Navigating the Loss of Your Business Best Friend

In business, we often hear about the triumphs and successes, but rarely do we discuss the profound emotional challenges of leadership. Sure it’s lonely at the top and all that, but really.

It is.

The pressure is intense, and the decisions…the list goes on forever. But what happens when you feel amazing one day and are devastated the next?

How do you run a business then?

Today, I want to share a deeply personal story about balancing emotions in business leadership. It’s when you immediately think “(@$%()*” and then have to juggle that with not falling apart. Fun times, but we’ve all been there.

This particular story began with a handwritten thank-you note and led to one of the most challenging periods in my 11-year entrepreneurial journey. It also answers the obvious question: where did Annie go?

In 2019, I hired Annie through a mutual friend. From the start, I knew she was special. That thank-you note she sent me after her first month sat on my pegboard by my desk until this winter. A daily reminder of the incredible partnership we once shared. Annie wasn't just an employee; she was the yin to my yang, my co-founder in every sense of the word, though not on paper.

Our dynamic was the thing you always wish for when looking for someone to lead alongside you.

• When I skewed pessimistic, she brought positivity.

• When my ideas veered over into far-fetched territory, she grounded me with realism.

• When I couldn’t do the talk, she could handle it.

• As travel partners, we were ideal companions, sharing the same approach to business trips and the inevitable snags of running a company.

Her insights, expertise, and enthusiasm balanced my leadership style in ways I hadn't known I needed until she arrived.

Then came the day that changed everything. When Annie told me she was leavingfor an opportunity that she felt she needed to take, it felt like all the air had been sucked out of the room. I was stunned, completely blindsided, and devastated in equal measure.

Happy for her, of course. But I couldn’t shake the feeling that the world was ending.

My initial reaction, as it often is with bad news, was to detach—to go cerebral and factual, to minimize the fallout and contain the disaster. But beneath that, I felt a profound sense of failure and an overwhelming sadness that felt beyond anything I had experienced so far running ALC.

Not-so-fun facts: professional breakups feel just like romantic ones.

Without Annie, the business suddenly felt hollow. The irony wasn't lost on me that we were experiencing our best performance ever, but it was too little, too late. For an entire weekend, I cried, questioning whether I even wanted to continue without her. I trusted her to tell me what she needed, but I realized too late that it was my job to ask the right questions—a failure I now own as a leader.

But as the captain of this ship, I didn't have the luxury of falling apart. So, after a weekend of crying, I put on my leadership hat and made a plan by Monday.

I broke the news to my people individually, starting with those I worked with most closely. Balancing wild internal emotions while maintaining a calm exterior was a new challenge. Nothing prepared me for how hard it was. Grief in business is not something for which there’s a support group. Especially when the best advice most people give you is, “This too shall pass.”

But what if it feels like it just…won’t?

Suddenly, it seemed the universe was conspiring to help. Harvard Business Review articles on navigating change started appearing in my inbox. I devoured them all, desperate for guidance. I had always said I never wanted to do this alone, and now I faced that reality. I needed time to sit with it, to see how it felt, turn it around in my hand before I cast it aside- determine if I could live with it, and most of all, be happy and at peace with it one day.

Five months later, I wish I could say I've figured it all out. The truth is, I'm still grappling with this loss in both big and small ways. One of the most complex parts is not being able to fully communicate or share these feelings with my team—another lesson in balancing emotions in business leadership. There is a delicate balance between honesty, candor, and professionalism, and I think about it all the time now. It can feel lonely and confusing.

But there have been silver linings. Annie's departure forced me to review everyone's roles and the business structure, ensuring they made sense in our rapidly growing business. Do we have the right people? Are we maximizing efficiency AND making sure everyone is happy? As companies expand, it's easy for things to become casual and loose. Her exit, coupled with our explosive growth, brought a new level of seriousness to our operations.

We still talk, and in many ways, she remains my business best friend. I am trying hard to find a new normal without her and a new narrative for my purpose and focus within Anchorlight and what I’ve learned from this whole process. I am still working that out.

While I don't know exactly what the future looks like yet, I've learned valuable lessons about failing, changing, and growing up in business—lessons that keep coming long after year one.

This experience has humbled me and shown me the importance of emotional resilience in business. I'm learning what it means to stand on my own feet without a hand to hold. But I've also discovered that I have many other business confidants to lean on when times get tough—more than I ever realized.

For other leaders facing similar challenges, remember that balancing emotions in business leadership is an ongoing process. It's okay to feel deeply, but it's also crucial to maintain composure for your team.

Just don’t become so busy that you don’t take time to really feel your feelings and take stock of what opportunities there are in change. There are always more than you think.

As I continue to navigate this new chapter, I'm reminded that entrepreneurship is as much about emotional growth as it is about business acumen. It's about learning to balance the personal with the professional, the heart with the head. Sometimes, it's about finding strength in vulnerability and growth in loss. It’s a new challenge that I don’t pretend to have figured out by any means, but I’m learning as I go.

To all my fellow entrepreneurs: Your emotions are valid, your challenges are real, and your resilience is all too often unacknowledged. But truthfully, I don’t know anyone as tough as us.

In the words of Maggie Smith: Keep going.