The Art of Not Freaking Out

Entrepreneurship will require everything you have, until you reach your limit, and it demands even more. 

If there was a disclaimer for being a founder, this would be the fine print.

Every founder faces do or die moments. They may be the price for admission. Still, nothing lessens the fear in your throat when your back is up against the wall. In an excerpt from my book, Fearless, I share our scariest You Can’t Make This Up moment — saving our business from bankruptcy in 24 hours — and how I learned to stay calm during a crisis. If messing up has taught me anything, it’s that when you fail (not if, but when), you have to face failure head-on. 

When the business was really starting to pick up momentum, I was sitting in Paris at the most glamorous restaurant I had ever been to in my life. The president of my company and I had spent the day in back-to-back-to-back sales meetings and it felt incredible to sit down. The insanely decadent truffle pasta and ridiculously delicious champagne made the nonstop work day all worth it. With the time change, New York was still working while we were at dinner, so I checked my emails from time to time, as one does. And then an email from my brother came through with no subject, but the preview text read, “The bank says they are done.” It was like time and space came screeching to a halt. The news wasn’t entirely unexpected, but to actually face the moment when the bank was no longer going to advance us funds for production and everything else was terrifying. 

The company had reached a point in our feverish growth escalation where the amount of money that we had coming in as an advance from the bank to fund future orders was more than the amount of money we had coming in for existing orders. The bank wasn’t willing to keep that up. But without that advance, we couldn’t pay for our next round of deliveries, and if we didn’t cover that, then the deliveries wouldn’t ship, and we wouldn’t have anything for people to order. It was a serious avalanche. 

I had to fight the urge to freak out. 

The reality of this perfect moment was that there were an unlimited number of worse scenarios that I could have been going through. It might sound fatalistic, but I like to imagine what rock bottom looks like so that I can come back to reality. Like, what if I were a well-known designer and no one wanted to work with me ever again because I went bankrupt? Or what if we couldn’t convince the banks to float us just a little while longer, and our cash flow ran dry and we had to lay off our entire team? It could mean having to hang up our bags and call it a day. Maybe the company I poured my blood, sweat, and tears into was going to end up in the hands of a coldhearted liquidator. Maybe it was over for me in fashion and I was going to head back to Florida and start answering the phones at my dad’s office. I knew at least he would hire me. 

The truth of the matter was, whatever happened, I was going to be okay. Even if I was devastated, I was going to make it through to the other side. I found my center. I reminded myself that they could take my company, they could take my apartment, but they couldn’t take my husband or my kids. At that moment, I knew that what mattered most were those that I loved and cherished — they were the only things that were irreplaceable. And in that instance, I knew that no matter what happened, I would bounce back. I would figure it out. 

Knowing the stakes and what I had the potential to lose was all the motivation I needed to get down to business. I could have thrown some Euros on the table and run out of the restaurant like my hair was on fire, but having gone through my worst-case scenarios in my head, I knew that there was nothing I could do to change the situation at that very moment, so I decided to finish my extremely delicious plate of pasta. I ordered two more glasses of champagne. (Priorities, right?) When I was finished, I went back to my hotel room and called my brother. It wasn’t time to fall apart. It was time to get to work. 

If you looked at just a snapshot of the numbers on paper, without taking anything else into account, business did not look great. We were a big brand with lots of overhead and tons of expansion. Sometimes there are just moments in your business life where you have way more money going out than you do coming in. The highs and lows are all part of the ride. There was no PowerPoint in the world that would convince a hardline businessperson that flowing us more cash would be a brilliant idea. 

When you’re in a jam like that, you need people to act from their human goodness. My brother and I had spent years building our personal relationships so that when things didn’t look great on paper, we’d be able to open the lines of communication to paint a bigger, more complete picture of the reality of what was really happening. Michael (our banking partner) and I had been working together for close to a decade. He had made the decision to support the business when we were just starting out, and he certainly bought into the potential and the dream. 

I was so grateful for him taking a chance on me that I made a concerted effort to make sure he was included in everything — not just the annual report emails. There was (and still is) a seat for him in the front row at every show, and there were always invites to all the parties and events we threw. When he was fundraising for charities that were important to him, we made donations or even hosted. He came along for every part of the journey. When we faced hardship or achieved a tough accomplishment as a brand, he was emotionally invested too. I knew I needed to make the call. 

On the phone with Michael and Uri, the discussion was much more than just “here’s the problem; please solve it with more cash.” Over the course of a few hours, we went over our entire strategy, including where we had come from, where we saw the brand going, and how we had gotten ourselves into this mess in the first place. 

Once Michael was able to get a better handle on the situation from a bird’s-eye view, we were able to envision our very bright, very sunny possible future, though we knew we would only be able to get there with his help. Before long, the three of us started getting somewhere closer to a solution. And eventually, with a lot of tough questions and honest answers, we came to a decision. It wasn’t money or numbers that saved us in the end. It was our longstanding relationship and authentic connection. No person or brand can win alone. There are a lot of people who have made my dream come true, and we all wanted, and continue to want, the brand to win. 

Being able to face a failure this big and not completely fall apart does not come easily. I had to fail a lot to get this good at it. You have to go through the exercise of confronting it. Each time you have a setback or a situation that seems uncomfortable, stare it in the face. Go on and look it in the eye. Snuggle up to it. Don’t be afraid to explore it, touch it, and feel it — really get in there. 

Don’t panic; evaluate the situation. Don’t judge it. Look at it objectively. What are the mechanics? What’s really going on? How exactly did you get here? What’s the very worst that can happen? What is your biggest fear? What would that be like? Is that the end of the world? Is it really so bad after all? Settle into the feeling of being unsettled, that woozy moment of truly not knowing what to expect or what exactly is going to come next. The only way you’re going to get out of it is if you really understand where you are and what you’re dealing with. Then you can start asking questions, like What’s missing from this picture? and What needs to change? 

By failing over and over again, I’ve been able to practice being more analytical when I am dealing with problems and less personal, less emotional, and less reactive. You’re going to fail as much as you succeed in business, and that’s part of the journey. Bad things happening is not the exception; it’s the norm. It might feel like the sky is falling, and it might be, but what are you going to do? Stand there and freak out while you get lost in the clouds, or look up and see what’s left? What matters most is what comes next, how you handle it, and what you learn from it. 

No matter how many times you fall, you have to get back up again with a smile on your face. 

I wrote Fearless for everyone who has a vision for their life and the change they aim to make in the world. It’s a collection of 21 rules that help me overcome my fears and turn my dreams into reality. I’m honored to share them and hope they do the same for you. You can learn more and pre-order it here!