Time off

"What were you doing when you took a year off?"

Let me tell you.

At the end of 2021, I was coming up on my six year anniversary at Remitly. It had been an incredibly fun, but stressful six years. I had a young family. Time was flying by. I was also burned out.

I needed a break! I decided that I needed to take some time off and recover.?

I had very little planned going into my sabbatical. The only thing that I knew was that I wanted to be extremely unstructured with my time. Up until that point, I had been incredibly regimented with my calendar. I wanted it to be totally different. I even cancelled my weekly therapy session.

A year (almost) went by, and I tried a lot of different things. Looking back on it, I was really pleased with what I did.

I also started having a lot of friends that found themselves in similar situations, and they started asking me about "What curriculum were you following?" What curriculum ???

But in truth, when I stopped and looked back on 2022, there were a few lessons that I could share about trying to get the most out of time off. There were a couple of major pillars, for anyone who is entertaining the notion of taking a break from their career:

• Take more time off than you think
• Spend time with family
• Reconsolidate your learnings
• Go deep into learning something that intimidates you

Take more time off than you think

First of all, you should take a hard look in the mirror and commit to taking a break. I will transparently admit that, as I was headed out the door, I had been telling people I was going to take a year off, but in my head, I really thought I could only last three months. I was going get bored right away and need something to do, or so I thought.

But in the first few weeks, as soon as I started to relax, I realized that I really needed it. Once I started to relax, I realized that it was good. And that’s when I fully committed to taking the full year off.

And so my first recommendation to anyone who is blessed enough to do so (like me) to take ample time to focus on the project of recovering and growing. My rule of thumb would be to give yourself three times the amount of time you initially thought.

If I had dove back into something in three months, I would still have been burned out. If I were to have joined another team, I would have started from an emotional and psychological deficit, and not been able to give 100% (not even close).

Ironically, it turned out that, once I had committed to taking the full twelve months off, I ended up being bored out of my mind by the month nine. At that point, I had exhausted all of my growth projects (see below) and was incredibly grateful to have something meatier fall out of the sky back at Remitly.

Spend time with family

"No amount of money ever bought a second of time." Tony Stark, Avengers: Endgame

You’ll notice that I reference “time” a lot in this. One of the most important realizations that I had during this time off was that time was the most important thing. I knew that I could work hard and make more money. But no matter how hard I worked, I would never be able to get a single second back. And as I looked at my young family, I knew that I wanted to prioritize that time with them over everything else.

Spending time with my daughter was one of the reasons I decided to take some time off. I wanted to be there for her in a way that could not be replaced with money. One of the first things I did was to buy annual passes to local theme parks like Legoland and Knott's Berry Farm. We spent a lot of time there and it was great bonding experience.

As someone who loves structure in my time, having regular scheduled activities was great in providing that structure and routine. I tried to make sure that I was there to pick her up and drop her off to day care and after school activities. I also tried to be there to cook breakfast as much as I could. It also provided me with the opportunity to spend more time with her.

It's not rocket science, just do it.

Consolidate your learnings

There is a David Friedberg quote that I love. I can't find it, so will paraphrase it here: “Four out of five days, you are failing and it feels like you are getting punched in the face and falling behind. But then on the fifth day, you have a massive breakthrough and have a massive leap ahead. If you compound that over several years, you do end up net ahead, but the feeling of the bulk of the time is one of struggle and failure.”

This is such a true statement, and precisely reflects my experiences at Remitly (and I’m sure many of my friends working at startups feel the same way). It felt like I was falling down most of the time. Walking away, I felt like I had barely started to scratch the surface of learning... anything!

But it turns out that was not true. During those six years of serving customers, shipping products, and building teams, I *had* learned a lot. But the predominant feeling of failure clouded the progression that had actually happened. It took an abundance of time for me to be able to consolidate the lessons that I had learned during those years.

There were a couple of things which I did to add structure to this initiative. While they may not be for everyone, I still think it is helpful to share.

First was angel investing. I was able to find a focusing and clarifying agent through investing in very early stage companies (often at what I like to call the “Gmail stage”). Being able to share lessons (often learned through painful mistakes) proved to be a way to even show to myself all of the things that I had learned. I talk a lot about this elsewhere, so I won't repeat myself here.

Second, I mapped out a series of conferences throughout the year that I thought would be great opportunities to grow my network and to learn. Now, I used to go to conferences all of the time for work. But this was the first time I was able to go with nothing to buy, and nothing to sell. I just went there to learn. (Btw, shout out to Capital Camp. If you only do one conference, go to that one.).

I felt like I was able to defrag and reframe all of the things that I had learned over the years and walk away with new insights.

Learn something that always intimidates you

Having had some really high stakes and interesting positions early on in my career, there were very few things that intimidated me professionally. There were really only two type of people that intimidated me. First, is people who can speak, read, and write both Chinese and English at a native level. Second, was software engineers.

Coding was always one of those things which felt so foreign to me, as to feel alien. The barrier to start learning felt insurmountable. Now, there are lots of resources out there now for free coding classes, but I could never get enough of a running start to get past through beginner modules.

But now I had the luxury of time and nothing else to do. I was very fortunate to have found a coding boot camp that was local to me, which was teaching an introductory Python for Data Science class. I was finally able to make enough progress in order to be dangerous in at least one programming language, where I felt I knew enough to build useful tools, at least for myself.

Doing the class also provided me with the added benefit of structure. I had class to go to and homework to do. This gave me a load of much needed structure.

Being able to learn something that I had been too intimidated to try to even contemplate learning, was one of the most wonderful things that I could have done. It felt like I had unlocked a part of my brain that I never knew existed. I understood so much more about building software products. I felt like I could appreciate my engineer colleagues so much better now and speak their language.

And the feeling of overcoming this mental barrier, is that I can really learn anything. Nothing is impossible.

And the timing of learning to code could not have been better.

Conclusion

Time is the most valuable thing.

I was incredibly blessed to have been able to enjoy a windfall of time in 2022 and I am glad that I was able to cobble together some semblance of a plan so that I did not squander it.

As I said, I went into it intentionally with no plan. But I had a notion that I wanted to learn and to grow. And I'm proud of myself for having done that.

I hope that this “curriculum” can serve as a useful tool for others that find themselves in such a privileged position. This is by no means an exhaustive set of things to do, you can write your own story.