Complete Entrepreneur Starter Kit Planning Collection

236 planning questions and 0 expert readings across 5 guides.

Planning Questions

• Write about the last 3 times in the past year when you felt most energized and "in flow" at work. What were you doing? Who were you working with? What made those moments feel different from your regular workday?
• Reflect on a typical Monday morning over the past 3 months. Write down the specific thoughts or feelings you have about starting your work week. When did this pattern start? What does it tell you about your current work situation?
• Document 3-5 moments in your career when you had complete control over HOW you did your work (not just what you did). What did you choose to do differently? How did that autonomy feel?
• Think about the last time you worked with a difficult colleague, manager, or client. Write down what made it difficult. Now reflect: would this situation exist if you could choose who you work with?
• List the last 5 times you've talked about money or negotiated price in any context (work salary, freelance rate, splitting bills, buying something). Which felt comfortable? Which felt awkward? What pattern do you notice about your relationship with pricing your own value?
• Reflect on your past 6 months of work. Write about 2-3 projects where YOU made the key decisions vs. projects where you executed someone else's decisions. Which type of work energized you more? What does that tell you?
• Document a time in the past year when you had an idea for how to do something better but couldn't implement it due to company constraints. What was the idea? What stopped you? What would you have done differently if you'd had full control?
• Think about your childhood or early career. Write about a time when you created something or started something from scratch (could be a lemonade stand, school project, side hustle, anything). How did you feel? What motivated you?
• Reflect on the people in your life (family, partner, close friends). List 3-5 recent conversations where you talked about work. What did you say? What didn't you say? Who knows you're thinking about freelancing?
• Write about your relationship with stability vs. uncertainty. Describe a past situation where something felt uncertain or unstable (job change, move, relationship). How did you handle it? What did you learn about yourself?
• Think about the last 5 times you felt genuinely productive (not just busy). Write down what you were doing, where you were, what time of day it was, and what made those moments feel different from your usual work.
• Document 3 specific moments in the past month when your productivity system (or lack of one) completely failed you. What was the situation? What broke down? What did you do instead?
• Write about your energy patterns over the past week. For each day, note: when did you feel most alert? When did you hit a wall? What were you doing during your peak vs low energy times?
• List every productivity method, app, or system you've tried in the past 3 years. For each one, write: how long did you use it, why did you stop, and what (if anything) actually worked about it?
• Reflect on the last time you felt "in flow" - completely absorbed in what you were doing, losing track of time. What were you working on? What conditions made that possible? How long has it been since you felt that way?
• Think about someone whose productivity you admire (colleague, friend, public figure). Write down specifically what they do differently than you. Not vague traits like "disciplined" - actual behaviors you've observed or know about.
• Document your biggest productivity guilt. Complete this sentence and expand on it: "I always tell myself I should ___, but I never actually do it because ___." What does this reveal about the gap between your ideal and reality?
• Write about the last week: What important task did you keep postponing? When did you finally do it (or are you still postponing it)? What were you doing instead? What does this pattern tell you?
• Reflect on your relationship with "productivity porn" - articles, videos, apps promising the perfect system. When do you consume this content? How do you feel after? Has it ever actually helped, or does it become another form of procrastination?
• Think about the difference between how you work alone vs with others watching. Describe a specific recent example of each. When are you more productive? When does the work feel more authentic? What does this tell you about accountability?
• Write about the last 3 times you had to speak in front of others (work presentation, toast, meeting, class, etc.). For each: What was the situation? What did you feel in your body right before you started? What's one moment from each that still sticks with you?
• Reflect on someone you know personally who seems comfortable speaking in groups - not a celebrity, but someone you've actually observed. What do they do differently than you? Write down 3-5 specific behaviors you've noticed (how they pause, make eye contact, use their hands, etc.).
• Think about the last time you had something important to say in a group setting but didn't speak up. What was the moment you decided to stay quiet? What story did you tell yourself about why you shouldn't talk? What do you wish you had said?
• Document 3 moments from your past (childhood, school, early career) when speaking in front of others didn't go well. For each: What happened? Who was there? What conclusion did you draw about yourself as a speaker? Do you still believe that conclusion?
• Reflect on the times when you DO feel comfortable speaking - maybe with close friends, family, or small groups. What's different about those situations? What are you doing in those moments that you're NOT doing when you're anxious?
• Write about a time when someone gave you feedback (positive or negative) about how you communicate or present. What did they say? How did it land? How has that feedback shaped the way you show up when speaking?
• List the last 5-7 times you were in a meeting, class, or group setting. For each, note: Did you speak? If yes, how long after the meeting started? If no, what stopped you? What pattern do you notice?
• Think about your "speaking voice" versus your "regular voice." How do they differ? When do you shift into "speaking mode"? What happens to your voice, pace, or word choice? Does it feel authentic or like you're performing?
• Reflect on the last presentation or speech you heard that genuinely moved you or stuck with you. What made it memorable? Was it the content, the delivery, the speaker's energy? What specifically can you remember about it?
• Document a time when you were explaining something you deeply care about (a hobby, idea, story) and got really animated. Who were you talking to? What made you forget to be self-conscious? What does that tell you about when you're at your best?
• Write about 3 times in the past year when someone (friend, colleague, stranger) asked you for help or advice and you thought "I could charge for this." What were you helping with? What made you think it had value?
• Reflect on your typical week over the past 3 months. List all the moments when you had free time but didn't know what to do with it - Sunday afternoons, evenings after dinner, Saturday mornings. What were you actually doing during those times? What pattern do you notice?
• Document 3-5 skills or activities where people have specifically told you "you're really good at this" or "you should do this professionally." For each, write: who said it, what prompted them to say it, and whether you believed them.
• Think about the last time you needed extra money (unexpected expense, wanted something specific, felt financially stressed). Write down what happened, how much you needed, how you handled it, and how you felt about your options at the time.
• List the last 5 times you spent money on a service someone else provided (haircut, home repair, consulting, coaching, creative work, etc.). For each, write: did you think "I could do this myself"? What made you pay instead?
• Reflect on hobbies or interests you've had over the past 5 years. Which ones did you stick with? Which did you abandon? What pattern do you notice about what keeps you engaged vs what loses your interest after the initial excitement?
• Write about a time when you tried to start something on the side before (side project, freelance work, small business, content creation). What happened? Why did you start it? Why did it continue or why did it stop?
• Document your current relationship with money and work. Complete these sentences: "I work my day job because..." "Extra money would mean I could..." "The idea of working more hours makes me feel..."
• Think about your energy patterns over a typical week. Write down when you feel most energized and creative (specific days/times), when you feel depleted, and when you're just going through the motions. What does this tell you about when you'd actually have capacity for side work?
• Reflect on the people in your life who have side income or run their own thing. Write down: who are they, what do they do, what do you admire about their situation, and what do you think "I could never do that" about their situation?
• Write about 3 specific moments in the past year when you thought "I could do this better as my own business." What were you doing? What frustrated you about how it was being done?
• Document the last 5 times someone asked you for help or advice in your area of expertise. What specifically did they need? What does this pattern reveal about what people struggle with?
• Reflect on a time in the past 3 years when you were so absorbed in a project that hours felt like minutes. What were you building or solving? What made it different from "regular work"?
• List every side project, hobby, or "just for fun" thing you've worked on in the past 2 years. Which one did you keep coming back to even when you were busy? Why?
• Write about your relationship with money over the past 5 years. When have you felt most financially secure? Most anxious? What would need to be true for you to feel okay with irregular income?
• Document 3 times you've started something new (job, project, relationship). How did you handle the uncertainty? What patterns do you notice in how you react to risk?
• Think about the worst professional failure you've experienced. How long did it take you to recover? What does this tell you about your resilience for business setbacks?
• Reflect on your current weekly schedule. Which 10 hours would you realistically cut to work on your business? What would you have to say no to?
• Write about why you want to start a business NOW versus a year ago or a year from now. What changed? What's the real urgency?
• Document every time in the past 6 months you complained about your current work situation. What specific patterns emerge? Are you running FROM something or TO something?

Expert Readings

Available Guides

• Building a Productivity System

  Create systems that actually work for you

• Building Side Income

  Generate extra income outside your day job

• Going Freelance

  Build a sustainable freelance career

• Public Speaking Confidence

  Overcome fear and speak with impact

• Starting a Business

  Launch your business from idea to first customers