Small Business Owners: Don’t Let Fear of Failure Hold You Back

June 2, 2017


As a small business owner, you’re bound to make mistakes. So you can’t let a fear of failure hold you back.

When it comes to running a business, most entrepreneurs and small business owners are learning as they go. Even if you have years of experience designing websites or writing creative copy, working for yourself is very different. So you’re bound to make mistakes. That’s why it’s important to overcome your fear of failure.

In hindsight, we all value our mistakes (think of all those articles by successful people owning their early slips and miscalculations) but in the moment, they don’t feel good. They feel like failure.

Understanding how to constructively deal with adversity is a learned skill, not something you’re born with. Here’s what you need to do to dust off and rebound after failure, in five steps:

1. Don’t Wallow in Your Failure. Take Action Instead

When you mess up, don’t get stuck wallowing in bad feelings or self-flagellation. Act quickly to make amends. If you’ve screwed up on customer service, think about how to make it right. Remember: The thing that stays with people is not service that’s mistake-free, it’s service that goes that extra mile when they get it wrong.

When you mess up, don’t get stuck wallowing in bad feelings or self-flagellation. Act quickly to make amends.

If you’ve made a mistake on a project, it’s critical to be transparent, candid and own up to the error. Don’t over-apologize or be defensive; the point is to be action-oriented and focus on the future. Explain to your client, coworker or teammate how your mistake will be remedied and how you will avoid making the same or similar error down the road.

2. It’s OK to Feel Bad, But Give Yourself a Deadline to Get Over It

Accept that mistakes and setbacks are unavoidable, along with the emotional fallout. Pushing all of your emotions down and pretending that you are OK is not OK. When you don’t deal with these feelings upfront, they tend to surface later on impacting your performance.

Once you’ve experienced a failure, it’s natural that your confidence takes a hit. But it’s important to keep things in perspective. One failure doesn’t lead to another failure.

Harvard Business Review has written about the importance of emotional agility, noting that everyone has an inner stream of thoughts and feelings that include criticism, doubt and fear. But the trick is not to let them hold you back and sap important energy that could be put to better use.



Take whatever time you need to be upset and grieve your losses, and set a deadline for accepting what’s happened. Then stick to it. The most successful “bouncers” don’t let themselves fall apart; they grieve, they own responsibility for the failure and then they move forward.

As entrepreneur and former world-champion skier Jeremy Bloom (who missed his shot at Olympic gold) writes in his book, Fueled by Failure, “limiting the time that we allow things to consume us strengthens our ability to control our thoughts and actions. That’s the key to using failures to fuel your successes. Setting deadlines for dwelling on failures can play a major role in whether we succeed at our future goals, or even go after them in the first place.”

3. Instead of Fear of Failure, Embrace Learning from Failure

You don’t want to repeat the error, so examine what went wrong prior and consider what signs you may have missed.

Replay events to understand what contributed to your gaffe: Did you not take the time to double-check a client’s expectations on a certain part of the project? Did you neglect one aspect of running your business over spending time on the tasks you love? Did you follow your heart instead of your head?

Be clear about what went wrong and don’t sugarcoat it. When you focus on the facts, you can call it like it is. Look at how you could prepare differently or how you might act on opportunities or react to specific obstacles in future.

Understanding what contributed to the mistake is key to getting a better result next time around.

Understanding what contributed to the mistake is key to getting a better result next time around.

Christopher Gergen, director of the Entrepreneurial Leadership Initiative at Duke University and co-author of Life Entrepreneurs: Ordinary People Creating Extraordinary Lives, nails it in this HBR article: The most useful thing you can do is “translate a mistake into a valuable moment of leadership.”

If the mistake happened on a team project, it’s important to address the underlying issue and resist the urge to finger-point. Work with your team to revise your process to prevent the mistake from happening again. This turns the failure into a learning experience that you can build on. You figure out how to “translate the mistake from a liability into an asset,” Gergen says.

4. Rework Your Business Strategy to Stoke Motivation and Take Action

Some mistakes lead right back to your original business strategy. Did you miscalculate finances for the first year of business? Did you neglect to do market research about who your customer really is and how to sell to them?

Uncover Your Billing Blindspots

A good business strategy isn’t static. It should evolve with new information. Now’s the time to course-correct by making adjustments to your business plan.

Take a look at your overall strategy to identify gaps and weaknesses. For example, maybe your small business is failing because you’re not attracting enough customers. Reexamine what you’re offering. Is there really a market for it? If there is, why didn’t you reach that market? How could you have done so? Don’t let your fear of failure stop you from experimenting with new tactics.

Or maybe your finances are flailing because you’re not using the right tools to keep track of cash flow. Step back, assess what tools can help (pro-tip: FreshBooks) and invest in a solution that supports your overarching business strategy.

Get super crisp on the area you neglected and make a plan to address that. Understand that you’re not alone here. There are always areas of business that are more challenging. Without self-flagellating, equip yourself with the right tools, seek mentors and resources to guide you over the aspects of running a business that caused blind spots.

5. Harness the Power of Sharing Your Mistakes

Many companies are becoming more transparent as consumers seek and trust brands they can relate to. In doing so, they find ways to own their mistakes and keep themselves accountable to clients, business partners and employees.



It’s also a sharp tactic: Transparency serves to deepen relationships and build trust in a very raw, human way. Millennials who grew up sharing everything on social media increasingly demand it.

As Forbes reports on the transparency trend, “Being transparent is a powerful thing, if you can trust yourself and be trusted by others… We are all living during a time when people want and expect their leaders to be more human, less perfect and at times a bit vulnerable—regardless of hierarchy or rank.”

Writing a blog post or posting a video that ‘comes clean’ about a mistake and shows how you changed your product or policies to improve can make for good PR, build rapport with customers and even establish you as a thought leader.

Remember to err is human. And small businesses are at their heart very human. If you embrace the journey you’re on, fear of failure is something you’re bound to feel. Don’t let it hold you back… see it as a self-challenge and embrace the process.


about the author

Freelance Contributor Karen Hawthorne worked for six years as a digital editor for the National Post, contributing articles on business, food, culture and travel for affiliated newspapers across Canada. She now writes from her home office in Toronto as a freelancer, and takes breaks to bounce with her son on the backyard trampoline. Connect with her on LinkedIn.