4 Lessons From 4 Years Since I Quit My Job
Why I carry two copies of my book everywhere I go 📕💋
Dear Wonderful Reader,
Tuesday, March 17th, 2026, marked 4 years since I freed myself from the shackles of my corporate job. Four years is a decent chunk of time. For the same duration as my undergraduate degree, I’ve been frolicking around Mexico City, perfecting my Spanish and waking up every day to the joy of being alive. How have I survived without a regular paycheck? And, more importantly, have I learned anything that’s useful to you?
It has been mostly a dream, but this quit-my-job-aversary comes at a particularly difficult time. I’ve barely made $2,000 this quarter, not even close to my personal OKR of $15k. Selling some of my index fund investments to pay my rent makes me feel like I’m failing at being an adult. Then again, I did take six months off client work to launch my second book, get it funded on Kickstarter in just 12 days, and get featured in The New York Times. Still, it’s hard to see the beauty in all that I’ve accomplished when reality is currently kicking my ass.
As you know, last week I was hit by a family emergency, causing me to fork out a couple thousand dollars more to fly to LA and say goodbye to my grandmother, who it seemed was on her deathbed. I sat with her in the hospital for five days as she went through a heart operation, reflecting on life in a mortal-imperative kind of way, while somehow helping to nurse her back to health. It was a close call. Not every day is sunshine and roses.
Sometimes those deeper, existential questions irk me. Am I really that much better off than before I burned my New York 9-5 life to the ground back in 2022? However, all it takes is a five-minute conversation with another software engineer who hates his life to knock my own sense back into me. I’ve definitely made the right choice.
I’m definitely not in the same place in this “creative career” as when I started. My direction is clearer and narrower in a way that’s motivating. I have a product to sell. I have workshops to teach. My path has a lot more shape, but it’s not easier. In fact, I’m still suffering. Yet I am following the advice of Graham Weaver, from my favorite episode of Lenny’s Podcast:
“Life is suffering, so make sure you pick something worth suffering for.” That’s how this feels right now. It’s a lot of work, but I’m much happier doing this than sending Sean a stupid, boring spreadsheet. (If you remember, in my corporate tech career, I worked with more men named Sean than with women on my teams, lol).
Here are four lessons I’ve learned in my fourth year of freedom.
1. Money still doesn’t really matter.
Yes, I’m a hypocrite. Aside from keeping the lights on and paying my rent, I still believe that money doesn’t really matter to me in my life. Through much self-reflection, I’ve learned that making money for money’s sake means nothing to me. I only make money to fund my creative projects and have control over my time. I couldn’t give a shit about owning a home. Sometimes I wish I had a bit more disposable income to travel, but that’s about it.
At the same time, the highest highs of my life cost next to nothing. Creating The Intimacy Journal in the second half of last year was pure creative bliss. Designing the pages, curating the erotic poetry, I had never felt so alive as I brought that book to life. Same with meeting up with a special group of incredibly talented poets and writers in Mexico City. Reading my work to them, experiencing their work, and feeling held creatively is absolutely fucking amazing. Enough said.
2. There are doers, and there are dreamers.
The other day, I was talking to a guy who planned to sell shoes from Mexico in the US.
“What shipping service are you using?” I asked him.
“Well, we haven’t actually done it yet,” he said, “We’re just developing the idea and exploring our options right now.”
Huh, I thought. So he hasn’t even really faced the issue, which is shipping stuff from Mexico to the US. He doesn’t know that Correos de Mexico, the Mexican postal service, isn’t permitting anyone to send more than a postcard. He doesn’t know they just digitalized their system and charge a shit ton more to send anything? Got it.
Something that continues to carry me through these years is that when I say I’m going to do something, I do it. Many people stand around commenting that what you’re doing is cool and that they’re doing it too, but then they don’t actually do it themselves.
You also don’t realize how much you will grow through this whole process. I look back, and I’m like: oh shit! I fulfilled 99% of the orders on my Kickstarter campaign. I hosted those workshops. I’ve done a lot of things, actually. And I’ve learned a lot, too. If you’ve been doing the things, you probably know a lot more than you think you know. By doing anything, you’re already way ahead of someone who hasn’t done anything at all. The same thing goes for reading books. A lot of people don’t read any books these days. Even if you just read one page of one book, that’s infinitely more than someone who just goes around saying how much they’d like to read more. Everyone talks a big game. When someone tells me about their dreams, but they aren’t actively doing them, I tune out. But when someone is doing something, even if they suck at it and they’re failing, I respect them.
3. Always be selling. Show, don’t tell.
If you bump into me on the street today, I am carrying 2 copies of my latest book, The Intimacy Journal. I have one sample copy and one copy in a gift-wrapped plastic sleeve. Why?
Well, when people ask me what I do, I don’t tell them; I pull the sample copy out of my bag and show them. I read them a line or a short poem, I show them the pages that I designed myself, and I tell them the story of how the book came about. I’m really proud of my book, and I think it’s beautiful. So I enjoy watching people interact with it for the first time.
What happens after that? Unexpectedly, they often want to buy one! And that’s when I sell them the gift-wrapped copy. This doesn’t always work, but I’ve sold about 42 copies of my book this way, which is about $1,250 USD in revenue for me (over a month’s rent!). Plus, people often add a little tip. It’s nice to have some extra cash on me. At times, it can get a little exhausting, and I feel torn or guilty if I’m not carrying copies of my book wherever I go. But I did sell 4 copies at my friend’s Christmas party. In fact, the last thing I did in 2025 was sell a copy of my book to a lovely gay man at a New Year’s Eve Party. Neat, huh? I keep track of how they pay me (Cash, Venmo, PayPal) and the currency they pay in (GBP, USD, MXN, EUR).
This is a true story: when I was a teenager, my family lived on the same street as the esteemed English fashion designer, Sir Paul Smith (he was knighted by The Queen years before). I only saw Paul Smith on my street a couple of times because he wakes up at 5am every day to go swimming. But one time, I ran into him and asked how he was. He immediately said to me,
“I’m excellent, thank you. I’m just picking out the furnishings for a new shop we’re opening on Albemarle, in Mayfair. You might like to go check it out.”
His words left an impression on me. He’s perhaps the most famous designer of men’s clothing in the world. His clothes are on billboards. He has shops in Tokyo and on Melrose in LA, and he’d been designing collections at Paris and Milan fashion week for longer than I’d been alive. As a 16-year-old girl, I wasn’t exactly his target demographic. And yet, here he was, imploring me to check out his new shop on Albemarle. I never forgot that he said that to me. And believe it or not, I did visit that new shop a few months later. And I liked the furnishings.
You’re not an obnoxious guy standing there with a big sign that you’re flinging around at a car depot. Don’t do anything tasteless. But if someone asks you what you do, or what kind of things you write, it’s about 1000x cooler to show them a beautiful book that you’ve created yourself than just about anything else.
4. Focus on one thing at a time.
One thing that has changed my life in the last year was deciding to focus on only one project: The Intimacy Journal. The world is a wide, complex, and distracting place, and each of us only has a limited amount of energy each day. When you work on 5 different projects, that energy is spliced out in 5 different directions. It leaves you too discombobulated and distracted to rise above the noise. And you need to do everything you can to rise above the noise because you’re competing with everyone else for people’s attention. If you put all your energy into one project, you have a chance of breaking out of your little bubble of people and reaching escape velocity.
Yes, I still wrote the odd article and kept up with my newsletter every week. But I concentrated all my energy into the journal. The launch. The Kickstarter campaign. The printing. Yes, I became a significantly simpler and boring person, but everything was more defined, and I found I made a lot more progress faster. My friends came back from the summer holidays, and I already had the first printed sample of the book to show them! A project like The Intimacy Journal is like a pillar. Once I got this book done, it opened up so many other revenue streams, including workshops, collaborations, podcast interviews, books, and audiobooks. I got a photo of me holding the book in the New York Times. Things just happened because I sat down and got that book done.
Whenever you feel that tug, that desire to ship this thing out into the world, and you’re excited about it in a deep way that makes you come alive, you just have to fucking do it. Because, like Elizabeth Gilbert talks about in Big Magic,
“Trust in the miraculous truth that new and marvelous ideas are looking for human collaborators every single day…Let them know you’re available. And for heaven’s sake, try not to miss the next one.”
The idea is yours for now. And if you don’t do it, the book, the song, the poem, whatever it is, will find another human subject to occupy soon. You’ll lose it, and you’ll wish you did it yourself.
I hope you found these lessons insightful, thought-provoking, and maybe even helpful. I seem to have driven home the point of being a doer rather than a dreamer here again a bit more. If that echoes what I shared in my list of lessons from last year, that’s because it’s proven to still be true.
I also hope that when I write to you again this time next year, I’ll have survived and thrived through this emotional rollercoaster and this dip in my bank balance.
Don’t forget to do something fun today!
Love
Tash
p.s. Visit tashdoherty.com for more writing, where I will be moving my guides and more SEO-focused articles shortly 👀
💌 ✍️
I hope the emergency is over. missed seeing you.