TL;DR
Learn, earn, or quit - Early on in your career, just earning is ok but learning is better. Doing both is best. If you’re doing neither, it’s time to quit.
Make people around you better - whether you’re an individual contributor or a manager, learn how to make others better, either through direct mentorship or indirect impact such as producing high quality reproducible work.
Maintain a brag document - always keep a document where you list your notable achievements at work. It’ll be useful in situations such as promotion talks, resume updates, performance reviews, etc.
Always be interviewing - constantly interview for roles even when you have a comfortable, well-paid job. There are many benefits to interviewing when you’re not actively seeking a job such as interviewing in a lower stress environment, and getting to measure your value in the industry.
Seek mentorship - extremely successful individuals almost always have mentors. It’s best to have two mentors - one who’s a few steps ahead and one who’s at the apex of your career path.
Be in places where you’re the dumbest person in the room - always make yourself uncomfortable and join teams/companies where you’re the dumbest. This gives you opportunities to learn and humble yourself.
Learning and earning
When you’re just starting your career, you might have the choice of a high paying job where you’re doing mundane tasks, versus a job where you’re doing something fun and exciting but it doesn’t pay well.
Usually, but not always, this choice boils down to a large corporate vs startup debate: do you work for a large corporation that pays well for doing something mundane or do you work for a startup where you’re building something exciting for low pay?
The decision is usually more complex. There’s an element of risk involved; not everyone can afford to take the risk to join an early stage startup. It’s also always not a dichotomy i.e. there are levels of pay and quality of work.
In most cases, for people that can afford the risk, the decision should boil down to whether you want to prioritize learning or earning. Early on, focus on learning over earning.
Because, your earning opportunities are not as high at the beginning of your career. Unless you’re very lucky and your moonshot succeeds, it’s very unlikely you’re going to become incredibly rich from a decision you made at the start of your career.
In most cases, your earning opportunities will be equity vs salary. Wealth from both of these options should be marginal compared to the earning opportunities you’ll get as your career progresses. Focusing on learning will give you opportunities to earn a lot more as your career progresses. It’s a worthwhile long-term investment.
What about jobs where you’re neither learning nor earning? I imagine a scenario where you’re an engineer building meaningless features on an outdated tech stack for a below industry average salary; your opportunities for learning are limited and your growth opportunities are stunted. In cases like these, it’s best to leave1.
Be a force multiplier
As an individual contributor (IC), it’s easy to fall into the trap of believing that you should only focus on your own work. After all, as an IC, my main contribution is my individual output right?
Amazing employees are force multipliers - they not only produce higher quality output themselves but they increase the quality of output of the team as well. This extends to IC roles as well.
One way of being a force multiplier is direct mentorship. Mentoring others isn’t just a one way transaction - it helps the mentor as well. It helps clear up concepts, learn new ways of doing things, discover new problems and work out new solutions to problems you might have never faced yourself. While it isn’t in every IC’s job description to mentor others, it’s always going to positively impact your perception in the workplace. It’s hard to disregard an IC’s impact on the team when the whole team performs better when the IC is a part of it.
The other way of being a force multiplier is indirectly impacting others. I’ve had colleagues that have made the team better by producing high quality reproducible work. These superhero colleagues reviewed other people’s work even when they were not required to do so. They produced tools to make everyone’s work easier. These colleagues also got promoted faster than everyone else - it was clear that they were force multipliers.
Even in managerial roles, it’s sometimes just easier to do the task yourself than to teach someone else. “After all, this is a one time task that I can do in 10 minutes, why should I spend 2 hours to teach the intern?”, you say to yourself, knowing very well this isn’t a one time task. Don’t fall into this trap. Always delegate and teach people how to do better work.
I’m not saying you shouldn’t individually grow but that you should learn to make others around you better as well; it’s this type of impact that helps you further down your career.
Maintain a brag document
If you do impactful work without documenting it, it might as well not exist. A brag document is where you summarize the big projects you’ve delivered in your job (or career) so far. You can be as granular as you want but the important bit is documenting it.
You will (or already have) run into situations where you know you did a lot of work but you can’t recollect it all. Documentation of past work and, more importantly, past successes is critical in so many scenarios:
You can highlight points from your brag document in your CV when you’re looking for a new job.
If you forget what you did last quarter for your performance reviews, you can pull up the brag document.
Trying to get a promotion? Pick out points from your brag doc to argue for it.
During layoffs, having a brag document will show the impact you’ve had on your company and, hopefully, help you keep your job.
Remember, your brag doc should only contain noteworthy achievements and should not contain things you can look up instantly e.g. pull requests, jira tickets, etc.
Always be interviewing
Even after you’ve landed a good job where you’re happy and well paid, it doesn’t hurt to interview for other companies. It’s actually easier to interview when you’re not actively looking for a job. This is primarily for a few reasons:
The stakes are lower because you already have a job you (hopefully) enjoy. This makes the interview a much lower stress situation so your performance should be better.
Your self worth is higher because you aren’t (desperately) seeking a job. It’ll take a substantial offer to convince you to switch. This is in contrast to desperate job searches where most candidates take the first offer they get.
You can gauge your value in the industry and use that to negotiate a raise or plan an exit if you’re getting underpaid.
You are constantly refreshing the knowledge and skills needed for interviews. Unfortunately, interview assessments rarely test what you do on the job so it helps to get a refresher on these topics.
Just don’t let these interviews negatively impact productivity at your own job.
Don’t underestimate the importance of mentorship
Early on in your career, find a few people in your industry that you look up to. This could be an influential individual in your industry, a thought leader or a top executive. Send them a text and tell them you would like to be mentored by them.
Rich elites have an incredible advantage in life in that they have access to powerful and successful individuals who can guide them. This ranges from a rich uncle to an alumni at their elite college to the executive coach that their parents hired for them.
Hatred for the rich aside, the point I’m making is that you can emulate one of the success factors of the elite; you can reach out to an influential individual and ask them to offer you mentorship. Sure, you can’t reach out to Mark Zuckerberg but you can reach out to a Fortune 500 tech lead, a top exec at the company you’re interested in or a alumni at your university who’s leading a startup.
These individuals have gone down your path and have made the mistakes you are going to make. It’s almost a superpower to have them guide you - a sort of time travelling machine where you can see the future and take steps to avoid future mishaps.
It’s also useful to have two types of mentors - one who’s just a few steps ahead of you and one who’s almost at the apex of the career path you want to be in. This will give you both short and long term guidance.
P.S. adplist.org helps to connect you to mentors across the world for free!
Be the dumbest person in the room
It’s important to be uncomfortable in the workplace; you should never be in a place where you’re the smartest in the room. If you’re not the dumbest person in the room, it’s time to change your environment. Join a different team, seek a promotion or switch jobs.
It’s important to always have opportunities to learn and you can’t learn if you’re the smartest person in the room. Seek opportunities to step outside of your comfort zone and go to areas where you’re more likely to be challenged.
I know it’s sometimes flattering and encouraging to be in a company/team where everyone looks up to you and thinks of you as the smartest person in the team. Unfortunately, this type of scenario can lead to complacency as you overestimate your skillset.
A lot of superstar employees from small startups usually get humbled when they join a larger company; they’re suddenly not the best employee anymore and they realize they’ve overestimated their capabilities. Then they start to learn from these smarter people and slowly, but surely, they become more skilled.
You should always put yourself in these uncomfortable scenarios. You’ll learn so much and be humbled in the process.
Further reading
Garry Tan is the founder of Initialized Capital and the president of Y Combinator. Garry gives career advice and industry insights on his Youtube channel. Kudos to
for recommending his channel to me. The first advice in this article came from this video:Steve Huynh is a Principal Software Engineer at Amazon and gives career advice for software engineers on his youtube channel. His content focuses more on software engineers aiming for senior positions (an uncatered niche in youtube) but is applicable to most career pathways. This video mentions the brag document advice:
I assume a scenario where you can take the risk i.e. don’t have dependents and are financially solvent. I also assume a scenario where you have other job opportunities available and the skills needed to get them.