12 Things I Wish I'd Known When I Started This Newsletter

Reflections on two years.

This week marks two years of writing this newsletter.

It started as an exercise in commitment—a promise to show up every week, with no real plan beyond that. Over a hundred essays, three dozen interviews, and hundreds of card readings later—roughly four books’ worth of words!—I’d like to tell you I know exactly what I’m doing. But nothing could be further from the truth.

I’ve made plenty of mistakes along the way. But in the immortal words of Alanis Morissette, you learn. Here are 12 things I wish I’d known when I started—about writing a newsletter, but also about patience and bravery and value and honoring your process. Maybe they’ll resonate with you, too.

1. It’s okay to own your sh*t.
I launched this newsletter like a cat burglar trying to avoid visibility at all costs. I didn’t make an announcement. I didn’t share it on social. I barely told my friends. I held my breath as I pressed publish, hoping someone would read it…while simultaneously fearing they might.

I’m going to state the obvious here, but this is not a good way to grow something.

Plenty of folks (all of TikTok) do not share the inclination to hide, but for anyone who does, I implore you: If there’s something you’re proud of, shout it from the damn rooftops. If shouting isn’t your style, recruit your loudest friend to do it for you. Take out an ad, post QR codes all over town, or charter one of those planes with the dangly custom banners. It may feel easier (and a lot more natural) to promote other people’s accomplishments, but you deserve that, too. And so does whatever you wish to usher into the universe.

Hindsight is 20/20.

2. Venture.
Somewhere in this wide world, I imagine there hangs a guidance-counselor-type poster about how “adventure” can’t exist without “venture.” And it would be right.

The word venture used to intimidate me (probably the fault of “venture capital,” as if every idea required a plan and a deck and a pitch). But now I see that it can be looser, messier, more casual. You wanna venture? Awesome. Just begin. A venture asks only that you show up and give it a shot, and you never know what could come of it.

3. When in doubt, make a list.
If there’s anything writing this newsletter has taught me, it’s that people love a list. The most popular posts have been lists—39 Things I’ve Learned in 39 Years; 10 Things I’ve Learned About Love; The Best Advice I’ve Ever Heard…If the human brain loves tidy, numbered bites, who am I to argue?

Need to write a speech for a meaningful day and don’t know where to begin? Start with a list. Feel freakishly overwhelmed by various stressors and want to confine them to one piece of paper? Try a list.

4. Slow is still progress.
Even though I know better, I’ll still expect projects to instantly catch fire, like the fast-forward growth on a Chia Pet commercial. In truth, so much of life is closer to the proverbial snail in the water pipe—two steps forward, one step back.

I recently stumbled across the below quote, which was apparently a favorite of Kobe Bryant and hung in the Lakers locker room for many years. If it doesn’t perfectly encapsulate my feelings toward growing a newsletter, finishing a book, building a career, running a marathon…I don’t know what does.

5. Somewhere between "F*ck" and "Yay" lies the truth.
The internet would have us believe that the world falls into one of two categories—f*ck and yay. Disaster and triumph. Birth and death. Honeymoons and breakups. Epic, shareable moments worthy of big reactions. But most of life happens in shades of grey.

It’s easy to get caught up in everyone else’s big moments. It’s also hard not to judge your own happenings by that metric. Is no one else working? Struggling? Watching the latest season of Love is Blind surrounded by a mess they are too tired to clean? They are, I promise. Into every day a little f*ck and yay must fall.

6. Take care of your people.
So much attention is paid to growth—attracting more eyes, building your audience. But whether we’re talking about readers, clients, customers, or friends, it’s every bit as important to treat your existing people well and with care. Focus on nurturing what’s in front of you, and growth will follow.

7. When you’re sad or stuck or scared to press publish, You Gotta Be by Des’ree is always a good idea.
All I know, all I know, love will save the day.

8. Give yourself the space (and trust) to follow your own process.
For a long time, I tried to follow a prescribed model of a “workday.” It involved sitting at a desk during “normal business hours” and continuously churning out words. After decades of office jobs, I felt confused and guilty doing otherwise. But that approach stood in direct opposition to how I actually work.

For example, I do some of my best writing on the move—while running or riding the subway—jotting lines in a notebook or the notes app on my phone. This isn’t ideal, as there’s only so much I can do on the go, typing with my thumbs. But when I allow myself the space to occasionally step outside the box, ideas flow, words get written, and work works a lot better.

Your process is your process. Your strengths are your strengths. Honor them.

Please enjoy this dog as a brief photographic intermission.

9. You do you.
Sometimes, when reading books or newsletters or watching biopics about inspiring people, I walk away wondering what I’m doing wrong. Could I change? Could I learn to become more like them—bold, brash, charming, charismatic, brave, outspoken, tolerant of risk? Could I train myself to be…different?

It’s tempting to want to “fix” ourselves, but in the end, leaning into your strengths produces a better result—for everyone. It’s authentic, it’s sustainable, but it’s also something no one else can replicate.

10. Value is always open for interpretation.
I’ve said it before, and I’ll say it again: numbers are not our friends. Not likes, not views, not subscribers or followers, not sales numbers, not ratings or reviews—and do not get me started on performance graphs.

Value comes in a lot of forms. Some are easily quantified. The ones that you can’t measure—impact, meaning, connection—count for a lot. The next time some number has you questioning your worth, remember that “value” is a word you get to define for yourself.

11. Nothing is as tidy as it seems.
Everything—people, art, essays, lists—is an awful lot like a needlepoint tapestry. No matter how smooth and impressive it looks on the surface, there are all sorts of messy stitches and loose threads behind it.

We’re all looking for connection—to be seen, known, counted—which stands in opposition to perfection. Some of the nicest words, to say and to hear, are “I made this for you.” Rough edges and loose threads are part of the deal.

12. Keep going.
Ready is often a myth. Showing up is half the game. Keep going, even when it feels hard or silly or pointless. Even when you question if it matters. You don’t need to see the whole picture. Take it one step, one stitch, one word, one breath at a time.

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Card of the Week

Here is this week’s card for the collective, as well as some thoughts to carry into the days ahead. As most modern readers will tell you, the tarot is not about fortunetelling, nor is it about neat, definitive answers. The cards are simply one path to reflection, a way of better knowing ourselves and others through universal themes. If this reading resonates with you, great! And if not, no worries. Take whatever may be helpful and leave the rest.

Featuring the Fountain Tarot, with art by Jonathan Saiz

We’ve all had that friend who goes on a date with someone who checks every box on their exhaustive list of requirements, yet still rejects them for some ridiculous reason, like their shoelaces.

This is Four of Cups energy. But before we judge it, it behooves us to remember that we’ve been there, too. In fact, there’s a good chance we’re there right now.

The iconic Smith-Waite tarot, with art by Pamela Colman Smith

We see a figure with three perfectly lovely cups before them. A hand emerges from a cloud to present them with a fourth cup, but they’re not having it. They don’t even seem the least bit impressed by the improbability of the scene. How is this hand emerging from the ether? Why don’t they care?

There are a number of ways to interpret this.

The first is that the character is stubborn, picky, or ungrateful. Why don’t they want this perfectly good cup? (Or any of the cups, for that matter.) Do they think they’re superior?

The second is that they simply know what they want, and they’re not interested in what society is selling them.

This card acknowledges that we live in a rather stressful and annoying culture (to put it mildly). We're offered up images and not-so-subtle suggestions as to how our lives could be improved, along with comparisons that can make us feel "less than." The Four of Cups reminds us that feelings aren’t facts (and neither is much of what we see in the media). Much like the person on this card, we always have a choice. We can accept the thing—the ad, the job, the date, the offer, the suggestion—or we can decline.

Both are valid.

Any choice is correct, as long as it comes from a place of truth. The trick is to liberate it from judgment.

It’s not greedy to say yes. It’s not disappointing to say no. There are no “right” answers beyond whatever rings true for you. This card urges us to examine not only what we want, but why we want what we do. Is it because society—our friends, family, colleagues, the media—encourage or expect us to? Are we agreeing out of fear or obligation, or from a place of genuine interest?

This week, the Four of Cups urges us to be honest about our desires. What is currently on offer, and how does it make us feel? What do we want to pursue, and can we give ourselves permission? Do we feel pressure to decide one way or another?

When all else is stripped away, what do we want?