The Biggest Regret People Have Early in Their Career


The most common mistake people cite in their career is staying too long in a certain job or industry and not switching sooner.

When I was younger, I thought I always wanted to be a lawyer.*

*Disclaimer: Asian parents.

But over time I realised I had a greater fascination in creating things. Whether it was drawing and designing works, writing stories or tinkering in random hobbies.

That was my first iteration. It made me change the entire course of the past 4 years of my life and how I spent my time.

This decision was probably easier than most people’s because I was much younger when I decided to iterate.
But most people veer away from this process of iterating because of sunk cost fallacy.We sometimes fall complacent because we think to ourselves:

“I’ve already put X amount of time/energy, it must be worth it.” or“It’ll get better soon.”It makes sense if you’ve spent a year or two on a certain trajectory or have accumulated thousands in course debt and subject credits.

But the time you spend in your 20s is crucial because the learnings you have in one job, degree, or field will compound.

Visually we might represent this as…

Treat complacency like a disease.

Internships, volunteering opportunities and entry-level roles should be seen as opportunities to sample careers and industries to find what you like/don’t like and iterate accordingly.

Once you’ve figured that out, double down.

good framework we’ve found to decide if you want to switch roles, degrees, etc. is the mnemonic, Am I Growing Complacent Currently? Where:

  • Accomplishment: Have I done anything noteworthy these last three months?
  • Impact: Would I write a line in my resume about the work or study I have done over these three months?
  • Growth/Future alignment: Have I acquired valuable insights or skills? 
  • Challenge: Am I pushing myself to be in a situation where I might fail?
  • Community: Do I wake up energised to see and learn from my teammates and peers?

Your evaluation should end up looking something like this:

Reflect on the past 3 months and see if that influences how you think about your current trajectory or what you’re working on.

Is it positive?

Or is it time for a change? If so, ask yourself: 

  • What is the gap that’s been missing for me in the past 3 months that needs to be filled? 
  • What things do I want to explore over the next year? How can I actively do so?
  • If I could work on only ONE project for the next 3 months, what would that be? 

This isn’t meant to scare you by any means to know exactly what you want early in your career. 

You don’t need to have it all figured out. And it’s always possible to make a switch. 

But if a certain pathway isn’t leading you to the outcomes you want, don’t be complacent. The time you spend waiting compounds. There’s guaranteed to be something out there more suited to you.

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