2020 Annual Review

By Trevor McKendrick 👋 - Have you read my free newsletter?

I’m very grateful for all the wonderful things that happened to me during 2020. While things didn’t pan out like I (or anyone) would have hoped, there’s been a lot of positives too.

This post includes my review for the year, some outstanding questions, and some goals for this year.

I’m very excited about 2021 on multiple levels. I’d never had a more clear vision of what I need to do, and I’m excited to get to work.

Highlights of the Year

Weight lost: 25 pounds

Newsletter subscribers: Passed 7,000 subscribers

Email Newsletters Sent: 52 - one every single week

Favorite book: O Jerusalem!

Favorite movie: Jojo Rabbit

Most popular tweetstorm:

Reflecting on 2020 - Things to Celebrate

I played 2020 very opportunistically. I didn’t have many explicit goals upfront, and so I did accomplish a lot around both my personal health and my newsletter.

Lost 25 pounds

My single biggest accomplishment was losing 25 pounds:

This was a huge win because it was as much a psychological victory as it was physical. Losing weight was always so hard - I’d tried countless times. So 2020 I thought would be no different - I literally didn’t think I even could accomplish this, and felt like I was stuck to be overweight forever.

Thanks to endless prodding from my friend Tommy to get a gym membership near our offices, this fundamental change became a reality this year.

I’m especially proud that it happened during Covid. Between the stress of the world changing, moving every month or so to a new Airbnb, work locations changing, etc., it would have been really easy to give up and justify eating a bunch of crap and stopping my exercise routine.

Instead I bought a used Peloton (also from Tommy) and dragged it in the back of my car everywhere I went during Covid. I was determined to keep the good habit going once Covid started, and I succeeded.

Riding in an Airbnb in San Diego

Riding in a hotel in Austin

More to say about this in a future post - it was an enormous personal win and I’m super excited to build on this in 2021.

Launched a new personal website

You’re reading it right now. I was curious about Webflow so I ended up teaching myself and doing the entire website. I probably should have paid someone to do this but it was a fun project.

This site is the foundation for my next decade of work. I am extremely long on the value of building an audience, and even with as much noise as there is today I think having an audience is still undervalued.

As the Internet becomes more noisy, the value of attention goes up. So having your own audience who listens to what you have to say every week is going to be come more valuable over time, not less. This also means today you can still “buy low” - attention is underpriced relative to its future value. Investing to build and grow my audience will be  the main theme for 2021.

I chose the colors you’re seeing purposefully - I wanted something distinctive and optimistic. You can’t miss the yellow, and the red and blue are light and playful. I used the same yellow for the background of my new headshot that you can see on Twitter.

This site also helps consolidate my newsletter How It Actually Works and my personal site TrevorMcKendrick.com. Previously they were separate, which I felt was diluting the attention I spent on each.

Launched a newsletter referral program

In trying to grow the newsletter I launched a referral program for my current subscribers.

If they signed up 2 friends, they got a set of content from David Perell, Eric Jorgenson, Nat Eliason, and Taylor Pearson that I customized specifically for my audience.

If they signed up 20 friends, they got a monthly coffee group meeting with me.

And if anyone ever gets 2,000 referral signups, I’ll put their name and domain on a billboard.

This was successful at launch and I’m working on making it a more active part of the newsletter going forward.

You can read the announcement email I sent out here - it was promoted by a bunch of referral companies as a great example of how to setup a newsletter referral system.

Launched Newsletter Sponsorships

By design this took almost no work. I added a PS at the end of my weekly newsletter to softly tell readers I was doing sponsorships. I only took sponsors who I thought would be a good fit for my audience and it still surpassed my revenue goal for the year, so I’m going to continue doing it.

BTW - if you’re interested in sponsoring the newsletter email me (first and last name @ gmail)

Launched the Subscriber Gifts Page

I wanted to do something different & fun for my subscribers, so I worked with 10 or so companies to create discount codes on their products just for my newsletter readers. I didn’t get a cut or anything, this was just something special for newsletter readers.

You can see the full page of offers here

In general I think a digital CostCo for millennials membership is a great idea. I don’t understand why The Hustle or Morning Brew haven’t tried this - they have the audiences to get suppliers interested & there is a massive aggregator waiting to be built here.

Another example is AARP, which is targeted at Baby Boomers and has something like 50 million members. There’s a membership company waiting to be built for the next generation.

Launched my book notes

I started publishing my personal notes to the books I read. I take notes using Readwise, either by taking pictures of physical pages or by syncing w/ my Kindle highlights. This is a low effort way to share what I’m thinking and reading about.

Created Optimism 2020

Optimism 2020 began in December of 2019, way before Covid was a real threat or anything close to mainstream.

It was a personal theme that I just started saying - to family, friends, coworkers. Anyone who would listen. 2020 was going to be the year of positivity and growth.

And then Covid hit - and it took on even more meaning. I joked that creating Optimism 2020 during the year of Covid was a pessimistic’s nightmare come true. “The one time I try to be positive…” But I think it actually took on more meaning. Instead of just being about me, it felt like a idea to hold on to for everyone.

I created the Optimism 2020 manifesto to document this theme.

Image credit Jamie Smallwood

I also created a personal flag for 2020 as a representation of the Optimism them. It uses the same colors as the website.

The final flag, in Los Angeles

Yes, 2020 sucked, but as humanity has done every year since its inception we managed to get through it. And I think we’ve all learned a lot this year - both about how the world works, and about ourselves as individuals. What we’re capable of, what we like/don’t like, who we truly love, etc.

I’m going to announce my 2021 theme soon, so stay tuned.

Goals for 2021

20,000 newsletter subscribers

Having an audience is the single most valuable thing you can do as a modern participant in the economy. It gives leverage to literally everything else you do.

Looking for talent to hire?

Want feedback on a product?

Seeking your first customers?

Looking for investors?

Having an audience enables all of the above and more, totally independent of the project. And as the Internet gets more noisy, the value of having an audience will continue to go up. The best day to plant a tree was 100 years ago. The next bets day is today. Which is why this is my most important goal for 2020.

I ended 2020 with just over 7,000 subscribers, so more than doubling is going to be a stretch goal, but I think with concentrated effort it’s possible.

To do this I’m going to double down on what’s working: 1) cross posting with similar newsletters (I see conversion rates of 30-50% when I do this), 2) being very intentional about what I put on Twitter, specifically around tweetstorms, and 3) creating longer form content on my own to act as pillars for what people can expect from me & to establish my expertise.

Ultimately having amazing content is what matters - I will be doing more with my own content in 2021 than I did in 2020.

4 Long-form Essays

Most of my current work tends to be relatively short, as far as essay standards go. This has worked well for me, and people appreciate the voice behind my brevity.

But if I want to stand out for the next 10-20 years I need to create content foundations that define my ideas & let readers go deep with me. Despite all the online noise, the appetite for quality & depth is absolutely there.

My goal is to do one long-form essay per quarter. I’ve already started on the first since this is a new muscle I’ll be building. I don’t know what the final lengths will be, but they will be longer than anything I’ve written before.

I expect these to both increase email subscribers and to clarify my brand so people know more about what to expect from me.

Much of the shorter content I used to publish on my site will likely go out as tweetstorms, or screenshot essays on Twitter.

24% body fat

I’m including personal health goals here because your health is to your body like an audience is to your job - having great health amplifies everything else in your life. It’s the single most important thing you can work on.

24% probably sounds high, but I’m being conservative because I’m hoping to knock this out of the park. I haven’t done any serious resistance training for the past 2-3 years, and I’m optimistic my body will respond quickly and positively to lifting weights again, as it has in the past.

2020 for my body was like buying a fixer upper and just cleaning it out. Now that it’s clean and decent, it’s time to start adding additional structure, decorating, and generally making it more pleasant and enjoyable.

I’ll be working with my friend Joshua Howland to put a program together to make this happen.

Areas to Improve

Important > urgent

In 2020 it was easy to get lost in the immediately urgent - whether that was checking email, responding on Twitter, checking my website stats, etc.

I’m thinking about what I produce in terms of a 10-20 year timeline - and therefore should be investing as much time as I can in that content.

The content is the important thing. Relationships are the important thing. The day to day details are not.

One of the most important skills I improved in 2020 was learning to recognize what’s actually an emergency versus what isn’t. The things that actually require your immediate attention are extremely few & far between. They just don’t happen that much.

But much of the world suffers from what I call Do Something Syndrome - X event happened that was bad, so we have to react and do something about it (Even if the action won’t be affective. Even if the bad thing wasn’t that bad. Even if there’s far more important & valuable things we could be working on)

When in doubt, I aspire to focus my time and attention on creating valuable content for my audience.

Writing Every Day

If content is that important to me and my goals, that should be reflected in my calendar and weekly priorities. Producing every day compounds over time.

Not all of my writing will be worthy of publishing, of course. It would be ridiculous to expect that.

But not everything has to be A Grand Essay. There are many different places to publish depending on the type of content. Specifically I’m thinking a lot about Twitter - Tweets, gifs, tweetstorms, screenshot essays, graphics - there’s a lot of creativity to be explored here.

And since Twitter is one of the main drivers of signups to my newsletter, writing every day will pay large dividends regardless of where the content ends up being posted.

Going Faster

My motto here is 10% aim, 90% shoot.

Sam Altman has emphasized multiple times the importance of speed, and I’m a believer, as they say. The part that’s most underappreciated, I think, is how it compounds over time:

If you write 50 essays in a year instead of 25, you might think you’ll earn 2x the following. But that’s just in the first year. The next year that content will continue to bring in 2x the value, AND (assuming production rates stay the same) year 2’s content will also bring in double. Each year’s output brings in benefit for many years to come, and therefore builds on itself.

To move more quickly I need to worry less about the immediate thoughts that come out of my head, and more about publishing frequently and regularly. I need to remove my ego and identity from what I publish, and focus on how I can be helpful and informative to my readers.

What’s wild to me is that usually going fast is less a skill and more an active choice. Choosing to do something now vs later. Choosing to publish now at 85% perfection vs waiting for 100%. Messaging that important person now. Etc.

This is a character habit as much as it is anything else. I aim to build more of it in 2021.

Open Questions

How to do all of this with a full-time job

This is a fair question but I think I can pull it off. I don’t have kids, which should give me a ton of time relative to people who do.

It’s more about focus - being extremely intentional about how I spend my time. This will mean being ruthless prioritization, especially about what I do in the evenings and on weekends. It will mean saying no to a lot of great things - TV shows, books that don’t help produce ideas into content, etc.

What is my niche? What topics should make people think of me?

The best content creators have all created their own area - a small island which they own, and most importantly that everyone else knows is theirs.

Right now a lot of my content is around personal growth, how to be great, etc. I like this type of content, but the topic area is extremely saturated and I want to expand. There are other areas to explore.

How will I monetize?

I expect my online presence to be the foundation of everything I build going forward. How that manifests as income can come in many different ways. It doesn’t (necessarily) mean charging my subscribers, or even sponsorships. There are a lot of ways to make money once you have a significant audience who trusts you.

And so monetization isn’t an immediate concern. Right now I’m optimizing for growing an audience who trusts me. I view everything I do here under the lens of a 10-20 year timeframe, so if I’m creating real value and building an audience of people who trust me - the opportunities will produce themselves.

If you liked this essay...

Then consider signing up for my newsletter, How It Actually Works.

It contains the best material I find anywhere – this means books, articles, podcasts, research, videos, Twitter threads... the most interesting stuff that will give you something to say.

1,000s of Silicon Valley executives, investors, and leaders read it every week.

You're in!
Ack – that didnt work. Try again...