James Hsu

A colleague recently gave a talk to our team about her career. She’s a well-respected leader with many years of experience in building and shipping successful software products. I was expecting it to be a straightforward talk about her accomplishments and learnings, but her sharing really blew my mind.

What struck me about her talk was her humility and willingness to talk about the times when she felt that she had made big mistakes. She talked about feeling like a failure in some cases, and being extremely fortunate in others. She found out that her project was about to be canceled days before her maternity leave – and not even knowing if she’d have a job when she returned! That’s a big one, which she recovered and grew from.

What really resonated with me, however, was when she talked about how to think about one’s career. She said two things that made total sense:

1. One’s career is usually not a straight line.
2. Think two jobs ahead.

What does the first point mean? The “straight line” trajectory suggests that we would stay in the same team or domain for a long time – but this is false. In our careers, we don’t always transition from junior level to senior level, and then live happily ever after. Think about how many folks join a smaller company or startup, only to rejoin a bigger company later. There’s an often-cited statistic that says the average person changes careers several times during his or her lifetime. Not just roles, but careers! I’ve found this to be generally true.

If career progression is not a straight line, then it means that the experience and learning derived from one’s current role is more important than one’s title. One could have a job title that is theoretically the same (or worse!) from the previous one, but is actually better in terms of being able to take on great projects. A janitor that learns on the job is better than a supervisor that does nothing. Don’t let the title define you. Define the role that you want, and don’t let others judge you for it.

Another way to interpret the first point is to think of Seth Godin’s “Dip” theory. Godin argues that success in life is about learning when to quit and when to persevere. Naturally, “dips” occur when one experiences lessened results despite a greater expenditure in effort. This often happens as one attempts to master something. Think about how easy it is to start blogging versus being one of the top five bloggers in the world. The path to greatness and mastery is challenging, and it is far easier to quit than to keep going. The key is to know what to focus on and what to leave behind.

Dips occur at a micro-level when one gets promoted to a new job level. The job feels hard and overwhelming, until one manages to rise above the dip and accelerate to a new level. But along the way, one questions whether this struggle is worth it – and that’s a longer discussion about mindset and motivation.

On a macro-level, getting to the dream job can mean taking one step back to eventually take two steps forward. It can mean changing careers entirely, and either having or lacking the conviction to do so. The tough part is that none of this is guaranteed. Nobody is going to swoop in and supply the answers we crave.

This leads into my colleague’s second point – thinking two jobs ahead. It is a great mental tool in terms of not allowing us to beat ourselves up at the first sign of trouble. The skills and systems one acquires at any given point can prove immensely valuable somewhere down the line, just not always now.

When I think back to my days working in Canada, I learned so many skills that I am putting to good use now. But that was a half-decade and five different jobs ago. Nonetheless, the skills toolkit that I’ve honed is absolutely cumulative and is now permanently part of my repertoire. The value that I bring to my current role, in terms of skills and mindset, will eventually allow me to level up.

Think about your current situation and what you are telling yourself. Are you fixated on the present job or a boss that you don’t like? Are you unhappy? Do you feel that you’ve plateaued? If the answer to any of these questions is “yes,” consider changing your mindset to play the long game.

In one’s career, we don’t always experience instant gratification. In fact, I would argue that only in rare cases does that happen. Half the battle is planning and plotting for future success. The only thing that is guaranteed to fail is to either do nothing, or to only think tactically.

Peace,

James