Two queens of Halloween costumes, Drew Burnett Gregory and Kristen Arnett, have previously rated their costumes for Autostraddle, and now it’s my turn. In Drew’s list, she mentions how trans people often use Halloween costumes to explore their gender expression, though she did not. That was absolutely the case for me though, whether it was conscious or not, because as I look at the list of costumes here, I dressed so frequently as men/male characters far before realizing I was trans.

I’m the youngest child of four, so there’s not many photos of me in general, and definitely not from Halloween, so there’s big chunks missing between 1996 and 2010. There’s also gaps in years here because I deleted so many photos from my Facebook after graduation and failed to save them elsewhere. Other photos were posted to my old private Instagram account that I no longer have access to (RIP). I don’t think we’re missing too much though.

1999: Simba from Lion King

I have no idea what I’m holding in my hand here. A leaf perhaps? I don’t remember what it was like to be Simba at three years old but I do remember that my mom handmade this costume, as she did for many of our costumes for Halloween and school plays growing up.

Rating: 10/10 I look cute as heck and it’s giving genderqueer kid.

2000 (and many consecutive years): Harry Potter

I was a huge Harry Potter kid and when I tell people I used to dress as Harry Potter for many Halloweens in a row they’ll ask “Oh were you Hermione?” and I have to be like “No… I was Harry Potter.” This Hedwig stuffy I had was so cute I could velcro his feet around my arm so he’d be perched like a real owl.

9/10: I mean look at the smile on my face! Deducting a point for transphobia.

2010: Playboy Bunny

I was a freshman dating a junior, so I was invited to a Real House Party where half the girls loved me and the other half hated me. I’m pretty sure my boyfriend at the time was dressed as Hugh Hefner in a robe and slippers, but I can’t find any photos. It was pretty bold of us to play into the age difference with our costumes considering I was fully 14-years-old here — but any excuse to wear my Victoria Secret Bombshell Bra!

Rating: 6/10 body was tea but deducting points for age-appropriateness and for those leopard print tights.

2012: Hooters Girl

This Halloween was kind of ruined by Hurricane Sandy’s untimely arrival. I forget what the limitations were but my friends and I weren’t allowed to do any big plans that year and instead stayed in my development trick or treating and probably drinking Four Lokos. I had a real Hooters Girl tanktop from visiting the Manhattan location with my late aunt and paired it with skinny jeans and a leather jacket.

Rating: 4/10 lack of creativity and wasted it on a Halloween I didn’t hang with any boys

2015: Walter White and Jesse Pinkman

My sophomore year of college, my brother came to visit and we were both obsessed with Breaking Bad. My brother is already pretty much Jesse Pinkman in many ways, so it was a no brainer he’d be him. I went back and forth on which Walter White I should be and of course landed on no-pants Walter White in the desert. In this photo, I’m wearing tights and two pairs of tighty whitey underwear because I was so afraid to actually be in my underwear. This mascara goatee would be the first of many, many handmade facial hair for me. This was also only a few weeks after I’d started hooking up with my eventual college boyfriend, and the party we were going to was at his frat. My brother and I did sooo much molly this night — it rocked. He hooked up with one of my sorority sisters.

Rating: 7/10 I should have committed to the bit and shaved my head.

2016: Lola Bunny and Bugs Bunny from Space Jam

This is one of the costumes locked in my old private Instagram account. Trust that I looked cute as HELL in that costume that I made for me and my ex from scratch, just for him to cheat on me with his roommate’s sister that was visiting for the weekend.

Rating: 5/10 cute but not cute enough for him to not cheat on me :/

2017: Jim and Pam from the Office (Company Picnic episode)

I’m not going to lie, this one was 100% my idea, and I absolutely loved it. My college boyfriend had graduated the year before me, so he came up to visit for Halloweekend and I thought this was so cute. Don’t let the innocence of this costume fool you, we were on sooo many drugs and absolutely got in some kind of screaming fight outside a frat house.

Rating: 4/10 basic as fuck

2017: Mia Wallace and Vincent Vega

WE BOTH LOOKS SO HOT IN THIS COSTUME. Truly so hot and so good and not enough 20 year olds attending SUNY Oswego had seen Pulp Fiction to appreciate this costume. That bob and bang wig was sooo cunt. The most annoying thing about this costume was I wanted to smoke cigarettes all night so bad, but my college boyfriend was so anti-cigarette despite regularly doing pills behind my back (lol) he got mad at me for smelling like cigarettes at the end of the night.

Rating: 10/10 I can’t lie it was a killer costume and we did the dance and everything.

2018: The Big Lebowski

The Big Lebowski is one of my favorite movies, and The Dude is one of my favorite characters ever. Luckily, my ex Vic was just as enthusiastic about this couple’s costume as I was and I really think we assigned the roles accurately. She did a reallllly good Walter. This costume was specifically for her hometown friends’ party, and I think we were a crowd favorite. I engineered my milk carton so that I could put my beer bottle inside and still drink from it, which was pretty cool if I do say so myself. This pic doesn’t show it well, but I was in a full floor length bathrobe.

Note: I have not covered up Vic’s face because when I texted her to see if she’d be okay with me using these images, I offered to cover her and she protested “then people will think there’s bad blood!” and that’s on being friends with your first lesbian ex <3

Rating: 10/10. We looked great, it was comfy as fuck, and may or may not have pushed me along on some kind of eventual gender journey.

2019: Dumb and Dumber

I remember having to concede to this costume idea because Vic really wanted to do it. I didn’t have any opposition to being Dumb and Dumber as a concept, but I really wanted to do it in a more literal way with oversized suits and not in a “girl version” way. But alas, that’s what we did. It ended up being a hit at the party we went to at her hometown friends’ house. We couldn’t find an orange cane for her, so I wrapped it in orange electrical or duct tape.

Rating: 5/10 really fun couples costume but I stand by that it would have been better if we had just worn suits.

2019: Bob Ross

Halloween while bartending is always a little bit tricky because you want something fun but practical. I was in grad school at the time and bartending at a lesbian-owned restaurant and cocktail lounge (shoutout Lost Dog Binghamton) where they’d play random things on the TV after hours for the drunk or high customers in the lounge. Sometimes it was a crackling fireplace or the POV of an Amtrak train, other times it was Soul Train or Bob Ross. I had pretty much the whole outfit needed for a Bob Ross costume and just had to get the painting supplies and wigs.

Rating: 8/10 it was great to be in jeans behind the bar and it was a little treat for the regulars at the restaurant.

2019: Eleven (bitchin’ era)

Okay so I had literally just done the Big Chop the day prior and received some immediate comparisons to Millie Bobby Brown. It was also my first few days — let alone first Halloween — with short hair and wasn’t entirely sure what to do with it. Reflecting now, I’m like, okay, why would I do this character costume two years after its relevance? But I think it was out of necessity in a time crunch.

Rating: 9/10 honestly proud of this one and the dedication to doing a photoshoot in my neighborhood liquor store for accuracy. Docking a point for being late.

2020: Dr. Alan Grant ft. Bo as Velociraptor

I have been in a few different relationships where I have requested me and my partner be Dr. Alan Grant and Ellie Sattler, and every single one has said no. Whether it was too nerdy or not cute enough or “I haven’t even seen that movie Motti,” no one was getting down with Jurassic Park. Well, I was single for Halloween in 2020, the world was pretty much shut down, and I had quite literally everything I needed to be Alan Grant in my home already so I finally got to do what I wanted.

Rating: 7/10 I think I did a good job but this costume is just not as good without either Ellie or some other character or dinosaur from Jurassic Park. Kristen and Kayla did it right for their 2023 costume.

2021: No Costume

I think I may have had COVID this year?

2022: Carmy from The Bear

This year, I was back in New York, bartending at a Colombian lesbian restaurant, and single. I didn’t put much thought into my costume because I knew I was working the closing shift and therefore wouldn’t be making any parties. The head chef at this restaurant only used the blue aprons like in The Bear, so I showed up for my shift in a white tee and black dickies, threw on the apron, and had a co-worker draw on Carmy’s tattoos with a sharpie.

Rating: 7/10 the gay girls loved having a masc lesbian Carmy serve them drinks all night but if I’m being honest, it’s some of my laziest work.

2023: BJ and Judy Gemstone

My girlfriend and I LOVE The Righteous Gemstones and are particularly obsessed with BJ and Judy Gemstone. The episode where BJ gets baptized to show his commitment to Judy and her superreligious family kills us, and we knew we wanted to dress up as that specific episode when we first started brainstorming. It took as a WHILE to find a dress close enough to Judy’s and even longer to find an accurate-ish outfit for BJ. We ended up assembling it ourselves, pulling each individual item from different places and modifying them to work together.

Rating: 10/10 this costume was so good the actors who play BJ and Judy reshared our posts

2024: Chappell Roan and a Passenger Seat

I mean… come on. Chappell Roan and a Passenger Seat (from the song Casual) is one of my proudest ideas yet. I’ve spoken pretty extensively about this costume after it went viral for the whole “I Hate Gay Halloween, What Do You Mean You’re ____” trend. My girlfriend, Britt, knew she wanted to somehow dress as Chappell Roan since she’s halfway there with her hair anyway, and I had the crazy idea to be the passenger seat she references being knee-deep in. I constructed the passenger seat myself from scratch and had so much fun putting it together. We turned heads everywhere we went that night, especially the multiple trains we had to take to our friends’ party in Brooklyn. It’s so funny that for most of these costumes, I dressed up as men, but as soon as I started identifying as a man, I dressed up as an inanimate object. I’m sure there’s something to dissect there.

Rating: 100/10 instantly iconic costume, will be referenced for decades to come. 

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It’s time for a little reflection and review. Each December, I conduct my Annual Review (this is my sixth year) and I’ve found the process useful every time.

As always, this Annual Review will answer three questions.

1. What went well this year?
2. What didn’t go so well this year?
3. What did I learn?

Before I begin, I should mention one thing: It’s always a little weird for me to share these Annual Reviews because when I talk about the good stuff it feels like I’m bragging and when I talk about the bad stuff it feels like I’m being strangely vulnerable with the world. That said, I still think it’s important because talking about how many workouts I did or articles I wrote provides proof that I am “walking the walk.”

While it is personally helpful for me to reflect on the last year, it also shows that I have skin in the game. I’m not just dishing out opinions when I write about things. I’m putting these ideas to practice in my own life.

Ultimately, every Annual Review is a personal process. This is what my year looked like, not a suggestion of what yours should include. Everyone runs their own race. That said, feel free to use this format for your own Annual Review and figure out what steps you want to take next.

1. What went well this year?

Let’s start with the good stuff.

Atomic Habits. I feel like I’ve told everyone within earshot at this point, but in case you haven’t heard: I published a book this year!

Longtime readers will know that this has been a multi-year battle. I announced the book deal in my 2015 Annual Review, I shared my writing struggles in my 2016 Annual Review, and I was (finally) nearing completion in my 2017 Annual Review.

I was still working on the manuscript in January and February of this year. If you had tapped me on the shoulder in the middle of my frantic final edits and told me the book would become a bestseller before the year ended, I almost certainly would have cried with relief.

As 2018 draws to a close, Atomic Habits has been out for 11 weeks (published on October 16, 2018). I did every single thing I could to make this book a success (starting with spending 3 years writing the best book possible), but the reception has outpaced even my high hopes.

Highlights include:

I don’t know what else to say, so I’ll just say “Thank You.” It means so much to me that you are finding the book useful and sharing it with others, and that my work is making some small difference in the world. If you’re interested in buying a copy, click here to see the different options.

Reach and Impact. It’s hard to quantify, but I feel like my work is making a bigger impact this year than in previous years. Maybe it’s just the excitement of seeing people read the book.

Regardless, I have said from Day 1 that I want to optimize for reach over revenue. I don’t care about making the most money. I just want to share the best ideas I can find with the greatest number of people. And this year we reached more people than ever before.

Here’s what the year looked like:

• 9 new articles published this year (browse my best articles)
• 241,827 new email subscribers this year
• 453,037 total email subscribers as of December 31, 2018
• 10,600,219 unique visitors this year
• 36,558,938 unique visitors since launching on November 12, 2012

Despite the success, there are some downsides hidden within these numbers. I’ll discuss them in the next section.

Travel. After not visiting a new country in 2017, I decided I would make travel a priority in 2018. And holy moly, did I travel this year.

My travel highlights for 2018 include:

• 7 countries (5 new): Argentina, Brazil, Chile, England, France, Japan, United States.
• 15 states (2 new): Arizona, California (4x), Florida (3x), Illinois (2x), Kansas, Massachusetts (2x), Nebraska, Nevada, New York (5x!), North Carolina (2x), Ohio, Pennsylvania, Texas, Washington (2x).

I continue to follow many of the strategies mentioned in my Ultralight Travel Guide, but I’ve also begun to implement some new approaches to accommodate for the number of speaking engagements I have do while traveling. I’ll update that page soon.

Speaking. I’m definitely a better speaker and presenter at the end of this year than I was at the beginning of it. Most of that is just due to practice. Thanks to the success of the book, I’m being asked to speak much more than I was previously. I’m excited to do more of this in 2019 and I put together a page with upcoming events. (If you’d like me to speak at your company or event, you can submit a request here.)

Charity work. Earlier this year, I settled on Against Malaria Foundation (AMF) as our primary charity partner. AMF distributes nets to protect children, pregnant mothers, and families from mosquitos carrying malaria. It is one of the most cost-effective ways to extend life and fulfills my bigger mission to spread healthy habits around the globe.

My plan is to donate 5 percent of after-tax profits to charitable causes, which means you are helping us contribute any time you buy my book or purchase a course or read an article. So far, our contribution has led to:

• 4,685 malaria nets distributed
• 8,433 people protected
• 87 years of additional life
• 2 lives saved

Now that we have this charity partnership, I like to remind myself that I’ll never have an unproductive day. Even if I fail to check items off my own to-do list, as long as the business brings in one dollar, some of that money will go toward making the world a better place.

2. What didn’t go so well this year?

And now the not-so-fun stuff.

Deadlines. I’m not sure I met a single deadline this year. Book deadline? Please. I blew that by more than a year. (Thank you to my publisher for being so accommodating.) Recording a revamp of my habits course? I originally planned that for the summer and it still hasn’t happened. Heck, even this annual review is going out a day late.

This problem extends to little daily “deadlines” too—like arriving on time to meetings. I’ve been told that I have a very optimistic view of time, which I think is the nicest way to say, “You’re continually miscalculating how much you can get done in each block of time.”

When some people have an extra 15 minutes before an appointment, they think, “Great! I can leave now and arrive early.” I think, “Perfect. I can do 15 more minutes of whatever I’m doing right now, leave at the last moment necessary, and arrive with one second to spare.”

To be honest, I’m not entirely sure what to do about this. I like having an optimistic view of time. The way I see it, I want to fit as much as I can into each hour. The upside is I get a lot done throughout the year. The downside is I have very little margin of safety. If everything goes to plan, I can get it all done. If something doesn’t go perfectly, a deadline is missed.

Weightlifting. In 2018, I exercised 141 times for an average of 11.8 workouts per month. Those numbers might look good at first glance, but both are a fair step down from last year (more on that in a minute).

When I broke the year down in detail, the issues became obvious. You can tell which months I turned in the manuscript (February), launched the book (October), and did a media tour across the US (December).

Workouts per month in 2018:

• January – 18
• February – 7
• March – 12
• April – 14
• May – 10
• June – 16
• July – 14
• August – 14
• September – 12
• October – 8
• November – 11
• December – 5

I am proud of myself in one respect, however. I could have said, “Oh, I’m launching a book in October so I can’t work out.” But getting 8 workouts in was better than zero. Managing to make it into the gym despite a crazy schedule (even if it’s only for 15 minutes) is important for maintaining momentum.

My best lifts of the year were:

• Back Squat – 400 lbs (181 kg) for 1 rep
• Bench Press – 280 lbs (127 kg) for 1 rep
• Deadlift – 500 lbs (226 kg) for 1 rep

These numbers are pretty good for me, but none of them are personal bests. I have been training fairly regularly for about ten years now and I believe this is the first time I have conducted an annual review and not hit a PR in at least one major lift.

Writing trajectory. I only wrote 10 articles in 2017, which was my lowest total ever. Somehow, I managed to lower the bar even further in 2018. The drop in output impacted other areas of the business too. Website traffic, for example, was highest in January and February and declined throughout the year.

In the short-term, it’s not a huge issue. But as I wrote in Atomic Habits, “It doesn’t matter how successful or unsuccessful you are right now. What matters is whether your habits are putting you on the path toward success. You should be far more concerned with your current trajectory than with your current results.”

The key point is not that millions are visiting the site right now (current results), but that the trend is headed downward (current trajectory). Now that the book is complete, I need to focus on rebuilding my weekly writing habit in 2019.

3. What did I learn this year?

Some of my major lessons from this year include:

If you don’t know what to do, focus on the fundamentals. Progress doesn’t need to be complicated. Skip all of the cutting edge tactics and focus on the key habits that deliver great return.

Here are a few habits that have a high rate of return in life:

• sleep 8+ hours each day
• lift weights 3x week
• go for a walk each day
• save at least 10 percent of your income
• read every day
• drink more water and less of everything else
• leave your phone in another room while you work

Mastery requires both impatience and patience. The impatience to have a bias toward action, to not waste time, and to work with a sense of urgency each day. The patience to delay gratification, to wait for your actions to accumulate, and to trust the process.

Curiosity is crucial. Increasingly, I feel an eagerness to learn is one of the most crucial skills in life. If you’re not curious, I’m not sure if there is much others can do to help you. But if you’re eager to learn, even if you aren’t particularly talented, then so much is possible.

Entrepreneurship is never as sexy on the inside as it appears on the outside. Whoever your entrepreneurial idols are, they have plenty of headaches behind the scenes.

You are only as mentally tough as your life demands you to be. Life will throw plenty of challenges your way, but there will be easy days too. An easy life fashions a mind that can only handle ease. Like a muscle that atrophies without use, mental strength fades unless it is tested. When life doesn’t challenge you, challenge yourself.

The margin between your best performance and your average performance is less than you think. In 2017, I averaged 15.7 workouts per month. In 2018, I averaged 11.7 workouts per month. At first glance, I considered it a modest difference. Only 4 workouts less each month? That’s about one less per week. And I was still making it into the gym consistently.

But then I realized I didn’t set a personal record in any major lift in 2018. Conversely, I hit PRs in nearly every major lift in 2017. One workout per week doesn’t sound like much, but that was the difference between my average performance and my best performance.

Move toward the next thing, not away from the last thing. Same direction. Completely different energy.

No is a decision. Yes is a responsibility. When you say no, you are only saying no to one option. When you say yes, you are saying no to every other option. One of my key themes in 2019 is to think carefully about what I say yes to and make sure I protect my time.

That’s it! As always, thanks for reading. Happy New Year! 1

The Annual Review Archives

This is a complete list of Annual Reviews I have written.