.

A few years ago, I interviewed Brad Hussey from Lethbridge, Alberta, Canada who left his full-time job with Sajak and Farki digital marketing company in Calgary to go freelance as a web designer and coder. As Brad told me, “…freelancing was up and down with inconsistent income.” He had to figure out how to create consistent streams so he went completely online and started teaching. He now has Code College, and is streaming the majority of his income online.  He teaches a globally based student body how to code and start their own freelance business so they too can quit their “real” jobs. He moved his portfolio career into a solopreneur business model.

Brad isn’t the only ones that have decided to steer away from a 9 to 5 lifestyle. This trend has become attractive to people from varying occupations, industries and socioeconomic backgrounds. Al and Denise pulled up stakes, quit their teaching jobs, sold their home outside of Calgary and moved to Mexico to work. They built a house in the province of Saskatchewan in Canada where they work in the summer and move to Mexico to work in the winter. They gave up a pension, stable work, and they haven’t regretted their choice. It wasn’t easy but in their experience, it was worth it. They have what they believe is the best of both worlds because they keep their toes in sand year round and never have to shovel snow.

Speaking of snow. From my experience meeting and interviewing portfolio careerists like me who have chosen not to climb the career ladder long term, no two are alike. However, our commonalities exist in our ability to adapt, create opportunity, meet needs and be open to customizing our work life. Consequently, we are often well positioned to adapt to the current shifts we are experiencing in the changing climate of work, and whether out of necessity or choice, we can pivot.

With an ever changing and evolving world of work, it appears the portfolio careers trend may continue to grow.

If you want to learn more about portfolio career strategy, Check out our Branch Out workshop series on our website.

Historical Reads

Statistics Canada Labour Force Survey https://www.statcan.gc.ca/eng/survey/household/3701

Chin, Jessica (2017, December). Less Than Half of Canada's Prime-Age Workers Kept aFull-time Job for All of 2015. Retrieved from http://www.huffingtonpost.ca/2017/12/01less-than-half-of-canadas-prime-age-workers-kept-a-full-time-job-for-all-of2015_a_23294345/

Vomiero, Jessica (2017, April 19). Inside Canada's Flexible Work Economy. Who's the real winner here? Retrieved from https://globalnews.ca/news/3385957/canada-flexible-gigeconomy-jobs/

Randstad's Workforce 2025 Report http://content.randstad.ca/hubfs/workforce2025/Workforce-2025-Randstad-Part1.pdf

Shulman, Michael (2017, January). Nearly Half of Canada's Workforce will be Self Employed by 2020. Retrieved from https://ca.finance.yahoo.com/news/nearly-half-ofcanadas-workforce-will-be-self-employed-by-2020-study-145943790.html

Jackson, Maggie (2008, January 27). Portfolio Careerists Revel in Change. Retrieved from http://archive.boston.com/jobs/news/articles/2008/01/27/portfolio_careerists_revel_inchange/

Greenspan, Michael (2017, May 4). How to Launch a Successful Portfolio Career. Retrieved from https://hbr.org/2017/05/how-to-launch-a-successful-portfolio-career

3 Reasons Why a Side Hustle is a Smart Career Strategy

You’re working full-time and have a part-time job on the side to save money to quench your thirst for travel. But, have you thought there may be more to a side hustle than just making some extra cash?

A side hustle is an extra income stream such as a casual or part-time job or an entrepreneurial venture that you do after working your full-time job.  Even though 70% of side hustlers say they are doing it for the money, I have three awesome reasons that prove money isn’t everything and side hustling can be a smart career strategy.

The Top 3 Reasons Why a Side Hustle is Smart

1.     Build skills that you possibly can’t build in your day job.

2.     Meet new people and create new connections.

3.     Scratch an entrepreneurial itch and test-drive your idea.

Building New Skills

One of the best reasons to take on a side hustle is the opportunity to build skills that you wouldn’t get to build in your day job. In some cases, this could be a specific professional skill that is related to your occupation and your long-term career growth. Several years ago, I worked full-time as an intercultural trainer and did some freelance consulting in my free time. I had specialized skills in the area of launching international student and second language programs and I had the opportunity to share my knowledge and expertise while I also built my consulting portfolio.  Today, I consult in a different area of expertise but I learned how to consult as a freelance side hustle earlier in my career.  

In other cases, your side hustle may be a personal interest that gets you up on your days off. Chris, a detective during the day, works with a carpenter on his days off. “I get to learn new skills that I apply to my own home,” he says. “I never need to hire contractors on my properties because of the skills I’ve built working on the side. I’ve saved myself a lot of money in renovations. And, as I see it, I’m getting paid to help out my friend.”

Making New Connections 

Side hustles can also be our opportunity to make connections with people we wouldn’t normally meet in our day job. When I decided to leave my teaching career, I worked .75 FTE as an international student coordinator, teacher and academic advisor. At the time, I was considering taking a leap out of working in a high school environment to working in the career development industry, but I didn’t know a lot of people. On my afternoons off, I took on a side hustle working as a vocational counsellor supporting injured workers in their work search. This helped me meet new people in the vocational rehabilitation and career development industry and allowed me the opportunity to test drive the two industries and talk to people to see if I really wanted to quit my day job and plunge into a new career.  

Scratching an Entrepreneurial Itch and Test-Driving the Waters

Since I was 14 years old, I’ve had an entrepreneurial itch that I have needed to repeatedly scratch throughout my lifetime in the form of entrepreneurial side hustles. These side hustles have helped build entrepreneurial knowledge and skills in safe ways before taking larger plunges.

One of my entrepreneurial side hustles developed while I was working full-time in Japan as an English Communication Instructor in a high school. There was a huge market for English tutors, so it was the perfect opportunity to run my own side business. I learned how to market my skills, create a fee structure, provide quality service and attract a clientele. It was my first real taste of running a small business.

In his Lendio blog post article, Do Side Hustles Lead to Legit Businesses, Grant Olsen writes, “Steve Jobs and Steve Wozniak may have had jobs at Atari and Hewlett Packard, but they relentlessly hustled their computer-building idea.” Businesses are not started over night. In many instances, people are doing their day job and hustling on the side to get their business idea off the ground.  

Steve and his wife Chrisa, agriculture entrepreneurs from Saskatchewan, Canada, were both working full-time jobs while they simultaneously launched The Duck Foot, a farming implement that Steve invented. While they test-drove the waters and went to trade shows in Saskatchewan, Australia and the US, they kept their day jobs. When The Duck Foot gained momentum and they started to get busy, Chrisa quit her job to look after operations and customers. They have now launched their product line in Canada, Australia, German, Brazil and the U.S.

Whether it’s building new skills, making new connections, building entrepreneurial skills, or starting a legit business, side hustles have their value. And, if you just want to make some extra money to pay for that trip to Spain, that’s a good idea too.

If you want to learn more about portfolio career strategy, Check out our Branch Out workshop series on our website.

Here are the Realities of Becoming a Freelancer

When it comes to being a freelancer, there are many advantages that make freelancing seem nothing short of a dream job. However, wherever there are advantages, there are also disadvantages. All of which I will be exploring throughout this post.

I am a freelancer who has been working alongside Purposeful Careers for the past six months. I graduated from high school in 2019, and I took a stab at News Broadcasting in the Fall. I decided it wasn’t for me, and so I took it upon myself to get a job working at a grocery store over the course of the holiday season. Then I got a part-time job working for a company called Jiva who had originally approached me because they wanted me to help them do video work. Unfortunately, the pandemic hit, and I got laid off. I didn’t want to have a huge gap in my work history so I approached Purposeful Careers, and asked them if they needed help. I have interest in social media, so we decided I would help create posts.

My job can be compared to that of a social media marketer because over the past several months, I have been working on a graphic design platform called Canva, creating and putting together content for both Instagram and Pinterest. In just six months, I’ve been promoted to taking a stab at writing a blog post. So, here I am.

Freelancing involves working independently for multiple people and/or companies on a contract basis. In other words, a freelancer is a self-employed individual who offers various services to their clients. I have learned over the last six months that being a self-employed freelancer has both advantages and disadvantages that everyone who is thinking about it, should know before they dive in.

Some of the Advantages

Being a freelancer means that you are your own boss, and that you have freedom to choose. You can choose your work hours. You can choose who you want to work for, and for how long you want to work for them. You can choose where to work, and you can choose when to call it a day. For example, I work part-time, three days a week from the comfort of my couch, but I don’t get to choose my hours. I start at 1:00 PM and end at 5:00 PM. During that period of time, I get a new assignment or I continue to work on the assignment from the previous day. I get to go to work in what I would call “picked-up-off-the-street” attire (basically whatever I want).

I also enjoy being able to work without having the commitment of the commute. Being able to wake up, and start work from the comfy cushions of a worn-out-couch is one of the joys of freelancing.  Being a freelancer means that you represent yourself, and your brand image, and the biggest advantages of being a freelancer is flexibility and freedom.

Another advantage is the fact that it’s been hard to find a traditional part-time or full-time job in this pandemic. Freelancing has given me the opportunity to learn new skills and get work experience that I wouldn’t normally be able to get. As well, because I don’t have a career direction chosen yet, I’ve been able to test drive social media content creation as a potential career.

Some of the Disadvantages

Keep in mind that as a freelancer, there’s bound to be disadvantages. You have your work cut out for you because it is your job to put yourself in the path of potential work, and find your own clients. As I mentioned, I approached Purposeful Careers after I got laid off. Purposeful Careers has now told other business owners about me so I could have potential clients in the future.

Your workload as a freelancer will vary, and you will not always have a steady stream of income. Not having a steady workload, and not being able to rely on a guaranteed stream of income can be a dealbreaker for some. In my experience, there will be days when my client suddenly decides that they don’t need me, and there will be days when my client is unorganized. For example, let's say I’m scheduled to work on Tuesday afternoon and on Tuesday morning my client says, “It’s okay. You don’t have to work today.” As you can see, being given short notice when it comes to when you work, and when you don’t work is something that freelancers have to deal with. Receiving short notice is a bummer, but in my eyes, it just means I can go back to bed. If you are the kind of person who needs consistency, and a steady income stream then freelancing is not for you.

Freelancing is a great opportunity to make money doing something that you want to, and already know how to do. Both the advantages and disadvantages are worth looking into if you are interested in becoming a freelancer. All in all, freelancing is a job that pretty much anybody can pursue, and if you were to give it a shot, you might find that it is a dream come true.

How to Change Careers by Asking 5 Smart Questions

With three major career changes under my belt that weren't effortless or without investment, I can confidently say that career changes shouldn't be made lightly. I've learned that a mid to late career change requires a thoughtful and pragmatic approach that answers the following questions:

1. How much and what kind of change can I realistically manage at this stage of my life?

2. What skills do I want to take with me and what would I prefer to leave behind?

3. Where am I financially?

4. Have I talked to enough people?

5. Have I learned about the “hidden gems” and the current trends?

These five questions have helped my clients navigate what can be a challenging decision.

How much and what kind of change can I realistically manage at this stage of my life?

From family responsibilities to finances, mid to late career changers have multiple layers of life to consider. Understanding the magnitude and type of change is critical at this stage of life. Typically, our choices are:

• Make tweaks to our current role (Ask for new tasks).

• Stay in the same occupation but change industries (The office administrator that moves from oil and gas industry to manufacturing).

• Stay in the same industry but change occupations (The engineer that stays in oil and gas but becomes a pipeline construction inspector).

• Change occupation and industry (The plumber who becomes a police officer).

With each change comes loss and gain, and each potential career changer has to weigh the impact on their lives.

What skills do I want to take with me and what would I prefer to leave behind?

The process of excavating skills and experiences can help mid-career changers decide the magnitude of change they want to make. When I made my first career change and moved from legal office administration to teaching, I made decisions about what I didn't want to do anymore (typing documents) and what I wanted to do (teach people). I also weighed the investment into building new skills. Did I want to go back to school?

Shedding skills I no longer wanted to use and identifying skills I needed to build helped me decide how much change I wanted to make. This process also helped me make decisions on where to investment my time and money when it came to retraining.

Where am I financially?

Executive Career Coach, Maureen McCann, has her clients “run their numbers”. Although Career Practitioners are not Financial Advisors, I believe that financial planning is a necessary and neglected area of the career planning process. Not knowing my financial facts stalled my first career change because I didn't think I could afford university. When I sat down with a financial advisor, I learned, over the long term, I would get my investment back and these facts changed my perspective.

In her article, Tips for a Successful Mid-Career Change, Madeline Burry writes, “Transitioning to a new career and industry doesn’t mean that you will need to begin from the bottom”. This can be true. However, when my husband and I decided to make mid-career pivots, our biggest concern was “Can we effectively mitigate the financial change?” I quit teaching and moved into career development and my husband quit teaching and moved into policing. We moved from mid-level salaries to entry-level salaries in our new occupations. To manage the change, we wisely took turns. He switched first, then I followed suit. We were excited about our new occupations but, it wasn't without sacrifices. As we transitioned into our new careers, we stopped traveling to help absorb the financial loss.

Have I talked to enough people?

Career Practitioners didn't exist in the high school I attended. Instead, my family of pragmatic farmers gave me simple and sound career advice. They said, “talk to people”. I contacted ONE person. My friend who was a legal secretary (which sounded sophisticated) said she liked her job. I thought if my friend liked it, I likely would like it too and I unwisely stopped my research. After a year of schooling and a year of sitting at a desk for 8 hours, not talking to people in a steno pool like the Dolly Parton movie Working 9 to 5, I started researching a new career direction. The job wasn't for me.

Although we build skills and experience from an ill-fit occupation, the investment of time and money mid-career can be far too costly. Forbes writer Brad Shorr, in his article 4 Important Things to Consider Before Making a Midlife Career Change, writes, “What you earn or don’t earn from the age of 50 to 65 is going to have a major impact on what you can afford to do in your golden years.” A major career change from the age of 35 to 65, can have a impact on our financial future for the better or worse.

After my stint as a legal office administrator, I went back to my pragmatic, fiscally responsible family for more advice about becoming a teacher and they said, “Before you spend that kind of money (on a university education), you need to talk to more people”. This time, I widened my research. I asked more people more questions. I covered education options, got a feeling for the career and trends impacting the industry. As a result of a more comprehension approach, teaching fit like a glove and the long-term financial gains outweighed the investment. More research ended in a wiser decision.

Have I learned about the “HIDDEN” gems and current trends?

Another important consideration when talking to people is to ask about the countless “hidden” occupations that never make it onto a database, have “hidden” career paths and are often well paid. We could be short sighted in our choices because we didn't do deeper research. In addition, emerging or growing industries have yet to create commonly used job titles or comprehensive job descriptions for emerging occupations. These occupations may not be on a career database and the only way to learn about them is to talk to workers or employers.

When I was working in Japan as a teacher, my American colleague had a friend that was a career counselor in the US. It sounded like a cool job but when I tried to research the occupation, I couldn’t find enough information to get a feel for the job. Career development was an emerging industry in Canada, so it was difficult to find comprehensive information on the role of a career counselor. A few years later, when I moved back to Canada, there was still little information. In order to learn more, I searched the Yellow Pages in my city and and set up information interviews with companies that had the word “career” in their business name. As I talked to people in the industry, I discovered a whole new world of possibilities with emerging occupations and entrepreneurial opportunities. I made the decision to take the leap and move from a career in international education to a career in career development.

In addition to hidden and emerging occupations, in a rapidly changing work world, mid to late career changers need to know how the occupation or industry they are considering will be impacted by trends and innovations. Retraining for an occupation that is sliding out of demand or will be replaced by Artificial Intelligence is obviously unwise, but I'm surprised by how many people don't do their research. Equally, moving into an occupation that is moving to an “on-demand” workforce, hiring independent workers for freelance or contract work may or may not be a good fit depending on the individual's personality and situation. Asking questions about impacting trends, new innovations, flexible staffing models and technology advancements in an industry before we make a commitment is a wise approach to a career change in a rapidly changing workforce.

With a more holistic, pragmatic and comprehensive approach, we can discover exciting and rewarding “next stage” careers.

If you want to learn more about independent work, subscribe to Career Corner Toolkit for FREE monthly injections of independent work and other career tips. To subscribe to Career Corner Toolkit or to have a free consultation, go to my home page.

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

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."