The Obstacle Course of Entrepreneurship: How to Fight, Pivot and Win Every Time

By Joey Gallagher

The backstory.

It started with a company meeting. I was just a year into my business — Gallagher Staging — and decided to take on a project that most young companies of my size would never have even considered. But I knew we were ready. We’d get it done.

So there I am, standing in front of my employees, discussing this challenging project, and instead of worrying about the complexities of what I was about to tell them, I stared into fifty sets of eyes and thought about the fifty families that were now counting on this company to succeed.

A good business owner goes to sleep and wakes up with the pressure of creating not only a prosperous, profitable business but also (and more importantly) a place that provides a better life for their employees and those who depend on them. If you can achieve both, I promise it’s a win-win.

You launch a business with the intention of working for yourself, which may seem glamorous in those motivational Instagram posts but while you think you’re building a shiny path to freedom, you’re actually building the most treacherous obstacle course you’ll ever experience. It’s why some people aren’t cut out to be an entrepreneur. And that’s OK. The genetic fabric of an entrepreneur is made from long days and big challenges, coupled with a special kind of resiliency not everyone can fully embrace.

Here’s the thing about the mental fortitude of an entrepreneur: You might not even know you have it until you’re on the obstacle course and someone throws a gigantic fireball at your head. While the non-entrepreneur runs away, the entrepreneur stands tall. They catch fire then forge on, transforming those flames into energy that pushes their company forward.

The mindset.

Solid leadership is the foundation for sustainable growth, excellent customer service, employee satisfaction … it’s everything. Take care of your team and your team will take care of your company and clients. It doesn’t matter if you’re running a local bike shop with three employees or a manufacturing facility with 250 employees, the philosophy universally applies.

Being a good leader means accepting and overcoming temporary challenges. Being a great leader is a lifelong commitment to personal and professional improvement.

A great leader is passionate, and has the distinct ability to help their team members become passionate about the work as well. They also have a positive mindset, and train their employees to operate with actionable optimism. There is no problem that can’t be solved if you focus on a solution.

Even the problems of 2020.

The pivot.

This year caused a complete shutdown of my business, which had expanded from those initial 50 employees to more than 160 employees. In 2019, we were building the main stage at Coachella and Stagecoach, and constructing multiple custom sets for some of the most famous entertainers in the world. Then the music stopped.

Instead of giving up, I decided — without hesitation — to fight. I created several new businesses utilizing my hard-earned knowledge and hard-working team. The difficulties I’d maneuvered through in the past prepared me for 2020 and its never-ending hurdles. (Remember, the bigger your goals, the bigger your obstacles.)

Flexibility is critical to the longevity of a business. I've constantly had to shift strategies to stay relevant and weather changes in the market. Pivoting could mean altering product lines, marketing tactics or even focusing on an entirely new marketplace. When you adapt to challenges or changes, you safeguard your long-term success.

My team and I were saved because I took immediate action and made the decision to survive. But years of tough decision-making prepared me for that moment, standing at the edge of a brand-new obstacle course with unimaginable twists and turns, determined to emerge victorious on the other side. Decisions a business owner implements along the way should be calculated ones. It’s extremely crucial to listen to your gut by utilizing what I consider to be my most powerful tool: my business sense. If you are constantly connected with your employees, clients and industry, your business sense will be strong. Use it and you’ll crush the obstacle course every time.

The balancing act.

Without balance I do not consider a business successful, no matter how impressive it may be on a balance sheet. Without real balance a business will consistently fail to realize lasting success. To give their best, team members need a healthy balance of work and home life, just as every manager or CEO does.

Nobody should spread themselves too thin. Responsibility should be delegated to the team and its managers with the appropriate systems in place to ensure accountability, productivity and performance.

Balance isn’t just about profitability, it’s also about employees’ mental wellbeing. We come in contact with people every day who are struggling in their personal life or at work — it could be a neighbor, a friend, a stranger on the street or one of your employees. Creating a workplace culture that accepts the messiness of real life (and the real people who live it) will bring a sense of humanity and humility to your organization. It’s truly magical and carries over to the product or service your company is providing.

Everyone has a bad day. Ridicule or attacks will never fix anything. I strongly recommend businesses establish a company-wide culture of support. Bad days get better, but it takes a family-like company culture to turn them around. When your company is defined by balance and empathy, a bad day — or an entirely bad year — becomes just another obstacle you can and will overcome.


This article was originally published in the Winter 2020/2021 edition of West Oceanfront Magazine. To view the full edition, click here.

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