Skip to main content
nine to five
The Question

I’ve been working for the same employer for eight years and I have a great relationship with my boss. He has promoted me several times and believes in my skills. I manage a team of six people as a department director, but I miss the simplicity of my former role as an analyst. I plan to quit my job and start a career as a freelance consultant. My industry is very small so I want to keep on good terms with my current company and do freelance work for them. But I don’t think my boss is going to take it well. What’s the best way for me to approach this resignation?

The First Answer

Yvonne Ruke Akpoveta, change management strategist and adviser, OliveBlue and the Change Leadership, Toronto

You mention you don’t think your boss is going to take it well. Is this what you assume your boss will do based on how well you know him? Or is this based on how you’ve seen him respond to other people leaving?

If you’ve seen how he has previously responded to others leaving, use that knowledge to help you determine how you approach your resignation in a manner that you believe he may be more receptive to.

You mention having a great relationship with your boss. If so, he is more likely to appreciate a candid and open discussion. Schedule time to have an open discussion. Express your gratitude for the opportunities you’ve been provided, outline your reasons for leaving and share your plans to start as a freelancer and why it is important to your professional development and goals. Have your resignation letter ready or send it immediately after the meeting. As well, agree on what the next steps will be in terms of sharing the news with your team, your notice period and the transition process.

Considering you are not leaving to a competitor or another organization, your boss may be more likely to graciously accept your decision, and be supportive of your plans and transition toward being a freelancer. Also, you could offer to give a longer than required notice period to help with transitioning your role to the right person. This will help build goodwill and capital for your freelance work and referrals.

The Second Answer

Colleen Clarke, workplace coach and career specialist, Toronto

Congratulations on plans for starting your own consultancy practice. You have flourished at the company, under the support of a great leader. Set a meeting with your boss before you give notice to anyone. Explain to him that, at least partially, due to his direction and support you are going to make this exciting change. And it would mean the world to you for him to give you his support and to continue working together and make great things happen.

If he is not as supportive as you would like, be prepared to outline to him how you came to make the decision. Give specific examples of how his guidance assisted you in preparing for this move. Ask him if he would be willing to act as a mentor in the early stages of your self-employment. Tell him you know it is difficult when people move on, but you know he will hire someone good to replace you.

If it is appropriate, offer to help recruit your own replacement. Chances are he won’t ask you to, but if made in good faith, that may help buffer the blow somewhat. The role of a great manager is to build strong individuals and teams, so they look good and the employees flourish and grow. Please don’t feel guilty. People leave jobs. This is business, this is not personal. Successful employees are an extension of strong leaders.

Have a question for our experts? Send an e-mail to with ‘Nine to Five’ in the subject line. Emails without the correct subject line may not be answered.

Stay ahead in your career. We have a weekly Careers newsletter to give you guidance and tips on career management, leadership, business education and more. Sign up today.