TL;DR: Break Bad Patterns with Six Transformational Questions for Entrepreneurs
Entrepreneurs often fall into destructive habits like emotional avoidance and procrastination due to high-pressure demands. One nightly ritual, asking six powerful self-reflective questions, helps identify these patterns and creates actionable change.
• Pinpoint daily avoidance to tackle unfinished tasks and decisions head-on.
• Differentiate busywork from productivity to realign goals meaningfully.
• Challenge limiting beliefs and take accountability for personal responsibility.
• Spot autopilot habits and redirect toward healthier practices.
• Reflect on improvements for the next day to refine success daily.
Start tonight: Commit to this 6-question journaling routine for one week to develop self-awareness and overcome barriers holding you back.
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I Stayed Stuck in Bad Patterns for Years Until I Started Asking Myself These 6 Questions Every Night
As a serial entrepreneur from Europe, I’ve faced my fair share of challenges in both business and life. It was painfully clear when my recurring bad patterns, emotional avoidance, procrastination, and lack of self-reflection, started impacting not just my ventures but my personal relationships. What makes this story different is that I didn’t get unstuck by reading one more self-help book or attending a seminar. Instead, the breakthrough came from a nightly ritual of asking myself six simple but powerful questions. These questions became the cornerstone of my mental clarity and success. Let me walk you through this transformational process that reshaped not just my businesses but my mindset.
Why Do Entrepreneurs Fall Into Bad Patterns?
Entrepreneurs often live fast-paced, high-pressure lives. The constant need to make decisions, meet deadlines, and innovate puts mental health and emotional resilience at risk. Studies show that over 70% of startup founders experience periods of depression and anxiety, often aggravated by a lack of self-awareness. When you’re deep in the weeds of running a business, self-reflection often gets pushed aside. The question is no longer about succeeding but managing the damage from recurring patterns. My personal experience was no exception.
- Emotional avoidance: Ignoring emotional struggles to focus solely on tasks, leading to burnout.
- Procrastination: Putting off key decisions or actions because they feel overwhelming.
- Lack of self-reflection: Neglecting mental and emotional inventory to “stay productive.”
My Six Nightly Questions: A Game-Changing Routine
These six questions transformed my evenings into personal coaching sessions. They forced me to confront my day without judgment. Here’s what I asked myself every night, and how it helped break the cycle:
- What did I avoid today that I’ll have to face tomorrow?
Recognize avoidance head-on. This question made me accountable for tough calls, unfinished tasks, or ignored relationships. - Did I mistake being busy for being productive?
This helped me focus on meaningful work instead of busywork, realigning with long-term goals. - What story did I tell myself today that wasn’t actually true?
We all rationalize actions (or inactions). Confronting this revealed limiting beliefs holding me back. - Who did I blame for something that was actually my responsibility?
Taking radical accountability was a game-changer for managing emotional and business failures. - What did I do today purely out of habit?
Habits can operate on autopilot, good or bad. This protocol helped me identify damaging ones. - What would I do differently if I had to live today again?
A reflective take on improving daily actions; helped me refine what “success” should look like proactively.
Can Founders Overcome Emotional Barriers?
Breaking free from cycles requires honesty and consistency. Founders often face stereotypes of fearlessness. Yet, behind these masks lie vulnerabilities that are rarely addressed. Investing just 15 minutes every evening to answer these questions gave me the tools to identify emotional blocks and pivot when necessary. For instance, I stopped defaulting to doomscrolling after failed pitches and redirected my energy toward actionable improvements.
It’s important to recognize that emotional resilience is not just a personal benefit, it shapes leadership. How you show up daily for your team and your company is directly tied to how well you manage your mental state. And yes, reflection is part of that equation.
Tips for Adopting This Ritual
- Consistency: Make it part of your nightly routine; treat it like brushing your teeth.
- Write it down: Journaling these answers makes the process tangible, with opportunities to track progress.
- Be honest: This is your private self-check, free from external judgment. The more honest you are, the more effective it becomes.
- Revisit weekly: Look back at your answers to identify recurring patterns that might need deeper work.
Common Mistakes to Avoid
- Overthinking: Keep it simple; don’t let reflection spiral into self-criticism.
- Skipping steps: Answer all six questions, even if some responses feel uncomfortable or repetitive.
- Procrastinating: Don’t delay answering these; the power lies in reflection before sleep.
- Being vague: Specificity in answers leads to targeted action.
It’s not about perfect answers but consistent self-awareness. Your growth unfolds one night at a time.
How This Changed My Life and Business
Within months of nightly reflection, key transformations emerged. My communication skills improved, not just personally but with my team. Business outcomes followed. For example, my ability to handle investor feedback without emotional avoidance resulted in a successful funding round after my second pitch attempt. Reflecting daily also allowed me to catch procrastination early, redirecting efforts to critical tasks that moved ventures forward.
Furthermore, accountability helped me repair damaged relationships, both personal and professional. What’s more, recognizing autopilot habits made it easier to bin unhealthy ones, like defaulting to caffeinated drinks late at night.
Conclusion: Are You Ready to Break Your Patterns?
If you’ve felt stuck or overwhelmed, I invite you to try this nightly practice. The questions are simple, but the results can be profound. Self-awareness is not a luxury, it’s the core foundation of your role as a leader. Entrepreneurs are not immune to emotional pitfalls, yet the key difference between thriving and struggling hinges on how you tackle these challenges head-on.
Your next steps:
- Commit to answering the six questions for one week.
- Keep a journal to track your progress and insights.
- Start small, prioritize one actionable change each day.
- Seek help when needed; emotional health is a team sport!
Your journey to clarity starts tonight. Reflect, act, and grow, one question at a time.
FAQ on Overcoming Bad Patterns Using the Six Nightly Questions
What led the author to create the six nightly questions?
The author, a serial entrepreneur, struggled with recurring bad habits like procrastination, emotional avoidance, and lack of self-reflection. These habits negatively impacted both personal relationships and business success. After realizing that passive consumption of self-help content wasn't creating meaningful change, the author decided to develop a nightly self-reflection routine. These six questions became a cornerstone of personal and professional transformation, emphasizing accountability and introspection. For deeper insights into this journey, read about the six questions here.
How do these questions help overcome procrastination?
One of the six questions asks, “What did I avoid today that I’ll have to face tomorrow?” This question forces honesty about tasks or responsibilities you might have delayed. By addressing avoidance head-on, it helps create accountability for moving past procrastination. Pairing this reflection with intentional next actions ensures better productivity. For further guidance on self-awareness techniques, Explore breaking procrastination habits.
Can these questions promote emotional awareness?
Yes. Questions like “What story did I tell myself today that wasn’t true?” and “Who did I blame for something that was actually my responsibility?” directly confront emotional narratives, limiting beliefs, and deflection habits. Practicing emotional responsibility helps entrepreneurs and individuals alike manage their mental state and improve relationships. This aligns with principles from emotional resilience experts like Brené Brown and Mel Robbins. Learn how radical accountability improves leadership.
How are these questions different from journaling routines?
Unlike generic journaling prompts, these questions are tailored for introspection that targets specific recurring patterns. For instance, the question “Did I mistake being busy for being productive?” focuses on identifying and reducing busywork, aligning actions with long-term goals. This method doesn’t just reflect on the day but offers a practical way to track incremental changes over time. Discover structured nightly reflection routines.
Is self-awareness enough to change bad patterns?
Self-awareness is the first step, but it must be paired with action. Questions like “What did I do today purely out of habit?” and “What would I do differently if I had to live today again?” help identify specific areas for change and prioritize actions. The nightly routine serves as a feedback loop, strengthening emotional resilience and enabling small, strategic improvements daily. Check out habit-formation strategies.
What role does journaling play in this process?
Writing down answers to the six questions reinforces reflection and provides a tangible record of patterns, progress, and recurring challenges. Journaling also allows you to revisit weekly entries to identify trends and track growth over time. This act of documenting creates accountability and solidifies the practice into your nightly routine. Explore why journaling aids transformation.
Can these questions improve relationships?
Absolutely. The questions, particularly “Who did I blame for something that was actually my responsibility?” foster accountability and self-awareness, which are foundational to repairing and strengthening relationships. As the author noted, this approach helped repair both personal and professional relationships by addressing emotional unavailability and improving communication. Learn how relationship reflection ties to leadership.
How can entrepreneurs apply these questions to leadership?
Entrepreneurs often face emotional challenges amplified by high-pressure environments. Implementing a nightly routine based on these six questions can enhance emotional intelligence, decision-making, and team leadership. For example, identifying narratives or unhelpful habits can translate into better responses to setbacks or investor feedback. Explore emotional growth for entrepreneurs.
Are there common pitfalls to avoid while adopting this practice?
Yes. Common mistakes include overthinking answers, skipping questions, and providing vague, surface-level reflections. For instance, instead of vaguely stating, “I want to be better tomorrow,” dive into what specific actions created challenges and how a different approach could help. Reflection should be honest and specific to yield meaningful change. For detailed error-avoidance tips, read here.
What are the long-term benefits of using this reflective practice?
Over time, using these six questions builds self-awareness, improves emotional resilience, strengthens relationships, and fosters consistent personal and professional growth. The author experienced both tangible results, such as improved investor meetings, and intangible ones like strengthened personal connections. By addressing underlying patterns daily, the practice ensures sustainable change. Uncover case studies on habit transformation.
About the Author
Violetta Bonenkamp, also known as MeanCEO, is an experienced startup founder with an impressive educational background including an MBA and four other higher education degrees. She has over 20 years of work experience across multiple countries, including 5 years as a solopreneur and serial entrepreneur. Throughout her startup experience she has applied for multiple startup grants at the EU level, in the Netherlands and Malta, and her startups received quite a few of those. She’s been living, studying and working in many countries around the globe and her extensive multicultural experience has influenced her immensely.
Violetta is a true multiple specialist who has built expertise in Linguistics, Education, Business Management, Blockchain, Entrepreneurship, Intellectual Property, Game Design, AI, SEO, Digital Marketing, cyber security and zero code automations. Her extensive educational journey includes a Master of Arts in Linguistics and Education, an Advanced Master in Linguistics from Belgium (2006-2007), an MBA from Blekinge Institute of Technology in Sweden (2006-2008), and an Erasmus Mundus joint program European Master of Higher Education from universities in Norway, Finland, and Portugal (2009).
She is the founder of Fe/male Switch, a startup game that encourages women to enter STEM fields, and also leads CADChain, and multiple other projects like the Directory of 1,000 Startup Cities with a proprietary MeanCEO Index that ranks cities for female entrepreneurs. Violetta created the “gamepreneurship” methodology, which forms the scientific basis of her startup game. She also builds a lot of SEO tools for startups. Her achievements include being named one of the top 100 women in Europe by EU Startups in 2022 and being nominated for Impact Person of the year at the Dutch Blockchain Week. She is an author with Sifted and a speaker at different Universities. Recently she published a book on Startup Idea Validation the right way: from zero to first customers and beyond, launched a Directory of 1,500+ websites for startups to list themselves in order to gain traction and build backlinks and is building MELA AI to help local restaurants in Malta get more visibility online.
For the past several years Violetta has been living between the Netherlands and Malta, while also regularly traveling to different destinations around the globe, usually due to her entrepreneurial activities. This has led her to start writing about different locations and amenities from the point of view of an entrepreneur. Here’s her recent article about the best hotels in Italy to work from.