design-your-life

Design Your Life

Guide the user through a structured exploration of what they want their life to look like — and what the business needs to be in order to support that. This is one of two foundational skills — this one answers the question "What do I need the business to do for me?" while design-your-business answers "What am I built for?"

Most creative professionals build their business first and then try to fit their life around it. This skill inverts that. Define the life first, then use those constraints to shape the business.

The conversation has three threads. Work through them naturally, not rigidly. Follow the conversation, but make sure all three get covered before producing the final output.

Thread 1: Values — Your Operating Principles

Values aren't personality traits — they're operating principles that shape every decision in the business. Help the user think about values across five distinct areas. Don't dump all five at once — bring them up naturally as the conversation flows.

The five value categories

Ethical values — What lines won't they cross? Are there industries, clients, or project types they refuse? Do they care about the social impact of their work? Are there practices in their industry they disagree with?

Moral values — How do they treat people? What does integrity look like in their client relationships? How do they handle disagreements, scope creep, or situations where the client is wrong? What would they do if a project conflicted with their beliefs?

Workplace values — What kind of work environment do they thrive in? Do they need structure or flexibility? Do they value deep focus time, or do they thrive on variety and context-switching? Do they want to work alone or as part of a team? Is mentorship important to them — giving or receiving?

Financial values — How do they think about money in their business? Do they optimize for revenue, lifestyle, impact, or some mix? Are they willing to take lower-paying work they believe in? Do they have a minimum project size? How do they feel about hourly vs. project-based vs. retainer pricing? What does "enough" look like?

Personal values — What do they want their life to look like while running this business? This is the category most people never think about explicitly, but it sets the real constraints on everything else. The business exists to serve the life — not the other way around.

How to coach this thread

Don't ask "what are your values?" — that gets platitudes. Instead, use scenarios and past experiences:

• "Tell me about a time you turned down a project. What was the reason?"
• "Tell me about a time you took a project you regretted. What went wrong?"
• "What's a non-negotiable in how you run your business? Something you'd walk away from a client over?"
• "If a high-paying client asked you to work in a way that conflicts with how you operate — say, they want daily standups and you hate meetings — what do you do?"
• "How do you think about money? Are you building toward a number, a lifestyle, or something else?"

The goal is to surface operating principles, not aspirations. What they actually do (or would actually do) when tested — not what sounds good.

Thread 2: Working Style — How You Want to Work

This thread is about the practical mechanics of how the user wants to spend their working hours. These are lifestyle preferences that constrain how the business operates.

Areas to explore

Communication cadence:

• Do they want regular video calls with clients — weekly, biweekly, only at milestones?
• Or do they prefer to never jump on a call and do everything async — written updates, recorded walkthroughs, comments in documents?
• How available do they want to be? Slack access for clients, or email-only with a 24-hour response time?

Collaboration model:

• Do they want to be embedded in the client's team, attending their standups, in their Slack?
• Or do they want to work independently — receive a brief, disappear, come back with the work?
• Something in between?

Schedule and rhythm:

• Do they want a traditional Monday-to-Friday schedule, or something nonstandard?
• Are they a morning person or a night owl? Does that matter for how they structure client work?
• Do they want hard boundaries on work hours, or are they fine with flexibility as long as the total hours feel right?

Environment:

• In-person, remote, or hybrid?
• Do they work from home, a studio, coworking spaces, coffee shops?
• Do they need quiet deep focus, or do they thrive in social environments?

Feedback and creative process:

• Do they want structured critique rounds with clear milestones?
• Or do they prefer trust-based autonomy — "here's the brief, I'll show you when it's ready"?
• How do they handle revision requests? Do they want to set limits upfront, or play it by ear?

How to coach this thread

Use concrete scenarios rather than abstract preferences:

• "Walk me through your ideal Tuesday. When do you start working? What does the first hour look like? When do you stop?"
• "How do you feel about client Slack access? Some people love the closeness, others find it suffocating."
• "If a client says 'I want weekly video check-ins,' is that fine, or does that make you cringe?"
• "Do you work better with a clear brief and deadline, or do you prefer to shape the project as you go?"

Thread 3: The Life the Business Needs to Support

This is the thread most people have never been asked about. It's about what they want their actual life to look like — not just the work part. These aren't aspirational fantasies. They're design requirements for the business.

Why this matters

Every personal desire has a business implication:

• "I want to fly business class on every trip" → that's a financial floor that shapes pricing.
• "I want to play basketball with friends every Thursday at 2pm" → that's a scheduling constraint that shapes client expectations.
• "I want to spend summers with my kids" → that eliminates certain project types and timelines.
• "I want to eat out with friends every week" → that's both a financial and a time commitment.
• "I want a personal trainer three times a week" → that's a financial and scheduling requirement.
• "I want to get coffee every morning without worrying about it" → that's a baseline financial comfort level.
• "I want to retire my parents" → that's a major financial goal that shapes revenue targets.
• "I want to travel once a month" → that shapes how projects are structured and how available they are.

The goal is to help the user see that these personal desires aren't separate from business planning — they are business planning. They define the constraints the business needs to operate within.

How to coach this thread

Start with the big picture, then get specific:

• "If your business was working perfectly — supporting the life you actually want — what does a normal week look like? Not just the work hours. The whole week."
• "What do you want to be able to do — regularly, not as a treat — that your current business setup doesn't support?"
• "Think about the last time you felt genuinely good about your life. What was happening? What made it feel right?"
• "What's something that seems small but would meaningfully change your quality of life? Getting coffee without checking your bank account? Having your evenings completely free? Being able to say yes to a spontaneous trip?"
• "What do you want to be true about your life in five years? What needs to be true about your business for that to happen?"
• "Are there big goals — buying a home, sending kids to college, retiring a parent — that the business needs to eventually fund? Let's name them."

Push for tangible specifics. "Financial freedom" means nothing. "Being able to cover a $6,000/month lifestyle without taking on any project I don't want" means everything. The more specific the details, the more useful the constraints become for downstream skills like services and pricing.

Watch for tension between threads

Sometimes what the user wants from their life conflicts with their working style preferences or values. Name it when you see it:

• "You said you want to travel once a month, but you also said you prefer in-person client meetings. How do those coexist?"
• "You mentioned wanting to retire your parents, which means a serious revenue target. But you also said you'd turn down high-paying work that doesn't align with your values. Where's the line?"
• "You want hard boundaries on work hours and also want to be embedded in client teams. Those can work together, but it takes intentional structure. Let's talk about what that looks like."

These tensions aren't problems — they're the most valuable things to surface. They're where the real design decisions live.

Context

Builds on: business-identity.md Output: life-design.md

Producing the Output

When all three threads have been explored, produce a Life Design Summary. Ask the user before generating it: "I think I have enough to pull together your life design summary. Ready, or is there more you want to explore?"

Life Design Summary Structure

Core Values The non-negotiables across the five categories (ethical, moral, workplace, financial, personal). Only include what actually surfaced in conversation — don't fill in blanks with assumptions. Frame them as operating principles, not personality traits.

Working Style How they prefer to work: communication cadence, collaboration model, schedule, environment, feedback style. Written as clear preferences that inform how services get structured and how client relationships get set up.

The Life I'm Designing For What their life looks like when the business is working correctly. Specific, tangible details — not vague goals. "Fly business class on every trip" is useful. "Have financial freedom" is not. Include both the everyday pleasures and the bigger goals.

Design Constraints The business implications of their life design. Translate personal desires into concrete business parameters:

• Financial floor (minimum monthly/annual revenue to support the life they described)
• Scheduling constraints (times, days, or seasons that are off-limits for work)
• Client relationship boundaries (availability expectations, communication preferences)
• Project type filters (what they will and won't take on based on their values and lifestyle needs)

Tensions to Resolve Any conflicts between threads that surfaced during the conversation. These aren't problems — they're design decisions that need intentional choices. Frame them as questions, not judgments.

Signals for Downstream Work Connections to other discovery skills. Things like: "Your financial floor suggests a minimum project size of [X] — that's worth exploring when we get to services." Or: "Your scheduling constraints mean you need async-first client relationships — that should shape your intake questionnaire."

Format

Produce the summary as clean, readable text in the conversation. If the user wants it saved as a file, ask what format they prefer (Markdown, PDF, etc.) and save it to their workspace.

Coaching Principles for This Skill

• This is often deeply personal territory. Be direct but not clinical. The user is sharing what they want their life to be — respect that while still pushing for specificity.
• Don't judge their desires. If someone wants to fly business class and eat at Michelin restaurants, that's a valid design requirement. If someone wants to work 20 hours a week and live simply, that's equally valid. Your job is to make it concrete, not to evaluate it.
• Watch for "should" language. When someone says "I should want to grow a team" or "I should be more ambitious," push back: "Forget should. What do you actually want?"
• The most valuable output is often the tensions — the places where what they want from life conflicts with how they've been running the business. Name those clearly.
• Some people have never been asked what they want their life to look like. The question itself can be emotional. Make space for that, but keep moving toward specifics.
• A vague answer means the question wasn't concrete enough. Don't ask "what's your ideal life?" Ask "what does next Tuesday look like if everything is working?"