What the Pandemic Taught Me About Coaching, Leadership, and Building a Self-Managing Business

One of the best parts of my work is getting to have real conversations with people who care deeply about helping business owners succeed.

Recently, I sat down with Joe Dimino on his podcast, Famous Interviews with Joe Dimino, to talk about how I became a business coach, what the pandemic taught me about leadership and resilience, and why personal growth is at the heart of every successful business.

We also touched on mindset, risk, curiosity, and how AI is reshaping the way we work.

I didn’t expect to live through a once-in-a-century disruption. But when 2020 arrived, it was clear: this was “the thing.”

Like everyone else, I started where we all did—uncertainty, Javex on the groceries, and a lot of questions.

I prepared clients for change, looked for the signal in the noise, and—unexpectedly—my business grew.

Owners finally had the time (and the nudge) to step back, recalibrate, and reconsider what they wanted from their companies and their lives.

Today, things have stabilized.

The lesson that stuck with me:

Disruption exposes what’s fragile and rewards what’s disciplined.

Coaching flourished because it helps owners become disciplined.

My role as a coach is to help skilled professionals become skilled owners.

You can be a superb lawyer, physio, electrician, or machinist—and still struggle with the business of your technical work.

My job is to provide the education, tools, and accountability so you can run the company you actually want to own.

Connecting the Dots Backwards

I’ve been wired to teach my whole life. As the eldest of eight, I was the “Johnny Appleseed” of books—on my bike to the library every three weeks, finding something age-appropriate for everyone.

In the early 1980s I learned the Socratic method of leadership: don’t dictate; draw the answer out of people so they own the action. That is coaching.

My corporate career sharpened the lens:

• Tip Top Tailors: sales to executive leadership—hands-on lessons in leading teams and stores that function like small businesses under one umbrella.
• President, BC Liquor Stores: 200 locations, billions in sales, and thousands of employees taught me what it means to steer a large, complex organization.

When I hung out the shingle as a coach in 2004, it felt less like a career change and more like recognition: I’ve been doing this all along.

“All Business Coaching is Personal Coaching in Disguise”

Most owners hire me for tactical help—time, team, or money.

We install systems, fix cash flow, and tighten execution.

But the lever that moves everything is personal growth:

• Mindset shifts (from technician to owner)
• Better leadership and communication
• True delegation (not abdication or micromanagement)
• Building confidence to make—and keep—decisions

Breakthroughs come in two sizes: boulders and grains of sand. Both count. What matters is consistent movement.

The Four Hats of Ownership (and Why You Feel Overworked)

Many owners get stuck wearing their technician hat while trying to grow:

1. Technician-Owner – “I do the work.”
2. Operator-Owner – “I run the work.”
3. Owner – “I design the systems and lead the team.”
4. Investor-Owner – “I build leaders who grow the business.”

If you still feel like “Chuck with a truck” even after you’ve added five trucks, you’re overdue for a hat change.

Systems run the business.

People run the systems.

You lead the people.

AI and the Next 25 Years

The AI train left the station a few years ago. You’re better off getting on now than waiting for perfect conditions.

I show clients simple, pragmatic ways to use tools like ChatGPT to buy back time, sharpen thinking, and turn ideas into assets.

Think back to the leap from AltaVista to Google—that’s the scale of change we’re in.

Evaluating Risk: Doors, Haircuts, and Tattoos

People tend to overestimate risk and underestimate opportunity. I like two simple filters:

• Bezos’ two-way vs. one-way doors: reversible decisions? Make them fast. Irreversible? Slow down.
• James Clear’s hats, haircuts, tattoos: some choices are trivial (hat), some regrow (haircut), and some are permanent (tattoo). Know which you’re making.

My own revenue breakthrough came when I asked, “What’s the highest and best use of my time?”

The answer: talk to clients and prospects.

So I redesigned my role to do only that—and delegated everything else.

Revenue followed.

4 Tips for Life and Business

Free Up Time with an Oh Sh*t List. If a task makes you say “Oh shi*t… I have to do receivables/payroll/that spreadsheet,” it belongs off your plate.

Stop asking “How can I get this done?” and start asking “How can this get done?”

Different question, different business.

Trust your intuition. Most of my mistakes came from ignoring it. With age comes clarity—I’ve become confident in what I hold to be true and far less concerned about external approval.

Find your version of paradise. For me, it used to be skiing on a powder day. My email address, @jadip.ca, stands for “just another day in paradise”—a reminder to find joy in ordinary days: a great conversation, a client breakthrough, a quiet morning with coffee.

And never give up on yourself. In 2011, I attempted suicide. In 2015, I shared that story in a TEDx Talk to help others understand mental health more compassionately. If you’re in a dark place, it can get better. I’m living proof.

How I Help

What clients say I do best: listen deeply, diagnose the real problem, and provide the right tool or framework to create movement. Then I hold you accountable to the actions you chose.

If the owner wants a better business, first the business needs a better owner. When you’re ready to become that owner, book a free 15-minute call with me. We’ll talk about what’s going on in your business and see how I can help.