Navigating Uncertainty to Find Meaningful Work
Breaking free
About 8 years ago, I landed a job that seemed like a dream. It had great pay, top-notch benefits, good work-life balance, and I was working with a great team. It was at a tech company in beautiful San Francisco which was an ideal place to build a tech career since it was a tech hub. The job was everything my parents had hoped for me and everything society told me I should want.
But something was missing for me. Despite this job being the perfect package, the work felt hollow and meaningless. I wasn’t motivated to do more than the bare minimum at work. I was asking myself questions such as: Why am I spending so many hours on THIS work? More than 2,000 hours just in 1 year of my life on THIS?
After already reaching the pinnacle of what many people thought was the ideal job, I concluded that it wasn’t for me. I couldn’t imagine myself staying on this career path for several more years let alone the rest of my life.
I realized maybe the things that some people say are good and would bring happiness aren’t necessarily the things that would make ME happy.
Back then, I didn’t know what I wanted to do. I felt empty about my work but I also had no clear direction forward. I wasn’t sure what my passions were other than maybe rock climbing, cycling, hiking, skiing, and reading (I used to read voraciously!). A year or two later, I was talking to a friend and she asked me something along the lines of: how do you feel when you think about staying? And how do you feel when you think about quitting? And I might have said something like…I feel relief, freedom, and excitement when I think about leaving. And I followed that answer through…so, I eventually quit my job with no idea what I might do next. Luckily, I had saved up enough to not have to work another job immediately.
And so, I started to go on a journey to discover my purpose and figure out a path that wasn’t dictated by anyone else’s values but my own. I had to spend a lot of solo time to discover myself and my values along the way because I had never spent the time to truly get to know myself. Prior to this, I had always been surrounded by family, friends, or romantic relationships, rarely spending time alone. For the first time in 2018, I chose to embrace some good old solitude! And boy has it been amazing to have this time to myself – maybe I’ll write about the importance of this in a future post!
It took me 5 years to discover something that resonated with me. And even now, I’m still in the process of discovery and refinement. And that’s actually a good thing! Because I don’t like feeling stagnant. I’m the type of person that likes to continuously learn and grow and experience new things, otherwise I get bored.
During those five years, I kept going back to corporate jobs, only to leave again. The back-and-forth wasn’t because I didn’t want change—it was because fear kept pulling me back to what felt safe and familiar. The biggest fear? Financial instability.
Despite having savings and budgeting for a couple of years to start a business, the reality of my expenses exceeding my income was unsettling. I wasn’t used to this in the beginning. And I wasn’t used to not making a lot of money! There were some weeks when I felt panicked and fearful about my survival.
It took multiple rounds of leaving, returning, and stepping away again to finally transform that deeply ingrained fear. I realized that I was actually ok and I could still live with a much lower income. When that happened, I started to feel a greater sense of stability. I felt ok with where I was financially, but more importantly, I learned that true stability wasn’t just about financial security—it was about self-trust. No matter what happened, I knew I would be able to pick myself back up because I had already fallen and failed so many times and gotten back up again to keep going. Going through failure is a good way to build resilience and confidence – don’t be afraid of it!
A lot of the work I had to do involved breaking out of generational and cultural conditioning around success and security. It wasn’t easy. It takes conscious effort and time to break generational cycles passed down through lineage and culture, but it’s so rewarding and freeing! (Perhaps I’ll write more about that in another post!)
During this transitional period, I did a lot of personal development work so that I could be the best coach and space holder I could be. Looking back, I feel like a completely different person. My friends used to say that I was stoic, very intense, and maybe even competitive. I had to unlearn old patterns and embrace a new way of being—speaking from my heart, allowing myself to be vulnerable, offering encouragement and praise, and practicing deep acceptance. Before I could do this for others, I had to do it for myself.
It always starts with the self and radiates outward!
When I finally found coaching and graduated from my certification program, I knew I had discovered something that I wanted to keep doing. It stuck, it matched all the qualities of what I had learned to become a better version of myself. And it was fulfilling and rewarding, yet it also pushed me to keep growing. I felt I was finally ready to say goodbye to the corporate world in 2024. I had reached a tipping point where staying in my comfort zone felt more painful than embracing the fear and uncertainty of stepping into a new and unfamiliar journey, with challenges and unknowns.
And just to be real, I’m happier about what I’m doing but sometimes doubts and fears still creep in (I just want you to know this is normal even for people who appear confident and successful). There have been days when I even browse corporate job postings. But the pull back to that old world isn’t as strong as it used to be.
The setbacks, failures, and challenges I’ve faced have all shaped me. They’ve tested me and always reaffirmed my commitment to this work/path. When I reflect on why I stay, it always comes back to how I want to feel.
When I was working a corporate tech job, I felt that I couldn’t fully be myself. I find myself being overly “masculine”, very logical, structured, fast-paced, a bit emotionless/stoic, and commanding plus demanding. But I like being “feminine”. I like being gentle, moving slowly, feeling deeply, uplifting others, and being sensitive. And as a coach and space holder, I am valued for being this way. Plus, I love helping people heal and step into their full potential, and that’s what keeps me here.
As I continued on this journey, my definition of success shifted. It wasn’t easy to shift at first, especially when we’re raised in a society that defines certain metrics of success so clearly like wealth or status. Now I think the most important generational wealth is having good mental, emotional, physical, and spiritual health.
Nowadays, I center my decisions around sustainability, joy, fulfillment, and what feels alive or right for me. I now believe it is my birthright to do work I love and make a living from it. And the more I surround myself with people who have built careers they love, the more I see what’s possible for me (and for you!).
Now, I truly believe that it’s possible to create a life, career, and relationships that bring genuine happiness. It takes dedication, courage, and a commitment to free ourselves from limiting beliefs and patterns.
And it is SO worth it.
Community Gathering Opportunity!
I’m hosting a virtual event on April 5th! Yay! This event is called Mosaic Gathering: Holding Space For Career Uncertainty And Transition. And your co-host is
. She’s been putting out beautiful poetry and helpful reflective questions on career grief and transition throughout the month of March, and it’s not too late to be part of that here: https://nyamadodoadji.myflodesk.com/mosaic-31-days.Description of the April 5th virtual gathering:
Have you reached a point where work no longer feels fulfilling? Wondering if there’s more to your career? Do you find yourself yearning to have a job where you feel you are allowed to be more fully you, valued for your unique gifts, and happy doing what you get to do every day? Maybe you feel a need for change but aren’t quite sure what that change looks like yet.
If any of this resonates, you’re in the right place.
This gathering is a space for those who feel a shift stirring in their professional life. You are invited to feel, connect, reflect, be witnessed, and be in community with others navigating similar questions. Here’s a permission slip to slow down, meet yourself right where you are, and honor whatever stage you are at in your career journey (even if what you are feeling is uncomfortable).
All parts of your experience whether it’s uncertainty, excitement, frustration, hope, grief are all welcomed. Every feeling carries a message, and together, we will hold space to learn what it is revealing about you, what matters to you.
How to engage:
Open up your voice. Maybe even notice when you want to share, or want to be heard, or want to participate but hold yourself back. In this space, you’re encouraged to share as much or as little as feels right for you. There is power in speaking your truth out loud.
Turn on your camera. It helps foster connection when we can see each other’s faces; after all, half of communication is non-verbal!
Bring something to write with. Bring paper and pen to write and have your favorite beverage nearby to sip. Let’s get comfortable!
Create a quiet space. Join this call from a quiet space where there will be no distractions. This time is for you!
Come as you are. All parts of you are welcome!
Let’s gather and navigate wherever you are in your careers, together.
If you wish to give back for the time and energy I put into holding this event for you, the suggested donation is $20. Your contribution is truly appreciated.
To register for this event, go here: https://lu.ma/mahi4gzv
Here are ways you can support me and my work:
I am a heart-centered coach who supports Asian millennials to deepen their relationship with themselves and gently free themselves from unhelpful expectations, patterns, and fears so that they can have the life and relationships they desire. Want to book a coaching session with me? Visit my website: alaliwei.com
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"True stability wasn’t just about financial security—it was about self-trust" Love this bit! It's truly powerful, as you describe, one of the problems people find when trying to pursue their dreams is that at the beginning, it's difficult and scary. But deep down, the fear in reality is not about money in your bank account, it's about how you feel about yourself. Thanks for writing your post, love to see there are more people like us in the world😉
Happy to have found your Meaningul Work post! Thank you for sharing your story!!! feeling that "relief, freedom, and excitement" when thinking about leaving a job that looked perfect on paper but just didn’t feel right is very relatable… but SO daunting. It’s lovely to read how you’ve shifted from fearing financial instability to trusting yourself :) And defining success for ourselves is incredibly important… focusing on mental, emotional, and spiritual health feels so much more fulfilling than anything external.
Wish you the best of all!🤗