Rebranding after a failed business? Here are 40 Questions Entrepreneurs should ask themselves

Throughout my 30 year entrepreneurial journey, I have experienced my fair share of failures. But these failures have been my greatest teachers. They taught me the value of perseverance, resilience and adaptability. I've had to learn it's not about avoiding failure but embracing it as apart of the journey.  In fact, according to statics, the average Millionaire goes bankrupt 3.5 times. 

As I look back on my career, I can see how much I've grown. My values and guiding principles have shifted and evolved overtime to reflect my personal growth and progress. Each stage has presented it's unique challenges and opportunities for growth, from self-evaluation to personal development, and from economic ups and downs to ending a business and rebranding. 

During this rebrand, I decided to write a Journal that would help me dig deep into what worked, what didn't, where I'm headed, why I'm going and how will I get there. In this blog, these 40 questions will help maximize your momentum into the next stage, moving past failure more faster, by asking the tough questions that move you away from unproductivity and strategically plan for a new or evolved purpose driven career. There will be some questions that you'll want to get your pin and paper out for you to write them down.  Let's get into it...

Contrary to popular belief, Business is Personal 

Self Evaluation. The first step of rebranding in entrepreneurship for me was self-evaluation. This involved taking a deep dive into my strengths and weaknesses. Identifying the skills and attributes that would make me a successful entrepreneur. I had to ask myself tough questions like "Am I really cut out for this anymore?" and "Do I have what it takes to succeed into todays market? This stage was critical in helping me to understand my motivations and abilities in building a solid foundation with the rebranding. 

1. What do I do exceptionally well?
2. What makes me uniquely valuable?
3. What were my values when I first started my business? 
4. Have my values and guiding principles changed? If so, what are they now? 
5. What is it about me that People like or support? 

Learning from Strengths and Failures. The next stage was learning from my strengths and failures. Every entrepreneur faces setbacks and failures, but it's how we learn from them that sets us apart. I had to learn how to take constructive feedback and turn it into a learning opportunity. I also had to learn to celebrate my successes and use them to propel me forward.  

1. What have I accomplished in the past 20 -10 years?
2. What have I accomplished in the past 5 - 3 years?
3. What problems have I solved? Articulate those solutions.  
4. What challenges have I had to overcome to build my previous business? 
5. What has led to failure in my business? Is it skill? personality? is it lack of healthy boundaries? lack of structure? discipline? language? conversation? communication style? 

Seasons of Business. As my business grew, I went through various seasons of business. There were times of growth and prosperity, as well as times of economic uncertainty and downturns. I had to learn how to pivot my business during these seasons and agile in responding to market changes. This stage taught me resilience and adaptability. 

1. What part of the process have I enjoyed?
2. What part of the process was the most difficult?
3. When business was slow, what did I do with my  time? Did it help or hurt my business? 
4. When my business was thriving, what habits did my incorporate to sustain them or myself? 
5. What do I still need to know or learn? 

Relationships. Building relationships with customers, employees, and other stakeholders have been a critical stage in my entrepreneurial journey. I had to learn how to communicate effectively and build trust with my customers, how to lead and manage a team  effectively and build trust with my clients, brands, while learning how to collaborate with partners and vendors . Building strong relationships has been key to my successes. 

1. What values are controlling me?
2. What problem solving style do I have?
3. How do I know when my values have been met?
4. What are my rules? Do I meet others values and rules?
5. Is my communication style helping or hurting my business? 

Personal Development and Personal Battles. Running a business has also forced me to confront personal development and personal battles. I had to learn how to manage my time effectively and balance my personal and professional life. I also had to work on my own personal growth and development, including developing my emotional intelligence and resilience. This stage taught me the importance of self care and personal development.

1. What questions do I ask myself that gives me insight into my life's purpose? 
2. What decisions have I made that contributed to inefficiency?
3. What are 4 of my short comings/flaws that have limited me?
4. What do I need to let go of? 
5. What has helped my confidence? what hurt my confidence? 

Ending a Business and Rebranding. Having to go through the difficult stage of ending a business and rebranding. Sometimes a business just doesn't work out or maybe you've been running the same one for over 20 years and it's just time, it's important to know when to cut your losses and move on. This stage required me to be honest with myself about what was and wasn't working, and to have the courage to make a change. Rebranding was also an important stage, it allowed me to pivot my business and enter a new season of growth. 

1. Where is my business or industry heading? 
2. What barriers to entry in this Business I may encounter?
3. How can I avoid difficult competitors?
4. What resources do I need?
5. How will I satisfy my existing /new customers?
6. In what ways can my product or service be more specialized?
7. What are my intentions? is this what I really want? 
8. How much time will it take or what am I willing to invest in it?
9. What will it cost? How will it enhance my life?
10. Who is my ideal customer and how can I add value to my existing or new customer? 

Take Risks. But the most valuable lesson I've learned is the importance of taking risk.. As we get older, it can be easy to fall into a sense of complacency and stick to what we know. But taking risk is what keeps us alive and growing. Whether it's launching a new product or entering a new market, being willing to take calculated risks has allowed me to stay at the forefront of my industry. 

1. What is the best that can happen in my rebrand? 
2. What's the worst thing that can happen?
3. What am I willing to do to make it what I want it to be?
4. What might I be doing that's sabotaging my own success?
5. What lessons have I learned?

Being a creative entrepreneur who's also from Gen X has given me a unique perspective on life. I've learned that age is not a limitation, but rather a badge of honor that represents a lifetime of experiences and wisdom. It's given me the confidence to speak my mind and share my values and my ideas with the world, knowing that my voice matters and can make a difference. 

You can find these questions and more in the 90 Day Journal for Creatives and Lifestyle Entrepreneurs: strategies to plan, prep, problem-solve, protect your time & scale profits while living a purposeful life. A powerful way to propel your life forward no matter what stage of business you're in on Amazon here. 

Overall, ending a business and rebranding has taught me to embrace the journey and enjoy the ride. Life is too precious to be consumed with worry and stress. I've been able to live a fulfilling life and inspire others to do the same. By focusing on the things that truly matter, like catering to your spirit, meaningful work that gives you purpose and with people in your life that make you feel valued.  Good luck to you on your next  entrepreneurial journey.. 

For more on topics like this, you might be interested in Survival of the most Competent a new paradigm.