34. What to Do When Life Doesn’t Pause for Your Business

Sometimes life throws you a curveball right when you need it least.

Just days before the most complex retreat I’ve ever planned, I got some difficult personal news that forced me to completely pivot.

The temptation in moments like these is to try to control every detail and predict every outcome. But I’ve learned that’s not what gets you through moments like these.

In this post, I want to share the three things I rely on when life forces a pivot, and why so much of entrepreneurship is really about who you choose to be when things don’t go to plan.

The retreat that couldn’t be cancelled

My colleague Dr. Matthea Rentea and I have been planning a five-day retreat for female physicians for six months. We’re hosting them in a home in Indianapolis, with a full schedule of vendors: a stylist, a makeup artist, a lighting coach, and a full-day branded photo shoot. Every detail has been thought through, documented, and locked in.

It’s the most complex retreat I’ve ever put together. And then I got the phone call.

My uncle had passed away. And his funeral services were likely going to fall right in the middle of everything I’d been building towards. I wasn’t going to miss the funeral. But I also couldn’t walk away from the retreat and the clients who’d committed to it, Dr. Rentea who’d be left to manage everything alone, and the months of work that had gone into making it special.

So I had to figure out how to honor both.

Why this happens more than we talk about

This is actually pretty common in entrepreneurship. We put our all into something, whether it’s a big launch, a retreat, a client project… and then life intervenes. Maybe it’s a sick kid, a family emergency, or a car that breaks down the morning of your biggest presentation.

Nobody really tells you this when you start a business. They make it sound like it’s all strategy and execution and hard work. They don’t tell you how much of it is toggling between contexts — holding something heavy in one hand while showing up fully with the other.

The real source of confidence

For a long time, I thought confidence came from having everything figured out, planning so thoroughly that nothing could go wrong, and being able to predict exactly how the story would play out.

But it turns out I’m not omniscient. And trying to contort myself to make sure everything played out exactly as I’d imagined? That wasn’t confidence. That was just fear dressed up as preparation.

Real confidence, I’ve learned, comes from self-trust built on experience. From doing hard things, learning from them, and being kind to yourself along the way. That’s the foundation that actually holds when things get difficult.

A three-part framework for handling any plot twist

When my kids asked me how I was going to handle hosting a retreat and attending a funeral, I realized I’d developed a framework over the years: three things I come back to every time a plot twist shows up.

1. Rely on good planning… then let it go.

We’d spent six months planning this retreat. We’d documented everything, vetted our vendors, and drawn on everything we’ve learned from running retreats before.

I can trust that work. What I can’t do is use it as a guarantee that everything will be perfect because there’s always room for things to go sideways. 

Good planning gives you a foundation. It doesn’t give you control.

2. Accept that there will be a plot twist.

Part of my job as an entrepreneur is to anticipate what might go wrong. But I’ll never be able to predict exactly what the plot twist will be or when it will show up. 

When it does, I need to get into problem-solving mode, not reaction mode. That shift in mindset makes all the difference.

3. Ask yourself who you want to be in this moment.

This is the most important one. In the middle of everything changing, I keep coming back to one question: how do I want to show up in this moment right now? 

This week, that means being present for my family when I’m in Chicago, and then heading to Indianapolis and being committed and thoughtful when I’m at the retreat. Holding both. Not perfectly, but intentionally.

The part nobody warns you about

Entrepreneurship has a way of expanding your capacity as a human being. Not just your capacity to strategize or execute, but your capacity to feel everything — grief and excitement, sorrow and commitment — sometimes in the same hour.

Sometimes we have to put a feeling on the shelf temporarily while we take care of business, then come back to it later. Other times we carry it with us and keep moving. Neither is wrong.

What I’ve learned is that the feelings aren’t the enemy. They’re sending me a message. And the more I’ve learned to listen to them, rather than being afraid of them, the better I’ve gotten at navigating moments like this one.

If you have something like this happening in your life right now, I hope this helps. 

To hear the full story and more on how this framework plays out in real life, listen to the full episode. And if you're navigating your own unexpected pivot, email me at [email protected] if you feel comfortable sharing.