We spend a bulk of our life and energy in our jobs and careers, so it's really important to be intentional about choosing the right job career.
1) Start with the big question. What life do you want to live? How would you live if there are no constraints?
This is the most fundamental question of your life and the answer to this should direct all your major decisions like career. Jobs and career are simply a means to the end of living the life you want. A good career maximizes the time that you spend on doing what you want to, or sets you up to do that in the future (with skills, money, network, or other resources).
This is not an easy exercise and your answers will change over your life, but don't skip it! The best you can do is to be thoughtful, long-term and regularly revisit your point of view and optimize/correct towards it, even as it changes.
One exercise that can work is to start with a smaller time window - 1, 3, or 5 years and think about what you want, and slowly extend it over time as you get clarity. You can also regularly reflect on what you enjoy - maybe keep a journal to keep track of moments of joy and satisfaction so that you can identify patterns. Another trick is to dream without constraints and explore diverse ideas of life to think very broadly and freely. Many of us are trapped into the life view and constraints that we were born into.
2) Be clear on what is actually important in a career
Break down your career/job goals into dimensions that matter to you. Here are some common ones:
1.The work and enjoyment: think of what you’ll do day to day, the conversations you’ll have, projects you’ll do.
Quoting advice from an ex-manager:
“As you know, startups are very hard work (as is any job), and at the end of the day I always give people advice to imagine what you are doing day to day. Imagine the actual work you will be doing, the meetings you'll be in, the users you'll be talking to, the colleagues you'll be working with. As ultimately, that is what shapes your happiness. At the end of the day, to be very successful, I believe you have to be passionate about the work you are doing, you have to love the people and the company you are working with, and you have to ask yourself how you will have a major impact."
2. Company/team potential: High tide lifts all the boats; you get disproportional rewards/recognition for your work if your team/co. Is doing well and vice verse.
3. Manager/team: Will you learn from them, are they nice people, do you connect well with them?, do you see them being friends in 5-10 years? can you form relationships that’ll connect you to your next gig?
4. Learning: What skills and capabilities do you want to learn? How do you see those changing after 2 years in the job. Earlier in your career, it’s good to optimize for learning velocity and both breadth & depth of exposure, as that set you up for more and better options in the future.
5. Compensation: What comp change will actually make a meaningful difference in your life and happiness? How much money do you need for a comfortable and happy life? What’s the comp potential in 3, 5,10 years? Compensation can provide both a comfortable life now, and earn you freedom and security in the future.
6. Recognition and reward culture: If you are a top performer, will you get proportionally rewarded? Do you report to someone and interact with people who have the ability and will to reward you?
7. Hours of work, vacation: Can you do other things outside of work? Badminton/travel/family etc. does this job make you optimize for career over everything else?)
6. Recognition and reward culture: If you are a top performer, will you get proportionally rewarded? Do you report to someone and interact with people who have the ability and will to reward you?
7. Hours of work, vacation: Can you do other things outside of work? Badminton/travel/family etc. does this job make you optimize for career over everything else?)
3) Rate your current job (1-10) on each of these dimensions
This exercise will help you understand what you value. Which ones are you okay with? (maintenance mode) Which ones do you want to improve on? Which ones do you not really care for? (like snack selection in the office).
4) Pick the top 3 things that matter to you
It’s easier to optimize with fewer dimensions. If you optimize across all dimensions, your outcome is likely to be average, and not great, on any dimension.
5) Explore opportunities that’ll move the rating of those top dimensions in a meaningful way
Ask friends, mentors and experts for recommendations that'll fit what you want. Most people are willing to chat and help!
Setup informational interviews with recruiters and hiring managers to learn more about different roles. In the interview process and conversations, ask questions that’ll help you rate the job on those dimensions.
Try to be upfront about what you’re looking for - it saves everyone time if you can decide if it’s a no-go earlier in the process. There’s not much upside in getting offers that you don’t want.
6) Be ready to pass on jobs that don’t meet your bar and those that you aren’t truly excited by
Find jobs that are significantly better in your top dimensions. Say no to everything else, if you aren't in a desperate situation.
You’ll only have the confidence to pass on offers if you have clarity on what you want (by doing steps 1-5). Otherwise, you'd find it hard to say no. Saying no gives you the chance to keep looking and find something that does.
7) Think 2 steps ahead
What’s next after this job? Is that what you want to do? If not, what is it? What’s the right next step that can take you closer to that?