Building a successful business is often a tumultuous journey filled with ups, downs, twists, and turns. Entrepreneurs and business leaders are all too familiar with the challenges that characterize this path. On an episode of my Family Office Success podcast, I shared personal experiences and offered strategies to stay motivated during chaotic and frustrating times. My hope is that these tips will help you through the “messy middle” of your entrepreneurial journey, providing actionable advice and thorough explanations.
Recognizing the “Messy Middle”
Understanding the Journey
The journey of building a business is rarely straightforward. It’s common to feel like no progress is being made, especially during challenging periods. From personal experiences of frustration and doubt, it is evident that these feelings are a natural part of the entrepreneurial process.
Drawing inspiration from successful entrepreneurs, it’s crucial to recognize the importance of the “messy middle” as a critical time, typically right before a big breakthrough. This period is often filled with uncertainty and obstacles, but it is also a time of significant growth and learning.
A few strategies for navigating challenging periods:
1. Celebrate Wins, No Matter How Small
One of the key strategies is celebrating wins, no matter how small. This practice can boost motivation and provide a sense of accomplishment during tough times.
Actionable Tips:
- Keep a Journal: Maintain a journal to document accomplishments – big, small, and in-between. Reflecting on these wins can provide a morale boost when you need it the most.
- Set Milestones: Break down long-term goals into smaller, achievable milestones. Celebrate each milestone to maintain momentum.
- Share Successes: Share wins with the team or your support network. Celebrating together can strengthen bonds and foster a positive work environment.
2. Focus on the Big Picture
It’s essential to focus on the big picture and remind oneself of your ultimate goals and long-term vision. This perspective can help maintain motivation and provide clarity during challenging times.
Actionable Tips:
- Vision Board: Create a vision board that visually represents long-term goals. Place it somewhere visible to keep your aspirations front and center.
- Regular Reflection: Schedule regular reflection sessions to revisit goals and assess progress. This practice can help you stay aligned with your vision.
- Affirmations: Use positive affirmations to reinforce commitment to long-term goals. Repeating these affirmations can help maintain focus and motivation.
3. Embrace the Chaos
Embracing the chaos is another strategy I recommend. Challenges are often necessary for growth and learning. When you can embrace the chaos, you can move through it more quickly and easily.
Actionable Tips:
- Reframe Challenges: View challenges as opportunities for growth rather than as obstacles. This shift in mindset can help you approach problems with a positive attitude.
- Stay Flexible: Be open to change and adapt strategies as needed. Flexibility can help navigate unexpected challenges more effectively.
- Continuous Learning: Invest in continuous learning and development. Equip yourself with new skills and knowledge to better handle the chaos.
4. Seek Support and Perspective
The value of seeking support and perspective from others who have navigated similar challenges cannot be overstated. Building a network of mentors, joining groups, or forming mastermind circles can provide valuable guidance and feedback.
Actionable Tips:
- Seek Out Mentors: Identify and reach out to potential mentors who have experience in the industry. Their insights can be invaluable.
- Join Groups: Participate in industry groups or online communities where experiences can be shared and lessons learned from others.
- Personal Board of Advisors: Build a personal board of advisors consisting of trusted individuals who can offer diverse perspectives and advice.
Building a successful business is not a smooth or predictable journey. By recognizing and appreciating the “messy middle,” celebrating wins, focusing on the big picture, embracing chaos, and seeking support, you can navigate the challenges and stay motivated. Reflect on progress, hold onto the vision, and let your passion guide you through the roller coaster ride of entrepreneurship.

