A lot of great projects have started in informal ways: a startup in someone’s garage, or a scrappy project run by volunteers. Sometimes people jump into these and are happy they did so.

But I’ve also seen people caught off-guard by arrangements that weren’t what they expected, especially early in their careers. I’ve been there, when I was a new graduate interning at a religious center that came with room, board, and $200 a month. I remember my horror when my dentist checkup cost most of a month’s income, or when I found out that my nine-month internship came with zero vacation days. It was an overall positive experience for me (after we worked out the vacation thing), but it’s better to go in clear-eyed.

First, I’ve listed a bunch of things to consider. These are drawn from several different situations I’ve heard about, both inside and outside EA. There are also a lot of advice pieces from the for-profit world about choosing between a startup and a more established company.

Second, I’ve compiled some anonymous thoughts from a few people who've worked both at small EA projects and also at larger more established ones.

Things to consider

Your needs

• Will the pay or stipend cover your expenses? See a fuller list here, including
  • Medical insurance and unexpected medical costs
  • Taxes (including self-employment taxes if they're not legally your employer)
  • Any loans you have
• Will medical insurance be provided?
• Maybe they’ve indicated “If we get funding, we’ll be able to pay you for this internship.” Will you be ok if they don’t get funding and you don’t get paid?
• Maybe they’ve indicated you’ll get a promotion after a period of lower-status work or “proving yourself.” If that promotion never comes, will that work for you?
• If you need equipment like a laptop, are you providing that or are they? Who owns the equipment?
• If you got a concussion tomorrow and needed to rest for a month, what would the plan be? If not covered by your work arrangement, do you have something else you can fall back on?
  • Medical care
  • A place to stay
  • Income
• If you need to leave this arrangement unexpectedly, do you have enough money for a flight to your hometown or whatever your backup plan is?

Predictability and stability

• How long have they been established as an organization? Newer organizations are likely more flexible, but also more likely to change direction or to close down.
• How much staff turnover has there been recently? There are various possible reasons for high staff turnover, but one could be a poor working environment.

Structure and accountability

• Will someone serve as your manager? How often will you meet with them? If there's not much oversight / guidance, do you have a sense of how well you function without that?
• Is there a board? If so, does the board seem likely to engage and address problems if needed?
• Are there established staff policies, or is it more free-form? If there’s a specific policy you expect to be important for you, like parental leave, you may want to choose a workplace that already has a spelled-out policy that works for you.

If living on-site

• Will you have a room to yourself, or will you ever be expected to share a bedroom or sleep in a common area?
• Is it feasible to get off-site for some time away from your coworkers? How remote is the location? Living and working with the same people all the time can get intense.

Work agreement

• Is there a written work agreement or contract? If there isn’t one already, you can ask for one. For example, in my state anyone employing a nanny is required to write out an agreement including
  • Pay rate
  • Work schedule
  • Job duties
  • Sick leave, holidays, vacation, and personal days
  • Any other benefits
  • Eligibility for worker’s compensation
  • Process for raising and resolving concerns (typically the option of a weekly meeting)
• Get things in writing. If you discuss your work arrangement verbally, and they haven’t sent you a written agreement, you can send a written message afterwards along the lines of “I want to be sure we’re on the same page. In our conversation just now we agreed on X, Y, and Z. Is that right?”
• Spell out the rate at which days off (holidays, sick days, etc) will be paid. If room and board is normally part of the package, how does that work during your holidays, vacation time, and sick time?
• Are there specific times when you’re not allowed to take vacation/holidays because of events or busy seasons at work?
• Is this an arrangement with set hours, or can you set your own hours, or is the expectation “work whatever hours needed to accomplish X”? What kind of hours do other people work?
• Are you expected to attend work-related functions in addition to normal work?
• Consider asking someone you trust (and who has had several jobs before) to look over the contract.

Communications

• Will you have permission to list this work experience on your LinkedIn, etc? There may be good reasons for not allowing this — maybe it’s a startup in stealth mode, or works in a sensitive area — but consider if you’ll be able to use the job for resume-building.
• Are there restrictions on your social media use? Will you need to avoid posting spicy takes on work-related topics? Will they expect you to take down any existing material you’ve written? (This may be more likely at more established organizations.)

Unpaid or barely-paid arrangements

• In some countries you can volunteer or intern at nonprofits and not be paid minimum wage. If you’re a volunteer, are you genuinely excited about contributing to the project’s work? If you’re an intern, are you gaining useful skills and experience? Or are you just very cheap labor?
• In EA, many (most?) projects pay their interns / fellows. If this project doesn’t have money to pay you, it might be a genuinely promising project that just hasn’t caught on with funders, or funders might have a reason for not being excited, or the project might not have tried to fundraise for these roles.

Travel

• If you need to move for this job, will any moving expenses be covered?
• Will you need travel medical insurance?
• Can you get items that are important to you in that location? (food to meet your diet, medicine?)
• If you see a therapist or other healthcare provider remotely, many of them have restrictions on operating across borders. 
• Will you be able to interface with locals if you don’t speak the local language?

Legal

• Will you be on a proper work visa, or are you expected to do work on a tourist visa?
  • If you don’t have the legal right to work in that country, how bad would it be if you get in trouble for your visa and are never be able to enter this country again?
• Does your status (as a contractor vs employee) match the kind of work you’ll be doing according to the country’s labor laws, or are you doing employee work but being called a contractor?
• Will you be expected to drive (including in a country where driving rules are different from what you’re used to)? Are you licensed to drive? Will you be expected to drive a type of vehicle (like a large van) you’re not experienced with?

Outside view

• Talk with someone who has worked for this organization or manager before, maybe especially someone who has left the organization.
• Is there someone you trust, ideally someone with related work experience, who you can talk over your decision with? What questions do they have about the arrangement?
• Once you’re at the project, do you have a social anchor outside that group you can stay in touch with?

Advice from a few EAs

This is a combination of lightly-edited thoughts from a few EAs who have worked both at small less-structured projects and at larger organizations.

A small project might be a better fit than a big one

I feel a bit on the edge about focusing so much on the informal projects — I am personally very unsure about my fit for a larger organization and my first year working at one has been challenging. I sometimes feel the meme spreading that working at a larger EA organization is better on so many dimensions, and even though it does provide some perks, I have had amazing times working at small informal projects and for me, one is not clearly better than the other one. Especially when you are in a time that you are more ok with taking risks I think it might be a good choice for proactive and problem-solving individuals. I learned so much at small projects and created super valuable friendships, and generally love the dynamism and sense of ambition.

Be picky

• Treat the choice of where to work (including within the space of “EA orgs”) as an extremely serious decision. For most EAs, the stakes are much(!) higher than the stakes for their donations. 
  • Take your time to figure this out, including e.g. calendar time delays to talk to potential references. 
  • Err against rushing this decision. If it is rushed, track that as a cost/potential source of error.
• Don’t assume that they’re impactful because they’re EAs.
• Reason about this for yourself, don’t defer to them. They are strongly selected for thinking that whatever they’re doing is great, even if ~no one else thinks this.

The organization’s reputation

• Ask around. What do other people think of this organization?
• Don’t just rely on references they gave you. E.g. “This intern can tell you how great their experience was.” Also seek out references they might not want you to hear. 
• Is it conventionally prestigious? (A more conventionally prestigious organization is likely to give you more flexible career capital)

Due diligence

• Don’t assume that they’re maximally transparent (even if they’re EAs) 
• What is their track record in terms of achieving objectively impressive things in the world?
  • Relatedly to the above, don’t trust them when they tell you about this. Try to do some amount of independent verification of claims. If they turn out to be exaggerated, that’s a major reason for suspicion.  
• Don’t assume that they’re necessarily cooperative in wanting the best for the world (or you) as opposed to locally trying to get you to do their work.
• Things that are unconventional or weird can sometimes be the right career choices. But the vast majority of "weird things" (including within EA nowadays I'd guess) just aren't that great. So the more something is unconventional, the more you'll need to do your own due diligence and independent thinking about it: if you just go work for Apple, you'll kind of know what you get and probably be ~fine if you don't pay attention to minor yellow flags or just don't worry about the details of your work arrangements etc. But if you go work for a small new org without funding, you'll really want to tune up your BS-detector.
• Did they get funding? Are their hiring rounds competitive? If not, be more suspicious/beware of adverse selection: perhaps other people don’t work there or fund them because they know stuff you don’t.
  • E.g. maybe they don’t have money to pay you, because funders don’t want them to hire/manage people, or funders just think they’re low-impact. This is one reason that getting a normal-ish salary and then donating is often better than taking a huge paycut, even if you’re altruistic.

Spell things out

It seems boring, but talk ASAP about roles, responsibilities, and expectations. It's ok to not know and to redefine for every project you start, but knowing that you are both thinking that you don't know seems valuable.

Interpersonal fit

• The smaller the organization and the more undefined it is, the more important it is that the collaboration is good. And not just nice, but that the collaboration is good when "shit hits the fan.” Conflicts will inevitably arise, and interpersonal conflicts are extremely likely to form in small, chaotic, informal teams. So the question is how you can handle these conflicts together, if you have good communication, if you trust each other, and if you are willing to step aside for the other person and help, even if this means doing things that you don't like / that you did not expect / that feel lower status.
• Ways I test interpersonal fit when I am forming small projects now:
  • conversations about feedback culture
  • three days in-person work test that are mostly about testing fit for working together (so not testing skills, but how do we scope together something that is very ill-defined and we probably have different ideas about?) and also hanging out informally (e.g.; having dinner, playing board games, etc.). 
  • an open feedback conversation that includes negative feedback at the end, to test if you could work through issues that could be emotional together
• I recommend having an outside person who can help you to process interpersonal fit. At [small organization] we followed the process where every team member had a conversation about the interpersonal work culture/dynamic with a board member at the start of the collaboration, and a similar conversation after three months. One of the goals was to surface issues before they were too big.
• I recommend having an outside person who knows all team members (decently) well and can play a helping role by talking with people and helping to process what's going on.

Test and adjust

• Have a three month (or other time interval) explicit 'testing' period. [Small project] usually works with three months of mutual (it's for both sides!) testing out. We have not needed to terminate, but having an explicit re-evaluation and clear moment of "It’s ok to leave, and we are probing you now to consider if you want to leave" seems good.
• If the project is not open to testing and shaping the working relationship, I would find this a red flag. I would like to know if they are open to suggestions along the lines of the above.
• Be ready to leave — sometimes it doesn't work out, and that's ok.