Some time ago, I ran a 30-day challenge. One set of questions a day — about your work, your career, and what you actually want from both.

No advice. No answers. Just questions worth sitting with.

Why? Because when it comes to your career, nobody else's answers are going to fit. The right question, asked at the right time, does more than the best advice — it helps you think differently about what's already in front of you.

Some of these questions sparked real conversations. A few kept coming back to people weeks later. So I've put all 30 days together here — go through them at your own pace, whenever the timing feels right.

Pick a day. Sit with the question. And if something clicks, do something about it — no matter how small. That's the whole point: through curiosity and a small bias to action, you get closer to the work and career that actually work for you.

 Day 1

“I have been through some terrible things in my life, some of which actually happened.” (Mark Twain)

-How can we change our career story?
-How can we choose to walk on the path of possibilities, instead of the path of limitations?
-How can we train our internal narrator to see what is already working, instead of focusing on everything that doesn’t work?

Day 2

“If you want to go quickly go alone, if you want to go far, go together.” (African proverb)

-What people can you bring in to help you grow and make an impact in your career?
-What roles can they play, beside mentor or “sparring partner” (e.g., coach, collaborator, connector, counsellor, encourager, information provider)?
-How could your “personal executive board” look like?

Day 3

“Courage starts with showing up and letting ourselves be seen.” (Brene Brown)

-How can you grow your #networking to explore new worlds, discover new perspectives on yourself, find new role models and expose yourself to new opportunities?

More specifically:

-Are there people you admire but you’ve never gathered the courage to talk to them?
-Have you met interesting new people but never followed up on the encounter?
-Are there things you could do that will bring you into contact with people from very different backgrounds?
-Do you know people connected to a wide variety of other people?
-Who does things in their career that are aspirational for you?

Day 4

“Go and make mistakes, make amazing mistakes, make glorious and fantastic mistakes. Break the rules. Leave the world more interesting for you being here.” (Neil Gaiman)

-How can you loosen your grip and allow yourself to experiment and make mistakes in crafting your job and career?
-How can you show more compassion to yourself?
-How can you strengthen your resilience to step into more unfamiliar, uncharted territories?
-How can you step out from your comfort zone to the stretch and growth zones?

Day 5

“Beware the barrenness of a busy life." (Socrate)

-How does busy-ness show up in your day to day work and life?
-How can you concentrate more on what really matters?
-How can you step away for all thus alluring, but nonetheless, unhelpful, distractions?
-How can you free up more time for what really matters in your work and life? What should you stop doing? What should you do less of?

Day 6

"Just one small positive thought in the morning can change your whole day." (Dalai Lama)

-Make a Good Time Journal: when do you feel engaged and energised at work? What are you doing in those moments?
-How can you do more of what you enjoy by crafting your tasks on the job?
-How can you do more of what you enjoy by crafting your work relationships?
-How can you bring more joy into your work and life? – positive emotions being an important part of work and career wellbeing.

Day 7

“Learning to choose is hard. Learning to choose well is harder. And learning to choose well in a world of unlimited possibilities is harder still, perhaps too hard.” (Barry Schwartz)

-Career exploration enables us to gain valuable insight into potential career paths and what it takes to get there. However, there is a moment in time when we need to focus on a choice. Otherwise, too many choices can paralyse us and make us unhappy. So, how can you avoid being paralysed by too many career options?
-How can you avoid the paradox of choice when crafting your own career?
-What are the alternatives when you cannot find all that you love in a single job or career?

Day 8

“Nothing in life is to be feared, it is only to be understood. Now is the time to understand more, so that we may fear less.” (Marie Curie)

What are the fears that stand between you and your career or life goals?
How can you hold space to learn more about what triggers the feelings of fear?
How can this awareness enable you to stand in your own power?
How can you become “fear-wise” instead of fearless?–because, sometimes, fear can show us aspects worthy to be taken into consideration.

Day 9

“If the path before you is clear, you're probably on someone else's.” (Joseph Campbell)

-If you see your career as an adventure, as a quest with you as a hero, what challenges do you need to overcome?
-What possibilities and rewards are achievable?
-Looking back at your journey so far, what becomes clearer about where would you like the next move to take you?

Day 10

Strengths = underlying qualities that energise us, and we are great at (or have the potential to become great at).

-What are your core strengths? Your emotional/ relational/ thinking/ execution strengths?
-Do you get to use your strengths at work every day?
-How can you focus more on your strengths at work?
-How can you use your strengths to boost your positive energy, confidence, and agility to deal with inevitable setbacks and unplanned changes?

„People who use their strengths every day are 3 times more likely to report having an excellent quality of life, 6 times more likely to be engaged at work, 8% more productive.” (Gallup)

Day 11

“The monkey mind is often like a bunch of little rascals creating mischiefs on Halloween.” (Due Quach)

-How can you be more aware of your own self-talk?
-What is the ratio between the voices in your head that tell you “I cannot make it”, “It is too complicated”, “It is not for me” and the helpful ones? How can you tip the scale in favour of a supportive self-talk?
-What happens when you replace a thought that drags you down with one that lifts you up. How much energy does that free up?

Day 12

“Where the needs of the world and your talents cross, there lies your vocation.” (Aristotle)

-Imagine yourself in three alternative realities, in each of which you can spend next year trying a job in which your strengths, values or skills meet the needs of the world. What three jobs would you be excited to try? You can craft them; they do not have to already exist. What can you learn about yourself by doing this exercise?
-What do you need to do today to use more of your strengths, skills, qualities at work, while serving the needs of the world?

Day 13

"Like most of us, I'm used to juggling about 52 roles in life.(...) Sometimes I feel a bit 'multiple-personality'."  (Sophie Kinsella)

-What are the life or work roles in which you are currently involved? How much time you spend in each of these roles, during a day/ week/ month?
-Now, I propose to you an exercise:
1.Rank your life or work roles using the values you consider to be important to you
2.Notice: is there a link between how much time you invest in each role and where they are ranked according to your values?
3. Can you identify:
-roles that conflict with each other?
-roles that are compensatory to one another?
-roles that complement each other

-With this knowledge, what do you intend to start/ stop/ continue doing?

Day 14

“Without the rich heart, wealth is an ugly beggar.” (Ralph Waldo Emerson)

-We all might have heart projects or money projects – how is your balance between those two?
-What do you need to do more of for expanding the overlapping of heart projects with money projects?
-Coming back to "the needs of the world", how would it be possible to do well and to do good, at the same time?

Day 15

“Perseverance and spirit have done wonders in all ages.” (George Washington)

-How can you bring more energy and spirit whenever you get frustrated and feel like giving up on something challenging related to you work or career?
-How can you take more time to reflect on how this challenge pushes you to grow?

Day 16

“Perseverance and spirit have done wonders in all ages.” (George Washington)

-How can you bring more energy and spirit whenever you get frustrated and feel like giving up on something challenging related to you work or career?
-How can you take more time to reflect on how this challenge pushes you to grow?

Day 17

“If your mind is empty, it is always ready for anything, it is open to everything. In the beginner's mind there are many possibilities, but in the expert's mind there are few. ” (Shunryu Suzuki)

-How can you start bringing more curiosity in your everyday interactions and let go of preconceptions, all kinds of labels and boxes you are accustomed to?
-How can you experience a greater sense of discovery, creativity, or connection in your work?

Day 18

“We might neglect our future selves because of some failure of belief or imagination.” (Derek Parfit)

-Who is the person you aspire to become?
-How can you align your career & life goals with this vision of your aspirational future self?
-How can you keep this vision steady in your mind every step along the way?
-How can you still leave space for the unexpected?

Day 19

„There is more wisdom in your body than in your deepest
philosophy.” (Friedrich Nietzsche)

-When thinking about the career and life you want, how can you listen to your full body? To your heart, in addition to your head?
-How can you tune in more to the emotions and energy of yourself and the people you interact with?

Day 20

“The best moments in our lives, are not the passive, receptive, relaxing times—although such experiences can also be enjoyable, if we have worked hard to attain them. The best moments usually occur when a person’s body or mind is stretched to its limits in a voluntary effort to accomplish something difficult and worthwhile. Optimal experience is thus something that we make happen. For a child, it could be placing with trembling fingers the last block on a tower she has built, higher than any she has built so far; for a swimmer, it could be trying to beat his own record; for a violinist, mastering an intricate musical passage. For each person there are thousands of opportunities, challenges to expand ourselves.”― Mihaly Csikszentmihalyi

-What could be some opportunities & challenges to expand yourself?
-Note when you are engaged and/ or energised at work - what are you doing during those times?  Are there any moments when you are in flow? (Look in the comments if you want to know more about flow)
-What small steps could you take to make more room for tasks and relationships that give you energy or, create a state of flow?

Day 21

“Do not be afraid of rejection. Finding your path is not easy. Closed doors simplify the search so you can focus on doors
that open” (Due Quach)

-How can you overcome your fear of rejection and politely make request from people who can support you in your career quest?
-How can you make friends with rejection? How can you hold space for the feelings or stories that might arise?
-How can you celebrate when taking the risk pays off?

Day 22

“In every person there is a sun. Just let them shine.” (Socrate)

-What is “your sun”? How can you let it shine more often, in your career and life?
-How can you appreciate more “the sun” in yourself and others?
-How often you neglect “your sun” and focus on “fixing the dark”?

Day 23

“It's never too late to be what you might have been.” (George Elliot)

For those who already have a plan to reinvent their careers and start anew:
-How can you make the connections between your past and present obvious to others?
-What are the hidden, underlying themes that connect your professional experiences?
-How can you explain your trajectory in terms of the value you bring to others?
-How can you keep your faith in yourself?

Day 24

“Self-limiting beliefs are cages we mindlessly lock ourselves inside” (Due Quach)

-Find one belief or story about your career that might be holding you back (look for “I can’t never do that”; “This is just not me”; “Maybe it works for others, but not for me.”; “This is how I have always did it.”; “I could never do that.” and other alike):
·     Is this belief or story true? All the time?
·     Is it helpful in any way?
·     How can you let it go?
·     How can you flip it and turn it into something useful and actionable?

Day 25

Just a job, a career or a calling? What it takes to be at the intersection of the 3 concepts?

While work means something different to each of us, most people see it from one of 3 angles:
1) work as a job required for financial compensation rather than for satisfaction or fulfilment
2) work as a career that is marked by status and advancement
3) work as a calling that is intrinsically rewarding and carried out for satisfaction and fulfilment rather than financial gain

-What is your orientation toward work – do you see it rather as a job, a career, or a calling?
-Are you satisfied with your orientation to work?
-Which of the 3 viewpoints would you prefer to hold? What are your reasons for this?
-What would need to change for you to hold this alternative view on your job?
-Can you be at the intersection of the 3 concepts?

Day 26

“Those who have a 'why' to live, can bear with almost any 'how'.” (Viktor E. Frankl)

-How can you go about finding a meaningful career?
-What does it take to overcome the fear of change and negotiate the myriad of career choices, especially in challenging economic times?

Day 27

Job crafting - taking proactive steps and actions to redesign what we do at work, mainly changing tasks, relationships, and perceptions of our jobs. The main premise is that we can stay in the same role, getting more meaning out of our jobs simply by changing what we do, how we interact with people and the ‘whole point’ behind our work.

Tasks Crafting
-First, map yourself on your strengths, skills, values & interests.
-Second, understand how you currently spend your time and energy.
-Then, think:
1.    How can you take on more or fewer tasks?
2.   How can you expand or diminish the scope of your tasks?
3.   How can you change how you perform a task?

Day 28

“Some people grumble that roses have thorns; I am grateful that thorns have roses.” (Alphonse Karr)

-When crafting your career, how can you choose to focus more on what is good or positive and complain less about the negative?
-How can you harness more the power of reframing?

Day 29

„(...)we can all benefit from having a little bit more interdependency in our micro- and macro-environments. For instance, instead of promoting “self-care” and implying that it is people’s own responsibility to sort through their own struggles, perhaps our culture could emphasise the value of caring for each other and create more safe spaces to allow open discussions about our challenges and imperfections.” (Xuan Zhao)

-What would it take to build safer, but courageous spaces where we can have discussions about our own career challenges and imperfections?
-In a (western) world where the focus is on individuality, how can you harness the power of “collectively” when designing your career?
-How can you release some of the pressure of „I have to make it on my own”, when thinking about your career?/ What is in fact in your control or in your influence? What is out of your control and should be only acknowledged and accepted?

Day 30

“We do not see things as they are, we see things as we are”. (ANAÏS NIN)
-How are your career perspectives influenced by your direct experiences?
-How can you expand your career perspectives through others?
-How can you appreciate more how others are seeing the world based on their own experiences?