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  • Writer's pictureHarshal

Using Stanford’s Design-Thinking Approach To Design Your Life

Updated: 6 days ago

My Pivot Trial In Aligning Career Ambitions with Personal Values

Do you ever feel torn between pursuing a well-paying career and one that aligns with your personal values? You're not alone.

Stanford professors Bill Burnett and Dave Evans teach a class on using design thinking for life decisions. They wrote a book, “Designing Your Life”. In this post, I share how I used this book during my career pivot.

I used it to design a path where my career and personal aspirations intertwine to bring me satisfaction and happiness.

I spent 2 hours 8 minutes writing this post and 3 hours 38 minutes doing the ‘designing your life’ exercise. You will need 16 minutes to read this post. So listen to 4 songs from your favorite playlist while you read this. Or, skim to find portions relevant to you.

Individual imagining the multi-verse of future career options using design-thinking.
Individual imagining the multi-verse of future career options using design-thinking.

Related:

7 Steps To Design Your Life

Here are the 7 steps:

  1. Audit your life.

  2. Reflect on your work and life views.

  3. Identify energizing or engaging activities.

  4. Create a mind map.

  5. Create 3 career plans.

  6. Get feedback on your plans.

  7. Conduct informational chats and search for the job.

Some of it follows the diverge and converge steps common in design-thinking. Thanks to Michelle Ovalle for the illustration. 

Divergent and Convergent steps in the ideation process.
Divergent and Convergent steps in the ideation process.

1 - Audit Your life

Write a few sentences about how things are going in each of these four areas. Rate each between 0 and full:

  • Health,

  • Work, 

  • Play, and 

  • Love.

Dashboard to mark my Love, Play, Work, and Health.
Dashboard to mark my Love, Play, Work, and Health.

My take:

I was close to full in Love, Play, and Health. I fluctuated between full and half-point in Work. I was getting quality family time and reaching my fitness goals. I was learning while building my business, making the time feel like Play.

I want to improve my ‘Work’ gauge. I started with a detailed review of my entrepreneurial journey here.

Gravity problems:

We cannot solve all problems. Recognize and accept that some problems are unsolvable. This acceptance will free up your mental and emotional energy to focus on areas where change is possible.

For example, I cannot work in a Bay Area startup but stay in Europe and work in an European timezone. I cannot work in a five-person startup and expect compensation that rivals my previous full-time PM salary.

2a - Perspective On Work

Keep these prompts in mind and write out one answer for your perspective on work.

  • Why work?

  • What's work for?

  • What does work mean?

  • How does it relate to the individual, others, society?

  • What defines good or worthwhile work?

  • What does money have to do with it?

  • What do experience, growth, and fulfillment have to do with it?

My take:

I like being known for the impact I create. I would love to continue working, even until the age of 100, in roles closely related to technology and its impact on people. When I was young, I dreamed of building amazing military vehicles or flying cars. Now, I think about developing software or hardware that helps businesses thrive.

I thought of my endless desires… I want to earn money from my work to afford a bigger house, a smart home, high-quality services, a warmer silent car, luxurious holidays, and prestigious schools for my children. I aim to be financially independent, meaning I have enough income to not rely on a full-time job. In an ideal world, I wouldn’t have to think about the cost when deciding.

Work is where I find an intersection of activities I like and activities that pay me. This includes full-time jobs, consulting part-time, or earning money from a product I launched. On one hand, I’ve realized that having a meaningful work profile boosts my social status. On the other hand, I’ve seen how meaningful work allows me to impact people's lives or help entrepreneurs. For example, I once wrote about creating wireless IoT sensors for small cottage industries to improve the utilization and efficiency of their machines.

I enjoy learning, and finding new things to learn is fun. In some ways, I have consistently moved away from my past experiences. For instance, after working with semiconductors, I moved to DSP algorithms, then to Cisco Tech, and later to telecom-related software. Now, I have shifted away from telecom.

I have always wanted to build or run my own company because I saw my father do it, and I wanted to achieve the same. However, I realized this wasn’t the right motivation to start something. Instead, it is an indicator I should look for jobs in small companies rather than large ones. I constantly think about decisions that will help me learn and grow, such as understanding engineering and business, marketing and sales, or making product and people decisions.

2b - Perspective On Life

Keep these prompts in mind and write out one answer for your perspective on life. The other side of the “work-life balance”.

  • Why are we here?

  • What is the meaning or purpose of life?

  • What is the relationship between the individual and others?

  • Where do family, country, and the rest of the world fit in?

  • What is good, and what is evil?

  • Is there a higher power, God, or something transcendent, and if so, what impact does this have on your life?

  • What is the role of joy, sorrow, justice, injustice, love, peace, and strife in life?

My take:

We are on Earth to continue the propagation of our species. But while I am here, I aim to make the best of that time and be happy.

Happiness comes from flow and maybe family too. I know friends are important, but I have mixed feelings about saying that I get happiness from friends. I am probably very left-brained and organized. I am happy doing things alone for long periods, whether it's online research, online games, or more. However, I realize I greatly missed face-to-face meetings from full-time work.

In the short term, if I were to eat lots of desserts and play computer games, I would be happy. But in the long term, eating macro-measured diets, exercising daily, and building my skills to become an industry leader will satisfy me more. This is because I will live longer, gain more prestige, and have more financial freedom to do what I want. I’ve trained my mind sufficiently that I feel guilt if I do short-term happiness activities at the cost of long-term happiness.

Humans are a social species, so individuals derive value from the relationships and contexts they create with others, whether as a child, parent, spouse, friend, or coworker. Every organization succeeds because it can have a group of people work together towards a goal. However, the same number of people working similar hours with the same skills could not achieve this if they were independent.

A country is a geographic and legal constraint. So if I am in Ireland, I am closed off from other countries, but this country is more open to me for jobs and friends.

I want to make my family successful. I don't want to hear from my kids that they need to start from zero money. I would like to make things easy for them the way my parents did for me by being able to sponsor high-quality, expensive education for them.

Good actions are those that help you or others. Evil actions are those that harm yourself or others. If you could do something that benefits you but harms others, then your actions can be categorized based on the legal system.

The only power transcendent in my mind is luck. We have our activities and processes, or inputs, in our control, but we do not have the output in our control, especially in business decisions. This is because similar business decisions in similar companies at similar times will result in different outcomes. And this is because the word "similar" is broader than it appears. Humans are inherently variable, impacting your company's success with consumers and the success your employees can create.

Because I believe luck as that power beyond, so my goal is to do my input activities well but also create a lot of opportunities for serendipity to strike.

Emotions are part of life, and it's been shown that humans without emotions are unable to make decisions. Having emotions like dopamine, happiness, sadness, and so on helps us live our life. There is also power in regret. The challenge with emotions is that you also face negative feelings. But it seems without those negative feelings, we would not appreciate the positive feelings.

2c - Merging Work And Life Views 

Keep these prompts in mind, and write out one short answer about how your work and life views complement each other.

  • Where do your views on work and life complement one another?

  • Where do they clash?

  • Does one drive the other? How?

My take:

I want happiness, but I keep thinking about work. Part of my reason for working is financial. If finances were not a concern, I would have more time to try out my business or be independent. I am exploring and learning every day, even though I do not have a full-time job. Ultimately, I want to create an impact, but I cannot do that without gainful employment.

3a - Good Times Journal

Over a few days, set random alarms. When your alarm rings, write what you are doing and how you feel about it.

  • How engaged do you feel in the activity from low (0) to high (5)?

  • When does the engagement feel like the state of flow? I consider high engagement as ‘flow’.

  • How energized do you feel from the activity, ranging from depleting (0) to energizing (5)?

My take:

I used my earlier evaluation of my activities and my daily journal notes to fill out the activity log.

Activity log table showing my engagement and energy levels with activities grouped in themes.
Activity log table showing my engagement and energy levels with activities grouped in themes.

3b - Reflecting On Your Activity Log

Use these prompts to review your activity log.

  • Activities. What were you actually doing? Was it a structured or unstructured activity? Did you have a specific role (team leader) or were you just a participant (at the meeting)?

  • Environments. Where were you when involved in the activity? What kind of place was it, and how did it make you feel?

  • Interactions. What were you interacting with—people or machines? Was it a new interaction or one you are familiar with? Was it formal or informal?

  • Objects. Were you interacting with any objects or devices—iPads, smartphones, hockey sticks, or sailboats? What objects supported your engagement?

  • Users. Who else was there, and what role did they play in making it a positive or negative experience?

My take on Activities:

  • Activities such as "Dance lessons," "Interviewing customers, analyzing data, visualizing data," and "Developing and iterating on PM resume checker" are both engaging and energizing. These activities often involve direct interaction with new knowledge, skills, or people.

  • Activities like "Find new clients" and "Admin work like taxes, legal T&C, contracts" score low on engagement & energy.

  • The time was structured and planned.

  • Some activities were unstructured. For example, analyzing data without knowing the outcome or writing something.

  • Interviewing customers was structured. I don’t like synthesizing interview notes, but that is also a structured activity.

  • I had autonomy.

  • I enjoyed marketing activities more than sales. I liked solo content creation over talking to humans.

My take on Environments:

  • High-scoring activities usually happen in dynamic or interactive settings (e.g., dance class, customer interviews, coding for product development).

  • Lower scores often occur in more static environments like office settings for admin tasks or client hunting, which might feel isolating or monotonous.

  • I liked sitting in the sun and soaking up the sunshine. But, I didn’t like having glare on my laptop screen like sitting in the sun.

  • I enjoyed sitting in the sun but disliked the glare on my laptop screen.

  • I liked working by myself in my home office but got distracted often.

  • I enjoyed discussions with colleagues in meeting rooms at WeWork a few years ago.

  • I liked interactive environments, such as discussions with clients, colleagues, or customers.

  • I did not like working alone via social media, like emailing or messaging people.

My take on Interactions:

  • I liked interacting with machines e.g. data analysis, writing.

  • Sometimes, I disliked interacting asynchronously with people via machines, e.g., emailing people or responding to messages.

  • I preferred my own time over meeting times but usually felt happier after meetings where I learned something new from someone.

  • I didn’t like data entry work or legal work.

  • I liked teaching candidates and doing informational calls.

My take on Objects:

  • I was engaged in activities where I could use tools and technologies, e.g., data visualization software, development environments.

  • I enjoyed using data visualization, my laptop, genAI, Google Docs, spreadsheets, and automations like smart home.

  • I did not enjoy CRM, LinkedIn messages, WhatsApp responses, or emails.

  • I did not enjoy commuting.

My take on Users:

  • Freelancers - delegating tasks “throwing over the fence” felt very liberating. Whereas cross-checking their work was painful.

  • Consulting or coaching Clients - It was great to talk to people in another company who were waiting for my input on something.

4a - Mind Map Using Your Activity Log

Mind maps have one central topic with branches forming a tree. Create three mind maps using activities where you felt highly engaged or energetic.

How to make mind map

  1. Pick a topic and start with it. e.g. I like content creation

  2. E.g. The book example starts with "being outdoors" from a person who enjoyed hiking in Redwoods.

  3. Note down related thoughts.

  4. Take the original idea and write down 5-6 related things.

  5. Write the first words that come to mind.

  6. Repeat with the words in the second ring, drawing 3-4 lines from each word and free-associating new words.

  7. Continue until you have three or four rings of word associations.

  8. Make secondary connections to create concepts.

My take:

I used Whimsical and Mermaid to create the mind maps. I preferred Mermaid because of its text-first interface. I created 3 mind maps.

Mind Map starting with content creation.
Mind Map starting with content creation.

One started with content. I am highly engaged when creating content. It reminded me of 

  • Lenny Rachitsky and Ben Thompson - two of the strongest content creators in the business of tech and influences on me.

  • My goal of researching the needs of my audience to improve my newsletter and LinkedIn content.

  • My high usage of ChatGPT or GenAI tools to speed up content creation or improve quality.

  • Creating video content on YouTube or Loom.

  • Potential of making money as a freelance writer or a technical writer.

  • Substack platform vs Medium, Wix, or LinkedIn.

Mind map starting with PM resume checker product.
Mind map starting with PM resume checker product.

I created my second mind map starting with PM Resume Checker. Here is the product. I am highly energized when iteratively building the product. It reminded me of:

  • Customer interviews.

  • Extending Product Management skills by joining as a FT PM in a startup.

  • Using Python or GenAI tools to parse resumes.

  • Hiring developers to enhance the product.

  • Pivoting to B2B.

  • Using bubble or no-code tools.

  • Marketing and feature ideas backlog.

  • Coding the product using GenAI.

Mind map starting with the activities of research, analyze, and visualize.
Mind map starting with the activities of research, analyze, and visualize.

I created my third mind map with ‘research analyze and visualize’. I am in a state of flow doing these activities. It reminded me of:

4b - Visualize Outer Ring Of Mind Map

After creating three mind maps, invent an interesting life alternative from each. Your life sketches do not need to be practical.

  1. Look at the outer ring of one of your maps and pick three distinct items that catch your eye. These items should intuitively stand out to you.

  2. Combine those three items into a possible job description that would be fun and interesting to you and helpful to someone else. It doesn't need to be practical or widely appealing.

  3. Name your role and draw a quick sketch of it, like the example shown here. For instance, someone sketched leading a Pirate Surf Camp for children.

  4. Repeat this exercise three times, once for each of your mind maps.

My Take:

I made three sketches using the outer rings of each mind map.

3 sketches using the mind maps.
3 sketches using the mind maps.

5 - Five-Year “Odyssey” Plans

You are in a multiverse, living multiple lives. Let's explore three possible paths for the next five years.

Life One

  • That Thing You Do

  • Plan: Expand your current life or pursue a long-held idea.

  • Goal: Focus on your existing idea, which is solid and deserves attention.

Life Two

  • If Life One Vanished

  • Plan: Imagine your first plan is no longer an option. Your Life One idea is suddenly over or no longer an option.

  • Goal: Consider an alternative path if your primary plan fails.

Life Three

  • Without Money or Image Constraints

  • Plan: What would you do if you could make a decent living and not worry about others' opinions?

  • Goal: Explore your true passion without financial or social constraints.

Create three alternative five-year plans, including:

  • Timeline: A visual timeline of personal and professional events.

  • Non-career Elements: Remember to consider elements beyond career and money, like family time and personal growth. Consider milestones like marriage, training for a competition, or learning a new skill.

  • Headline: A six-word summary of each timeline.

  • Questions: Two or three questions to test assumptions and explore new insights. A good designer asks questions to test assumptions and reveal new insights.

  • Dashboard: Assess time, money, skills, contacts, likability, confidence, and coherence with your Workview and Lifeview.

  • Considerations: Geography, experience, impacts, role, industry, and other relevant factors.

More details on the dashboard:

  • Resources (Do you have the time, money, skill, and contacts to pull off your plan?)

  • Likability (Are you hot or cold or warm about your plan?)

  • Confidence (Are you feeling full of confidence, or pretty uncertain about pulling this off?)

  • Coherence (Is the plan consistent with your Workview and Lifeview?)

More details on possible considerations:

  • Geography—where will you live?

  • What experience/learning will you gain?

  • What are the impacts/results of choosing this alternative?

  • What will life look like? What particular role, industry, or company do you see yourself in?

My take:

I made 5 plans instead of 3. Some are too detailed, whereas some are incomplete.

Plan 1 - Product Manager in EU startups then co-found funded startup.

Why? This helps me towards my goal of being a startup person and builds long-term savings (vs solopreneurship).

5-year path towards founding startups.
5-year path towards founding startups.

Here’s the dashboard review for it.

  • Time: No, too much to handle.

  • Money: Yes, will get.

  • Skill: Definitely yes. I’m comfortable in my Product Management skills.

  • Contacts: Yes. I have contacts in startups or Product Management. But only some in EU. Good enough.

  • Likability: Warm, positive.

  • Confidence: Low. Too many things in the plan - content, network, speaking.

  • Coherence: How will I have family time vs rest? My life view includes family time and an emotionally connected family.

Plan 2 - Startup PM roles don’t exist. So, consult companies in business strategy.

Why? I can help companies this way too. It’ll help me reach FIRE fast as part of an established consulting firm.

5-year timeline towards consulting.
5-year timeline towards consulting.

Here’s the dashboard review for it.

  • Time: Yes

  • Money: Yes

  • Skill: Uncertain.

  • Contacts: Some

  • Likability: Lukewarm because of the negative image of consultants.

  • Confidence: Yes, because it is a job change. I am confident in executing the process of an industry and function switch.

  • Coherence: No, because it's not tech. My workview involved staying in tech till old age.

Plan 3 - Scaled marketing/growth consulting agency owner.

Why? Achieve financial independence (FIRE) and flexibility.

5-year timeline towards marketing agency.
5-year timeline towards marketing agency.

Here’s the dashboard review for it.

  • Time: Yes

  • Money: No, because I may not make profits for a long time.

  • Skill: Yes. I am also comfortable with sales now.

  • Contacts: Yes

  • Likability: Less than warm

  • Confidence: Low

  • Coherence: Yes, aligns with tech and upskilling. It will be B2B, which I know.

Plan 4 - If money were not a concern - lifelong learner.

My end goal would be to be a writer, thinker, researcher, and lifelong learner. I’ll pursue my passion for content creation and learning.

Here’s the dashboard review for it.

  • Time: Yes, have a lot of time for this.

  • Money: No, not at all. But not relevant.

  • Skill: Yes

  • Contacts: No, I am not connected to a lot of top-tier content creators.

  • Likability: Warm

  • Confidence: Low. My content is not popular.

  • Coherence: Yes - learning, balance, and tech.

5-year timeline as a content creator.
5-year timeline as a content creator.

Plan 5 - Grow my dad's small business

I didn’t create a plan for this but I realized this is also a viable plan.

6 - Prototyping: Getting feedback on plans

The book provides multiple ways to prototype plans. I chose to seek feedback from experienced individuals. The book also offers guidance on preparing a conversation script.

Get feedback from friends, family, or professional connections who are knowledgeable and willing to help.

Intro script

  • Explain the concept of Odyssey Plans.

  • Share why you’re presenting these plans to them. Highlight that you value their insights and seek feedback rather than mere approval or critique.

  • Inform them that you have multiple versions of your future plans and are exploring different possibilities. This sets the expectation that you are in an exploratory phase and are interested in feedback on various alternatives.

Prompt script after sharing plans

  • General Impressions: 

  • "What is your initial reaction to this version of the plan?"

  • "Which parts of this plan do you think play to my strengths?"

  • Specific Feedback:

  • "What do you think are the most realistic elements in this plan? Why?"

  • "Are there any parts of this plan that seem unclear or less feasible?"

  • Comparative Insights:

  • "Compared to the other versions I've shown, which plan do you feel is more aligned with who I am?"

  • Exploratory Questions:

  • "Can you think of any challenges I might face in this scenario, and how I might address them?"

  • Encouraging Storytelling:

  • "Have you ever considered something similar, or do you know someone who has pursued a similar path? What was that like?"

7 - Onwards For Job Search Or Career Pivot

I am comfortable with the steps the rest of the book explained. There are also better books for the rest, including:

Connect with people in roles you aspire to. Aim to understand their experiences and gain insights.

Who to approach:

  • People in your target roles and industries.

  • A diverse range of professionals, from early-career individuals to seasoned veterans, and those happy and unhappy in their roles.

How to approach them:

  • Express your interest in learning about their career experiences.

  • Use mutual connections when possible.

  • Request a short, specific time frame for the conversation (e.g., 30 minutes).

  • Offer goodwill gestures, such as a cup of coffee.

What questions to ask:

  • Career path and choices:

  • "Can you share how you started in this field and what your career journey has been like?"

  • "What were some of the pivotal moments in your career?"

  • Day-to-day reality:

  • "What does a typical day look like for you in your role?"

  • "What do you enjoy most about your work? What are the challenges?"

  • Insights and advice:

  • "Looking back, what advice would you give to someone just starting out in this field?"

  • "Are there any decisions you would have made differently?"

  • Future perspectives:

  • "Where do you see this industry going in the next few years?"

  • "What skills do you think are crucial for success in this area?"

  • Personal reflection:

  • "Can you share a significant learning experience you've had during your career?"

Application Strategy:

Realize you are choosing one path you like but cannot pursue every path.

Your Next Pivot?

How do you feel about your life gauge? How close are you to full in health, work, play, and love? What are your next steps?

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