July Moments - Uncertainty, 90s Vibes, & Looking Ahead

As leaders, we often fall into a trap when facing uncertainty: We try to control everything... except what actually matters.

Here's what I mean:

• Uncertain about your business taking off? You might obsess over your daily schedule. (Color-coded to-do lists, anyone?)
• Worried about the market? You might spend too much time thinking about minor costs. (Those paperclips? Probably not THAT crucial.)
• Concerned about elections? You might post your opinions, hoping to change minds. (Because nothing says "productive dialogue" like a Facebook argument, right?)

But here's the hard truth: None of that actually addresses the root of our uncertainty. It's like trying to stop a leaky faucet by repainting your kitchen – sure, it looks nice, but you're still going to need a bucket.

I've been thinking about this a lot this month, especially through the lens of grit. How can we navigate uncertainty with resilience and focus? The answer, I believe, lies in understanding what we can truly influence and taking meaningful action.

If you're in a period of uncertainty right now, I hope you find this newsletter useful. Remember, it's not about eliminating uncertainty – it's about building the grit to face it head-on, making smart choices, and focusing on what truly matters.?

Let's dive into some key insights from this month that can help us all navigate uncertainty – with a little grit and a lot of grace ??

The Power of Perspective: My "Acquisition Moment" Confessional

About four years ago, CoverHound was being acquired. Suddenly, uncertainty became our unwelcome houseguest:

• Will there be layoffs?
• Will they keep certain aspects of the business?
• Are they going to sell it off or close it down?

The "what ifs" were real. But through this experience, I learned some valuable lessons:

1?? Mindset is everything.

I had a choice: focus on all the bad things that could happen, or choose a different perspective. I decided to focus on what I knew: my worth, what I bring to the table, what I'm capable of, and what I can produce.

2?? It’s best to keep moving.

Even when uncertainty felt paralyzing, I committed to making CoverHound the best damn business I possibly could. I kept putting one foot in front of the other, regardless of what might happen.

3?? Your network is your lifeline?

I reminded myself of my contacts and my network. These relationships were a source of strength and opportunities, regardless of the acquisition's outcome.

4?? Embrace the unknown?

I learned that it's okay not to have all the answers. What matters is how you approach the uncertainty and keep pushing forward.

In the end, we not only survived the acquisition, but we've continued to grow and evolve. The journey hasn't always been easy, but it's been incredibly rewarding.

To everyone facing your own "acquisition moment" (or any major uncertainty)...

It's okay to be scared. It's okay to be unsure. Just keep putting one foot in front of the other, and you might be surprised where you end up. Remember, every step forward is progress, even if the path isn't clear yet.

?? Leadership in Times of Uncertainty: Taming the 'Urgent' Beast

As leaders, we've all been there. An idea strikes at 11 PM, and suddenly we're reaching for our phones to share it with our team. After all, in these uncertain times, every thought feels crucial, right?

But here's a gentle reminder: Your midnight burst of inspiration shouldn't become someone else's 6 AM panic attack.

I'll be the first to admit, I've been guilty of this. Just last week, I caught myself about to hit 'send' on a late-night "just wanted to share before I forget" message to my team.

Here's the thing: In our always-on world, it's easy to forget that:

• We're ALL accessible 24/7 now (but that doesn't mean we should be)
• We assume others know it's not urgent
• We might inadvertently be turning our to-do list into someone else's stress list

So, how can we lead with consideration? Here are some strategies I've been working on:

1?? Urgent but not an emergency? Write it down or schedule send for working hours.?

2?? Not urgent? Keep a running list for your next 1-on-1 or send a consolidated update.?

3?? True emergency? Ask yourself: Will the business fold? Is someone at risk? Are we facing significant revenue loss?

Remember, "It might get worse if we wait" doesn't automatically equal "emergency."

As an insurance exec, I've seen how poor communication can lead to real emergencies.?

And as a grit coach, I know that true resilience comes from respecting both our own boundaries and those of our team.

Let's challenge ourselves to communicate thoughtfully. It's not about stifling ideas – it's about sharing them in a way that respects everyone's time and energy. That's what I call leadership grit.

??? Time-travel leadership hack: No DeLorean required!

Remember the '90s? When "urgent" meant something quite different from what it does today?

I've found a simple yet powerful way to gain perspective on our always-on, hyper-connected world. When I'm grappling with a boundary issue, I ask myself:

"What would I have done about this in the '90s?"

It's fascinating to consider how we handled "urgent" thoughts after hours back then:

1?? We'd jot it down for the next workday?

2?? We'd wait for the next scheduled meeting?

3?? If truly urgent, we'd make a phone call or stop by in person?

4?? And sometimes... we'd forget, and the world kept turning!

Sounds almost quaint now, doesn't it?

As an insurance executive, I've seen how constant urgency can lead to burnout and errors. And as a grit coach, I know that true resilience comes from managing our responses, not just reacting to every impulse.

So, here's a challenge for you: The next time you're about to send that late-night "urgent" message, pause and ask yourself, "What would I have done in 1995?"

You might be surprised at how often the answer is "wait until tomorrow." And that's okay. In fact, it might just be the key to more effective leadership in our hyper-connected world.??

And finally, what about the businesses that are on the up and up? I generally love to read fiction, but part of my job is to keep up with small business trends. I recently read Bank of America’s Business Owners Report to help me with that aspect of my work.?

In this issue I found that a whopping 87% of mid-sized business owners expect revenue growth this year. Exciting times, right?

But here's the thing – as your revenue grows, so does your level of risk. It's like upgrading from a bicycle to a sports car; sure, you can go faster, but you also need better insurance.

Whether you're a CPA advising clients or a small business owner managing your own finances, regular check-ins are crucial. Think of quarterly reviews as your business's health check-ups. And during these check-ups, don't forget to consider your insurance needs.

Here are some questions to ponder:?

?? How much has your revenue changed? Is it up by 10%? 20%? What does that growth look like in real terms??

?? What's driving this change? New hires? New equipment? New clients? Remember, each of these exciting developments also increases your exposure.

This is where your insurance partner becomes your new best friend. Imagine the conversation: "Hey there! In the last quarter, I hired two more employees and invested in a shiny new cherry picker. As a result, my revenue's up by 20%!"

Your insurance partner can then help you navigate these new waters, ensuring you're protected as you grow.

The key? Stay proactive. Protect your growth. After all, you've worked hard for this success – let's make sure it's well-guarded.

Curious for more insights? Check out the 2024 Business Owner Report. It's a goldmine of information for growing businesses like yours.

Looking Ahead: The Permission Slip Conference

Exciting news! CoverHound is sponsoring the upcoming Permission Slip Conference in Knoxville this November. It's all about giving ourselves permission to GROW – to be better, to be different, to finally admit that we don't understand… [can you add a cultural reference?!]

As we cruise into August, I challenge you to reflect on what you would do if you gave yourself permission. Start that business? Scale to seven figures? Finally learn how to fold a fitted sheet? (If it's the last one, please teach me!)

Remember, true grit isn't just about pushing through. It's about smartly navigating challenges, building the right support systems, and protecting what you've worked so hard to build. When we combine an unbreakable spirit with smart protection, there's no limit to what we can achieve. Except maybe folding that fitted sheet. Some things might be beyond even grit.

Until next time, keep pushing forward with a little grit and a lot of grace.

Caitlin

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