Stage 4: Strategy | Career Design

The Career Identity workbook helped you understand who you are at work. This one is about what you do with that knowledge.

Most career advice assumes you need to find the perfect job. This is impossible as even the most well-matched career will have misaligned pieces, boring days, and hard trade-offs. What actually works is designing your career actively: reshaping your current work to fit you better, prototyping possible futures before committing, and making decisions based on your internal compass rather than external pressure.

The research in this workbook comes from 3 traditions: design thinking applied to careers (Burnett and Evans at Stanford), job crafting psychology (Wrzesniewski at Yale), and planned happenstance theory (Krumboltz at Stanford). Together, they give you a practical toolkit for designing a career that fits your life.

You already did some of this work in the Odyssey Plans topic. This workbook goes deeper, with career-specific exercises that build directly on your career identity profile.

What the research says

Design thinking and career decisions

Bill Burnett and Dave Evans ran the Life Design Lab at Stanford for over 15 years. Their "Designing Your Life" course became one of the most popular electives in Stanford's history, and more than 570 universities have since adopted the approach.

Their core argument was that the tools that designers use to create products (empathy, ideation, prototyping, testing) work just as well for designing a life and career. The most important principle is that you can't think your way into a career - you have to build your way into one.

Burnett and Evans found that people get stuck in career decisions for 3 predictable reasons:

• Gravity problems. Trying to solve a constraint that can't be changed. "I wish I'd studied medicine" is a gravity problem at 45. You can't go back. You can only design forward from where you are.

• Anchor problems. Fixating on one solution and refusing to explore alternatives. "I just need to find the right company" narrows your field when you might need a different kind of work entirely.

• Lack of prototyping. Making permanent decisions based on imagination instead of experience. People quit jobs, move cities, or start businesses based on a fantasy of what the new thing will feel like, without ever testing it first.

The fix for all 3 is to generate multiple options (not one "right answer"), prototype them through small real-world experiments, and use what you learn to make better decisions. This is the career equivalent of the "little bets" you will explore later in this stage.

Job crafting

Amy Wrzesniewski at Yale studied hospital cleaners and discovered something researchers didn't expect. Some cleaners described their work as boring and meaningless. Others, doing the exact same job in the exact same hospital, described it as deeply meaningful. The difference was that the second group had actively reshaped their work. They'd taken on extra tasks (rearranging artwork for patients, chatting with visitors to make them feel welcome) that transformed their experience of the role. Wrzesniewski called this job crafting: the active process of reshaping your work to create more meaning, engagement, and satisfaction.

Job crafting has 3 dimensions:

• Task crafting. Changing what you do: adding tasks that play to your strengths, dropping or minimising tasks that drain you, redesigning how you approach existing work.

• Relational crafting. Changing who you work with: seeking out collaborators who energise you, reducing time with people who drain you, building mentoring relationships, creating new connections across teams.

• Cognitive crafting. Changing how you think about your work: reframing a task from "filing reports" to "keeping the team informed," seeing your role as part of a larger purpose, connecting your daily work to your values.

The research shows that job crafting improves work engagement, job satisfaction, and resilience. And it works at every level, from entry-level to executive. You don't have to wait for someone to redesign your job for you. You can start reshaping it yourself. This is great news especially if you're not ready to leave your current role. Job crafting is career design you can do right now, inside your existing situation, without anyone's permission.

Planned happenstance

John Krumboltz at Stanford spent decades studying how people actually make career decisions (as opposed to how career theories say they should). He found that most significant career developments happen through unplanned events such as a chance conversation at a party, a colleague mentioning an opening, a side project that unexpectedly takes off.

This doesn't mean career planning is useless. The most successful career builders are the ones who create the conditions for good accidents to happen. They stay curious, try things, talk to people, and remain open to unexpected directions.

Krumboltz identified 5 skills that help people benefit from unplanned events:

• Exploring new learning opportunities even when they don't seem directly relevant.

• Continuing effort despite setbacks and uncertainty.

• Being willing to change attitudes, circumstances, and plans.

• Viewing new opportunities as achievable regardless of uncertainty.

• Risk-taking. Acting in the face of uncertain outcomes.

So, alongside deliberate career design, build habits of exploration, go to the thing, have the conversation, and just say yes to the odd opportunity. Your next career move might come from a direction you haven't even considered yet.

Exercises

Access your Notion workbook here.

Exercise 1: Job crafting audit

Before designing your future career, see how much room you have to redesign your current one. This exercise uses Wrzesniewski's 3 dimensions of job crafting.

Task Crafting:
Tasks you could add or expand (that play to your strengths and energy):
What's stopping you? How could you start?
Tasks you could reduce, delegate, or redesign (that drain you):
How could you reduce your time on this?

Relational Crafting:
People you want to work with more (who energise you):
How could you create more opportunities to collaborate?
Interactions you want to reduce (that drain you):
How could you set boundaries or restructure?

Cognitive Crafting:
A task you currently see as meaningless or draining:
How could you reframe it in terms of your values or larger purpose?

Now think about your 1-month job crafting plan: what's the first small change you'll make in each dimension?

Exercise 2: Career odyssey plans

In the Odyssey Plans topic, you explored 3 different possible lives. This exercise focuses specifically on 3 possible career paths. Each should be a genuinely different direction, not 3 versions of the same plan. Use your career identity from the previous exercise as a filter: which paths honour your career anchor, match your RIASEC code, and protect your energy?

Career path 1: The current trajectory extended

If you stayed roughly on your current path for the next 5 years and things went well, what would that look like?

• What would you be doing day-to-day?

• What kind of environment would you work in?

• How does this path match your career anchor?

• How does it match myour RIASEC code?

• How would it affect your energy (based on your work energy map)?

• What would you gain?

• What would you lose or sacrifice?

• Confidence level (1-10): how realistic is this path?

• Excitement level (1-10): how alive does it make you feel?

Career path 2: The pivot

If your current path disappeared tomorrow, what would you do instead? A genuinely different direction.

• What would you be doing day-to-day?

• What kind of environment would you work in?

• How does this path match your career anchor?

• How does it match myour RIASEC code?

• How would it affect your energy (based on your work energy map)?

• What would you gain?

• What would you lose or sacrifice?

• Confidence level (1-10): how realistic is this path?

• Excitement level (1-10): how alive does it make you feel?

Career path 3: The wild card

The option you haven't let yourself consider seriously yet. The one that excites and scares you.

• What would you be doing day-to-day?

• What kind of environment would you work in?

• How does this path match your career anchor?

• How does it match myour RIASEC code?

• How would it affect your energy (based on your work energy map)?

• What would you gain?

• What would you lose or sacrifice?

• Confidence level (1-10): how realistic is this path?

• Excitement level (1-10): how alive does it make you feel?

Looking at all 3 paths, which one are you most drawn to? Why?
Which path best honours your career identity?

Exercise 3: Career experiments

Burnett and Evans call these "prototypes." Krumboltz would call them "planned happenstance." The principle is the same: test your career ideas in small, reversible ways before making big, permanent decisions.

For each career path you're considering (or for the one you're most drawn to), design 2-3 small experiments you can run in the next 30 to 90 days.

Types of career experiments

• Conversation prototype. Have a 30-minute conversation with someone who's already doing what you're considering. Ask them what a typical day looks like, what surprised them about the work, and what they wish they'd known before starting.

• Experience prototype. Get a small taste of the work. Volunteer, freelance, take a short course, shadow someone, or take on a side project that simulates the role.

• Skill prototype. Test whether you enjoy building the skills the new path requires. If you're considering UX design, spend a weekend on a design project. If you're thinking about coaching, coach a friend through a problem and notice how it feels.

Experiments you want to test

For each new experiment, answer these questions:

• Which career path is this testing?

• Type of experiment (conversation / experience / skill)

• What specifically will you do?

• What question are you trying to answer?

• By when will you do this?

• What would "success" look like? (What would confirm this path is worth pursuing?)

• What would "failure" look like? (What would signal this path isn't right?)

Exercise 4: Career decision filter

When a career opportunity appears (a job offer, a promotion, a freelance gig, a business idea), use this filter before saying yes. It's built from your career identity and designed to prevent reactive decisions.

Build your personal filter

Using your career identity work, fill in your personal career decision criteria. These become your checklist for every future opportunity.

Does this honour my career anchor? My anchor is: ___. This opportunity would need to...
Does the environment match my RIASEC code? My code is: ___. The environment would need to...
Does it respect my energy patterns? Based on my energy map, I need...
Does it fit my values? (from Stage 1) My top values are: ___. This opportunity would need to...
Does it fit my life vision? (from Stage 3) My vision includes: ___. This opportunity would need to...
Does it protect my lifestyle needs? I need: ___ hours/week, ___ flexibility, ___ location...
What am I gaining?
What am I giving up?

The gut check

After filling in the filter, answer these 2 questions:

• If you imagine yourself in this role 6 months from now, on a regular afternoon, how do you feel?

• Are you saying yes because you want this, or because you're afraid of what happens if you say no?

Save a blank copy of this filter. Use it every time a significant career decision appears. The filter doesn't make the decision for you, but it makes sure you're deciding from self-knowledge.

Reflection

Use these when you want to think more deeply about your career direction.

• If money weren't a factor for the next 2 years, what work would you choose to do? What does that tell you about your real interests?

• What kind of work have you been doing for free (helping friends, side projects, volunteering) that you've never considered as a career?

• Which of the 3 career paths excites you the most when you imagine telling someone about it? Which one do you feel defensive about?

• What's one career experiment you've been avoiding? What are you actually afraid of finding out?

• If you could apprentice under anyone for 6 months, who would it be and what would you want to learn? What does that tell you?

• What parts of your current work would you keep even if you changed everything else?

AI companion (optional)

How to use: Share your career identity synthesis from the Career Identity exercise, your job crafting audit, your 3 career odyssey plans, and your planned experiments. The AI will help you evaluate your options and strengthen your experiments. It will take around 25 to 35 minutes.

Copy and paste the prompt below into Claude, ChatGPT, or any AI assistant:
You are a career design strategist using methods from Stanford's Life Design Lab (Burnett & Evans), Amy Wrzesniewski's job crafting research, and John Krumboltz's planned happenstance theory. I'll share my career identity profile (career anchor, RIASEC code, values, strengths, energy map), my job crafting audit, my 3 career odyssey plans, and my planned experiments. Your job is to:
(1) Evaluate each career path against my career identity. Be honest about which paths genuinely fit and which ones I might be pursuing for the wrong reasons (status, external pressure, fear, inertia).
(2) Strengthen my career experiments. Challenge me to be more specific about what I'm testing and what success/failure would look like. Suggest experiments I haven't thought of. Push me toward experience prototypes over pure research.
(3) Help me spot my gravity problems: constraints I'm treating as problems to solve when they're actually fixed. And my anchor problems: places where I've fixated on one solution when I should explore alternatives.
(4) Based on Krumboltz's planned happenstance, suggest specific actions I could take in the next 30 days to create conditions for good career accidents. Who should I talk to? What should I show up to? What conversations should I have?
(5) Review my career decision filter and challenge any criteria that seem vague.
Help me make each criterion specific enough to actually use. Be direct. If a path doesn't fit my career identity, say so clearly.