How to Turn Your Agency Failures Into Growth Opportunities

By Jason Swenk on November 27, 2022

What big agency failures have you had? How did you overcome them? Most people don’t like to talk about failure but we all know it’s part of being an entrepreneur. The road to growing your agency is filled with them and it’s good to reflect on how we deal with failure. It’s also important to look back on things that seemed like the worst-case scenario can turn out to be blessings that lead us to new and exciting paths. Today’s guest has turned his past failures into an opportunity to share the lessons that can come from failures.

Justin Skinner is a self-proclaimed professional failure. He’s also an entrepreneur, author, and podcast host. When Justin’s dream of becoming a professional baseball player didn’t take off, he focused on graphic design and photography. He ended up working at a couple of digital agencies and eventually became a real estate entrepreneur. Neither of these careers was what he thought but he found great success and happiness in this unexpected path. Most recently, Justin has been spreading the word about the benefits of failure with his book and podcast, The Professional Failure.

In this episode, we’ll discuss:

  • Trying to minimize the risks when growing his agency.
  • Learning from his failures as a leader.
  • The big failure that changed his career path.


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The Road to Growing an Agency is Filled with Failures

In the agency business, the road to growth and success is normally filled with a list of failures. People normally want to hide those failures and not talk about them. The truth is even big names like Frank Kern has experienced some failures in their incredible career. It’s an inevitable part of learning and growing.

Agency owners may get to the point where they want to give up and see no way out other than selling. Jason sees this type of exhaustion all the time when advising agency owners. However, he believes discussing failures can help you realize you’re not alone and find solutions faster.

There are many different ways to go about building an agency. For Justin, it made more sense to grow with contract workers. According to him, this allowed more flexibility and freedom from project to project. The agency did end up having one key employee who did a great job. However, they end up never adding other employees.

The benefit of course is that they didn’t have to worry about employees in slow months. It definitely depends on how you want to manage your agency and the vision you have for its future. In Justin’s case, it was the best decision because it provided clarity on their bottom line and allowed them to forecast net earnings for the year.

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Biggest Failure Turned into a Huge Success

Justin has had several failures in his career. One that turned out to be a big success down the road was his dream to play professional baseball. He played in high school and college and had several friends who got drafted so he assumed he would too. This dream never came true. Although he was crushed, he now realizes his life wouldn’t have led to him growing a successful business and becoming an author if he had continued to pursue a career in sports. Losing this dream led to many opportunities he couldn’t have imagined at the time.

It’s all part of learning to identify yourself with who you are rather than what you do. Justin realized he wanted to be a resource for others, whether he was an agency, owner, baseball player, or realtor. This has really helped him find joy in whatever he’s doing. Pivoting is part of life and sometimes you’ll find you no longer enjoy what you’re doing, so it’s good to know you can pivot to something else.

Lessons in Agency Leadership

One of his biggest failures was when he hired the agency’s one and only employee. Since he was used to working exclusively with contractors, it was hard for him to manage someone else’s time. He didn’t know how to train an employee and wasn’t clear on the tasks required for the job. Without clear direction, the employee had nothing to do sometimes, which led to frustration for both.

Justin had to learn how to become a better leader who is clear about his expectations.

When you hire someone you shouldn’t assume they’ll know what to do. Keep in mind why you are hiring this person. You’re probably trying to save time. However, if you can’t figure out how to communicate their tasks properly, you’ll find yourself giving instructions over and over. The result of this poor communication actually adds more work, instead of saving you time.

Jason has struggled with this in the past and he realized he needed someone to manage and guide these new employees. He recognizes he doesn’t have the patience to do it himself but he still makes sure new employees receive proper training.

On the flip side, Justin thought he was empowering his employee by giving them the freedom to choose how to organize their day. In reality, the lack of clarity and direction left ambiguity as to priorities.

This “failure” turned into 2 huge lessons:

  • Be more organized, and
  • Give clearer instructions and realize we’re all different and everyone has different ideas about which are the boring or interesting tasks

Next time you feel like you’ve experiences a failure, consider what lesson it’s actually teaching you.

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