Why It's Normal To Feel Doubt In Your Business

When was the last time you faced an unexpected challenge at work? For most of us, it was likely a few hours ago.

The most therapeutic part of hosting my podcast Superwomen is bonding with leaders about the struggles of building a company. I always walk away relieved, thinking: ‘It’s rough for them too. This is normal.’ The challenges are so common that I want to create a “You can’t make this up” club where we share the unanticipated difficulties we face every day. The majority of a leader’s role is answering hard questions about how to get where you need to go. Questions are always accompanied by uncertainty and a spectrum of doubt we learn to manage to pave our path forward. 

Ordinary doubt is the questions you face every day. Should we launch this new product? Did we make the right hire? How will the tariffs impact our business? They range in intensity but your hands are on the steering wheel. 

Doubt on the other end of the spectrum is when you feel a lack of control or decisiveness leading your company. I’ve been through it a few times; When it feels like nothing is working and you don’t know which direction to go. It is unhealthy and raises an immediate red flag. These experiences are often transformative and the overwhelming advice I received is to stay true to your integrity, no matter what happens. 

One of the most uncertain periods for our brand was during the recession when retailers told us we wouldn’t make it unless we lowered our prices. We made the crucial decision to keep our handbags in stores and didn’t make any money for five months. It was a scary journey of asking: How are we going to recover from this? We couldn’t revoke the decision and for months moved through a cycle of: Well, that didn’t work. What are we going to do now? 

As a founder, every day is about figuring it out. How do you confidently lead amidst the uncertainty? 

The first step is to decide that you can do something about it. Train yourself to develop a problem-solving mindset. Avoidance is part of human nature but it doesn’t work in business. There is no time to feel like a victim or wander aimlessly. If your house was on fire, you wouldn’t sit around saying: Oh no! I can’t believe I left a candle on. You would put the fire out. Respond to business challenges with the same urgency. 

Refinery29 Co-founder and Global Editor-in-Chief Christene Barberich offered a valuable question to ask in these moments at Female Founder’s Day: Am I avoiding this because I am afraid? ‘90% of the time we know the right answer but we’re afraid to confront it,’ she shared. ‘It is a lifelong process to train yourself to confront the things that scare you and move through them with grace.’ 

The early problems you face as a founder feel like your first break up. Your heart aches for months. Then, it happens again and you think: This really sucks. I didn’t sleep last night but we’ll figure it out. Resilience is a muscle. The more you fall, the easier it is to get back up. Your recovery and bounce back period decrease every time. 

I rely on a mental Rolodex exercise to help me evaluate my choices in tough situations. When I’m facing a challenge, I step away from the office (and usually into a massage chair) and keep flipping through the Rolodex of possible solutions until I gain clarity, often through an a-ha moment, on the right one. 

During the early years, especially in the do or die moments, there can be a longing that the journey will get easier over time. The truth is the obstacles escalate — $100 million only means 100 million problems. 

Challenges will arise in your business every day. Face them head-on. Dissect every aspect of them, personally and with your team and advisors, so you can overcome them as quickly as possible. The more closely you inspect them the easier they are to surmount. The essential thing to remember is that: There is a solution to every problem. It may not be the one you want but you will always find a way forward. 

How do you manage uncertainty as a leader? Let me know in the comments!