A rideshare driver's aunt left him a bookkeeping business, not just its shares

The situation

The envelope sat on Soo-jin's kitchen table for two days before she opened it. Inside was a letter from a Thunder Bay law office, informing her that her aunt Tigist had passed away and that Soo-jin was named in her will. Soo-jin drove for a rideshare service most days of the week and had not spoken to a lawyer about anything more complicated than a lease before, and the formal letterhead alone was enough to make her put off opening it. She eventually brought the letter to our office with a friend translating parts of the conversation, since her spoken English, while functional for daily life and for the driving work she did, was not built for legal terminology or the weight of what the letter was actually describing.

Tigist had spent close to fifteen years building a small bookkeeping practice in Thunder Bay, serving a loyal roster of local trades businesses and sole proprietors who valued her by name and had stayed with her through every tax season for years. The practice was not large by any standard. Between its client contracts, modest office equipment, and a small operating account, Tigist's estate, including the business itself, fell somewhere between $120,000 and $300,000, most of that value tied up in the ongoing relationships the business had built with its clients rather than in any physical asset that could simply be appraised and sold.

Tigist's will, prepared years earlier by a different firm entirely, left the bookkeeping practice to Soo-jin, but not outright and not immediately. Because Soo-jin was still young at the time the will was written and had no bookkeeping background herself, Tigist had structured the gift as a trust, naming her long-time friend Dawit as trustee, with instructions that the business be held and eventually transferred to Soo-jin once she was ready to take it on, or sold for her financial benefit if it turned out she was not interested in that path.

The problem surfaced within days of Tigist's death, when Dawit, trying earnestly to do right by his old friend, discovered that the trust document said almost nothing about what he was actually allowed to do with the business on a day-to-day basis. It named him trustee of the shares in clear enough language, but it was silent on whether he could sign new client contracts, pay the practice's part-time assistant, or make the ordinary operating decisions needed to keep the business functioning while everyone else figured out what Soo-jin's role would eventually be.

What was actually at stake

A testamentary trust, the kind created by a will rather than during a person's lifetime, can hold almost any kind of property, including shares in a small operating business. But holding shares and running a business are two very different things, and a trust document that only grants a trustee the power to hold property does not automatically grant the power to operate it in any active sense. Ordinary default trustee powers are built around managing investments prudently and conservatively, not around signing contracts, hiring or paying staff, or making the daily judgment calls a small service business needs simply to keep functioning from one week to the next.

Tigist's will fell into exactly this gap. It transferred the shares of her practice into the trust cleanly enough on paper, but the powers clause, drafted years earlier without much thought given to the fact that the trust's main asset would be an active, client-facing business rather than a passive portfolio of investments, gave Dawit authority to hold and eventually distribute the shares but said nothing at all about operating the business in the meantime. Without express authority spelled out in the document, Dawit was left in a genuinely uncertain position: acting too boldly risked exceeding his authority as trustee and exposing himself personally, while acting too cautiously risked the practice's clients quietly drifting away to another bookkeeper within a matter of weeks.

The stakes were concrete and, importantly, time-sensitive rather than abstract. A small bookkeeping practice's value lives almost entirely in its client relationships and in the trust those clients place in continuity of service from one season to the next. Several of Tigist's clients had year-end filings due within two months of her death, and if Dawit could not confidently sign engagement letters or communicate with the tax authority on the practice's behalf during that window, those clients would reasonably look elsewhere for help, and the business Soo-jin was meant to eventually inherit would be worth only a fraction of what it had been.

There was also a real question of what Soo-jin herself actually wanted out of all this. She had no bookkeeping training and had never expressed any interest in running the practice herself before the letter arrived, and the will's language had anticipated that possibility by allowing a supervised sale for her benefit as an alternative. Sorting out the trustee's powers mattered regardless of which path Soo-jin eventually chose, because a business that had lost its clients while everyone waited would not be worth transferring to her or selling on her behalf for anywhere close to its real value.

What we did

1. Reviewed the trust language in Tigist's will against what the business actually needed day to day, identifying the specific gap between the power to hold shares and the power to operate the underlying practice, so we could describe the problem precisely rather than in general terms when advising both Dawit and Soo-jin at their first meeting with us.
2. Arranged a professional interpreter for our meetings with Soo-jin so she could participate fully and confidently in decisions about her own inheritance, rather than relying on a friend's informal translation for a decision this significant, and confirmed her understanding of each option available to her, in her own language, before any irreversible step was taken.
3. Advised Dawit on his interim authority as trustee under general trust law principles, identifying which day-to-day actions, such as paying the practice's part-time assistant and maintaining existing client files, were defensible as reasonable preservation of trust property even without express operating powers written into the will, while clearly flagging which actions carried real personal risk for him.
4. Applied to the court for directions confirming that Dawit could take specific, clearly defined steps to keep the practice operating through the transition period, giving him formal protection for decisions that the will's own language did not clearly authorize on its face. The application spelled out each power being requested rather than asking for open-ended authority, which let the court respond quickly and gave Dawit a document he could point to if a client or family member ever questioned his authority.
5. Prepared a short-term operating protocol for Dawit to follow in the meantime, covering client communication, fee collection, and permitted use of the practice's operating account, so the business could keep serving clients through the busy year-end filing period without Dawit exceeding the authority the court had confirmed for him. The protocol gave him a written reference to check any borderline decision against, rather than calling our office every time a new situation came up during the busiest weeks of the year.
6. Met with Soo-jin over several separate sessions, spaced out over a few months, to walk through what actually taking over the practice would involve day to day, against the alternative of a supervised sale, so her eventual decision was genuinely informed rather than made hastily under the pressure of the surrounding uncertainty.
7. Drafted a formal variation of the trust powers, agreed to by Dawit and approved through the appropriate court process, expressly granting the trustee authority to operate the business, sign client engagements, and manage staff until the shares were finally transferred to Soo-jin or sold on her behalf. Getting the variation formally approved, rather than relying on the interim protocol indefinitely, gave the arrangement a permanent legal footing that would hold up regardless of how long Soo-jin took to decide.
8. Coordinated the eventual share transfer to Soo-jin once she confirmed her decision to keep the practice, including basic corporate filings and a handover plan with Dawit so client service continued without any visible interruption during the changeover. Dawit stayed on informally through the handover to introduce Soo-jin to the practice's clients personally, which mattered for a business built on long-standing relationships rather than on paperwork alone.

The outcome

The practice kept every one of its major clients through the transition period, including the group with year-end filings due within the first two months after Tigist's death. Dawit, now working with clear and formally confirmed authority, signed the necessary engagement renewals and kept the part-time assistant on staff throughout, and the business's revenue through that period held roughly steady against the prior year rather than dropping off, which it plausibly could have done during a prolonged period of unclear authority.

Soo-jin ultimately decided, after several months of reflection and with a much clearer picture of what the work would actually involve, that she wanted to keep the practice rather than have it sold on her behalf, and began training informally under Dawit's supervision while continuing to drive part time to cover her own expenses in the meantime. The shares were transferred to her once the trust's terms allowed it, by which point the business was worth close to what it had been at the time of Tigist's death, rather than a diminished, client-depleted version of it.

The file was, in the end, a clean example of catching a drafting gap before it quietly cost anyone anything real. Tigist's will reflected genuine care and thought about who should ultimately receive her business and under what conditions, but it had not been drafted with a close enough eye to keeping that business alive and functioning during the months a trust would actually hold it. The court application and the operating protocol together closed that gap in time to matter, and the practice Soo-jin now owns is, by every meaningful measure, the same one her aunt spent fifteen years building, not a shadow of it.

What you can learn from this