Wills, Estates, and the Quiet Craft of Succession Planning

Ask a room of law students what kind of lawyer they want to be, and you will hear litigator, corporate deal-maker, maybe Crown prosecutor. You will almost never hear "I want to draft wills." Which is a shame, because wills and estates is quietly one of the most rewarding corners of the profession, and one of the few where you get to sit with people at the actual turning points of their lives.

I did not plan to end up here. I fell into an estates file during articling because someone senior was on vacation, and I stayed because the work turned out to be nothing like I expected. It is not dusty. It is not slow. It is careful, and there is a real difference.

What the work actually is

Strip away the stereotypes and estate planning is about one deceptively simple question: what happens to a person's life once they are no longer here to manage it. That pulls in a surprising range of law. Property, tax, family, trusts, capacity, and a fair amount of plain human psychology.

On a given week you might draft a will for a young couple who just had their first child, help an elderly client set up a power of attorney before a surgery, and untangle an estate where three siblings have not spoken in a decade. The legal instruments repeat. The people never do.

There are broadly two sides to the practice, and most solicitors lean toward one:

• Planning. Drafting wills, powers of attorney, trusts, and beneficiary structures while the client is alive and well. This is proactive, relationship-driven work.
• Administration. Guiding executors and families through the process after a death, including probate applications, gathering and valuing assets, paying debts, and distributing what remains.

Some lawyers also drift toward estate litigation, which is a different animal entirely: will challenges, dependant support claims, and fights over capacity. If you want the courtroom, that door is open too, though it tends to sit closer to the litigation bar than the solicitor's desk.

Why the craft matters more here than almost anywhere

In a lot of solicitor work, a small drafting slip gets caught and corrected. In estates, the person whose intentions you captured is often gone by the time anyone reads the document closely. There is no calling them back to ask what they meant. The words on the page have to carry the full weight of a life's wishes, on their own, possibly decades later.

That changes how you work. You learn to write with almost obsessive precision, because ambiguity in a will is not an inconvenience, it is a lawsuit waiting for a grieving family. You learn to think several steps ahead: what if this beneficiary dies first, what if the client remarries, what if the estate is worth ten times more than it is today.

An estates lawyer I trained under used to say the client is not the person sitting in front of you. The client is the family sitting in your boardroom fifteen years from now, and you will never meet them. Draft for them.

That line reshaped how I approached every file. You are not just recording wishes. You are building something that has to survive contact with real people, real grief, and real money.

The human part is the job, not a bonus

Here is what surprised me most. The technical drafting is maybe half the work. The rest is sitting with people through conversations most of us instinctively avoid.

Clients come to you thinking about death, sometimes for the first time in a serious way. They arrive with old resentments, guilt about favouring one child, second marriages with tangled loyalties, a business they built and cannot bear to imagine handing over. Your job is to hear all of that clearly enough to translate it into a plan that holds.

This means asking gentle but direct questions that other people in their life will not. Who did you leave out, and why. What happens if your spouse remarries after you are gone. Are you sure you want your son, who has never managed money, as your executor. These conversations require patience and a steadiness that no course teaches you. You develop it by doing it, badly at first, and then better.

If the idea of that appeals to you more than it frightens you, that is a strong signal. It is also worth reading a little about protecting your own mental health in law, because holding space for other people's hardest decisions has a cost, and estates lawyers carry more of it than they usually admit.

Skills that quietly compound

Estate planning rewards a specific mix of traits, and the good news is that most of them are learnable:

1. Precision in writing. Every clause is a small act of engineering. If you enjoy getting language exactly right, you will feel at home here.
2. Patience with detail. Asset lists, beneficiary designations, and tax implications reward the person who checks the boring thing twice.
3. Emotional steadiness. You will meet people on some of their worst days. Calm is a professional skill, not just a personality trait.
4. Long-term thinking. The best planners see around corners, anticipating problems that may not surface for a generation.
5. Discretion. You will know more about a family's private life than almost anyone. That trust is the whole relationship.

None of these show up on a transcript. All of them show up in whether a client refers their sister, their neighbour, and eventually their adult children to you.

What a career here can look like

One underrated feature of this practice is its shape over a lifetime. It is durable. People will always need wills, and the demographic reality of an aging population means demand is not going anywhere. It also tends to offer more humane hours than deal-driven practices, which is part of why it draws lawyers who want a sustainable career rather than a sprint.

You can build it almost anywhere. A solo practitioner in a small town can run a thriving estates practice serving the whole community, while a specialist at a larger firm might handle complex cross-border trusts and estate tax planning for high-net-worth families. The range between those poles is enormous, and it is one reason the small firm versus Bay Street question plays out so differently in this area than in, say, corporate work. Estates practice genuinely thrives at both ends.

Compensation tends to be steady rather than spectacular, closer to the solicitor's range than the peaks of high-stakes litigation or M&A. What you trade for that is a practice you can grow for thirty years, one relationship at a time, without burning out in the first five. For many lawyers that is a very good trade.

If you are still exploring where you fit, browse the other practice area guides to compare the texture of the work, and keep an eye on current articling and legal job postings that mention wills, estates, or trusts. Firms that do this work well are often smaller and easy to overlook on the big recruit calendars.

How to get a foot in the door

If this practice interests you, a few concrete steps help more than good intentions:

Seek out a firm or a solicitor who actually does estates work and ask for exposure to it during articling, even if it is not your main rotation. Many students never see a will drafted end to end, so a little curiosity stands out. Community legal clinics and pro bono programs sometimes run simple wills projects, which are an excellent low-pressure way to learn the mechanics and to find out whether the client conversations energize you or drain you.

Read real wills and estate plans, not just casebooks. Precedent files teach you how experienced drafters actually structure things, and the gap between a textbook clause and a battle-tested one is instructive. If you want to understand how any solicitor's file gets staffed and billed, the billable hour explainer is worth a read, because estates work is often billed in a blend of hourly and flat-fee arrangements that trips up newer lawyers.

Finally, talk to someone who has practised in the area for a decade or more. The provincial law societies, coordinated through the Federation of Law Societies of Canada, can point you toward sections and mentorship programs where those practitioners gather. Almost all of them will tell you some version of the same thing: they came for the law and stayed for the people.

The quiet reward

Litigation gives you the adrenaline of the win. Corporate gives you the thrill of the close. Estates gives you something slower and, in my experience, more lasting. A client sits across from you, unsure and a little frightened about the future, and leaves with a plan that lets them stop worrying. Years later their family opens a clear, careful document at a moment when clarity is the kindest thing they could possibly receive.

That is the quiet craft of it. You spend your career making sure that when people are no longer able to speak for themselves, their wishes still do, gently and exactly. Not many kinds of law let you do that. This one does, every single day.