Work, Career Change, and Leadership

What if your work life felt as deliberately designed as your personal growth? Many of us feel we “have to” operate by default at work – chasing what success is supposed to look like, absorbing stress as a given. But what if you approached your career and leadership with the same freedom-by-design mindset? Have you clarified what you truly value in work? Do your daily job choices reflect that? Are you leading (even if you don’t have a formal title) in a way that aligns with your agreements, or are old misconceptions guiding you?

This chapter invites you to redefine success on your terms, to craft how you show up professionally according to clear values, and to apply the tools of intentional design – like experiments and feedback loops – to navigate changes and opportunities in your career. Whether you’re considering a major shift or simply want to lead more authentically where you are, the process is similar: know what matters, make concrete plans around those priorities, and communicate and learn as you go.

Clarify top three work values and behaviors: First, identify what truly matters to you in the realm of work. Values could be things like: Creativity, Work-Life Balance, Growth, Financial Security, Helping Others, Autonomy, Collaboration, Influence, Learning, Integrity, or Fun. Choose your top three (the ones you couldn’t stand to sacrifice long-term without feeling miserable).

Once you have them, for each value, brainstorm at least one concrete behavior that exemplifies it in your current work context:

If one value is Deep Work/Focus (perhaps under a broader value of Excellence or Mastery), a behavior might be “I preserve one uninterrupted 2-hour block per day for high-priority work.”

If Family or balance is a value, a behavior could be “I leave the office by 6pm and don’t check email after dinner.”

If Learning is a value, a behavior might be “I will spend 1 hour a week reading industry articles or taking an online course to develop skills.”

If Integrity is a value, a behavior could be “I speak up when I see something unethical, even if it’s uncomfortable,” or “I only promise what I can deliver and I follow through on my word.”

Write down the three values and one specific behavior (this week) you will do for each. To ensure you follow through, schedule or announce these if needed:

For example, block your calendar for that deep work, or set an alarm to leave by 6, or sign up for a course to force that learning time, etc.

By translating values to actions, you align your work more with who you are. This also acts as a compass: if you find a value that has no possible behavior in your current job (say, creativity, but your role is extremely rote and offers no room for it), that’s a red flag that either something needs to change in your approach or maybe in the role itself long-term. It points to where friction might be.

Decision scorecard for opportunities: When facing career decisions (a job offer, a project, a promotion, a partnership), it’s easy to get overwhelmed or swayed by one factor (like money or prestige). A scorecard helps you evaluate opportunities holistically against your criteria.

Decide on a few key criteria important to you. Common ones:

Learning/Growth: Will this challenge and develop me?

Alignment: Does this align with my values/purpose?

Energy: Does the idea of this energize me or drain me?

Compensation: Does it meet financial needs (including benefits, etc.)?

People/Culture: Will I be working with people I can respect and learn from?

Flexibility/Work-Life: Does it offer the balance I want?

Impact: Will my work make a positive difference that I care about?

Pick the top 3-5 criteria that matter most for you (some above may overlap with your values identified). Now, for a given opportunity, rate each criterion on a simple scale, say 1 to 10 or even High/Medium/Low.

For example, you’re considering a new job:

Learning: High (8/10) – new skills and industry.

Alignment: Medium (5/10) – the company mission is okay, not deeply inspiring, but not opposed to my values.

Energy/Interest: High (9/10) – role itself sounds exciting.

Compensation: Medium (fair salary, slight raise).

Flexibility: Low (2/10) – known for long hours in office.

Now you see on paper: High in growth and interest, low in lifestyle, moderate alignment. Now you can weigh – maybe for a few years, growth is worth the hours, or maybe not. It at least makes the trade-offs clearer.

Or deciding whether to take on a leadership role in a volunteer organization:

Impact: High.

Time commitment (Effort): Medium-high (but do-able).

People: High (great team).

Personal growth: Medium.

You might test it on one choice or compare multiple options side by side. The scorecard helps remove some bias (like getting seduced by a big paycheck alone or by a fancy title) and reminds you of what you decided matters.

Actually test it: think of a pending decision in your career. List your criteria and score each option. It might not give a definitive “answer” – but it will highlight strengths and weaknesses of each choice and provoke the right questions. For instance, if one option scores low on alignment, maybe you consider how to mitigate that if you take it, or lean towards the one with higher alignment.

30-day job crafting experiment (10% time shift): You might be in a job that’s okay but not fully utilizing your strengths or passions. Before leaping to a new job, try “job crafting” – proactively reshaping your current role. A classic approach: steal back about 10% of your work time for projects that give you high value or energy.

Plan a 30-day experiment:

Identify tasks in your job that energize you or add a ton of value when you do them (these typically align with your strengths and interests). Also identify tasks that deplete you or seem low-value.

Find ways to spend 10% more time on the good and 10% less on the not-so-good (renegotiate, delegate, streamline, or straight up drop if feasible).

Maybe that means dedicating Friday afternoons to a side project innovation you think would help the company, and automating a report to free that time. Or volunteering to take on a duty that you find enjoyable but wasn’t originally yours (and offloading something else with permission).

Track your energy and performance changes. Possibly even note how you feel before and after at baseline vs. during the experiment (maybe even use a simple scale daily to score your job satisfaction or exhaustion).

At the end of 30 days, assess: Did shifting 10% of my time toward higher-value tasks increase my engagement? Did anyone notice a positive difference (or negative)? Did the lower-value tasks being reduced cause any issues, or were they not missed?

If positive, you can make this a permanent shift and even negotiate role changes over time (“I’ve been doing X project and it’s yielded good results; I’d like to formalize doing more of that and less of Y”).

If negative or neutral, you learned something: maybe it’s not the tasks, it’s something bigger like the environment or field that needs change.

Leadership agreement – be impeccable with your word: In leadership (or simply within a team), trust is currency. Making clear promises and keeping them is crucial. Adopting an explicit agreement with yourself to be impeccable with your word at work can set you apart:

That means if you say “I’ll email that by end of day,” you do it. If you can’t, you proactively inform the person before the deadline passes and renegotiate.

It also means choosing your commitments carefully. Don’t overpromise to look good in the moment. Better to under-promise and over-deliver.

It might involve publicly acknowledging trade-offs: e.g., in a meeting, “If we prioritize Project A (which I think we should), we may need to delay Project B by a week. I want to be transparent about that trade-off so we set realistic expectations.”

Encourage your team (if you manage one, or peers if you have influence) to do the same and create a culture of update if things change rather than hide delays.

A practice: Keep a small log of commitments you currently have (could be a page in notebook). Check it at day’s end to ensure you followed through or updated on each. This habit helps nothing fall through cracks and shows others consistency. Over time, people know they can trust your word – an invaluable leadership trait.

And if you miss something, own it (ties back to repair and integrity metrics in later chapters).

Assume positive intent, verify with questions (meeting habit): In the workplace, misunderstandings and conflicts often erupt from assuming worst intentions behind someone’s words or ideas. Adopting “Assume positive intent” as a mini-agreement can transform meeting dynamics:

When a colleague suggests an alternate approach in a meeting, instead of thinking “He’s trying to undercut my idea,” assume they want what’s best for the project and are genuinely adding perspective.

Then verify with questions: “That’s an interesting suggestion, can you walk me through your thinking?” or if you feel some tension, “I sense you have concerns about the current plan; could you elaborate your perspective so I understand better?”

This does two things: it prevents immediate defensiveness or dismissiveness, and it invites clarity. Often you find they weren’t attacking you at all (or if they were, the question forces them to articulate in a more reasonable way).

Make it a habit in meetings to ask at least one question before counter-arguing someone’s point – especially if you feel emotionally triggered by it. Also, if someone’s email comes off curt, assume they might be busy, not that they hate you, and perhaps pick up the phone to clarify details if needed rather than stewing.

Team culture improves when people feel their intentions are assumed good until proven otherwise, rather than everyone on guard. As a leader, you can model this: when two team members have friction, facilitate them asking each other questions to get on the same page rather than trading accusations.

Monthly stakeholder check-in (keep/start/stop): Whether you’re an employee with a boss, a manager with a team, or collaborating with peers, regular feedback helps course-correct and align expectations.

Schedule a short meeting perhaps monthly or quarterly with key stakeholders (boss, or if you manage, each direct report, or cross-functional peers on a project).

Use the prompts: “What should I keep doing? What should I start doing? What should I stop doing?”

This structured ask opens the door for constructive feedback:

“Keep” tells you what’s valued that you should continue (good for confidence and clarity on strengths).

“Start” surfaces things you aren’t doing that they would like – opportunities for growth or new responsibilities.

“Stop” gently invites pointing out something that’s not working for them (without them having to frame it as harsh criticism; it feels like fulfilling your request).

For example, with your boss: “I’d love your brief feedback to help me improve. Is there anything I should keep doing that’s working well? Something I’m not doing that I could start? Or anything I do that you feel I should stop or do differently?”

Or if you lead a team, ask your report those questions about your management: “Please be candid - I want to be the best manager I can. What’s working that I should keep? Anything you wish I’d start or do more of? Anything I do that maybe I should stop or adjust?”

Listen actively and thank them for sharing, even if feedback is hard to hear. Use it as design input for your work style. It keeps you in tune with others’ evolving needs and prevents small issues from festering unspoken.

Low-risk career test (before big leap): If you aspire to a career change or a different role, design a small experiment to dip your toes in:

If considering a new field, try freelancing or volunteering a few hours in that field (on weekends or evenings) to get a taste and build some experience.

If you think you want to start a business, create a prototype or run a pop-up event rather than quitting your job immediately. Gather data: do you enjoy the work? Is there interest from customers?

If moving from individual contributor to management intrigues you, take on a leadership role in a small context (maybe lead a small project, or mentor an intern) to see how you like guiding others.

If relocating to a new city, maybe try a 2-week working remote from there, or a long vacation to check lifestyle fit.

If a completely different sector, consider informational interviews or shadowing someone for a day.

Frame it as an experiment with specific questions: “Will I enjoy [X]? Am I any good at [Y]? Does the reality match my expectation?” Afterward, evaluate. This agile approach prevents dramatic leaps based purely on fantasy – you get real feedback to make an informed decision.

Design one small test for your next big career idea. Put it on a timeline (e.g., “Over the next 3 months I will spend 5 Saturdays doing [related work] and then decide.”). Not only does it reduce fear (because you see it’s manageable and reversible), it also gives you momentum; you’ve started, which is often the hardest part of a big change.

Weekly leadership reflection: Whether or not you have a titled leadership role, you lead your own life and influence others. The key to effective leadership is learning continuously from your decisions.

Each week, pick one decision you made (big or small) and reflect:

What guided that decision? (values, data, fear, assumption?)

How did it turn out (so far)? What does that indicate about your process?

How could I align even more with my principles or goals next time?

For a manager it might be, “I assigned tasks very aggressively last week. Guided by urgency and pressure. Outcome: team got it done but morale seemed low. Next time, I’ll involve them in the timeline discussion (aligning with value of collaboration).”

For an individual, maybe, “I decided to forego a networking event to work on my side project. It was guided by my value of creativity over socializing. Outcome: I finished a chapter of my novel – feel proud. Next time someone invites me out, I might communicate my priorities clearly or compromise one social event per week.”

Writing this in a journal or a digital note helps track your growth as a leader/decision-maker.

This habit ensures you’re iterating on your design. You don’t just set values and forget them; you actively check your real choices against them and refine.

As you bring clarity and intention to your work and leadership, you may notice something powerful: work stops feeling like a separate beast and becomes another avenue for your self-expression and values. By designing how you show up in your career, you become more authentic and effective, which often leads to opportunities that fit you better. Colleagues will start seeking your input because they notice you lead with integrity, or maybe you’ll realize a career path you hadn’t considered is now visible because you’ve clarified what you truly want.

The more you apply these practices, the more your work life will feel like it’s on your terms. And if eventually you decide a big change is needed, you’ll do so from a place of knowledge and self-trust, not desperation. Now, even with all this alignment, fear and self-sabotage can still creep in – especially when we stretch ourselves. In the next chapter, we’ll tackle those internal loops of fear head-on, and design strategies to heal and navigate them so they don’t derail your progress toward freedom.