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THE QUESTION
I’m a data analyst working for a small company. I plan to resign and become a full-time freelancer. I have a feeling that the company will struggle when I’m gone. I would like to offer my support as a freelancer while they transition to finding my replacement. I could really use the additional income, too, as I grow my freelance career, so it feels like a win-win. What are the ramifications of this? Should I ask at the same time as resigning or afterward? Do you think HR is likely to shut this down? How do I go about offering my freelance services in a tactful way?
THE FIRST ANSWER
Dr. Candy Ho, board member, CERIC; researcher and educational studies instructor, Kwantlen Polytechnic University, Burnaby
What stands out to me in your question is the combination of empathy and organizational awareness. You recognize that your departure may create a gap and you’re proactively thinking about how to support continuity.
There typically aren’t major ramifications to making the offer (unless you are being pushy). The bigger question is whether your employer sees value in it and whether there are internal policies (sometimes driven by HR or procurement) that shape how external contractors are engaged. In some organizations, this kind of arrangement is straightforward; in others, it may take more time or approvals. This is beyond your control.
I would suggest raising this at the same time as your resignation. It plants a seed early and frames your departure as a transition plan. Don’t over-explain; simply express that you’d be open to supporting the team on a freelance basis during the handover period. Then give them space to consider it.
It’s also worth doing a bit of homework beforehand. Has anyone in your organization made a similar transition? Having precedence can make your proposal easier to accept.
Speaking from personal experience, these situations can unfold in different ways. Sometimes the answer is no at first, only to become a yes later, once the reality of the gap sets in. Other times, leaders get creative with short-term contracts or retainers. Once, a former supervisor added two additional days to my last paycheque for me to facilitate training for my former team. Flexibility on both sides helps.
Ultimately, this is an early opportunity to practice what freelancing will consistently require: articulating your value and advocating for your work. You’re on your way to positioning yourself as a strategic partner – well done.
THE SECOND ANSWER
Julie Labrie, President, BlueSky Personnel Solutions, Toronto
This could be a win-win situation, but only if you handle the timing and frame your offer carefully.
Raise the freelance offer at the same time as your resignation, not afterward. Coming to the table with a solution on the same day signals professionalism and goodwill – it shows you’re thinking about the company’s continuity, not just your exit.
Before that conversation, review your employment contract. Many agreements include clauses around non-compete arrangements, intellectual property or post-employment restrictions that could affect how you structure freelance work with a former employer. Understanding what’s in your contract lets you walk into that meeting informed. If you do find a restrictive clause, it’s worth getting clarity on what it means for your situation before the conversation – being caught off guard in that meeting is the last thing you want.
Be prepared for the fact that some companies, once notice is given, will walk you out the same day – it comes down to company policy. Go in with realistic expectations and have a plan in the event this happens. They may or may not accept your offer for freelance work and you must respect their decision.
If they are open to hiring you as a freelancer, they will most likely establish a timeline with you. If no end date is provided, it is advisable for you to propose a reasonable end date. Setting a clear final deadline encourages the company to seek and onboard a suitable replacement promptly. Without such boundaries, there is a risk of ambiguity between contractor and employee roles. A well-defined agreement benefits both parties and, should additional support be required beyond this period, terms can be renegotiated accordingly.
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