Last week, we said goodbye to two of our sheep—Joe and Katie. They weren’t just livestock. They were part of the family. We’d cared for them for over 15 years, ever since rescuing them from a shelter. They had names. They came when called. They’d nuzzle in for a fuss like a dog would. We loved them deeply.

As tough as their passing was, it brought something unexpected: clarity. In the middle of grief, I started thinking about business—about how often we, as entrepreneurs, ride emotional rollercoasters of our own. Wins, losses, plans that go sideways. It’s all part of the journey.

Joe and Katie’s final week reminded me of five key lessons every business owner needs to revisit—especially when things don’t go according to plan.

Let me share what I took away. I think you’ll see how relevant these lessons are to the world of business and entrepreneurship.

1. You Can Do Everything Right… and Still Face a Loss

When we realised Joe and Katie were struggling, we did what most entrepreneurs do when we sense a problem—we acted fast.

We moved them to a paddock closer to our house, sourced a new shelter, arranged everything so we could keep a closer eye on them. We invested time, money, and care into giving them the best chance at comfort and recovery.

But a few days later, the vet told us it was time. They were suffering more than we’d realised. No treatment would help. Letting them go was the kindest thing we could do.

And here’s the hard business truth in that moment: You can put everything in place, follow the plan, and still not get the result you hoped for.

That doesn’t mean you failed. It means you tried. You led with care. You made the tough decisions. And in business, that counts for a lot.

2. Your Plan Is Just the Starting Point

We had a plan. A solid one. We found a shelter, recruited help, handled logistics, and executed quickly. We did everything right. But still, reality had other ideas.

Sound familiar?

As business owners, we’re constantly planning—launches, campaigns, new hires, product development. But the truth is, your ability to pivot matters more than the plan itself.

Execution is important, but adaptability is what keeps you in the game. I’ve learned that building a “resilience muscle” is more important than building the perfect strategy. Because when something doesn’t go the way you’d hoped, it’s your resilience that gets you through.

3. Surround Yourself With People Who Have Your Back

When things got hard, people showed up. Friends helped unload the shelter, the vet was compassionate and clear, others helped clear fencing and reset the paddock. Our support system made a huge difference.

This made me think: Who’s on your team—not just on your payroll, but in your corner?

In business, this is one of the biggest differentiators between those who burn out and those who bounce back. Whether it’s a mentor, a peer group, a coach, or simply friends who understand what you’re building—surrounding yourself with the right people is essential.

You don’t have to do everything alone. And truthfully? You shouldn’t.

4. Gratitude Anchors You in the Chaos

After the loss, I felt this overwhelming wave of gratitude. For the years we had. For the people who helped us. For the fact we did all we could.

It made me realise how rarely we, as business owners, stop to feel grateful. We’re always moving, chasing, building. But stopping—even briefly—to appreciate the journey is one of the most powerful ways to stay grounded.

Celebrate the lessons, not just the wins.

Be grateful for the team member who tried even if the project didn’t work out. Be grateful for the client that challenged you. Be grateful that you’re still in the game, learning, evolving, growing.

Gratitude gives perspective. And perspective helps us make better decisions.

5. Keep Moving Forward—One Step at a Time

After everything settled, we cleaned up the paddock, listed the shelter on Facebook Marketplace, and began clearing the space. Moving helped. It gave us momentum again. It didn’t fix the sadness, but it reminded us that life (and business) doesn’t stop.

In business, especially after a setback, the most important thing you can do is keep moving.

Momentum is powerful. Even small steps—posting on social, sending an email, calling a supplier—can shift your mindset and rebuild your confidence.

So whether you’ve just lost a client, missed a goal, or had to shelve a passion project—just take the next right step. Then another. That’s how progress works.

In Business and in Life, the Lows Matter Too

Joe and Katie were sheep, yes. But their final chapter left a big mark on me—not just emotionally, but professionally. Because running a business isn’t just about revenue, metrics, and growth. It’s about how we handle the setbacks, the pivots, and the moments when things don’t go as planned.

So, if you’re in one of those seasons right now—where things feel uncertain, heavy, or frustrating—remember this:You’re doing your best. That matters.Your ability to adapt is more powerful than any plan.You are not alone—ask for help.Gratitude can change your perspective.Keep moving forward, even when it’s hard.

Those lessons didn’t come from a boardroom or a webinar. They came from two aging sheep who reminded me what it means to lead with care, to act with integrity, and to keep showing up—even when the outcome isn’t what you wanted.

If you’re riding out a tough patch in business right now, I get it. I really do. And if you’d like to talk—no pitch, no pressure—just a conversation, feel free to book a free 30-minute call with me here: TimeWithSimon.com

Sometimes, a good conversation is the best first step to getting back on track.Here’s to embracing the whole journey—ups, downs, and everything in between.

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