Epistemic status: my personal experience, YMMV
I'm Sam, executive director of the Jewish Social Impact Network (JSI, formerly known as EA for Jews). I started in this role about two years ago, so I thought I would share some learnings now that I've had a bit of time to get oriented. I don't mean to suggest anything here is universal, it's just my experience that I hope others at early stages can learn from.
Running JSI has been a very different experience from just about every other kind of work I've done before, but it's a common type of experience in this community. It's been incredibly valuable and I'm very glad I chose to do it, but it's also very hard. In a sense, this has been the first time I've ever felt deeply challenged by my work. Every prior stage in my life had clearly defined steps, and like some other people I know in EA, I didn’t struggle much with any of them. This was completely different, in ways that have been both stressful and generative. After I started I felt like I'd thrown myself into the deep end. Honestly, I floundered for a while.
But struggling has taught me a lot. With lots of support, and more experience under my belt, I think things are in a stronger position now. If you're looking for inspiration to get you from zero to "maybe this will turn out alright," this might be the post for you.
I hesitated to write this because in some ways it's hard to act on. I remember getting lots of advice early on that I could tell was good advice at the time but still struggled to put into practice for a while until I had directly learned it myself through trial and error. Even things I endorsed intellectually and intended to implement were difficult to really internalize to the point that I could apply them to my specific context, incorporate new habits in my working style, and prioritize between competing approaches. Some of the advice I heard is even repeated in this post, which led me to wonder: if an abstract understanding of the "right" way to approach a project is no match for direct contact with reality, and the only way to figure things out is by doing stuff, is it worth giving advice at all?
I tentatively concluded that my reflections might be reassuring to other people who are feeling overwhelmed by the rapid learning and growth necessary in the early stages of a project (or their careers in general). The problems we face often seem less daunting when we see that others struggle with them too and they can be overcome, especially if we have tools to help us solve them.
So here's what I learned.
I'm more confident this section generalizes broadly.
Seriously, if you can avoid it, don't take on your big project solo. If I could go back two years and change one thing (among many worthy contenders), it would be not having a co-"founder." The value of teamwork may be a universally known applause light, but I don't think I was able to appreciate the necessity of collaboration until I took on a project without it.
I encountered two big problems as a result of going it alone:
All that said, I'm not sure finding the right collaborator would have even been possible at the time because talent is scarce. I hear people say this all the time, but my experience working in the effective careers field has reinforced the lesson. Obviously, there are many people in the world who are good at what they do, but people who bring the right set of (rare) skills for a very niche role in a highly uncertain environment for under-market pay are hard to find.
Relatedly, there are no bonus points for lone wolves. You can and should use whatever outside support is available. I'm glad I got help from two coaches (as well as other informal advisors), but I wish I'd done so from the start. Early on, I didn’t appreciate enough that while having oversight from my advisory board was helpful, it is not the same role as a coach or mentor. Often, you need someone to help you navigate your work who's looking at it from your side, including in your interactions with other stakeholders like your board. (h/t to Sarah Pomeranz for recommending Andreas Setzer and for her own periodic coaching, as well as to Kelby Kupersmid for his helpful executive coaching)
Lots of startup advice focuses on the importance of understanding what problem you’re solving and how you solve it (this is known as product-market fit), but it’s ok for this to take time. It's often an iterative process. Some projects start as one thing and pivot to something completely different, while others hit on the right idea at the outset. For me, it was something in the middle: I came into an existing early-stage organization, experimented with a few things, and ended up settling on a direction that was a modest pivot. When I started, EA for Jews was a broadly community-building focused organization that ran dinners and general learning-oriented fellowships. Now, JSI focuses more narrowly on providing career development programs and a network for Jewish professionals focused on impact. That pivot took a year and a half to settle on, and I get the sense that isn't unusual.
It just takes time to build context and skills in an ambiguous, self-directed job, even if you’re qualified for it. Unfortunately, there isn't much you can do to change this: you don’t know what you don’t know, and some knowledge only comes from experience. Just like you can't become a skilled medical researcher solely by reading a biology textbook, you can't become an effective community builder solely by reading the forum (as great as the forum is).
Maybe I’m just deficient in this way and this is easier for other people, but it was hard for me to implement textbook "best practices" until I had tried things and built up my own experience. There was just too much to absorb at once, and I didn’t know where to start on the list of things I needed to do. The only way I found to break through when I felt lost was trial and error, patiently building up my hard-earned knowledge.
This phase can be uneven. I knew there would be some adjustment period, but it was a lot longer than I expected it to be. Definitely over a year, probably more like a year and a half. But when the switch flipped, things changed quite a bit. Settling on a clearer, more realistic direction that I felt confident in based on my initial exploratory months of experience re-energized me. Instead of dreading the blank space that was the future of my organization, I started feeling really excited to get to work every day. I went from struggling with bouts of procrastination to noticing workaholic tendencies in myself (that I know aren’t sustainable long-term and I’m working on solutions to that).
I was already on board with the importance of evaluation when I started, at least in principle. Intellectually, I would've said I was open-minded about pursuing whatever direction seemed best based on the information I had, and in many ways, I think I've acted accordingly.
However, I underrated how difficult it would be to put this attitude into practice operationally and psychologically. It takes effort up front (to design a system, collect relevant data, and iterate on the program and evaluation strategies if early results aren't promising) that you don't always feel like you can spare, and opens the possibility of direct confrontation with failure. The pressures of following through on commitments to funders, stakeholders, and myself; the desire to project stability and consistency in the organization; and fear of uncertainty that comes with change all probably warped my decision making to some extent. It's very easy to tell yourself a story about how all that M&E stuff is a luxury for more established organizations while you "just need to execute on things" until you find stability. But paying attention to early indicators is how you determine which plans are worth executing. Resisting the temptation to put this off speeds up the process of iteration and saves the trouble of bigger problems later.
In my case, I initially didn't have a structure for tracking the outcomes from my career advising and fellowship programs, like people starting new high-impact jobs, applying to promising opportunities, taking steps toward a transition like attending EAG, etc. This made it harder to see which parts of the fellowship design were and were not working, prioritize activities I wasn't spending enough time on (like finding new career advisees), write strong funding proposals, and adjust organizational strategy. Giving more thought to this structure helped me align my day-to-day with a more promising high-level strategy and monitor progress so I can course correct along the way.
This job often forces me to confront my weaknesses while taking my strengths for granted. In this way, it's an inversion of a typical job. In my past experiences, I was put in roles aligned with my skills and given work that drew on my strengths while covering for my weaknesses. Here, I take advantage of my strong suits, but spend much more time thinking about and finding ways to mitigate my areas of weakness.
This is burdensome (read: this role is not for everyone), but it's also been highly valuable to me psychologically and professionally. No other experience in my life has fostered so much learning and growth so quickly. In addition to the skills it has taught me, it has also rigorously tested my ability in several areas, giving me a much better calibrated sense of my professional value. This experience has helped me make a few useful updates, such as updating positively on my aptitude for entrepreneurship and advising and negatively on social media marketing and project management (at least, at my current skill level).
EA is often described as having a "bias toward action." To the extent that I adopted this bias, I'm glad I did. I’m glad I said yes to lots of things when I didn’t know what exactly to do. In particular, I’m glad I took opportunities to immerse myself more deeply in the EA community (that’s probably especially valuable to me doing community-building work, but I’m sure it’s a robustly good idea). Trying things is a way to increase your surface area for serendipity.
Things I'm especially glad I did:
While there's value in trying different things, you still need to prioritize when you allocate precious time and resources. My agreeable disposition made this a challenge for me. If you also have this sort of disposition, you'll need to resist the urge to enthusiastically embrace every idea you're presented with. You can't be all things to all people, and it's better to disappoint someone gently up front than to take on too much, fall short of your commitments at a later stage, and burn yourself out. Sometimes the best thing to do is hear someone out, acknowledge the merits of their suggestions, and explain why you aren’t prioritizing them right now.
When people on the outside of your project make suggestions or pitch you on initiatives, they usually mean well, but they don't have the necessary context to gauge what you can realistically take on. You are the only person in the best position to make prioritization decisions about your work. Making these decisions is also one of the most important (and likely most difficult) parts of your job. It can be lonely, so seek outside advice when you can, but ultimately you are responsible. If you have a tendency to succumb to the planning fallacy and overextend yourself, err on the side of narrowing to fewer activities and saying no to more awesome ideas potential distractions.
There's a fine art to managing the balance between prioritizing the most important activities and testing lots of ideas. I think I should've struck that balance by testing more hypotheses relevant to the specific core program that was my top priority, rather than letting myself drift. Specifically, I should've turned down ideas like external partnerships to run a series of events that required substantial time and effort on my part without clearly being able to yield lots of direct benefit. Because I find it hard to say no by disposition, I was biased toward trying to make everything work, which for a while resulted in not much working at all. I rationalized this bias by telling myself that it was a good idea to test out lots of options because I was in an exploratory phase. There may have been some truth to this, and I did learn from it, but it probably set me back compared to a counterfactual where I focused on what seemed most important. Other people with different natural inclinations may need to adjust in a different direction, so it's important to notice which biases you have to account for them properly.
A related thought pattern I found myself falling into is what I'll call the "just around the corner" fallacy. I noticed myself thinking "I've been meaning to get to task x, but I'm really busy with y. That's temporary though; once I'm done with y, I'll be able to get back to it." I perpetually felt busy for months on end, but in the moment it would feel like just a temporary thing with the end just around the corner. Instead, things would usually languish on the back burner for a while, because task y would take longer than expected and then task z would arise before I ever got caught up. The busy-ness was a more fundamental problem of limited time and insufficient prioritization, not a short-term crunch specific to a given month's agenda.
One strategy that can help with this is to set a regular check-in point to look back on how often you're actually getting back to those less-urgent things within the amount of time you expected. If you’re often falling short of your own expectations, or the to-do list is growing faster than items are being checked off, re-assess whether the things you wanted to get to “eventually” are really as high priority as you originally thought. If they still seem to be just as high priorities, look at the things you’ve been doing in the meanwhile to determine which of them need to be explicitly moved down the priority list, then adjust your agenda accordingly. Keeping too many things "high priority" results in more stress while treating all of them as low priority in practice.
Listen to that inner voice nagging at you. Even (or especially) if it feels uncomfortable or you don't know what to do about it.
It's easy to forget that you aren't alone even if you're doing solitary work. But once you've paid attention to the "off" feeling enough to identify something that seems like an issue, external mentors and thought partners can help you figure out the solution. I should’ve listened to this voice more, and I think part of the reason I didn’t was that it didn’t occur to me that I could seek support when I didn’t know the answers. I now feel silly looking back on how, at various points, I felt uncertainty about my strategy, financial management, and ability to get things done but didn't think to seek the obvious sources of help. Although it can be difficult to swallow your pride and ask for help with something that feels basic, you might get much farther ahead if you do.
The most important nagging doubt I had was about my strategy. Early on, the voice in my head was trying to tell me it was too sprawling, with a fellowship, events, and 1-on-1 networking to advance goals of career transitions, effective giving, and more general community-building. It saw a red flag every time I struggled to give someone an elevator pitch-length explanation of what I was working on. I should have listened sooner: narrowing my focus has been by far the most important thing I've done to improve my effectiveness. JSI now has a much greater volume of people coming through the fellowship and/or 1-on-1 advising, and a much greater volume of high-EV actions taken as a result.
This section is more personal, so I'm less confident it will be applicable to most people, but I'm sure some readers can relate.
This experience has been seriously humbling. I never doubted my overall ability, but I have seriously questioned whether I was in over my head in this role and needed to go back to the drawing board before I’d be ready to run an organization. There was no point when a switch flipped from feeling this doubt to no longer feeling that way. Instead, it came in waves, and with time they generally got less frequent. Anxieties that arose every day at first slowed to once a week, then once a month. Eventually, I stopped feeling it at all, apart from occasional normal work stress.
Now that I'm growing something from an early stage, I see more clearly how much effort goes into any substantial project, no matter how simple it sounds. As a result, I have much more respect for anyone who builds just about anything of their own. I'm really glad I gave myself some tangible exposure to this perspective and I expect it to be useful later in my career.
Despite the truism that learning and growth require trying new things, I think this lesson may be under-appreciated in career development. It was for me, at least.
In my prior job, while I learned some subject-matter knowledge and sharpened the technical skills I used every day, when I left I wasn't a meaningfully different person from who I was when I started. My work at JSI, on the other hand, requires me to learn something new most days and to grow continuously in several different areas. I don't think that would have been possible if I hadn't taken on a difficult, open-ended project that came with some doubt.
It took pushing myself to the edge of my professional comfort zone to really begin developing skills beyond the ones I took away from my academics and the limited set of familiar domains that had come to feel safe. With greater risk came greater reward.
Many weaknesses can be overcome through some combination of outside mentorship, upskilling, experience. But some can’t, and we only have finite effort we can devote to self-improvement. Obviously, imperfection is fundamental to being human and an inevitable constraint on our effectiveness no matter how growth-oriented we are.
While this observation is a cliche, it can be difficult to accept in an optimizing culture like EA. It can feel like there's always someone out there somewhere who’s optimizing something you suck at optimizing, and at least for me, being confronted with that can often lead to insecurity, stress, and anxiety. It’s great to learn from others’ strengths and advice, but only up to a point. If you shy away from doing things at all for fear you won’t do them optimally, you’ll never make progress or grow. I really admire the ability I see in many members of this community to prioritize ruthlessly, but it does not come naturally to me. I’m pretty sure I’ve improved on this front, at least at the scale of high-level strategy (though I haven’t exactly measured it), but I feel confident I’m still below average when it comes to my day to day routines.
I plan to continue doing what I can to get better (for example, I’ve long meant to test the hypothesis that Adderall would help with my executive function issues, but, fittingly, I haven’t gotten around to it), but I’ve also come to feel more comfortable with the possibility that I’ll never be awesome at this for three reasons:
This community is full of excellent advice for improving your work and yourself. But I wish, alongside this advice, someone had told me that it’s ok to accept your weaknesses, and it’s also ok to accept that you may never try the 'solutions' to some of them.
While I've learned a lot, progress in my weakest areas can be slow. I'm still disorganized and expect that I'll need to hire to improve JSI's internal systems. And despite having thought about prioritization a lot and feeling like I've come a long way over two years, I'm sure I could still do a better job prioritizing. Continuing to improve in that area would probably reduce my stress and increase my impact further, so I plan to keep focusing on that in the years ahead.
If you read this far, thanks for your time and I hope this was valuable to you! I'm also really grateful to everyone who was part of this journey, helped me, and stayed patient with me along the way. In particular I'd like to thank Hillel Ehrenreich for his incredible work pioneering EA for Jews before I joined; my formal and informal advisors for offering candid feedback and support to help me steer this project; people I spoke with at EAGs or virtually when I didn’t have a clear ask other than soaking up their knowledge; the EA Infrastructure Fund for their patience with me and providing the funding runway that has been essential as I onboarded and figured out what I was doing with my organization; Coefficient Giving for supporting JSI's next stage to make the project more sustainable; and most of all my wife Samy, for always serving as a second set of eyes on my work and for her support as I took on a risky and demanding project.
