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Preparing Workers for the World of Freelancing

How career development professionals can support clients

By Tammy Donovan


It is commonly accepted knowledge that the world of work is changing considerably. Full-time jobs are becoming less common and a growing number of workers are expected to make a living by freelancing, or combining part-time and project-based work. Statistics Canada data indicates that all jobs created in 2016 and a large majority of jobs created in early 2017 were part-time jobs. The shift from lifelong employment toward freelancing raises an important question for career development professionals (CDPs): how can we help prepare workers for the changing nature of work?

A good place for CDPs to start is by considering some big picture issues and differences between freelancing and full-time employment that are likely to have an impact upon the type of help required by freelancers.


Big picture issues

There are at least two big picture issues that are likely to influence the type of help freelancers require: stage of career and motivations to freelance.

CDPs are likely to work with late- and mid-career workers transitioning into freelancing, and aspiring workers who build careers out of freelancing and never hold full-time jobs. These groups are likely to have overlapping concerns and distinct needs. For example, all workers may need help coping with anxiety arising from a lack of job security. Transitioning workers may need help with learning to self-promote, and adjusting to unstructured workdays and working independently, and mastering technology that allows them to work remotely. Aspiring workers may need help learning practicalities that previously would have been learned in the workplace, such as negotiating, resolving complaints diplomatically and navigating organizational cultures.

CDPs are also likely to help workers with a range of motivations for freelancing. Highly skilled workers may want to freelance to boost income or increase autonomy/flexibility, and seek help with marketplace analyses or business development. Low-skilled workers may need to freelance due to unavailability of full-time employment, and seek help with devising long-term plans to build up skill sets, and obtain more stable or lucrative employment.


Differences between freelancing and full-time employment

There are many differences between freelancing and full time employment that are likely to have an impact upon the type of help freelancers require from CDPs:

• Organizational knowledge

Freelancers possess less organization-specific knowledge than employees and do not understand organizational culture as well as employees. HR staff often complain these factors render freelancers less capable of making immediate contributions to projects.

CDPs can help freelancers by providing information about the benefits of developing organizational knowledge and understanding organizational culture, and teaching efficient strategies for researching organizations.

• Entrepreneurial skills

While entrepreneurial skills are relevant to employees seeking to advance within organizations, freelancers cannot succeed without them.

CDPs can help freelancers by working to change prevailing views regarding entrepreneurship. In a labour market that will force some workers to freelance, it is helpful to frame entrepreneurship as a set of skills that can be cultivated, rather than an innate quality.

CDPs can also help freelancers to develop and enhance skills associated with entrepreneurial success, such as continuous learning and development; marketplace awareness, trend-spotting and innovation; opportunity seeking and career insight (i.e., knowing which jobs to accept to build a strong reputation and resume); persuasion and negotiation; creative problem solving; tolerance for risk and failure and resiliency; and understanding value propositions and market differentiation (e.g., differentiation based on quality vs. cost of products and services; specialization vs. range of products and services; innovative vs. traditional products and services).

• Career Identity and satisfaction

Given the piecemeal nature of project work, freelancers may find it more difficult than employees to map out clear career paths, develop a sense of professional identity and understand how their work contributes to organizational goals and society as a whole.

CDPs can help freelancers understand their motivations and values, build professional identities and foster awareness of their contributions.

• Career progression

Employers are willing to invest in the training and growth of employees, but seek to hire only experienced, job-ready freelancers. Given this, freelancers may find themselves accepting routine, unchallenging work and struggling with career progression.

CDPs can teach freelancers about ways to secure skill-building work, such as volunteering; discounting fees; seeking projects with small skill-building components or that may lead to other skill-building work;; describing previous work to potential employers in ways that highlight similarities to skill-building work; and building collaborative relationships that may lead to referrals for skill-building work. An innovative way for freelancers to build collaborative relationships (while combating isolation) is through joining co-working collectives that are popping up in major cities or participating in business incubator programs.

• Balancing doing work and getting work

Most employees spend their time completing work, not getting it. Freelancers need to balance doing work and getting work. Too much focus on doing work can lead to extended gaps between projects, lower income and increased anxiety. Too much focus on getting work can lead to rushing to complete existing projects, doing mediocre work and feeling overwhelmed.

CDPs can help freelancers develop different work habits and reconfigure work schedules to achieve balance.

• Collecting fees and mitigating risk

Unlike some employees, all freelancers need to be comfortable with discussing and collecting fees from employers and to be aware of the difficulties involved with collecting overdue payments from employers (especially ones in other countries).

CDPs can help freelancers by providing coaching about how to discuss fees and collections, and providing information regarding risk mitigation strategies, such as requiring retainers, collecting interim payments, or implementing short billing cycles.

• Feedback and promotion

Unlike employees, freelancers do not automatically receive project feedback or performance reviews. Given this, freelancers need to find ways to obtain feedback that can be used to improve their work and promote themselves to potential employers.

CDPs can help freelancers by coaching them on how to boost ratings on online work platforms like UpWork and Freelancers; how to secure testimonials and respond to feedback; and how to build work portfolios.

• Benefits, supports and legislative rights

As independent contractors, freelancers do not enjoy the same extended benefits or legislative protections as employees. As freelancing becomes more common, we can expect to see changes to relevant legislative frameworks and new organizations emerge in support of freelancers. For example, Ontario is currently reviewing its legislative framework (see for information); freelancers can opt into the Employment Insurance regime; organizations supporting freelancers have appeared (e.g. Canadian Freelancing Union, CMG Freelance, Urban Worker Project), and benefit packages designed for freelancers are available (e.g. COHIP). CDPs can help freelancers by staying abreast of these developments and educating both young freelancers (who may not be aware of legislative rights or supporting organizations) and older freelancers (who may not be aware of legislative changes or new organizations).

Based on this brief review, it is clear that as the world of work changes, workers will require different forms of support and the role that CDPs can play will evolve in exciting ways.



Tammy Donovan is completing a Master’s of Counselling Psychology. She is a former lawyer who looks forward to helping people with everything from job applications to major career transitions like hers. She is also interested in building a stronger community of career counsellors in Vancouver, BC and would love to hear from others looking to do the same. You can reach her at

Lucie Morillon
Lucie Morillon is the Bilingual Content & Communications Co-ordinator for CERIC. With a passion for quality content, she connects with her online communities and provides strong resources to engage members – and always encourages new ones to get involved. She identifies, creates and curates the content destined for the ContactPoint website, the weekly CareerWise newsletter and Careering magazine.

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