My previous post, “Never Waste a Good Crisis,” shared the story of a long low period in my life. Many people have gone through, or are going through, slumps of different lengths. Hardship is a normal part of life. What matters is how you use the present moment to plan a path that better fits the future you want, so that ten years from now you can look back and feel grateful for the turn the crisis gave you.

Today I want to look at this from the opposite angle. What if everything is going fine for you? Your family has not been hit by the pandemic, you have not been laid off or taken a pay cut, and apart from the inconvenience of not being able to go out and have fun, life feels much the same as before. Should you try to change now?

Some readers have asked me about this. They are doing fine at their current jobs. For a long time they have wanted to learn programming, or go abroad for a degree, but they worry about giving up everything they have accumulated to chase a goal they might not reach.

I think there is no standard answer, because everyone’s situation is different. Some people are the main earners in their families. Some are waiting for a green card (if they are in the US) or an H1B work visa lottery. Some have constraints of their own that keep them from doing whatever they want. Suppose none of that applies to you, and you are free to make a change. Is now a good time?

Should You Think About Change When Things Are Going Well?

Bert Lance famously said, “If it ain’t broke, don’t fix it.” If something is not broken, do not try to fix it. And this is an especially scary time: in the past nine weeks, initial jobless claims in the US have totaled 39 million. Out of a workforce of roughly 150 million, that works out to an unemployment rate of about 25 percent, far above the 10 percent of the 2008 financial crisis. (Note: the 39 million was the cumulative count of initial jobless claims over those nine weeks; the official unemployment rate peaked at about 14.7 percent.)

If hardship from outside forces pushes you into a slump, using the moment to think about your direction and make a change makes sense (that is the logic of my “Never Waste a Good Crisis” post, XD). But I also believe that thinking about the future and planning your life is not something to avoid just because things are going well. We are living through an unprecedented crisis, and the crisis is accelerating many changes that were already coming (like the remote work trend in tech that I wrote about the other day). If you are not struggling right now, you actually have the luxury of planning calmly, and of using the resources you have built up to find a better position in the wave that is coming.

A reader once described this dilemma to me. In Taiwan, this reader had already become a tech lead running a team, but had also gotten an opportunity in Silicon Valley, and could not decide whether to move the whole family over and start again from scratch as an engineer. Another reader was not an engineer at all, had taken some online courses, wanted to keep going deeper, and was unsure whether to quit a nicely paid job and go all in on a career change.

My blog is called 「半路出家軟體工程師在矽谷」, the software engineer in Silicon Valley who changed careers midway (nobody ever gets the name completely right!). But I am not telling everyone they have to become a software engineer, or that they have to come to Silicon Valley (or is that just the answer everyone wants to hear? :)). Most of the time, I ask people what their ideals and goals are, what preparation and effort they are willing to put in, and how they are framing it mentally. Very often, the answer is a plan: once I have a few more years of experience, once I get promoted to a certain level, once I have saved a certain amount of money, then I will officially start moving toward the goal.

“Waiting for the Right Conditions” Usually Means Never

Maybe it is because I have seen a few more cases now, but here is my sense of it: people who say they need to wait until some condition they set is met before acting rarely follow through once the condition is met. After all, you worked so hard to reach that milestone. Are you really going to give up the new achievement, and everything you have accumulated, right away? Or would you rather enjoy the hard-won result for a while, and push the conditions for the dream a little further out? Every time you postpone, the switching cost you face next time gets higher, and over time you may simply stop wanting to change at all.

I have postponed changes myself. A year after I got my first full-time job in the US, I started to feel that my learning, both at work and studying on my own after hours, was getting less efficient. Maybe my approach was wrong, or my learning was not systematic enough. I thought about going back to school to study properly, but I was scared: I had spent over a year landing that full-time job, and I felt I should save more money before making a change. That hesitation dragged on for almost a year before I finally committed to studying full-time. In the end, I chose the shorter option, a coding bootcamp (the one I wrote about in my Coding Bootcamp post), as my way to level up.

After I got to Silicon Valley, I mostly stopped having this problem. People here are highly action-oriented. I saw people working a job while doing an MBA, and people working during the day while building their own startup plans at night. Everyone seemed energetic, unafraid of change, and determined to live life on their own terms. That atmosphere rubbed off on me, and I tried a lot of things too, like writing after work, and switching jobs a year and a half into my first Silicon Valley role.

At Facebook, I Got Comfortable Too

After joining Facebook, I went through a period of impostor syndrome. Everyone I met was smarter, stronger, and harder-working than me, and working there was intensely challenging. But after pushing through for a while, I adapted to the pace, the standards, and the way of working. I started mentoring new hires, took on more projects, and built a bit of a reputation, so that people would come to me with questions.

Work still held plenty of uncertainty, but I could roughly size up most challenges and prepare accordingly. And that was exactly when I started to feel comfortable. Comfort is not a bad thing. After my daughter was born, a large part of my time went to her and to family matters. If there were too much uncertainty and too many unpredictable challenges, I would have been miserable.

But I am also someone who needs different challenges. Stay in the same role and the same work for too long, and I start wanting a different kind of technical challenge, or a new domain to learn. Over the past few months I have been going back and forth on this, and I asked several more senior people for advice. Every one of them said the same thing: go pursue new challenges. If my life is fairly stable right now, my dear wife has been working for a few months and things have settled, and my daughter is sleeping through the night (which gives us a few full hours of sleep at night), then if I do not try now, when would I ever?

Knowing is easy; doing is hard. I can be perfectly objective when advising others, but facing a similar decision myself, I kept finding different considerations. Since the pandemic started, everyone works from home, so I cannot properly get to know a new manager and new teammates face to face. Or, if the broader environment turns bad and the company unfortunately has to lay people off in the future, my output and importance on my original team would certainly be higher than on a new team, which would be relatively safer (though nobody can say for sure). That is also why, in my earlier post on why I recommend you start writing, or creating anything, I encouraged everyone to write or create content. Sharing my past and current struggles here is my way of showing that I hesitate too, and that I am not always so action-oriented.

My Move: A Hack a Month

But if I only wrote about my struggles and took no action, writing this post would have been pointless. So let me share this: I recently did a hack a month at work. At my company, engineers who have been there for a year can switch teams freely. If the receiving team’s manager is willing to accept you, your original team’s manager cannot block the internal transfer (the idea is to let talent move freely inside the company, instead of leaving for another company). Before transferring, many people try a hack a month, which basically means spending one month doing another team’s work to find out whether you like the new team.

Some people do a hack a month and decide to transfer. Some may do several hack-a-months in a row, with different teams. And some discover that their original team was better after all, and go back. Either way, it is a mechanism that gives people a chance to try a new job. I am one week into mine. I am relearning different projects and picking up new technology, and there are many moments when I feel quite dumb, but having a new challenge always excites me.

I am sharing this post because even when we are not in a low point that forces us to reflect, we still have many goals and dreams waiting for us. The title of this post is “If Not Now, When?” If not now, when will we make the change? We keep setting one condition after another, waiting until we are ready, or until a better moment arrives. But let me ask you, reading this: is there ever a moment when you are one hundred percent ready? Is there ever a road toward your goal where every light is green? For me, most of life cannot be fully prepared for. Exams can always be prepared for a little more; interviews can always be practiced a little more; and the same goes for confessing to someone you like, deciding when to marry, when to have kids, moving house, changing jobs, switching teams. I am not saying we should not prepare. I am saying that, with limited time, once you are prepared to a reasonable degree, maybe it is time to start trying.

I hope that when you face your own goals and ideals, and ask yourself if not now, when?, you have a clear answer!

This post was originally published on my former blog, 「半路出家軟體工程師在矽谷」, on May 23, 2020. The blog is now offline, and the text is preserved via the Wayback Machine. It has been lightly edited for this site.