Each new year, the world gets a little bit older...and so do we. This end to an era nudges us to take a step back and reflect on “how we’re doing” – to consider what we’ve accomplished, to evaluate the delta between our hopes and reality, and to assess whether we’re focusing on the right things altogether.

I like to call it “a look in the mirror”.

This article is mine.

Each Year Passes Differently


I’ve come to appreciate that each year passes in a unique way.

2018 was a hard year to beat. It was my year of sponge, filled with a lot of growth. Perhaps more importantly, it was a year without expectation. No one knew who I was or cared what I was doing. All that fueled my progress was the “time anxiety” of turning 25. And somehow, that was enough to make 2018 the year that I learned to code, launched 4 projects, and started leading a 20-person team while traveling the globe.

2019 was also a great year, but in a very different way. Most notably, it was the year that I launched my blog which has now been read my hundreds of thousands. I also had the opportunity to speak at my first conference (and my second). But outside of those accomplishments, the other milestones likely seem less “impressive” to an outsider, despite being equally meaningful to me.

In 2019, I made the difficult decision to walk away from leadership and switch things up, founding Integral Labs. I also spent more time with my family and found myself in a new relationship. And just like 2018, I kept reading, coding, and creating – albeit at a slower pace. More on all this later in the article.

If 2018 was my year of sponge, I’m not sure what I’d call 2019. It was the year where I stopped moving at full force and learned to appreciate that direction is even more important than speed. 2019 was the year where I learned more about what motivates me (and what doesn’t), where I want to be in the long-term, and how I need to invest my time to get there.

I’ll reflect on this change of pace as I look forward to 2020, but first, in true “open” fashion, here’s how I fared on my explicit goals.

2019 Quick Recap

I publicly stated my goals, so I might as well publicly reflect on them (plus a few extras). I’ll be leaving up the 2019 results for a few days, while I await getting my Mac back and then I’ll do a complete open page revamp.

✅ Goals achieved:

  • 🌀 Learned illustration
  • ✏️ Wrote and built blog to 2k+ subs (goal: 1k)
  • 🎤 Spoke at multiple conferences (goal: 1)
  • 🔑 Created resources for women in tech
  • 💼 Incorporated my own business
  • 🍁 Spent a summer with my family

❌ Missed goals:

  • 📚 Read 12 books (goal: 24)
  • 📈 $378 MRR (goal: $1k)
  • 🏃‍♀️ Exercised 169 days (goal: 182 days)
  • 💻 1 new coding course (goal: 3 coding courses); coded 89 days vs 125 in 2018
  • 💸 Spent $26k (goal: spend <$24k)
  • 📹 Didn’t ship projects live (goal: ship 2+ projects live)
  • 🚙 Didn’t learn to drive (still can’t 🙃)

🔮 Unexpected happenings:

  • 👩‍💻 Left my job at Toptal
  • ✍ Wrote 18 articles, with an average of 3500 words each (or 63590 altogether), leading to 395k pageviews
  • 📈 Trended on the Hacker News homepage 4 times
  • ✈️ Traveled to 14 countries, including 3 new! (South Africa, Turkey, New Zealand). Very cool Nomadlist view
  • 👫 A relationship

The Lessons Behind the Goals

Instead of simply stating what I was able to accomplish and what fell short, the more valuable approach would be to share what I’ve learned. Here are my top 5 lessons from 2019:

1. The power of writing

Almost exactly one year ago, I decided to launch my blog. The impetus at the time was simply to distill my thoughts and have a medium to share them. More tangibly, I really just wanted to write this article about remote work. However, something unexpected happened almost immediately: people cared.

To respond to this attention, my blog quickly became a focus throughout my year. I started the year with 0 subscribers. By the new year, I had over 2k people allowing me into their inbox and 395k site pageviews.


Perhaps most rewarding were the connections and opportunities (including my current job), that were due to my decision to launch this thing. This is something I’m proud of.

But the lesson here isn’t about me. It’s simply that this wouldn’t have been possible 30 years ago. In an age of infinite leverage, the ability to share your ideas through mediums like the Internet, is unprecedented. And the best way to do so? Through writing.

Prior to 2019, I was under the impression that there was just too much content out there. I’ve now come to realize that the truth is, there is too much low-quality content out there. When used with care, I see more opportunity than ever in the written word. (If you're interested in launching your own blog, I would very much recommend Ghost)

2. Old habits die hard

I started the year wide-eyed and in South Africa. I wanted to get the travel bug out of me, so that I could spend the rest of the year staying relatively put and ultra-productive. Despite my intentions, I found myself hopping around just as much as ever. What’s more concerning is the fact that I had the same intentions and outcome in 2018.

The choice to continuously be fickle (yes, I’ve grown to believe that being fickle is a choice to not commit to something) has eaten into my productivity and more importantly, my ability to lead the life that I want. Said differently, I’ve consistently prioritized my short-term desires over my long-term goals. But I’m recognizing with more conviction that even though nomading is fun, we all yearn for the same things in life: routine, relationships, and balance. In 2020, I’m choosing to be less fickle and prioritizing these aspects of my life.

3. Career enmeshment

This year, I learned a valuable term and an equally valuable lesson. Google defines enmeshment as “a relationship between two or more people in which personal boundaries are permeable and unclear”. The term career enmeshment was recently coined by Janna Koretz, but is something that I and many others have long experienced.

In 2018, I was lucky enough to get the opportunity to lead a 20-person team at the ripe age of 24. It wasn’t until I went looking for new roles this year when I realized how deeply I defined myself by my title. Instead of searching for work that I found truly motivating, I found myself sifting through other job titles or companies that would give me similar accolades. My career had become my identity. It took me a while to process this and gain the confidence to step away from leadership and explore a new role that would let me refocus on my skills.

4. The delicate balance of monetizing

I had a goal in 2019 to reach $1k MRR. I did not hit this goal and quite frankly, found this the hardest goal to make substantial progress on.

I find my struggles in this area particularly interesting. Why? I’ve helped companies on both sides of this coin: building products and scaling products. For some reason, I’ve struggled to translate these results to my own projects.

When I reflect on this, I think it’s because I hold my own work to a different standard. I’ve been operating off of the mentality that I should only work on things that I’m deeply passionate about. I’m also very protective over what I’m willing to put my name on and conservative in what I'm comfortable a price tag on. At a high-level, think this mentality is mostly good.

However, I have to be honest and say that sometimes I see people working on things that they’re either a) not passionate about or b) not super proud of, but they’re killing it. And at those times, I wonder whether I’m being too restrictive of myself. I have no intentions of launching dropshipping business or joining an MLM scheme, by any stretch, but I’m openly admitting to finding it difficult to find the right balance between sticking to my values and monetizing. I'm not sure if there's a lesson here, but rather something to ponder. We’ll see how this progresses in 2020.

5. Three core priorities

Perhaps the most important lesson of 2019 was one that I wrote about in February, but quickly forgot in the context of my own life.

My first article to go “viral” was You Don’t Need to Quit You Job to Make. The article focuses on the ability for people to work full-time while creating things, but more broadly speaks to the possibility to fashion one’s time more optimally in order to achieve more.

However, it does so under the pretence of being able to focus on three core priorities at a given time. For reference, these were my cited priorities in the article, including my hopes for 2019:

  • 2017: Work, Travel, Relationship
  • 2018: Work, Learning to Code, Building Side Projects
  • 2019: Work, Scaling Side Projects, Sharing Ideas (Writing, Speaking)

I started 2019 with ambition to build a product or two and write for my blog, while still working full-time. It sounded tough, but doable.

As the year went on, so did my appetite to take on more. I wanted to continue learning to code. I wanted to attend and speak at events. I wanted to write weekly instead of monthly. Despite thinking I wanted to slomad, I still found myself hopping around. And in the wake of all this, I changed jobs and entered a relationship, while still wanting to keep up with my exercise and reading goals. I quickly went from having three focal points, to way too many.

Original

  • Work, Scaling Side Projects, Sharing Ideas (Writing, Speaking)

Reality

  • Work: Transitioning job, team offsite
  • Products: Creating Upread, taking another coding course
  • Writing: Publishing weekly, growing blog, monetizing
  • Other: Speaking, new travels, new relationship

Candidly, I spent a few months spinning my wheels trying to find a solution that would encapsulate all of these goals. I genuinely thought I could.

But even when I was succeeding in one arena, I would feel bad about my progress in others. I would open up my google tracking sheet, only to see that it had been X days since I last coded or I was Y% off my exercise goals. By the end of the year, I came to the uncomfortable realization that I couldn’t just “do it all” and decided to deprioritize most things.

I focused back on three: my new job, my new relationship, and making the most out of the travels I had chosen to take. For a few months, writing, coding, and products were off the map. It somehow both alleviated and induced stress. But, it was the right decision.

That’s led to me consider how I’ll tackle 2020. I still want to make. I still want to write. And just like 2019, there will likely be many other things that fall into my plate. But I’ve learned that KPIs start to lose their importance if too many run in parallel; if everything is a priority, then nothing is a priority.

In an effort to find a path forward, I remembered a comment that ironically was posted on the Hacker News submission of the exact same article. At the time, I must admit (as you can tell from my comment), that I didn’t really find it pertinent to my life. But now, I think it’s just as relevant as ever.

The idea is simple: approaching your life in epochs or seasons, so that you can not only focus more effectively on one particular area of your life, but also have peace of mind when you put some things on the backburner. With this concept in mind, I’ll have overarching goals, but will focus on one, maybe two key projects outside of my core work. The rest? It’ll have to wait until the next season.

Looking forward: A New Decade

In 2019, I came to the sad, but freeing realization that I can’t just “do more” or “optimize better” to achieve my long-term goals. Instead, I need to be more realistic and prioritize doing fewer things, but better. In order to get there, these are some areas I’m focusing on:

1.0 Learning to automate

I’ve had a lot of fun coding over the last two years (I can’t believe it’s been that long!), but something that I haven’t focused on enough is automation. I see this as a huge opportunity for me. I know there are repeatable elements to my life, which a computer can do much more effortlessly than I can. The only thing blocking me from accessing this "superpower" is the lack of attention that I’ve dedicated to it. In 2020, that will change.

2. Outsourcing

For things that can’t be automated, some can be outsourced. I recognize that I’m extremely privileged to even have this as an option, but I want to explore it for two reasons. One is simple: to free up my time. The second is less obvious: to learn to give up some control. My decision to outsource isn’t so much about location arbitrage or becoming hyper-efficient, but instead about seeking help and learning  to build something bigger than myself.

I’m constantly impressed by what other people are able to do around me when they trust people with their businesses. I just need to get there mentally. At this point, I’m not entirely sure what I should outsource, but that’s a priority for me to figure out.

“At first, it was hard for me to imagine anyone else being able to do these tasks that seems so ‘proprietary’ to me, but I quickly learned other people could do it, and they could even do it better.” - Pat Walls, 2019 Recap

3. Deprioritizing

Not everything can be automated or outsourced. And unfortunately, I want to do far too many things in life. So across those that I can’t automate or pay to get help with, I need to be more pragmatic about what I can achieve.  In order to deprioritize, I’m minimizing shallow work and focusing on productivity over business.

In his book Deep Work,  Cal Newport comments on a habit that I’ve increasingly faced: using busyness as a proxy for productivity. Many people use busy activities like hitting inbox zero, to convince themselves or those around them that they’re productive. But busyness is not productivity. This surfaces for me personally in surfing Twitter, reading a boatload of email newsletters, or rewriting my todo lists. I make excuses about why these are beneficial to my existence, but in reality, they are distracting me from the things I truly want to create or achieve.

“If I organize my life in such a way that I get lots of long, consecutive, uninterrupted time-chunks, I can write novels. [If I instead get interrupted a lot] what replaces it? Instead of a novel that will be around for a long time… there is a bunch of e-mail messages that I have sent out to individual persons.” - Deep Work

In order for me to achieve the things I want, I must no longer trick myself into being productive, but actively deprioritize things that aren’t driving me towards my core goals. As a more concrete example, I’m choosing to completely deprioritize speaking this year.

Another thing that I must admit has warped my sense of productivity is sharing everything openly. When you start building a following and sharing mini-milestones, it’s exciting that there are so many people cheering you along the way. It’s really a beautiful thing. But, it’s often not an accurate reflection of reality. For example, in the last three months, I did nothing especially notable or impressive. I worked and traveled a bit. I wrote zero articles. I built zero products. But I still had people reaching out congratulating me on X, Y, or Z, making me feel like I was productive and contributing throughout the entire period.

I think the pros in sharing openly still outweigh the cons, so I will continue to share, but just try to have a more objective view of my success judged solely by myself.

4. Slowmading

Every year, I tell myself that I’m going to slow down. And each year, regardless of my intentions, I still find myself swept up in nomadic indecision.

But this year, I’m moving in with my partner. Who knows exactly what that will look like and for how long. Some might even say I’m quitting the nomadic life. But I view being able to work remotely as the ability to be exactly where you want to be. And for now, that means a little less on the road, allowing me to focus on other things during the first few seasons of 2020.

5. Taking myself more seriously

The past year or so brought me a lot of unexpected ‘success’. I use the term success because I can’t put my finger on another word that would communicate the attention that many of my projects and articles have gotten. I couldn’t be more thankful. But what has also come from that is a lot of people seeking my advice. In 2019, I tried to respond to everyone and offer help in essentially every scenario. But it was draining and unsustainable.

In 2020, I’m trying to see myself as a professional and say no more often. In some cases, even charge for my services (inspired by Anne-Laure’s consulting page).

Taking myself more seriously also feeds into the types of projects I want to work on. This year, I hope to get started on a full-length book. For a long time, I thought that I wouldn’t write a book until much later in life or perhaps not at all. But, according to Google, a typical book is 90k words. This year, across just 18 articles, I wrote over 63k words, or ⅔ of a book! This makes me realize that with some dedication and focus, a book isn’t outside the realm of possibility, even at this stage of my life.

6. Taking other things less seriously

While I try to take things more seriously in work, I want to take things less seriously in play.

Speaking again to my “unexpected success”, I want to touch on the unexpected part of the phrase. As I built projects or wrote articles at the beginning, no one was watching. And I had a lot of fun expressing myself in boundless ways. I did things because I thought they were great and felt great creating them.

But as they started to get attention, I felt a deep seated pressure to continue on that path. Each article had to be as highly researched as the last and just as profound. I found myself asking the question, ‘What will the response to this article be?’ or ‘Could this article trend on Hacker News?’ instead of asking myself, ‘Do I think this is interesting?’.

In 2020, I want to fall back in love with the things that got me that unexpected attention again. I want to view my passion projects as exactly that: projects that I’m passionate about. The types of activities that I’m excited to have time for, instead of ones that feel like a drain on my day. I want to go down rabbit holes and create projects, even if they are just projects and may never become products.

I look back on 2018 very fondly. Why? There were no expectations. I was just learning and creating. I want to get back to that mentality.

7. Living a little

I remember sitting down in Singapore with a guy I met at a conference earlier this year. We got into the topic of personal development and I explained to him my philosophy of tracking nearly everything. He seemed overwhelmed and quite honestly a bit disturbed by the prospect of tracking things so precisely. At the time, I didn’t really understand his reaction.

But moving into 2020, I think I do. I still want to be tied to results, but also want to focus on some other things that won’t be another number in my spreadsheet. These include:

  • Spending more time with my parents
  • Investing in my relationship
  • Developing a daily yoga practice
  • Spending less time on social media
  • Smiling more :)

My 2020 Goals

Finally, it’s time to share my tangible goals.

At first, I looked for ways that my 2020 goals could look distinctive from 2019. Surely, if they look the same, that means I’m not growing, right? Well, if I truly believe that being great is just being good repeatably, then that’s exactly what they should look like. I should continue hacking away at the things that I can see myself doing in 2 years, 10 years, or a lifetime.

So, these are some of the goals I hope to tackle this year:

And the first epoch? My blog. I miss writing and have a laundry list of topics to cover. A few goals for “season 1”:

  • Biweekly posts
  • Grow to 3k subscribers
  • Double organic traffic

So that’s a wrap. Here’s to a new decade filled with mini epochs and hopefully a lot more passion in my projects.

Thank you so much to everyone who spends the time following along my journey. It’s a beautiful thing to get to share your life with others.

I’ll be in Bali for the first two months of the year, but then I’ll be heading toward San Diego. If anyone lives around there, I’d love to connect!

‘Til next time.

PS: If you liked this article, you might also enjoy my podcast on all types of things like tip culture, technology people feared, or the the most influential artist you've never heard of, or my latest project.