You're Not Alone: The 5 Most Common Questions from Business Owners After They Sell

Selling your business is a landmark achievement, but it's often a strangely isolating experience. The people in your life, while supportive, likely don’t understand the unique cocktail of emotions and anxieties you're navigating. The identity you held for years has vanished overnight, replaced by a complex new reality.

If you’re feeling a mix of elation, uncertainty, and even a little bit of fear, know this: you are not the first person to feel this way. In our work with entrepreneurs who have navigated this exact transition, we’ve found that the same core questions surface time and time again.

You’re not alone in your concerns. Here are the five most common questions business owners have after a sale, along with the perspective you need to start moving forward.

1. "Did I just make a huge mistake?"

This is often the first question that whispers its way into an entrepreneur's mind, usually in the quiet moments after the initial celebration has faded. It’s a shocking thought. You’ve just achieved a life-changing goal, yet you’re second-guessing the entire thing.

The Short Answer: No, you didn't. What you're experiencing is completely normal. It’s the emotional whiplash from shedding a core part of your identity. For years, you were the builder, the problem-solver, the leader. Now, that structure is gone. This question isn't really about the financial transaction; it's about the loss of purpose and routine. The key is to recognize this feeling for what it is—a natural part of the transition—and give yourself the grace to sit with the uncertainty for a while.

2. "How much money do I actually have?"

You see the number in your bank account, but it feels like an illusion. You know a significant portion will be lost to taxes, but the finality of that number is a massive unknown, which makes every potential purchase feel reckless.

The Short Answer: You cannot know your true net worth until a tax professional has done a thorough analysis. The proceeds from your sale are subject to capital gains tax at both the federal and provincial levels. The calculation is complex and depends on many factors, including whether you can leverage your Lifetime Capital Gains Exemption (LCGE). Until you have this after-tax number, the real answer to "How much can I spend?" is "Less than you think." All major financial decisions must wait until this figure is crystal clear.

3. "How do I protect this money from myself (and others)?"

This question reveals a deep-seated fear common among entrepreneurs. You know how to take risks to make money, but you’re terrified of taking the wrong risks and losing it. You’re also keenly aware of the new "friends" and "opportunities" that have suddenly appeared.

The Short Answer: You protect it by creating structure and process. In the short term, this means following the Capital Preservation Play we outlined earlier this week: park the proceeds in secure, liquid vehicles like Government of Canada Treasury Bills or high-interest savings accounts in a separate institution. In the long term, it means building a comprehensive financial plan and an Investment Policy Statement (IPS). This document acts as your financial constitution, defining your goals, risk tolerance, and the rules of engagement for your portfolio. It’s the framework that protects you from making emotional decisions.

4. "What am I supposed to do every day?"

This is the big, terrifying, existential question. Your calendar, once packed with back-to-back meetings, is now a blank canvas. The fire that drove you seems to have been put out, and you’re not sure how to reignite it.

The Short Answer: For a while, the answer should be "Not much." Resist the urge to immediately jump into a new venture, start an angel investing career, or commit to a dozen charity boards. Your first job is to decompress and rediscover who you are outside of the business. This is a time for exploration. Travel. Reconnect with family. Pick up an old hobby. The "next big thing" will emerge, but it will come from a place of clarity and renewed purpose, not from a frantic need to fill the void.

5. "Who can I even trust to help me with this?"

This is the most critical question of all. The world of wealth management can feel opaque and self-serving. You’ve spent your career sniffing out bad deals and asymmetrical partnerships, and your alarm bells are ringing.

The Short Answer: You need to build a new personal Board of Directors. The team that helps you manage wealth is different from the team that helped you build it. You need a coordinated group of specialists—a CPA, an estate lawyer, and a Personal CFO—who understand the specific challenges of sudden wealth in Canada. Trust is earned through transparency and expertise. Take your time, ask tough questions, and demand absolute clarity on how they are compensated.

These questions aren't just common; they're foundational. The journey you're on is about more than just managing money; it's about redesigning your life with a new set of resources.

The first step is always to arm yourself with knowledge. Every question you have, big or small, is valid. And now, you can get answers instantly and confidentially.

Have a question about your own post-sale journey? -> [Ask Georgia Anything]