For over five years, I've been running Life Worth Loving Coaching, where I help individuals navigate work transitions with confidence. Many of my clients arrive feeling scattered—caught in cycles of indecision and overthinking about what they “should” do next. Together, we ground them in their personal needs and desires, providing a clear decision-making framework and encouraging them to experiment to gain insights beyond their own internal dialogue.
While my work tends to attract people from the tech industry—such as developers, data scientists, and CTOs—I have also coached students, retirees, academics, medical students, finance professionals, and many others. Feeling stuck and yearning for work that is both sustainable and energizing is a challenge nearly everyone faces at some point.
If you find yourself in this situation, this post (and the following two in the series) may be for you. Based on everything I’ve learned and experienced, here is my process to follow if you want to hate your work less, and love your life more.
If there’s one key takeaway from this post, it’s this: you might be unhappy with your work and dissatisfied with your life because they are not aligned with what truly matters to you, and you’re held back by fears, outdated beliefs, and uncertainty. Honest self-inquiry and courageous experimentation are the antidotes—they help align your values with your life and transform fears, blocks, and uncertainties into allies rather than obstacles.
The First Instinct Might Not Be the Wisest
When people realize they dislike their work, they often start by seeking the simplest and most obvious solution: looking for a new job. However, more often than not, the problem isn't the job itself. One sign that the job might not be the source of your dissatisfaction is if you've already switched jobs multiple times in a short period, hoping that this next one will be different enough to scratch the itch of dissatisfaction. Another sign would be that the job appears impressive on paper—it seems to be everything you thought you wanted, yet something just doesn't feel right and you can feel the exhaustion setting in slowly but surely.
Start with Honest Self-Inquiry
Instead of immediately searching for a new job—which will likely leave you burned out and frustrated again within a year—start by engaging in self-inquiry to understand why you feel this way. Although this may seem obvious, many people skip this step in their desperate desire to "do something" about their work situation. Action without reflection leads to burn out but reflection without action stifles out our confidence and leads to analysis paralysis.
The goal of this is to help you gain clarity about what you truly want and what is important to you right now in both your life and work so you can take meaningful action. This clarity will enable you to say "yes" with enthusiasm and "no" with conviction. Self-inquiry for this purpose divides into two large categories of questions: zoomed out questions about your life & questions that are specific to work.
Big Zoom Out: Questions Reflecting on Your Life
Since work is not siloed but part of a larger system with feedback loops, you need to understand the entire system before making changes. To understand the system that you are, begin with the following questions:
What is a good enough life for me?
Not a life of endless striving, but one where, at the end, you can look back and say, “That was a good life.” Think of it as writing your own eulogy.
What does "success" mean to me?
Define success on your own terms—not according to your friends, parents, or society, but solely by your own standards.
Whom or what am I envious of? Why?
Envy often signals our unspoken desires, the ones we’re reluctant to voice. Embracing this feeling can offer valuable insights. If you’re struggling to articulate your envy, try this prompt:
“I hate to admit it, but I’m envious of … because …”
What is the lifestyle do I want? How does work fit into that?
Instead of trying to shape your lifestyle around work, consider how you can design your work to complement the life you desire.
What does my ideal week look like?
Reflect on your ideal routine: How do you spend time with your family? Are you indoors or outdoors? Do you prefer hands-on work, collaborating with others, or working independently?
What do I truly care about?
If you had to name the five most important things in your life, what would they be?
One of my favorite and most reliable methods for answering the final question above is the Values Exercise. In this process, you identify your top five values by reviewing and narrowing down a list of approximately 90 options. The journey of reaching those five words is just as valuable as the final list itself. If you'd like to give it a try, here is the values exercise I use with all my clients.
Values are a useful tool for articulating what matters to you, but ultimately, they're just words. They gain power when used as reminders or lenses through which to view the life you want to live and the work you wish to pursue. There is no right or wrong set of values—only what is important to you. Moreover, values evolve over time. The more you align your life with your values, the more you will see your life transformed. For example, my value of autonomy evolved into interdependence and later into synergy as I experienced more of each in my life. Because values are such a broad topic, I wrote a blog post that dives deeper into them.
Once you have a list of your values, share them with someone. Explain what each word means to you and have them ask questions. Then, evaluate the extent to which you are currently living these values in your life and work. Your work should either directly support your values or at least not detract from them. The degree to which your values and your work align can be a strong indicator of why you might dislike your work and feel unfulfilled in life.
Zooming In: All About Work
Now that you've taken a step back to see the broader context of your life, it's time to ask some work-specific questions. Let's start with the basics:
What does work mean to me? Why do I work?
What constitutes good, worthwhile work for me?
What is a good job? Is there a difference between the two?
What did I learn from my parents or caregivers about work?
What was their relationship to work?
What needs do I expect work to fulfill?
Common needs include money, social interaction, a sense of contribution, mastery, belonging, self-expression, and structure.
In the words of Mark Manson: What "shit sandwich" am I willing to eat?
What are things I am willing to do in exchange for what I want? Remember, loving 100% of your work 100% of the time is a myth. Aim to like most of your work most of the time.
How important is money to me?
As Paul Millerd puts it, what are you not willing to leave on the table for money? Reflect on your values and your "shit sandwich" as you consider this question.
The Goldmine of Your Own Experience
Next, consider something you may not realize: your personal experiences are a goldmine of information about what you love—and what you dislike—doing. If you are unsure of what you want to do, create a list of all the projects, jobs, and experiences that have brought you joy and fulfillment. For each item, describe the context, the actions you took, how you executed them, and with whom you worked. Then, use that list to identify patterns in what you enjoy.
Similarly, compile a list of the jobs, projects, and experiences you hated. Describe each situation in detail and look for recurring themes.
These patterns are what provides you with starting points on what work worth loving might look like for you.
If you’re feeling extra brave, ask your friends or collaborators to recall moments when they saw you light up or truly excel. Send an email asking people to respond back with a time they've really seen you shine. Talk to three of your close friends about what strengths they admire in you. They might have noticed qualities or patterns that you haven't yet recognized.
MUST HAVE, AWESOME TO HAVE & CAN’T HAVE List
Now, take everything you've reflected on so far and compile it into your MUST-HAVE, AWESOME-TO-HAVE, and CAN'T-HAVE list—your filter for all work opportunities.
This list is straightforward. Consider the next work opportunity you want to invest your energy in, and note down what the job MUST HAVE, what would be AWESOME TO HAVE but isn’t essential, and what it CANNOT HAVE. Include factors such as salary, the amount of freedom you desire, remote versus in-person work, the type of work you want to do, and the importance of mentorship or learning opportunities. Reflect on how your values will influence your work, how you want it to fit into your life, and what you enjoy and dislike.
Write everything down and keep it somewhere easily accessible. This list serves as a reminder of what you are not willing to compromise on and what you will enthusiastically say yes to. It will change over time as you learn more about yourself but it is a starting point to work off of.
With this solid foundation—knowing what you care about, the life you want to live, and the work you desire—it's time to start experimenting. You might not feel completely ready, but if you're 70% sure, the remaining 30% will be learned through doing.
The post is divided into three parts. You can check out Part 3: The Ways We Get Stuck here.
This is a post adapted from a Threadapalooza thread I wrote on X in Dec 2024. You can check out the thread here.
If you want to work with me check out my coaching page.
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