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How to change your career


I noticed this a lot when I talked to friends: they are not passionate about their careers but they don’t know how to change it. A high-paying career is especially dangerous because it makes all other things less interesting.

It’s okay if you’re not passionate about a job. A job can be something that fuels other important parts of your life. But I think in terms of careers we should strive for something that’s fulfilling.

While I can’t declare I have successfully changed my career yet, the post existed at least means I’m on my way. I didn’t have any strategy when I started. Writing online is just something I wanted to do.

But I recently read Working Identity by Herminia Ibarra, a professor at London Business School, and find it really valuable in guiding us through the process. I’ll share what I learned in this post.

You don’t have to figure out your true passion first #

Most articles advise you to start by finding your true self, either through introspection or doing personality tests. But people rarely find their passions this way. Let me explain.

I wanted to learn piano since I was young. I never got the chance until I had a job. I started it very passionately for one year, but then the pandemic hit, and my teacher switched to online teaching. It became less stimulating without social interactions. Then I gradually lost the drive.

What I learned is passion can get us started, but it’s not enough to sustain it. Just like starting a business, an idea is not as important as execution. My writing journey went the other way, fortunately. If I hadn’t gotten positive feedback when I was uncertain about my ability, I may have given up already.

In The Second Mountain, David Brooks argues that calling is only obvious when looking backward:

Often people feel a call but don’t really understand it, or they forget the call or just wander off. It’s only later that they make up a neat linear narrative of their life to describe how they took the road less traveled.

This made me wonder, as each of us went through life and experienced zillions of events, is it really true that there is only one calling for everyone?

We’re many selves #

I start to realize there are many things I’m passionate about. And as I explore, I discovered even more things interesting.

In the book, Ibarra mentioned the adult-development theory. The theory says that as we age, we shift priorities. We rediscover values and interests we had previously ignored. For example, in early adulthood we may be victims of other people’s expectations. As we mature we “transcend pressure for social and organizational conformity in order to become ‘our own person.’”

I don’t think looking inward is useless. But the problem with trying to find one true passion or one right career is that it often paralyzes us. We say to ourselves, “I don’t want to do anything until I arrive at the insights”.

But we learn in practice, not in theory. We grow in iterative, multilayered ways. A better use of the introspection tool is to generate options, rather than find the one thing. And because there are many possibilities, we try them and find out which one leads us to the place where we want to be.

Trying out many options #

Creating options is important because life is more like a complex terrain rather than a single mountain. To find the best food, animals would start by searching randomly before committing to their niches. To climb to the highest hill, the best algorithm is not going upwards from where you started, which only gets you to a “local maximum”, but surveys the terrain before committing the climb. You’re more likely to discover new solutions you couldn’t see before.

The career landscape has what Taleb calls “convexity bias”. There is much less downside in trying out options compared to the huge upside. We want to try a lot of things, keep the ones that work, and discard the ones that don’t. He writes,

Take the most opaque of all, cooking, which relies entirely on the heuristics of trial and error, as it has not been possible for us to design a dish directly from chemical equations or reverse-engineer a taste from nutritional labels. We take hummus, add an ingredient, say a spice, taste to see if there is an improvement from the complex interaction, and retain if we like the addition or discard the rest. Critically we have the option, not the obligation to keep the result, which allows us to retain the upper bound and be unaffected by adverse outcomes.

Notice for this strategy to work, the downside needs to be small. We don’t have the time and resources to try all the careers or industries we’re interested in, but we can take small steps and make quick iterations.

This strategy also helps us psychologically because big problems often overwhelm us. Taking small steps and making small wins set us in motion for the next steps toward bigger success.

As Ibarra suggests, instead of asking “Who am I”, ask smaller, more testable questions like “Among the many possible selves that I might become, which is most intriguing to me now? Which is easiest to test?”

Finding new connections #

Experimenting should take most of the time during career transitions. Along the way, there is one important thing: making new friends.

My fellow writers are both my mentors and teammates (although I never told them). They lead good examples and introduce me to new people. And I don’t feel alone.

I used to find it awkward to say that I lost connections to many friends in real life as I started writing online. Ibarra says this is a part of the transition:

When it comes to reinventing ourselves, the people who know us best are also the ones most likely to hinder rather than help. They may wish to be supportive but they tend to reinforce—or even desperately try to preserve—the old identities we are seeking to shed.

People we meet give us support and show us what’s possible. They also share valuable information. Harvard sociologist Mark Granovetter discovered that most people find their jobs through weaker social connections. These weak ties are helpful not because of the closeness of the relationship, or the power of their positions, but the likelihood that they know different people and give us different information.

Finding the people we look up to and the people we want to emulate also clarifies who we want to be like. Derek Sivers had a revelation when he asked himself “who are my heroes?” Although he spent most of his time being a programmer and entrepreneur, he realized he actually wanted to be a writer because his heroes are writers.

Making sense #

In its deepest sense, a career change is an identity change.

I recently talked to a friend who seemed to be stuck with his demanding job. He knew he should quit, but emotionally he was not ready.

That is normal. Once we start exploring, we’ll begin our “long and chaotic period of transition.” Ibarra describes such a psychological zone as “in which we are truly between selves, with one foot still firmly planted in the old world and the other making tentative steps toward an as-yet undefined new world.”

During this period, we try new activities, not only learning what kind of jobs or possibilities exist, but also sensing how we’re doing in those concrete contexts and situations. We meet new people, asking ourselves if we want to be like them or if we can be like them.

And there is one more thing that is happening, often hidden from view: we create new narratives of ourselves.

(Layers of career change, repurposed from the graph about behavior change in Atomic Habits)

As we experiment and meet new people, we start to discover the part of ourselves that was hidden. We’re moving away from the external rewards that gave us only transitory happiness. And towards internal drives that align with our values and characters.

A deep change starts to happen inside. We start to make sense of all the experiences we gathered. We start to see a clear path. We encounter epiphany. This is when the heart aligns with the head.

Insight is an effect, not a cause… There is not much we can do to manufacture the turning points that lend dramatic form to our stories. But when events happen that serve our purposes, we can weave them into the fabric of our reinvention narratives to use them to explain—to ourselves as much as to others—why we are changing.

The oft-cited key to a better working life, “knowing yourself,” turns out to be the prize at the end of the journey rather than the light at its beginning.

Seize windows of opportunity #

When do we decide to make the change?

Ibarra reminds us there are windows of opportunity that open and close back up again. If we don’t take advantage of the insights we gain, “old routines will reassert themselves, leaving basic problems unresolved until urgency builds the next time around.”

I’m not there yet, but one heuristic that might be helpful is the “Stop, Flop, or Know” I learned from Shane Parrish. We take the jump when we stop getting useful information, when we first lose an opportunity (“flop”), or when we have gathered a critical piece of information that makes the choice clear (i.e. gut feeling).

Summary of strategies #

As you can tell by now, changing careers is not a linear process. It takes trial and error. We go back and forth. It involves both interacting with the outside world (trying out activities and meeting new people) and working out the narratives about ourselves.

I hope you find these strategies helpful:

  1. Create options and act, then reflect
  2. Experiment by taking small steps and cherishing small wins
  3. Find people and communities
  4. Weave experiences into new narratives about ourselves
  5. Seize windows of opportunity
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