Into the Unknown

Written on 04 July 2021

Since I left my job at Buffer, a few people have asked me about the leap of faith as they consider making a move from their companies. I can’t help them (or you) make the decision but I can share my thought process and experience so far.

I left a comfy, well-paying job that many people want for a more stressful, lower-paying job.

I spent about 5.5 years at Buffer. It is my first job since college. I got to a point where life was comfy: I was paid more than most of my peers in Singapore, could do my job relatively easily, and only had to work four days each week. I even had the time to start side businesses such as Yeti Distro and Open Atlas. I knew everyone, had a lot of context about many things in the company, and was used to the systems and tools. The people, culture, and perks were all great too. The company wasn’t growing much but at $20 million ARR, it is nevertheless still a successful business.

On the other hand, I received a job offer from ReferralCandy that is in line with my career goals and would give me a step up in my career. I would have the chance to lead and grow a team as the Head of Marketing while working with the rest of the management team (if I'm good enough). But I had to take a substantial pay cut. And there was a lot of unknown. As much as I tried to find out during the interviews, there are many things that I would not know until I experience them myself—such as the people, culture, processes, and pace.

A big struggle was: Do I want to give up all that I was enjoying for an uncertain opportunity for growth? Would it not be nice to just keep working at a well-respected tech company, enjoy all the perks, and have little stress?

Several books I read in the past guided me to the decision.

Working hard as my life philosophy

The first is A Guide to the Good Life: The Ancient Art of Stoic Joy. My main takeaway is I should decide how I want to lead my life—my philosophy of life. Instead of doing things because other people say it is good or because it will get me results more easily, I want to be making decisions according to my values and principles. For example, some people prefer not to work too hard and just enjoy life. I do not think that is absolutely wrong and it is great for them if that is what they want. But that is not what I want (at least for now).

(I have given insurance agents a hard time because of this. They would ask me when I want to retire to reverse engineer how much insurance and investments I should get. I would always say I do not want to retire.)

The other book is The Art of Doing Science and Engineering: Learning to Learn and specifically the last chapter, You and Your Research. Richard Hamming has inspired me to want to do something significant with my life and to work hard at it. I will be doing Hamming a disservice by trying to summarize his ideas, so I recommend you read You and Your Research if this intrigued you.

Books like Poor Charlie's Almanack: The Wit and Wisdom of Charles T. Munger, Benjamin Franklin: An American Life, and Edison and those people, Charlie Munger, Benjamin Franklin, and Thomas Edison, have also inspired me to want to keep learning and doing valuable things throughout my life.

I want to be working hard and learning even if it means I will have more stress or less leisure time. That outweighed most of the other considerations. I’m very thrift so the pay cut wouldn’t change my lifestyle. The perks I would lose (e.g. unlimited free books, annual retreats around the world, stipends for various things, sabbatical, and family leave) are amazing but not that important to me—at least for now. Working five days a week is largely the norm anyway, and I wouldn’t mind working more on things I enjoy and want to work on. I had been spending my Fridays, Saturdays, and Sundays working on things I like, and I much prefer being able to do that from Mondays to Fridays too.

Eventually, I knew that I should leave the safe shore of Buffer and sail into the unknown because I felt I wasn’t learning and working hard anymore.

It is not as scary as I had expected

I had to apply three times to get my job at Buffer. That made me worry that if things do not turn out well and I need to apply for new jobs, I would struggle to find another job that matches my criteria.

Fortunately, things have been well so far. But I also realized I was over-worrying. When I got my job at Buffer six years ago, remote work was a novelty and there were fewer exciting tech companies. Times are so different now. Furthermore, the job market seems very liquid now. I have several friends who have or are changing jobs, and I received several recruiting messages. If I have to find a new job, it will not be as hard as I was imagining. It might not be easy but I do not think it will be as hard as I had thought. If I had known this earlier, I would not have worried so much about the unknown. I could find another job if the new job does not work out.

The other fear I had was "yeah, I could find another job but what if I cannot find a company as good as Buffer?" But as I dug deeper, I realized the people, culture, and perks are good but staying is not good for me. I was becoming complacent and not learning on the job. I did not want to waste my career (and life), one comfortable year at a time.

I should add that I did not come to all these realizations myself. My wife, friends, and colleagues listened to me, asked questions, and shared their perspectives with me.

Owning the decision

Ultimately, we need to make our own decisions. Nobody can decide for us because nobody knows our dreams, preferences, and concerns better than ourselves. And owning the decision is not just about making the decision but also making it work.

Since joining ReferralCandy, I have been working a lot harder than I did in the past. It is partially because I made this move to grow and learn, so I have been taking challenges head-on. It is also partially because the change in environment rekindled my interest and curiosity in marketing, management, and more.

I think any job change will be hard. But so far, I have found this job change to be worthwhile.

P.S. Working hard can be a controversial topic. I like Paul Graham's essay on this topic.