A Reflection on '23

Without a doubt, 2023 was the craziest year of my life.

I accomplished professional goals that I’ve held for years.

I met thousands of people from every culture and background you could think of, a small fraction of whom have become close friends.

I filled my days with experiences that most people can only dream of ticking off their bucket lists. 

I witnessed extreme wealth and extreme poverty, often not too far away from each other. 

I felt the most alive and the most lonely I’ve ever felt, often at the same time. 

If you stumbled upon this annual review and don’t know me, let me briefly catch you up to speed: 

a) In April 2022, I left my full-time job in product development to pursue a career as a freelance writer. 

b) A single tweet changed my life, leaving me with a full calendar and a thriving business nearly overnight (but don’t be mistaken, this was not an overnight success).

c) I spent 12+ hours per day holed up in my studio apartment writing. I quickly realized that the “freedom” as an entrepreneur is something that is earned, not given. With more work than I could handle myself, I launched a content marketing agency, Third Wall Creative, and began to learn the power of leverage and delegation.

d) Feeling stagnant in New York, I booked a one-way ticket to Prague in January 2023 to solo travel around Europe and build my business.

From January to June, I lived in 14 cities across 7 countries (full list below). I fit my entire life into one large and one small backpack – ten shirts, two pairs of jeans, two hoodies, two light jackets, some underwear and socks, and a laptop.

But most impressively (imo), I did all of this while still running (and growing) Third Wall.

Why You’re Here

Writing this annual reflection post is as much for me as it is for you.

For me, it serves as a cathartic review of my year, taking note of where I excelled and more so, where I came up short — no punches pulled. 

For you, it’s purpose is two-fold:

1. To give you an in-depth, entertaining, and honest, update of what I’ve been up to beyond the standard social media highlight reel.

2. To help you learn from my mistakes and apply some of these lessons to your own life.

On we go. 

On Changing Environments

Over four years ago, I wrote about Relocation Therapy (yes, that’s a real thing) in my book.

Any writer will agree that the best way to escape writer’s block is to change environments. The simple change of setting, even moving up a few floors in the same building, makes a world of a difference. 

Changing up my entire lifestyle? Immediate force multiplier.

I was immediately invigorated by the energy of working from random coffee shops, libraries, and hostel lobbies. The novelty was contagious and the ambiguity was exhilarating.

I was fully in a flow state and, as a result, I made some serious progress in my business:

• Built out three defined offers (still figuring this out, but progress!)

• Landed 10+ new clients

• Launched a new website and branding

• Built a custom agency operating system on Airtable, complete with a CRM, Content Management System, Learning Management System, and hiring tools.

• Hired and trained my first full-time employees

• Put in a ton of automation that has drastically freed up my time and made operating the business itself quite easy.

Due much in part to these improvements, I surpassed my entirety of the 2022 revenue by the end of July.

With five days left in 2023, we’ve shipped 350+ pieces of content across 17 clients.

Even better, revenue was up 57% YoY.

If you’re feeling stuck, don’t be afraid to change up your surroundings.

Better yet, take some time to travel alone. It’s been by far the best decision I’ve ever made, and will be something that I continue to do (in much shorter sprints) for years to come.

On Agency

I’ve come to learn that most people underestimate how much agency they truly have in their lives.

If you’re unhappy with something, there is rarely anything stopping you from taking action towards making a change.

Unfortunately, most people don’t want to put in the work.

Hate your job? Start applying.
Want to get stronger? Hit the gym.
Unhappy in a relationship? Talk about it, end it, do something. 
Want to start a business? Go for it. 

Will this change happen overnight? Probably not. But it sure as hell won’t happen if you don’t start making moves. 

I wear a ring with the phrase ‘This is Your Life’ inscribed on the inside.

What once started as a cool Shark Tank-inspired purchase has now become a core part of my being. I feel off when I don’t have the ring and often find myself subconsciously running my fingers over the text when I’m stressed or unsure of a decision.

I’ll leave you with one of my favorite images that echoes the same sentiment of this ring, courtesy of Tim Urban. Soak it in.

On Parkinson’s Law

I’ve highly encouraged all employees to implement timeboxing into their calendars, and in combination with Parkinson’s Law, I’ve watched it turn even the most stubborn procrastinators into efficient workers.

Of course, I did the same thing with my own calendar. With so much to see, I knew I didn’t want to spend my entire day working or, even worse, procrastinating.

I wanted to meet new friends, see new things, and do cool shit.

I needed to fit work into the time I allotted for it. I knew that if work started to suffer, I was hopping my ass on a flight back to New York.

The time difference was also a huge factor. At all times, I was anywhere between 5 to 7 hours ahead of EST and 8 to 10 hours ahead of PST.

I could wake up at 7am (my time) and immediately jump into deep work without needing to think twice about being distracted by friends, family, or US-based clients. Most of my employees were in the Philippines, so this time difference was better for our communication as well.

Even communication with clients in Israel and Australia (where EST calls were sometimes tricky), became instantly easier.

Everything ran smoother.

*I first learned about timeblocking from Nir Eyal’s book – Indistricatable. Highly recommend. 

On Commitment

Five years ago, a friend asked me a question that would go on to change my life:

“If you apologize for everything, then what are you truly sorry for?”

The same applies to commitment. Promises must be treated like apologies. They shouldn’t be taken lightly. A (wo)man is only as strong as their word.

I pride myself on following this code and throughout my life, I’ve done a very good job of sticking true to this.

This year, I let myself slip. Big time.

Warren Buffet is famous for his quote, “It takes 20 years to build a reputation and five minutes to ruin it.”

The same concept applies to habits. It’s amazing how hard it is to build a habit and how quickly that momentum fades once you begin to slack off. 

Coming into 2023, I was determined to consistently publish my writing. For the past two years, I have published one or more newsletters a week. Over 100 weeks straight.

Because of the immediate uptick in client work, I let it fall to the wayside. I went completely dark on my email list with no warning.

When I set out on my travels, I sent my email list a long update that concluded with this paragraph.

I'll be using this newsletter to document my travels, along with some other thoughts about life, business, and psychology. No consistent cadence. I'll be writing when inspiration strikes, but I promise I'll be active.

And guess what? I wasn’t active. 

I published twice, and then I gave up. I also stopped publishing my newsletter and writing for Digital Fashion Daily, even after giving my readers my word I’d continue.

This one was more of a case of over-extension, but still. My word is my word.

The real problem was that I did the same thing in my business. At the start of each day, I would send ‘Daily Briefings — short articles to my team to keep them engaged and educated about the world of tech, content marketing, agency life, whatever.

For a few weeks, it stuck strong, and then I forgot to send it once. Then twice. Then it went eight days in a row without an update. Momentum gone.

Then I brought it back and made it my word to continue. Then it fell off.

My least favorite type of people are those who only talk about ideas. They’re unreliable and never take action. It pisses me off.

This year, I saw myself start to become one of those people.

No lie, I’ve lost sleep over these things. It’s something I refuse to let happen again. 

On Compounding

Everyone tries to overoptimize their habits. But the real hack is to do simple shit and let it compound.

To show up, even when showing up is the last thing in the world that you possibly would want to do. 

To commit to getting 1% better every day.

These small efforts compound into larger efforts, and the next thing you know, you’re fucking crushing it.

My friend Tommy Clark is the epitome of this. Since June 2018, he hasn’t gone a day without publishing a piece of content. 

It’s not surprising that his content agency, Compound Content, has scaled like crazy, completely organically, immediately after launching.

On Optionality

Much of this year’s inconsistency was a product of too much optionality.

While having some choices is crucial, an abundance of them leads to significantly diminishing points of return.

This paradox of choice runs rampant in our daily lives, from supermarkets to online shopping and content consumption.

Above all, we see this in dating apps, where the majority of twenty-somethings struggle to commit to an option that “checks all the boxes” because an “even better” one might be just a swipe away.

As a single, 26-year-old with no lease, earning a great U.S. salary, and traveling to countries where the dollar was crazy strong, I was overdosing on optionality.

Yes, of course, I’m grateful to have been in that position. But trust me, not all that glitters is gold.

Money is often seen as an amplifier of opportunity, freedom, and optionality. But if you look at many of the most “successful” people who can do anything they want but have no:

• Relationships (Family + Friends)

• Structure

• Purpose

They fall into dark, dark places. 

I could live almost anywhere in the world, work on many different projects, and eat at any restaurant. But yet with all that choice, I had no idea what I wanted to do.

My shiny object syndrome kicked into overdrive and I was constantly wasting brainpower on trivial decisions that ultimately ended up distracting me from the responsibilities that allowed me to create freedom in the first place.

As someone who has been described by one friend as a “creature of habit”, having absolutely no routine was tough.

I had nowhere near as much money as these guys and luckily I have great family and friends, so I didn’t come close to any rock-bottom, come-to-Jesus moment. 

But on a significantly smaller scale, I already got a taste of that feeling.

My good friend Jason Levin recently wrote a blog on a similar topic, titled Digital Nomad = Overrated.

While I disagree with the extent of some of his ideas and personally find solo travel to be one of the most rewarding experiences of my life, most of what he wrote was true — especially this passage.

While my version of settling down is quite different from Jason’s (he has a fiance and a dog, while I have a new girlfriend and still forget to regularly feed myself) the concept is the same.  

Probably the most important lesson I learned this year….

Just because you have all the optionality, doesn’t mean you should use it. 

On Momentum

Momentum is everything in business. And I’m not gonna lie, business was booming this summer.

Back-to-back-to-back record-breaking revenue months, hiring new employees to meet the demand, launching our new websites and offers — everything was clicking.

I should have slammed my foot on the gas, buckled down on fulfillment, gone balls-deep on our sales push, and continued to dial in our operations. 

Instead, I got complacent. I came back to New York. I relaxed, I caught up with friends, I partied, I slept in.

My biggest fuckup? I let sales fall onto the back burner.

All the productivity I had built up when I was away? Gone.

And our pipeline? Weaker than ever.

This mistake set me and the company back by ~4-6 months and contributed to us missing our projections for the back half of the year.

I’m still dealing with some of the repercussions. 

On Hiring & Managing People

Coming into this year, I had no hiring or managerial experience. In March, I hired my first full-time writer. Two months later, I hired two more. 

As you can imagine, I made a lot of mistakes.

By no means am I an expert on this (I honestly think it’s one of my biggest weaknesses right now), but here are a few of my biggest learnings:

1) Go with your gut. Always trust your intuition. If something seems off about a candidate or too good to be true, it probably is. 

2) Bad talent is costly & good talent pays for itself.

You pay for bad talent multiple times over — the actual cost, the time it takes to fix their shitty work, any issues with unhappy clients, poor company morale, the list goes on. 

3) Always ask for samples and references. Don’t let the social proof of credible institutions fool you.

Always ask for samples of writers’ first drafts, not published pieces. You’d be shocked how many freelancers submit samples of published work that has been heavily improved (read: basically re-written) by a talented editor.

The same goes for references. Always, always, always ask for & follow up with references.

4) Be specific. Overcommunicate everything.

In elementary school, we were given a task to write step-by-step instructions on how to make a peanut butter and jelly sandwich for someone who has never done it before. 

The goal was to teach us the importance of communication. How we often underestimate how much we know and assume that others know the same.

You’d tell them to spread the peanut butter on the bread, but you never told them to find a knife. 

Stuff like that.

The same thing applies to business. When it comes to training and delegation, throw all assumptions out the window. With all employees, but especially overseas talent.

If anything, default to the idea that most people will likely not know what you’re talking about, especially if they’re a junior employee or only recently starting in a role. 

Overcommunicate and document everything upfront. Write your SOPs like you’re teaching someone to make a PB&J. 

It will save you and your team members so much time. 

And lastly…

5) People are fucking nuts.

We are all irrational monkeys floating around on a rock in space, but let me tell you…

Some people are certainly more irrational than others. 

I had a candidate (who APPLIED for a role at MY company) curse me out when I told her that I was unable to extend her an immediate, on-the-spot offer because I needed to give other candidates a chance to interview. 

I still have the audio from that conversation, always gives me a good laugh.

On Strangers

We spend our whole lives being told not to talk to strangers, while Uber and Airbnb are built on the backs of putting our lives in the hands of people we don’t know.

The same people telling you not to speak to strangers are those who didn’t have the balls to do so in the first place or who default to the ‘all people are inherently bad’ mindset.

Either way, stay clear of these people.

On the 80/20 Rule

The 80/20 rule (also known as the Pareto Principle) states that roughly 80% of the outcomes come from 20% of the causes. You can also think of it as where 20% percent of inputs is driving 80% percent of outputs.

It’s widely apparent in my life, and I can almost guarantee yours as well. Maybe not to the exact percentages, but close.

Even when living out of a single backpack, I still favored 20% of my clothing. Halfway through my trip, I gave around ~20% of the total items I brought with me back to my parents. I hadn’t touched them once in months.

85% of our annual revenue came from 35% of our clients.

The last few reps in the set are responsible for the most gains.

Heading into the New Year, I’ve spent a lot of time auditing my day-to-day life and figuring out where this rule applies.

Take a second to do the same, and then double down on that 20+%.

On Goal Setting

Here’s the funny thing about goals: Everyone talks about how to hit them. No one tells you what to do after you’ve achieved something. 

For as long as I can remember, I wanted to be an entrepreneur. To experience a life where every day was different. To not have to answer to a manager. Certainly, not to be told how I need to dress.

This year, I achieved all of that and more. Now what?

Did I set my goals too small? Too broad? What even we’re my goals? 

Looking back, I used to set a lot of goals, like 10-20 per year. They either fell into two buckets:

a) I smashed them out of the park
b) I didn’t even attempt to achieve them

The conclusion from “A” goals is rather straightforward: Set more ambitious goals.

The goals that fall into bucket “B”, required a little more to unpack. These were the goals of others, not mine.

Let me explain. 

Over the last twelve months, with the help of Luke Burgis’ Wanting, I’ve been carefully taking note of the motivation behind my desires. 

Are these desires a product of mimesis or are they original aspirations that I truly want? 

Recognizing how much of my goals and desires are driven by external models has been an eye-opening experience.

It’s like walking in on your parents having sex. Once you see it, it haunts you forever.

That's why setting my goals for 2024 has been centered around a terrifying question…

What do I really want? 

And more importantly, why do I want it? 

This has led to the more terrifying answer(s) of: I don’t know. 

I do know that I want to optimize my life for freedom. Doing the things I love to do (whatever that may be at the time) with people who I love to be around, and I certainly don’t want to work for anyone else ever again.

But what that looks like 5-10+ years from now? I have no fucking clue.

At 26, maybe I’m not supposed to know. But it feels a bit like navigating a maze without a clear view of the entire layout, relying instead on intuition and the occasional hindsight insight.

This doesn’t exactly sit right with me, but at the time of writing, I don’t have a better answer. 

That said, I’ve broken down my 2024 goals into four categories: Business, Health, Hobbies, and Travel.

Each bucket has two simple, actionable goals. They're straightforward in theory, yet challenging in practice, requiring dedication and a steady commitment to growth and learning.

Simple, but not easy. 

Business

a) Double Third Wall’s revenue while still keeping profit margins above 70%

b) Launch Klipboard (more on this coming soon) and get 200 paying users.

Health

a) Hit the gym at least 208 times (4+ times per week)

b) Gain 10-15 pounds of muscle

Hobbies

a) Publish 1+ piece of content online every day. Publish a long-form piece of writing at least once every two weeks.

b) Become fluent in Spanish (I’ve been taking two 1:1 lessons per week since August). 

Travel

a) Take one 10+ day solo trip to a foreign country. It’s looking like Peru will be this year’s destination (so I welcome any and all recs)

b) Austin, Texas — never been to Texas + have a bunch of internet friends down there that I should probably go see.

The crazy thing is that these are only a few of my takeaways from this past year, but for the sake of your time and sanity, that’s all I’ll share.

I’ll be spending the last few days of the year winding down, relaxing with loved ones, and preparing for what I hope to be the happiest, healthiest, most successful year yet. 

I encourage you to join me. 🤝

See you in 2024,

Randy