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.

No Job Title? Seriously.

Through my career services work, I have had the wonderful opportunity to meet hundreds of people from around the world who have come to Canada to live and work. I have learned, from these international job seekers, that job titles can have significant meaning in cultures, creating an important marker of status, value and prosperity. In North America, our job title is also important, giving us a sense of identity and worth.

As a career practitioner and portfolio careerist, although I see the benefit and structure job titles create in the work world, they also can have a negative impact on our sense of self-worth, skewing our decision making in the work search process. Several years ago, I was facilitating an interview skills workshop when I met a man from Africa who had a degree, but when he came to Canada as a refugee, he couldn't find work in his field. At his time of arrival, he had very little English, no Canadian experience and no Canadian education. These factors created barriers, making it difficult for him to access his field. For years, he studied English and eventually found work as a security guard, also doing odd jobs on the side. When he found himself in my interview skills workshop, he was out of work for the first time. As participants practiced accomplishment stories, he quietly confessed that he felt like a failure, and he could not identify one accomplishment since his arrival.

This lovely man adapted to a new culture, learned a new language, found a job when he had little English, raised his children, paid his bills, contributed to his new country and had saved to put his children through university and he felt like a failure because of his job title. When we pointed out all of his accomplishments and his personality traits of tenacity and adaptability, his countenance changed. The participants in his group affirmed his value through his work and the challenges he had overcome. They brainstormed his accomplishments in a new way and he left that workshop with a new sense of pride and purpose, having never looked at his accomplishments through this lens.

Job titles can undermine our sense of value and they can also skew our decisions. Recently, I have met job seekers in our current recession in Alberta who have turned down jobs, preferring to pay bills on credit rather than accept a job that is "beneath them" (their words not mine) in title and pay. I have also met job seekers who have asked me if they should travel for long lengths of time on their severance package, not because they can afford it, but because they are concerned about filling a gap in work history. They wonder if travel is better to put on their resume than a job that doesn't carry weight in their industry.

I understand the underlying concerns job seekers have around working outside of that job title box, the monetary value and the career ladder they are trying to climb. I also understand that folks are worried about the "what ifs". What if I get a better offer in six months? What do I do when the economy turns around and I want to go back to what I did before? These are all legitimate questions. However, I am left to wonder how long people can wait for that perfect fit. I'm left to wonder how long folks can go without work and still make their bills. I'm also left wondering when did a good day's work and just the simple act of supporting ourselves regardless of title stop being enough?

Zappos and Gusto are two companies, featured in the below links, that wondered the same thing. They got rid of job titles in their organizations because they believed it would strengthen their company culture and put the focus back where it needs to be - on a good day's work. They claimed titles created barriers, unnecessary power distance and prevented the flow of creativity and growth. I give these organizations props for test driving this "No Job Title" idea. It's a brave thing to do.

However, as career practitioner, I'm in the business of work search and career management so I clearly understand that job titles are still used for necessary markers of negotiation, promotion and access into higher paying positions within an organization. However, as a portfolio careerist (someone who streams income from multiple sources) I don't pay as much attention to job titles because I'm not necessarily looking to climb a ladder. I'm building a portfolio tree where the focus is on creating income streams, building relationships and looking for opportunities to add benefit and value. The portfolio style of work does blur the boundaries that bind us to job titles, and challenges us to view work in a new way.

This doesn't mean we have to end all job titles in the workforce. That isn't realistic. However, if you read the articles below on organizations that have eliminated titles, it is an interesting concept to just get rid of them altogether to see if that frees us up to work differently. Personally, I would just like to see us relax a little around job titles in our culture. It would be really nice for a job seeker to feel comfortable taking a lower paid job that has less status because for them it is a wiser thing to do for their long term financial freedom. I would prefer that job seekers not be scared of what that "outside of their industry" job would look like on their resume, or be concerned about what their friends would think.

In our current economy, many career development specialists and recruiters suggest that job seekers become open, flexible and be willing to do something new because these are valuable skill sets that employers prefer to see in potential candidates. I know we aren't going to completely eliminate job titles, at least not yet. It appears the world of work is not yet ready for Zappos CEO's Holacracy concept. I guess the "No Job Title" idea was too confusing. Nonetheless, could we please just relax a little and meet the needs of an organization that needs our help? 

I would like to end with two quick stories. I met a woman a few months ago who was a laid off accountant from the oil and gas industry and she was helping out her friend who owns a restaurant. She was serving, working in the kitchen, and doing whatever needed to get done. She said she didn't necessarily have a job title, but she added, "I quite like the variety and I can't believe I'm saying this, but I don't know if I'm going back to what I did before." She was exploring new options.

I recently learned that an old family friend had lost their job. He worked for oil and gas too. Surprisingly, through connections, he landed a new job building sets for a film. After building one set, he now has more projects in the film industry lined up. Who knows, he may be headed in a new career direction. 

What I learned from these stories? If we just relax a little around our job title and meet the needs around us, we not only can find work, we just never know where something new may lead us.

Click on these links for articles on eliminating job titles:

Companies without job titles: Gusto

Impact of job title removal: Zappos

Here are the Benefits of Working Multiple Part-time Jobs

Having difficulty breaking into an occupation? Do you need flexibility in your work life? Would you like to get started in an industry? If job seekers are strategic, streaming income from multiple salaried part-time jobs can have countless benefits. It can be beneficial to new graduates starting their careers, job seekers moving to a new city, province or country and for people who are transitioning into a new occupation or industry. Workers can leverage opportunities, build a larger network, gain valuable experience and pay bills (not a bad idea).

I have had three major career changes in my life, and I have used this strategy to break into a new occupation and industry each time. Out of high school, I trained to become a legal office administrator. I was test driving law as a potential career direction. After working in the industry, I decided this wasn't a path I wanted to pursue with a degree, and I retrained to become a teacher. After five years of studying, I graduated into a recession with stiff competition from laid off, experienced teachers. School divisions were downsizing and there were few full-time jobs. I did get interviews but no jobs offers. The response from employers, "We hired someone who had experience."

It was an extremely frustrating experience because the logic didn't add up. How was I supposed to get experience when no one would give me a job? I clearly needed a strategy. After a few days of sitting on the couch watching old reruns of Oprah, I pulled myself together and strategized. I pieced together four part-time jobs to help me financially weather the recession, while building skills and a much needed network into the teaching industry.

To accomplish this, I tapped into my contacts and through my roommate found a part-time job in a daycare to build experience working with younger children. I then talked to a teacher who informed me that the entry point into teaching was through subbing. I applied for the sub-list and worked two jobs as a substitute teacher to build my network into schools. I kept my part-time banking job (that put me through university) because I could work evenings and weekends, plus it provided me with full dental and eye care benefits. It was also my back-up career plan.

I will admit, it was a juggling act, and I sometimes answered the phone at the bank using the name of the daycare. However, it was worth it. Within 10 months, I was offered a temporary full-time teaching job that turned into a permanent full-time position six months later. In the interview, the school division was impressed with my ability to juggle multiple commitments. They apparently believed if I could juggle four jobs, I could manage a classroom of 30 grade three children.

““I will admit it was a juggling act and I sometimes answered the phone at the bank using the name of the daycare.” ”

I have also worked multiple jobs to launch a career in another country. Fast forward a few years to when my husband and I moved to Japan to teach. We did our research, talked to teachers coming back from Japan who encouraged us to work multiple part-time jobs. With this style of work, we would have the freedom to work for whomever we wanted and take more vacation time (big bonus). Upon our arrival, we pieced together part-time work, and a private business, creating six streams of income and the ability to create our own schedule and have more time to travel throughout Asia. This strategy also eventually increased our network leading to a full-time job and more lucrative part-time contracts.

I have also worked multiple jobs when I have transitioned from one occupation and industry to another. Fast forward again to when I decided to move into the career development field. I was working as an academic/career advisor/international student coordinator/ESL teacher (yes, that was one job) in a high school when I decided to move into the career development field. I quit my job so I would have time to explore other options.

While researching and talking to people in the career development industry, I worked part-time teaching English as a Second Language to adults. I wanted to add adult education experience to my skills and I needed to pay my bills. It was through my part-time work that I was "discovered" in the lunch room by Carol, a supervisor of a work placement program. She offered me the opportunity to job shadow which turned into a full-time job offer. By having a conversation in the lunch room, I had tapped into a hidden opportunity in the career development industry through my part-time teaching job. From this experience, I learned that we can't underestimate the power of just getting ourselves into the building.

Savvy portfolio careerists know that working for multiple companies part-time gives them more opportunity to share their skills, double the potential for promotion, a larger network and double the potential to learn and be mentored. It also provides the opportunity to explore various industries, learn first-hand about potential career pathways, jobs that are dying out and work that is emerging within the hidden job market.

Strategizing and working multiple part-time jobs can create opportunity and beats sitting on the couch watching Netflix and the bills stack up. However, nothing is perfect. And, because nothing is perfect, in my next post, I will hash out the challenges associated with working multiple part-time jobs.