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When is it time to start your legacy career?

February 16, 2023

Contract work is gaining traction after full-time careers

From SeasonedPros.ca Insights Lab

Increasingly Canadian workers are trading the responsibilities of full-time careers for the freedom and flexibility of contract work. 

Sometimes they work in the same job or industry as a freelance consultant. 

In other cases they start a whole new type of job, applying the skills and experience developed through their corporate career. They might want to work for a start-up or give back to a favourite nonprofit.

This is defined as a legacy career

Legacy workers tend to fall into two broad categories: those who can’t afford to live on current savings and those who aren’t ready to give up work because they want to stay engaged and active.

Even if they qualify for pension benefits, it doesn’t mean that a life of leisure is going to be financially sustainable or personally satisfying. 

A legacy career can be full-time, but more often these jobs are contract-based.  Seasoned professionals work in roles that are fractional, interim or project-by-project. A legacy career can also be volunteer work. 

Here are a few reasons professionals decide to transition into legacy careers:

  • No longer enjoying the time and demands of a full-time career 
  • Laid off but don’t wish to return to full-time
  • Want the variety that comes with multiple contracts
  • Stay in touch with former work colleagues 
  • Remain mentally engaged and stimulated
  • Need income to cope with inflation, economic uncertainty and a longer life expectancy
  • Seeking a sense of purpose
  • Wanted to give back to a non-profit or charity
  • Desire for more freedom and flexibility of remote and occasional work


Once someone has made the decision to leave a full-time career, they need to ask themselves questions and do their research.

How do you prepare for a legacy career:

  • Decide what motivates you 
  • Do you want to do the same work or try something new?
  • How many hours do you want to work in a week or a month?
  • How much time off do you want and when do you want it?
  • Review your skills and research jobs that match them
  • Take a course to upgrade your skills
  • Dust off your resume and research different presentations styles and formats
  • Review your finances to be sure that a legacy career will be financially sustainable
  • Set up an efficient, quiet home office for remote working and video calls
  • Research the costs and benefits of private health and dental insurance
  • Speak to your accountant to understand tax implications
  • Consider whether you are prepared for the precarious nature of contract work


The key to developing a successful legacy career is to prepare in advance. 

Do the research and talk to other legacy workers and contractors to find out what this work and lifestyle are really like. Be sure that you are ready to leave the security and benefits of full-time work. 

And open your imagination to a horizon of new possibilities.

SeasonedPros.ca is an on-demand business talent source. Clients with an immediate need for experienced talent trust us to source professionals for project, interim and part-time roles. Each professional in our national database has 20 + years of business experience. We provide our clients 2-4 four vetted professionals in 10 business days or less.


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