Rituals: How I’m navigating the “messy middle”
When happens after your life blows up
Note: Tomorrow is Independence Day in the US 🇺🇸. As a content entrepreneur who has largely worked from home and/or anywhere in the world, the tenets of independence, autonomy, and freedom are some of my core values. Were it not for my parents coming to the states decades ago from Taiwan, I wouldn’t have all the opportunities I have now. It takes courage to be independent and change—yourself, your job, your environment, to lead others—for better. Here are some fun resources on the history of America: my US History AP textbook (actually an immersive read), a mainstream view, and a contrarian view. Now to regularly scheduled programming…
In 2023, two major events blew up my life.
They combined to form a cataclysm to a life I’d known for so long—and from which I feel like I’ve finally had a bit of time to recover.
First: In January, the sale and exit of the company I’d founded in 2016 were finalized, and the calculation of my last payout came through.
The months leading up to this were some of the most stressful of my life, in that I didn’t know—even in the month prior—whether I’d earn nothing or something after years of building and hard work.
Second: In December that same year, I finally left and moved all of my things out of my ex-partner’s condo in Miami.
We had a “conscious uncoupling” conversation about a year before that and started leading separate lives.
We spent the next year mostly apart, in a grey area of not knowing each others’ status, but also confronting hard truths about long-held resentment, mismatched goals, and timelines.
This was facilitated by said unlivable condo, plagued by delayed renovations, permits, and contractors.
I wish things could have worked out, because this was a life-changing relationship; I love and had a special bond with his children. I’m grateful for some of the best moments of my life with him and them.
But, I almost let another whole year go by (after a decade) to be shown something different—not just in words but also actions.
When nothing changed, not really, I had to leave—or continue living someone else’s life.
And then, my heart was truly free again and I was single. Not young, not old, and with no children of my own.
Content entrepreneur | Agency Founder & CEO | Bestselling author Featured in Forbes, The Wall Street Journal, Business Insider, Bankrate, Cheddar TV, and HuffPost | Join more than 6,480 people on the internet who follow me for discerning lifestyle, travel, and money content:
The messy middle begins
I have no idea where the phrase “messy middle” came from, but I believe it started as a marketing phrase to describe a buyer’s journey from when they first see something, to when they buy it.
Today, it’s morphed into something that describes the “in between” phases of life: In between relationships, jobs, companies, and starting new ones.
It’s the part when people grieve past lives, hindsight the fuck out of things, figure shit out, work on themselves, plan, optimize, and come out the other side, supposedly more resolved.
The messy middle is also bubbling up, making waves across LinkedIn lexicon.
I wish it could be rebranded as something a bit more positive.
“Messy” connotes negativity, sloppiness.
And while that might be the metaphorical case, how about “Peaceful Pause” or “Restful Respite”?
I don’t know, I just made those up, but they sound pretty good, eh?
Peaceful Pause, Restful Respite
Today, I've found that working for yourself is actually great, but what you do with the in-between time is perhaps even harder:
After the invitations to speak here and there stop coming in
After the incessant pings that once required your attention are now…silent, and no one needs you anymore for key decisions, and yet deep, deep down you kind of miss it
After the ‘biz dev’ and ‘coffee’ and misc. requests, that once flooded your inbox, no longer appear
Yes, it’s a really peaceful place to be.
You welcome, embrace, get used to, and indulge in this new quiet space.
But it’s also a little frightening.
There’s now no structure to your days. It’s all on you to figure out what’s next.
You wander around, sometimes aimlessly, get distracted by things, go down rabbitholes, and absorb, absorb, absorb knowledge.
You consider business opportunities, attempt to travel, and connect with friends who have completely different lives than just a few years ago…
In order to stay above the malaise and functional depression, you go to therapy, fill your days with new habits, communities, writing, and learning worky skills—meanwhile rediscovering creative pursuits and hobbies that once filled your soul.
Trust me, the muscle memory is still there.
And maybe, just maybe when you least expect it, want to fight and deny it, push it away for fleeting, easier situations because it triggers real, secure emotional intimacy, and something you didn’t know was possible…
You might even find a new, soul-filling love.
More from the Shindy-verse
📺 Shows I’m watching
The Gilded Age (on
MaxHBO) - continuing thisStill watching the forever trainwreck of And Just Like That… on
MaxHBOSquid Game, Netflix - it’s the last season and it’s super gory
Trainwreck: The Cult of American Apparel: A quick watch, solid nostalgia. Ah, the many times I walked to multiple American Apparels across Manhattan (esp. the West Village location). I still have key pieces which I’ll never let go of
📚 Books I’m reading
The Power of Positive Thinking, by Norman Vincent Peale
Just started this to see what it’s all about. It’s a little church-y (the author is a Methodist minister) but I’m curious to see what I can learn.
What about you?
How have you navigated a messy middle?
I’d love to know!
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Until next time,
Shindy
On Instagram + TikTok
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Rituals is a section where on the first Friday of every month, I’ll cover a regular daily, weekly, or monthly personal habit that has become ritual. It may be a lifestyle, wellness, or work practice that has become a valuable and beneficial part of my life. Enjoy!
I love the photos of you and Mr. Bean!!!!
The first thing I thought of when reading about your, “Peaceful Pause” because you’re so young! The second thing I had to have misread is “unlivable condo!!!”
That could not be the way you lived!!! You’re so organized, meticulous, and such a perfectionist, this has to be an error!!
Terrific post as always!!