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

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.

Is it a good idea to vacation now and postpone retirement?

Two words that go together well. Summer vacation. It is time to unwind, sit out on the front porch or back deck with a cool drink. Chill on the beach with a few friends. Ride that motorcycle through the foothills of the Rocky Mountains or take a long hike to the top of a mountain to breathtaking, panoramic views. Aww...summer. 

The summer is a time to get away from our work lives and contemplate other passions. Clear our heads of work place cobwebs and enjoy our hobbies, family, friends. Last night, I was on the patio of a good friend, she had a nice fire going and we started to contemplate our lives. Fire pits seem to fuel work talk and the thought of fleeing to better winter climates. Both of us have taught English in Japan and are fairly well travelled. Could we set up a small coffee shop in Belize? What about teaching English again overseas - Spain, perhaps? Are we too out of shape to wrestle sheep on a farm in Australia? Maybe we could do what Al and Denise do (see previous Portfolio Careerist article) and live half in Mexico and half in Canada. That sounds good...summer all year long. Seems like early retirement to me.

We concluded, after a bottle of wine and a dead fire, that we are grateful to live in a beautiful city like Calgary, next to the Rocky Mountains, an amazing playground of free activity. We are equally grateful for our work, health, family and good friends. We also concluded that it is okay to think about the possibilities and exciting opportunities that await us. We both love our work and, of course, there is always something to complain about - the workplace drama and the industry politics. But, it is good work that we do and we recognize that there is good work to be done in other ways and in other locations. Having changed up our work lives in the past, we have the experience to know that shaking things up brings new opportunity. 

Are either of us moving to Belize? Not any time soon but my husband and I have a financial plan to take a break in 3 1/2 years for 6 months. We have no idea what we are going to do - we're taking suggestions - but we'll take a 6 month break, refuel and then see what the future holds. In a recent article by Kate Ashford for Forbes called Millennials: Traditional Retirement May Not Be in the Cards, Ashford interviewed Morag Barrett who discusses the concept of short sabbaticals over the course of our work life rather than the concept of traditional retirement plans. It's an interesting article and worth the read because it redefines our work life, vacation time and retirement. We've been conditioned to take that two - three week vacation yearly and retire as early as possible, but is that still feasible? Is this the way of the future for the next generation? 

My friend and I concluded that there's nothing wrong with shaking up our work lives - moving to Costa Rica and working from our laptops seems like a venture within reach. We don't want to wait until retirement to enjoy our lives - we figured that out long ago. However, we can also relate to Morag's approach to work and retirement. Work longer but vacation longer; doesn't sound great written like that. However, when you unpack the concept, it leaves room for more interesting options. In my opinion, this way of thinking fits better with the portfolio careerist mindset. If we are redefining how we work, why not redefine how we vacation and how we retire?

I could get on that boat...floating down the river of summer contentment. Flies and mosquitos not included. A long vacation every three years. Sign me up for the financial plan for this idea. Where can I meet a financial planner that even knows how to plan for this concept? Another industry that will have to adjust to the new way of working and retiring that will be the future. 

To read Kate Ashford's article, click on: retirement.