Lounge Access: Addicted to Optimization

Over the last year I’ve received quite a few media features, including being named a Condé Nast Traveler Top Travel Specialist. A single one of any of these individual features had once been a goal, and now I’ve accomplished multiple of them.

I let myself feel it for roughly the length of time it takes to read an email. And then, almost immediately, I thought: what’s next?

I’ve been thinking more lately about how quick I am to optimize, and not because I’ve decided the striving is a problem to be solved. I want to be clear from the start, because I know the direction this kind of essay usually takes: Woman achieves things, woman burns out, woman discovers stillness, woman recommends stillness to you in five easy steps. That isn’t where this is going. I actually quite like the part of me that wants more. In fact, she’s who built everything I have today.

But in that, I’ve noticed something else I don’t love, and I see it in the way a lot of us travel too.

I spend my working life overseeing a team of people who, collectively, all plan how other people spend their most precious weeks of the year. We are constantly fielding requests to cram three countries into one week or to book every single meal of their entire trip (all at highly acclaimed restaurants). Then, somewhere in the onboarding process, we also hear “we just want to relax.”

I don’t judge them for the contradiction because I get it. This trip we’re planning is sacred time off, and no one wants to waste it. I have been that traveler, and I’m in no position to be superior about it (I’m also going to 4 destinations across Italy next week, so I’m often guilty myself!)

But I also know that trying to cram so much into one trip turns a holiday into some sort of extraction operation with photographic evidence. (For what it’s worth, this can usually be resolved with an incredible hotel that you don’t want to leave, forcing you to slow down and get that desired relaxation).

But even if we fall prey to over-optimizing our trips now and then, travel has an end date. What I’ve found much harder is the same instinct applied to other areas of life.

If it’s not clear already, I love to optimize. It’s my first reaction to nearly any situation: I know how this could be better! (thought to myself with much excitement!) I’m not an overly critical or joyless person by any means; I actually find it incredibly satisfying. I am someone who loves to imagine what is possible. I set goals at the start of every year and at the start of every month. I write myself a to-do list every morning (often an idealistic one). I am, on any given Tuesday, in the middle of trying to improve something in my life: my hormones, my macros, my businesses, my friendships, my skin, my wardrobe, my knowledge of global affairs…you name it.

People sometimes frame this as ambition, and sometimes as anxiety, but I think it’s closer to a single combined instinct: I find joy in becoming the best version of myself, and because of growth, that continues to evolve. You can be the smartest you’ve ever been in your life, and there is still always more to learn (the same example could be used for any category named above, really). Optimizing and tenacity are kind of the same muscle in my opinion. Optimization notices the gap, while tenacity refuses to leave it alone.

But here’s the part I won’t apologize for: everything I have is a result of that. It took me four years to get my UK visa. Four years of applications and lawyers and near-misses and starting again, for the right to live in a city I’d decided was home. I’ve built two businesses over more than a decade, through years when it would have been reasonable to stop. I did not coast into any of it. I had to fight tooth and nail for all of it.

So when people talk about the tyranny of self-improvement, I understand the critique, and I also know what my particular version of it has afforded me. A younger version of me, the one in Nashville who had barely been anywhere yet, would find my home, marriage, work, my whole life, quite frankly, to be astonishing. Every part of it. I don’t take that for granted!

The trouble isn’t the engine. It’s that I never turn it off.

So below: what happens when you realize you’re a bit addicted to optimization, but certain areas of your life don’t bend to it? I’ve been learning a lot about this (seemingly, the hard way) lately.