tips for major career decisions

Summary

sketchy notes related to escaping flatland not ready for widespread consumption. Notes mostly pertain to startup engineering careers since that’s what my specific decision-making need was.

background

these are thoughts that have solidified after my process of deciding where to join full-time.

at the time I had the choice between 3 offers:

1. return offer from late-stage (series C/D) startup I interned at and enjoyed a lot
2. offer from small/medium-sized (series A/B) startup with product-market fit
3. offer from tiny pre-product, pre-series A startup

I ended up deciding on option 3, though there are definitely parallel universes where I’d have accepted any of the three offers, and leaned all three ways at various points in the decision-making process.

These were a few things I was decided upon prior to the decision-making process:

1. I wanted to get some more work experience rather than going immediately to grad school (and/or taking a gap year to apply). I’d enjoyed my time working so far, and looked forward to continuing my journey for at least a while longer.
2. I wanted to work at a startup rather than a larger company. I prefer chaos/uncertainty and high workloads over bureaucracy and low-impact work.

In the process, I discovered that the three most important things I was looking for in my next career move were, in order of importance:

1. optimizing for learning: I wanted the opportunity to work on a wide variety of things I hadn’t done before, and be able to wear lots of hats at once (bonus: have the chance to do some non-engineering work too, like product/design/sales/support). This heavily favored Option 3.
2. strong team/mentorship: Being early-career I wanted the chance to work with very talented, experienced engineers who would be willing to provide the support and feedback I’d need to learn the right habits from and grow in the right direction. This favored Option 1 (since I enjoyed the care/quality of mentorship in my previous internship), with Option 3 taking second place (since I had friends/connections who worked with the team previously and held them in very high regard).
3. filling in the startup gaps: so far I’d had the opportunity to work at a pre-product startup, a later-stage B2B startup with 1000’s of customers, and a large market-leading company. I was curious about the type and stage of startup I was missing experience in: going from 1-1000s of customers, and/or building consumer-facing products. This favored Option 2 (which was exactly the missing stage, but B2B) and Option 3 (still pre-product but would grow quickly into the missing stage if successful; consumer-facing) about equally.

Non-issues for me were:

• salary: all three of them paid a comfortable base salary; and because startup equity is so unpredictable, there really wasn’t any way of telling which one would end up being better so I just didn’t factor it into my decision at all.
• location: all three were within comfortable commuting distance and had similar policies for being in-office.

If you are reading this and you aren’t me, then your specific circumstances may be very different— but I hope that my personal reflection on this type of decision-making process can help provide an extra data point for you.

know your values

• if you can clearly state what your career and life goals are, you can use your values as an unbiased mediator for decision-making.
• rank the importance of at least the top 3 things you’re looking for in your next job. (stable income? learning opportunities? chance to work on impactful projects? strong mentorship? good wlb?).
  • communicate these preferences to potential employers so they can understand whether their opportunity is the right fit for you. great recruiters will turn you down, even if you’re qualified, if they know they can’t offer what you need— be flattered that they’re saving everyone a lot of time!
• it’s ok if these change during your decision-making process (if anything, you should be actively looking for holes to poke in your value system!).
  • lean on friends, family, and trusted peers during this time- ask for their opinions and take time to talk through your decision with a large number of people who have little to no stake in your choice besides wanting the best outcome for you.
  • AVOID discussing your values with managers, potential employers, and anyone else who does have stake in your choice until you have a strong conviction. they will often try to coerce your decision-making in a way that benefits them/their company (hopefully not nefariously; it’s literally their job!!).
    • identify when they’re trying to change your values vs. offer concessions towards them. the former is a red flag; the latter is helpful and can realistically change your decision without changing your values.
      • positive example: you’re considering switching jobs b/c you want to move closer to family; your company offers to relocate you to a closer office.
      • negative example: you want to switch jobs for better work-life balance; your manager warns you that your career will suffer if you start slacking off and offers you a raise instead.

maximizing two-way doors

• one-way doors: there’s no going back. you have to be really sure of yourself before jumping through them— the grass is not always greener etc.
  • examples: getting a phd in an unrelated field, canceling visa to stay in home country, burning bridges w/ toxic acquaintances, leaving for a direct competitor
• two-way doors: allow you to come back in, though often with some effort.
  • examples: switching teams, taking a year off to get a master’s, leaving amicably to go to a non-competing company
• most one-way doors can be coerced into two-way doors with the right planning and circumstance. doing so is often the first step in your transition, since it makes the burden of decision-making far lighter and lets you turn high-risk high-reward options into low-risk high-reward options.
• jumping through one-way doors can still be low-risk if you identify safety nets that can catch you if you fall.
  • do you have backup plans and savings?
  • can you revert to a similar, but not identical, position you were in before the decision?
  • does the opportunity on the other side provide you with any outcomes you can depend on?

expand your option pool

• even if you’re mostly set on one of a small set of options (perhaps even just the one), it’s worth spending time to open up competing offers and choices.
  • this makes negotiation much easier- if you have a secondary offer that’s giving you more of something you want, you can bump up your primary offer to be even better (even though you were going to take it anyways).
  • sometimes in the process of exploring alternatives, you realize that there are aspects of them that you wish you had for your main option. (or conversely, you’ll realize that most of what you originally wanted is also available elsewhere!).
  • generally expanding your community, knowledge base, and surface area for luck into more diverse planes is a good thing even outside of your career!

controlling information flow

• as engineers, we innately value transparency and speed of communication— if someone knows/learns something, or you need help w/ something, you should go talk to your teammates and tell them everything!!
• this is NOT true in a general business sense. many great deals, politics, hiring decisions, etc. are made through information asymmetry. as an employee, you can use this fact to your advantage (but it’s also easy to get taken advantage of from the other direction).
  • salary: learn how to negotiate. a few awkward minutes of discussion could be life-changing. it costs very little in relative terms to a company to potentially an outsized benefit to you. it’s not a zero-sum game. (employers also tend to value their employees more if they’re getting paid more!)
  • when weighing competing offers, whether you should leave a company, etc., be honest + firm when discussing the competition with a potential employer. your job is to tell them every reason why the competition is better; their job is to win you over by one-upping what they can offer.
  • avoid over-sharing your decision making process with recruiters/employers— even if you’re 100% set on taking/rejecting an offer, keep the doors open for as long as allowed and needed.
    • Employers will often try to rush you since it’s in their advantage to get you to start earlier and have a smaller period of uncertainty. They’ll appreciate it if you get back to them in a timely manner, but be very careful not to let yourself feel anxious about the deadline. If it’s just not enough time to gather all the information you need to make an informed decision, then don’t be afraid to ask for a few extra days— they’ll be happy to give it to you (and often set up additional opportunities to chat + get more info) if they genuinely want you to join their company.
• this also does not give you a free pass to lie or stretch the truth (though, you may need to omit certain details where needed). trust is difficult to build, yet gets irreparably broken the instant either party shows a lack of respect towards the other.
  • conversely, any potential employer that directly lies to you or withholds crucial information until after you make a decision is a huge red flag. no matter how many goodies they’re offering you, run far far away!!!