In Episode #43 of the The Cultivating Business Growth Podcast, as we wrap up the final episode in our Working with an Advisor series, we focus on how to challenge yourself and your business to continue improving. 

While in the midst of challenges it often feels as if you are trucking uphill on a windy road that leads to a dead end. The good news, many times at the end of that journey you’re pushed somewhere you didn’t want to go, or didn’t know you needed to go, and you find innovation. We want to help set you up for success so when you face a challenge, you can tackle it head on, and be confident in where that challenge leads you and your business.


What we cover in this episode: 

  • 05:19 – Challenge births innovation
  • 14:37 – Strategies to challenge yourself
  • 15:48 – Be prepared
  • 19:34 – Establish a sounding board and utilize it
  • 22:22 – Be resilient
  • 23:23 – Calculate risk
  • 27:46 – Hold yourself accountable
  • 30:10 – Know your end goal

Challenge births innovation

Jami shared with us a story about her father and his experience in the agricultural trucking industry. Jami’s father’s job was to transport crops to the appropriate elevator after they were harvested. In the 1980’s, regulations changed and farmers were eligible for different subsidies which led to farmers purchasing their own trucks. After decades of being in business, these changes in the industry meant there was no longer a need for Jami’s dad’s trucking business; he had to find a new way to survive. So, he examined his needs, his business needs, and his desires. He knew his business was successful at transporting, rapport had been established with his drivers, and saw an area where there weren’t many competitors. He took the opportunity to trust his gut and pivot his business from hauling crops to hauling dangerous chemicals necessary for successful farming. He embraced discomfort, focused on the big picture, evaluated the risks and accepted the opportunity to change his business. Ultimately, the challenge led him to further success in his career.

Safe does not mean success

This story highlights the importance of challenge and embodies that entrepreneurial spirit that every business owner needs to have at their core – the willingness to face uncomfortable and sometimes scary challenges, and the resiliency to come back repeatedly despite the risks. All business owners should know that the chance for success may mean going out on a limb every once in a while. 


From our perspective, if you own a business you have to have integrity. Period. There is no wiggle room with this statement. We want business owners to feel good about what they are doing and serve people in the right way. To do this, you must operate with integrity. 

There are ways to take care of people while taking care of yourself. It’s up to you to find ways to achieve your goals without jeopardizing your morals, ethics, and relationships. Be prepared for others who may not like your approach or your decisions because that will happen. At that point, you can step back and reflect on how you made the decisions you did, and why, and know you did it in good conscience and intentions.

Strategies to challenge yourself

As you learned with Jami’s dad, sometimes challenges are great. In fact, sometimes competition is great. What’s not always great is the timing of challenges. You may not be able to predict when a challenge may arise, but if you follow our recommendations below you should be able to overcome challenges successfully.

1. Be prepared for the unknown. Make sure your business strategies are sound and know them well. Having the knowledge and understanding of your business, what it can do, and what it can withstand gives you a strong foundation. When challenges come your way, you can step back, assess the situation, and then you’re able to respond soundly one step at a time.

2. Be resilient and don’t let obstacles stop you. Look at failures as learning opportunities; this can lead to innovation. 

3. Establish a sounding board and utilize it. Hearing from people who are able to look at the issue you are having and help you see it through a different lens is invaluable. It’s imperative for you to have an honest, educated sounding board that understands your goals and has your best interests in mind. Go to them to listen, answer questions, give you things to think about, and ask you questions. Allow them to point out things you haven’t noticed and/or share ways they’ve seen similar challenges be tackled successfully. 

4. Calculate risk. There are things you need to be willing to risk. Before moving forward, it’s important to understand the magnitude of the risk. Some risks are high and you need to determine if there is a way to bring that risk level down. Truly think about the risk or liability and make sound judgement. Ask yourself important questions like “What are the long term risks?” and “What are the short term risks that could provide immediate gratification?” Be intentional with sacrifices. Identify the sacrifices you will have to make to get to where you want to be and determine what are the right sacrifices to make. 

5. Hold yourself accountable. Recognize when you make a mistake and own it. In order to have the ability to own your mistakes, you need to be cognizant of what is going on around you and also be cognizant of the people around you. There are times when you take action where it wasn’t needed or you don’t take action when you should have. There are times when action is needed, but the action you took just wasn’t hitting the mark. It’s ok! We’ve all been there. If needed, apologize to yourself and/or someone else. Be responsible to others and yourself. It will refine you so you can press on and can keep going.

6. Know your end goal and feed that fire. There will be challenges you run into that may not be worth overcoming because they’re not in the interest of your vision. In order to decipher which challenges are worth overcoming, and then actually taking action, you must know your end goal. If you haven’t thought about what that looks like, take some time and ask yourself these important questions like, “What do I desire?”, “What is my long-term vision?”, “Who am I and what is important to me?”, and “What is my dream?” If you would like to further define your vision and long term goals, listen to episode #01 and complete the free workbook provided with that episode


Challenges aren’t convenient, no matter how big or small. They can look like hiccups with technology, difficult clients, changing careers, and even starting a new business or new business line. Regardless of the shape and size, everyone faces challenges. Our hope is that the tips we shared today will help you overcome challenges when they come your way and help you think of new, innovative ways of handling your business. 

Links mentioned in this episode:


cultivating business growth itunes
Listen on Google Play Music
cultivating business growth stitcher
cultivating business growth spotify