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Earlier this year, I connected with Rachel Gold, the co-editor of the newspaper for the Ontario Bar Association's Tax Section and an associate at KPMG Law LLP. The result of our collaboration was this Q&A session WOMEN LAWYERS IN TAX: Q&A WITH ANNA MALAZHAVAYA, SOLE PRACTITIONER AT ADVOTAX LAW, published on the OBA website on May 30, 2020.

Although the original article was published in the Women Lawyers in Tax section, I believe our discussion with Rachel raises issues that may be interesting to anyone entering the profession. Today on the blog I am sharing an excerpt from the Q&A session.


"What advice would you give to your younger self when you started out as a woman in tax law?

I would have been frank with my younger self and have told her that the first five years would be rough. There are no shortcuts to becoming an excellent tax lawyer. If you are a tax planner, technical proficiency takes time. Work hard, read, write, present/speak, then read some more. Find a good mentor. Publish at least one article per year and be strategic when choosing a topic. Become an excellent writer. Stay current on everything coming out of the courts, the CRA, and the Department of Finance.

If you are a tax litigator, find a good mentor. Take pro bono informal procedure cases. Check the TCC’s hearing schedule and make time to watch the best tax litigators in action. In your practice, know your facts. Know the evidence rules. Be organized. Know the law. Know the judge assigned to your case. Keep a list of all the practical/strategic things that worked for you in the courtroom. Stay current on all developments. Practice, overprepare, ask for feedback, and practice again. 

Prepare yourself for the possibility of major bumps on the road, especially if you plan to have or if you have young children and don’t remember what “not tired” feels like. Keep things in perspective: your tax law career can last 40 years, but your babies won’t stay up all night and keep you exhausted for 40 years. You still have decades of an exciting and rewarding career ahead of you. If you love the practice of tax law, don’t quit.

What strategies have you used to progress in your career? I see you began your career at a large law firm and then transitioned to a small firm environment. Do you have an ‘a-ha’ moment that you can share.

You can (and should) customize a career plan for yourself. Your firm’s generic plan for tax associates’ professional development is probably excellent, but their vision of your professional success may or may not be similar to your vision. Make sure to have your own plan.

Consider these questions: How do you imagine an ideal day/year/decade of your career? How much money do you want to make? Do you want to be recognized in the tax publishing community? If so, in what area of tax? How important is it for you to have your own book of business? If it is, what kind of clients can you attract? If it is not or if you want to avoid marketing at all costs, how do you make sure your job is secure? How many hours do you want to bill per year? How many weeks of vacation do you want? How much time are you willing to spend commuting to work? How important is it for you to challenge yourself with complex cases? What kind of people do you want to work with? Do you want to be home before dinner every day (or most days)?

Write down the answers to all these questions, analyze them, talk to people, and eventually you will know your ideal role/job in the tax legal community. Now that you know where you are going, figure out how to get there, and when you do, enjoy your “a-ha” moment.

In my case, as a young lawyer, my goal was to have an opportunity to learn from the best lawyers in the country. As a more senior tax lawyer, my mission is to provide Bay Street quality service to my own book of small and midsize business clients. My commute is 10 minutes door-to-door, and my hours are quite flexible most of the time.

Have you had mentors or sponsors during your legal journey? Are they tax lawyers or lawyers in other areas? If so, how has your relationship with them changed over time?

Mentors are vital. Every good tax lawyer I know is fortunate to have had an equally brilliant mentor. They are your teachers, your biggest critics and supporters, and your “Phone a Friend” lifelines. If you’re really lucky, over time, they may become your friends.

All my mentors are tax lawyers. Chris Norton, Ken Snider, Richard Yasny (to name a few)—thank you, I am forever grateful.

If you do not have a mentor and don’t know where to start, check out the book, Lean In by Sheryl Sandberg. It has an excellent chapter about mentors. If you are still struggling, send me an email!"


The full text of the Q&A session can be found here.

I was serious about inviting struggling new tax lawyers/law students to send me an email then, and I am still serious about my offer now. My email is I'll be happy to have a coffee over Zoom and chat with anyone entering the profession. The Canadian tax legal community is small but mighty.

Nothing in this article constitutes legal advice and no solicitor-client relationship is created. If you require legal advice pertaining to your specific situation, please contact our tax lawyer.

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