Freedom from “Should”

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Hi Everyone,

I’ve got something special for you all this week—a guest article from my friend and fellow real estate investor Jaime Lee. Jaime is the CEO of Jamison Realty, a powerhouse firm and one of the most incredible immigrant success stories in all of LA history. She’s also a prominent civic leader, the youngest ever Trustee for the University of Southern California, the former President of the Port of Los Angeles, and a board member of many other prominent local organizations. The LA Times recently featured her in their list of the most influential leaders in Los Angeles and many people around town consider her an eventual shoe-in for elected office.  

Jaime is all these things and more but I know her best as a devoted Mom and a great friend. We often meet to compare notes on things like real estate market dynamics and local politics but always end up talking about our kids, parenting, and the deeper contours of the search for the good life. As you’ll see in what follows, Jaime has a unique perspective and much to contribute.

Happy Valentine’s Day.

It’s already mid-February, and yet, in LA, it feels like the beginning of January all over again. The City of Angels is taking a hard reset on 2025 after an apocalyptic and devastating start to the year. Rain is finally blanketing the embers, and it’s time to get back to work, but even through the charred hellscape, we continue to face new levels of volatility, toxicity, and unease. From hateful Super Bowl ads, worsening tariffs/supply chain outlook, disjointed markets, and literal toxins swirling through our environment (can we drink the water or not?); it feels like the zone could not be more flooded, and yet, each day we wake to more inputs that shock the conscious, spike anxiety, and leave us wondering what could possibly be next? The mantra that many of my friends have adopted when asked by people outside the region is: “We are safe, but no one is ok.”

Where do we go from here? Whole industries have been disrupted, communities destroyed, and while local leadership is notably absent, national leadership has never felt more omnipresent in our lives. What are the long-term implications for a place like Los Angeles, uniquely positioned as a progressive, diverse, and creative haven of industry between a state government that tells us one thing, and a federal government that says the opposite? And finally, how do we rise, like a phoenix from the ashes, with so much uncertainty and trauma around us, with so many competing factions of leaders trying to claim authority and control, and so many citizens, more faint of heart, who have already pulled up stakes and fled?

Whether in good ways or bad, the theme of this year seems to be about stripping things down to their essence: institutions, businesses, governments, relationships, and even literal neighborhoods. Fire, while destructive, can have a cleansing element to it as well as a nourishing one. Breaking down the basics and getting back to authenticity, might be exactly what we need to thrive. 

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When the Sunset Fire broke out in Runyon Canyon, one of my most treasured places in the city and a little too close for comfort, we decided to leave our home and drive south. I was surprised by the choices I made in what to pack in the car. Just the day before we had witnessed dozens of friends and family members fleeing their homes on a moment's notice. For some, the time between their evacuation order and their home being engulfed in flames was a mere 45 minutes. They spoke of grabbing old photo albums, trophies, surfboards, baby keepsakes, a favorite jacket, documents— things they thought of as irreplaceable or precious. My husband and I had discussed then what we would pack if we needed to, covering a wide range of options from the necessary to the practical to the sentimental. 

Suddenly, we were putting our conjecture into practice and actually packing. I suggested splitting up into two cars to create more space, and he insisted on staying together as the traffic around us was building. This meant that in one vehicle with two adults and three children, there was very little room for cargo. When push came to shove, my packing choices ended up reflecting a mixture of zombie apocalypse survival tools and easily replaceable creature comforts for the kids. There was zero consideration for anything sentimental. No artwork or baby books, no ticket stub collections or mementos from faraway travels. No valuables. It was pure survival (water jugs, food, headlamps, cash, blankets, anything resembling a weapon) and keeping the kids comfortable (pajamas, toothbrushes, one stuffie each, and books). When I look back on it, I ask myself if I really thought that we would have to sleep in the car or fend for ourselves, or that credit cards would stop working or stores throughout the southland would be overrun. I’m not sure, but my mind went to the extremes. In that moment all I cared about was being with my family and protecting my kids. I knew then that I could lose everything, but as long as I still had the people I cherish, everything would be ok. It was an important and comforting realization that cut to the core of finding my authentic self.

The experience pushed me to contemplate all the ways that life can assert a kind of control on you. As a first-born daughter of Korean immigrant parents, my entire life has been predicated on “shoulds.”

You should take care of your brothers, you should study more, you should go to law school, you should work in the family business, you should marry a Korean doctor…

Eldest Daughter Syndrome is in full effect in my psyche along with the deeply ingrained fears of shame, judgement, and imperfection, and it has taken a lot of work to start detaching myself from expectations to find the root of what truly drives me. And so, I will posit that in order to build our city back up, in order to calm the anxiety of these turbulent times, and in order to know what to do next, we need to drill down to the authentic base of what truly matters in life and the passions that dictate, not what we should do, but what we innately, desperately, feel compelled to do.

In the book “The Three Regrets”, author Tenzin Kiyosaki, an interfaith hospice chaplain, explores the deepest and most common regrets of the dying as she guides them through their final moments. Chief among them is not living one’s dreams. Nearly every person on their deathbed has a regret around living life according to other people’s expectations and not following their passions. We’ve all heard some version of questions like:

“What would you do if you knew you couldn’t fail?” or “What would you do if you weren’t afraid?” 

I’ve been asking myself a slightly different question to spur myself into action: “What would I work on if I didn’t have to tell anyone?” because I’ve realized that judgement and fear of failure have ruled my life spectacularly. No more!

In this moment of crisis for our city, I’ve found opportunities for renewal and created a list of all of the projects, courses, investments, and businesses I would pursue if I didn’t have to tell anyone I was working on them. I’m learning what life would be like if I could just set aside the fear of ridicule or playing small, if I stopped caring about opportunity cost calculations, unfavorable market dynamics, and limited time and instead focused on the simple idea of waking up every morning and being utterly lit up by my work. It’s been as liberating as getting in the car that night with my family and realizing I had everything I could ever need or want right there. 

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