Here’s how making mistakes — and encouraging your team to do the same — can become your business’s competitive advantage
8 min read
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When you’re building a business, a lot of people will offer you advice. But, I’m going to bet that you won’t hear this often: Make lots of mistakes. They might say, “Take risks!” or, “Don’t hold back!” but they probably won’t make the business case for how this mindset can actually give you an edge over your competition, make you a stronger leader and set you and your team up for greater success in the future.
At Away, we’ve built a culture that celebrates our mistakes. In fact, we made a pretty major one before we even launched: We realized there was no way that our first production run would be ready in time for the holidays, a major issue when you’re in the retail business.
We could have panicked, but instead we came up with a Plan B and launched with a book that was full of travel stories from a range of influencers, sold along with a gift card that would be redeemable for our first product, The Carry-On, in the coming months. What was a mistake on our side ended up being a huge win for two reasons: First, it gave us an opportunity to define the brand and really show people what we stood for beyond just a great product, and second, it allowed us to get a clear grasp on interest, which helped us determine inventory needs in a way that’s pretty rare for startups.
We’ve known from the beginning that there’s no playbook for what we’re creating at Away. We may fail at a few things along the way, but we’re willing to take thoughtful risks and embrace failure when it happens because we know those moments enable us to iterate and grow as a team.
Here’s why (and how) you should embrace your mistakes, too:
If you’re never failing, you’re probably never really winning either.
This might sound counterintuitive to some but, to me, it’s the most important point on this list. It should set the foundation for how you approach everything you do. Think about it: if everything you do is working, you probably aren’t taking enough risks, which means that even if you’re achieving small wins every day, you aren’t challenging yourself to achieve big wins that will set you apart in a meaningful way.
In fact, we took a pretty big risk just a few months ago that ended up being a huge success. When airlines introduced new regulations regarding luggage with batteries (like some of our Carry-Ons), we made a huge investment of time and resources to proactively respond. Even though our bags have always had removable batteries — making them compliant at any airport — our newest iterations were designed with batteries that were ejectable from the outside of the bag, so we decided to develop a retrofit program that would allow customers with earlier versions to upgrade their bags at no cost to them. By leaning into the risk and accepting that it’s possible we fail, we were able to deliver a thoughtful solution for our customers, and one that ultimately gave us a competitive advantage in the industry.
And you probably aren’t learning much more than what you already know.
We know that we don’t know everything, and it’s why we’re always seeking out new perspectives that challenge our assumptions, and using data to inform our gut feelings. We also know that we’ll make better decisions for the business when everyone is empowered to bring their unique perspective to the table, even (especially!) when that means people disagree. Our rapid growth wouldn’t have been possible if we weren’t constantly learning by soliciting those insights, testing what we think might work and then iterating based on what we discover.
Here’s an example: When we were first starting out, our hypothesis around brick and mortar was that it wouldn’t make sense for our business, since our product didn’t have a fit component, was a large item to walk out of a store with and we offered free shipping and a generous return policy for customers buying at awaytravel.com. But, with our test and learn mentality, we decided to test out our hypothesis — and we were quickly proven wrong. Today, all of our retail stores not only build community for our brand and lift web sales in the markets we open them in, but they’re all standalone profitable as well. If we had relied on our assumptions and let fear of failure stop us from opening our first store, we would have missed out on a huge business opportunity.
When someone on your team fails, talk about it — and even celebrate it.
It’s much easier to talk about failure in hypothetical terms than it is to actually embrace it, but highlighting these moments when they happen helps ensure this mindset becomes an active part of the culture you’re building. At Away, that means creating a space where it’s okay to publicly share what went wrong, and what the team can learn from that failure for next time.
That might sound totally terrifying to some, but here are important conditions to ensure you’re doing it right: First, it should start from the top (if junior members of the team see their bosses talking about failure, they’ll be more likely to feel like they can, too); second, it should happen often (as opposed to waiting for the “right time” to have a tough conversation); third, it should be delivered thoughtfully and one-on-one, initially (it’s not about how you prefer to deliver feedback, but how that person will receive it in a way that’s beneficial to them); and fourth, it should be framed as a benefit for the company (“Guess what we learned that we wouldn’t have otherwise!”).
I recently listened to an episode from Adam Grant’s podcast, WorkLife, where he talked to guests about the unconventional concept of loving criticism and how embracing constructive feedback actually helps people become better at their jobs. What Grant calls “improving mode” — the idea of knowing you’re a work in progress and that you always want to know how you can get better — is exactly what we lean into when we talk about embracing mistakes at Away.
Again, it starts from the top.
A culture can’t be defined by one person, but it’s important that a company’s leadership actually embrace the benefits of failure to drive whether or not this mindset is actually adopted. As a leader, I share my failures in order to set the expectation with my team that they can feel comfortable doing the same, and to show them how these moments can make us stronger. Lead by example by having regular, open conversations when mistakes happen to keep a no-pressure dialogue about the reality of mistakes. Occasional failures are a guaranteed outcome of trying something new and a good signal that you’re rightly pushing some boundaries, so it’s better to practice resilience and be good at problem-solving than to be bad at failing.
Ultimately, your life and your career is made up of many small, but innately important choices: some of them will be the right ones, and some of them won’t be. Keeping this in mind can help to ensure that you maintain necessary perspective and don’t view every failure as a major setback, but just a helpful piece of the bigger picture.